The Weekly Reid: How to overcome an IMPOSSIBLE task

Every so often, we are faced with what seems to be an impossible challenge. A task so large and so complicated and so difficult, its hard even to imagine what a win could look like. These don’t come along very often – thank goodness. Maybe once every five years or so in my experience. But when they do come along, the journey they provide tends to change the course of your career. Your response and actions and attitude when faced with an impossible challenge, give you character – they define you as a leader – they shape the future (better) you.

I should say, in my career, it’s the impossible challenges that I go back to over and over again. These moments have become the stories I tell my team when we’re up against it. They are the stories I share with my friends and former colleagues. I should also say, not all of these stories are of victory. That’s the exquisite beauty of an impossible task. Even in failure there is greatness to be found (which is a good thing, because failure happens a lot when you take on impossible things).

I don’t have a nicely packaged set of tips to overcome whatever impossible task you are facing. Unfortunately, it doesn’t work that way. That’s the nature of the impossible task – it’s impossible. I can’t change that for you anymore than I can change it for myself. But what I can do – what I hope to do – is share some of the lessons I’ve learned over the years that have helped me make it through some pretty daunting challenges. And in so doing, I hope I can help make your next impossible challenge a tiny bit less impossible.

Observe your situation from a distance

When you’re right in the middle of an impossible task – stressed to the max, taking heat, working around the clock – you can easily lose perspective. You can get sucked into a crashing wave of work and worry that makes it hard to know which way is up. Days and weeks can go by in the blink of an eye. And if you’re not careful, this wave can push you off course – your mind and your work.

I find it helpful, when I’m facing an impossible situation, to observe myself and my situation from a distance. What do I mean by that? It’s about detaching yourself for a moment and watching yourself as an outside observer would. It’s about being aware of what’s happening – in the way a scientist would be aware of an experiment. It’s about noticing what’s going on. It is far different from being inside the situation. It’s actually about taking yourself outside the situation (to the extent that’s possible).

If you can detach yourself for an hour or even a few minutes, you can gain valuable perspective on your mental state and on the tasks at hand. You’ll find in doing this, you can see things in a different way. You can relax a bit more. You can notice flaws in your logic. You can find wins you didn’t realize you had.

Cut everything until you find something to win at

If you are a regular reader you will not be surprised to hear this one. I have always been a huge proponent of doing less - ruthlessly prioritizing. I have spoken out against multi-tasking on several occasions. But sometimes, when you have an impossible challenge, with eight million components and complexities, it’s impossible not to multi task a little.

The risk, when your volume of challenges is so great, when there are so many problems to deal with, is that you end up accomplishing nothing. You improve ten issues by ten percent instead of one issue completely. From an outsider’s perspective, you haven’t actually accomplished anything. But you worked so hard. The effort it took to advance those ten issues by ten percent each was huge. You’re tired, your team is tired, and yet it appears like nothing has been done. This is a massively demoralizing situation.

When I have a huge number of tasks to take on – all of which seem to be urgent – I still apply the same ruthless prioritization approach. The first thing I do every morning is make a list of my major issues, and then I cut everything out until what is left is something I can realistically win at that day. I refuse to let a day go by without finding a win. The benefit of this approach is that I win at something. My team wins at something. We see progress. Outside stakeholders see progress too – as fractional as it may be. And with that progress comes a hit of energy to fuel the next push.

The challenge with this approach is I have to let things wither and die. Important things. There is no other option when you’re faced with an impossible task. So, I quarantine issues where I can. I tie off problems, so they don’t spread or get worse. It takes a lot of strength to do this, I can assure you. As much as I can, I speak openly about my choices and sacrifices with my manager, so she understands the situation and is not surprised or embarrassed by the issues I’m not able to focus on yet.

Embrace the lessons learned

When I’m feeling particularly stressed out or overwhelmed by the impossibility of a situation, I remind myself that the lessons I’m learning have value. And that, so long as I make good choices and apply sound judgement, I will have nothing to regret when I look back on the challenging period. I try to take note of the lessons I’m learning even as they are happening and point to those as wins in and of themselves.

My recommendation, for those of you facing impossible tasks, is to take note (like actually write down) the lessons you’re learning. Be grateful for that. Find a win in that. It can have a profoundly positive impact on your perspective and energize you for the daunting challenge that lies ahead.

Put yourself in the best possible mental and physical state

I won’t dwell on this one because it’s been written about a thousand times. But, if you’re not careful, you can let the stress and anxiety of an impossible challenge make that challenge even harder to overcome. There can come a point when you start getting anxious about being anxious. Getting stressed about being stressed. Allowing the fear that you are failing manifest the very failure you fear. This can snowball on you. You may think this is easier said than done (perhaps it is) but you need to try to present your best self in front of an impossible task.

Sleeping well, eating well, doing some physical activity – these things can make all the difference in the world when you’re in front of a seemingly impossible challenge.

Every so often, as leaders, we are faced with an impossible task. The deck is just stacked against us. Inevitably, these are the moments that define our careers and give us the toughness to lead others through difficult challenges. There is no magic list of tips to make impossible things possible. Sadly, it doesn’t work that way. We can only put ourselves in the best possible mindset each and every day, make good choices, and stay positive. I hope this perspective is helpful to you as you take on your next impossible challenge.

The Weekly Reid: 3 Tips to Lead Through Change in 2019

How do we lead a team through uncertainty and change?

This question gets to the heart of what it means to be a leader. The answer to this question is the answer to just about everything. Here’s my perspective:

A former mentor of mine used to tell this story during periods of change.

When you’re on an airplane, and it starts going through turbulence, the first thing people do is look up at the flight attendants. If you look up and the flight attendant is calm and happy and serving customers, you calm down, you relax, you assume everything is going to be ok. But if you look up and the flight attendant is nervous or panicking or visibly concerned – if, when turbulence hits, the flight attendant blinks - you start to panic, you start to worry.

Our job, as leaders during times of turbulent change, is not to blink.

This anecdote has always resonated with me. I remind myself of it whenever my team is faced with change. It has served me well, and I hope it will serve you well too.

What does it mean to “not blink”? It boils down to three specific things for me:

Be purposeful, not reactive

Inexperienced managers react to change. They take in a flow of inputs – complaints, concerns, frustrations – and they try to react to each one as they come. They favor speed of response over substance of response. They try to move quickly. They are uncomfortable in a state of flux. They exacerbate tension and anxiety with their own frantic energy. That leads to more panic, more chaos.

Experienced managers, on the other hand, are purposeful. They’ve been through change. They have the patience and calmness to sit amidst a chaotic, frenetic environment and make sound decisions. They communicate effectively, purposefully. They don’t react just to feel like they’re taking action. Instead of making 100 frantic reactions, they make 3 or 5 strong, purposeful moves.

Next time you’re in a crisis or managing through change, stop reacting. Stay calm, don’t blink, and take purposeful actions only.

Explain the context to everyone

One of the primary contributors to anxiety during change, is a lack of understanding for WHY the change is occurring. In the absence of proper context, people speculate – often leaning towards the worst-case scenario. The company must not be doing well. We’re definitely getting laid off. This is surely just the first of many changes.

When you don’t give people proper context, this is where their heads go. It’s a natural reaction. It’s understandable. But it’s also deadly if you’re trying to make productive, positive change.

My advice to leaders is to give people the full context for change as soon as you possibly can. Tell them why. Give them the business context. Empathize with their position. Walk them through the logic that has led to the current situation and decision making. Some leaders mistakenly assume people won’t understand or don’t need to know the context for change. I think this is misguided. Give people context – early and often.  

Be honest and direct

Another mistake inexperienced managers make when leading through change, is to sugar coat things. Or to speak of changes in a manner that is unclear or convoluted or patronizing. They assume (wrongly) that people can’t handle the naked truth. That they need to be placated. In my experience, this is not the case.  

My advice to managers, when leading through change, is to be completely honest and direct in communication. Tell people what is happening, what it means for them. They can handle it. It’s much better for people to have an accurate picture of what is happening, than it is to preserve some false sense of security.

With the beginning of a new year, we almost always see changes. Our teams change, our goals change, our industry changes. Things change, and most people struggle to handle the uncertainty and anxiety of it all. I hope these tips for leading through change were as helpful to you as they have been for me.

Happy New Year!

The Weekly Reid: Is your team strategic? Advice for managers who want to say "yes"

It never ceases to amaze me how few managers can describe their function (and team) as an integrated system. When I ask them about their teams, they tell me about activities, projects, tasks, people. When I ask them to draw me a picture of the system they’ve built and the strategic purpose of that system, I too often get blank stares in return.

The truth is, there are levels to management. To thinking about management and developing a team. To becoming “strategic”. And, in my experience, the upper levels don’t even reveal themselves until you’ve built a strong enough foundation to understand them. I am sure there are many levels I can’t yet comprehend because I haven’t learned enough to be aware of their existence. I don’t know what they are yet, but I’m pretty sure they’re out there waiting for me.

 Today I’m going to walk you through how I think about the various levels of management and team development (at least the levels I’m aware of). I hope it’s helpful as you build a vision and model that makes your team more strategic.

 Level 1 – Activity Centric

Early in a team’s development they tend to chase activities. This is especially true in early stage companies, where established systems and processes do not yet exist. Teams move from one activity to the next, focused almost entirely on the execution of those activities. They tend to measure success by the individual successes of the activities. Did we run a good event? Did we write a good report? Did we close a deal?

The biggest challenge with an activity-centric approach, (aside from it not being strategic) is that it doesn’t scale. You can’t continue applying the soccer game model as your team and company grow. It won’t work. Moreover, the activity-centric approach tends to be disconnected from the real goals and objectives of the company. When you assign intrinsic value to any one activity e.g. an asset or event or project, you miss the point. Tactical activities actually have no intrinsic value – their only value is in how they connect to a strategic business outcome. You can miss this entirely if your team is too focused on activities.

 Level 2 – Function Centric

At a certain point, a manager, and her team by extension, come to realize an activity-oriented model is insufficient. Typically, the leader wakes up one morning with the painful realization that while their team can execute activities, they lack expertise and knowledge of best practices for key functional disciplines. At one time it may have been enough to have generalists working together to execute sequential activities, but that isn’t enough anymore. The best companies in the world have expertise in every function, they have specialization, they have depth. And so, we start building out functional excellence on our teams.

The biggest challenge with a functional-oriented approach is that while it may add quality to your activities by applying best practices, it is still largely disconnected from key strategic business outcomes. Now, your functional teams operate well, but they operate in silos. Instead of assigning intrinsic value to activities, they now assign intrinsic value to functional processes. They aren’t integrated. They are functions that aren’t connected to a higher-level system or process.

 Level 3 – Outcome Centric

Once you’ve moved away from a fixation on activities to develop functional depth, the next level is to integrate those functions to achieve strategic business outcomes. The challenge with both the activity-centered and functional-centered approaches, is they are inherently wasteful. Resources are not efficiently aligned towards the pursuit of high priority business outcomes, they are aligned either towards activity execution or functional best practices.

There comes a moment in every manager’s life when she realizes just how disconnected the team’s efforts (and budgets) are from the actual outcomes the company cares about. They are directing resources and energy towards building expertise and best practice, but that’s not what the business is really about. And so, we re-engineer our organizational structures and processes and KPIs to focus on the pursuit of real business outcomes e.g. revenue acquisition, customer value expansion etc. We build a real architecture and model for our teams and tactics work together in an integrated system with a focused business outcome in mind. This makes a big difference and tends to bring with it, new levels of resource efficiency and connectedness between employees and strategic business initiatives.

Level 4 – Leveraged Model

Now that you have an organizational structure and model that is oriented around delivering to business outcomes, you can begin to scale it. Scaling too early only results in pain and problems. Too many teams try to scale poorly architected models and wonder why its ineffective. Too many managers get infatuated with new trends and the promise of technology and overlook the prerequisite steps to be able to take advantage of them.

But once you have a solid system and model in place, you can begin to apply leverage through the use of data and technology and automation. You can find new levels of scale. You can begin to add additional value to the business as your focus moves away from fundamental model design and towards incremental value creation. You can be strategic.

There are levels to management; to team development; to becoming “strategic”. I am sure there are more than four. I just don’t know what they are yet. My advice to managers is to plot your team against these levels and build a vision for advancing – one step at a time. I hope this was helpful to you and, as always, I’d love to hear your thoughts in the comments section.

The Weekly Reid: 3 Things Every Manager MUST Do in December

We’re winding down the year. It’s easy to take your eye off the ball. It’s easy, in between the holiday parties and family festivities, to overlook a few best practices that can be very important to your team’s momentum and your own career advancement.

Today I’m going to share three things I do every December to put the cherry on top of the current year, and to set my team up for success in the year to come. They won’t take you a ton of time, but in my experience, doing these things can be extremely valuable.

Publish a year-end highlight real

It’s very easy for your boss and other company leaders to forget all the great things your team has done this year. Even you may have forgotten some of them. If you’re not careful, some of your great efforts and accomplishments can be inadvertently swept under the rug.

One of the most important jobs you have as a manager is to create visibility for the great work your team has done. That recognition is critical to building a winning culture where people feel their work has value. It’s great for the culture of your team. It’s also great to set you up for a strong performance review in the new year, since your accomplishments will be top of mind.

Each December, I create a highlight real to summarize my team’s greatest accomplishments for the year. I spend time on it. I go back to projects from January and February and March so I don’t overlook anything. I find wins from across the team, and I remind everyone of them.

A highlight real can take several forms … a PowerPoint deck you present at a team meeting, a booklet you distribute to your team members and leaders in the company, a fun video you make with your team. It doesn’t matter so much what format your highlight real is in. What matters, is that you take the time to summarize all the great things your team did this year and tell people about it.  

Publish a vision for next year with key strategic initiatives

Too many teams start slow in January. Some teams barely get going until February. A slow start makes the rest of the year harder. You can lose momentum. It can cause the leaders in your company to question your vision and plan for the year. It can make you appear to be stagnating. It can cause anxiety on your team.

Every December, I bring my entire team together to share a vision for the year to come. I try to paint a picture for how we will evolve and change to get better. I give context for why this change is important, and how it relates to the highest-level goals of the company. I break this vision down into key strategic initiatives so every member of my team can understand what we are doing and how they factor into it.

By sharing a vision for the year to come, you allow your team members time to process and understand it. This way they can enter the new year with confidence and purpose vs. questions and concerns. By sharing a set of strategic initiatives, you demonstrate to your team (and to leaders in your company) that you have a plan, that you’re evolving, that you’re improving. Every leader needs to do this.

Individually thank your team members

You may think this one is obvious. Maybe it is for you. I’m not sure it is for every manager. We can all agree it’s important to thank our team members for a great year. But I want to highlight how important it is to do this individually – personally. I don’t think it’s enough to send a “thank you” email to your team or hand out some templated holiday cards. I think you need to do more.

I’m not talking about expensive gifts or grand gestures. Quite the opposite. In my experience, the most impactful thing you can do to show your team members how much you value their contributions, is to personally thank each of them. I write a personal letter to each of my direct reports to thank them for their great work and partnership. I spend time on this. I think back on the year, where they’ve come from, what they’ve had to overcome – the ups and downs – and I put it all in there. They’ve worked so hard, on so many things, they deserve this depth of acknowledgement.

My recommendation to managers is to get a little more personal this year. Spend a little more time on your recognitions. It will mean a lot to your team members.

December is an easy month to get distracted. But that is akin to slowing down at the finish line. If you’re not careful, you can dull the impact of all the great things your team did this year, and lose momentum going into next year. I hope these three tips are helpful to you, as you close out another great year. 

The Weekly Reid: 3 tips to make your boss care about your projects

It’s hard to make progress if your boss doesn’t really care about what you’re working on. I get questions about this all the time.

My boss cares about everyone else’s work but mine. How do I change that?

How do I get my manager to focus on my projects even for half an hour a week?

I work my butt off on these initiatives and nobody seems to care. Can you help?

My boss refuses to pay attention to my project until the last minute. And then he blames me!

If you feel like this, from time to time, take solace in the truth that you’re not alone. We all face it at some point over the course of a career. But let’s start with some tough love. There are some realities we have to accept. If the projects you work on aren’t directly associated with generating revenue, if they aren’t part of a hot new product release, or in support of a big deal or partnership, it’s going to be tough to command sustained attention. That’s just part of the deal. But it doesn’t mean you CAN’T get your boss to care about your work. You just have to be more purposeful in how you go about things. I hope these three tips will help you.

Tip #1 - Start with your boss’s priorities and work backwards

This one is about tactical empathy. If you haven’t read my article on the subject, I suggest checking it out here. Too many people in the workplace focus only on themselves and not enough on others (I’m sure that’s universally true in life and in work). We tend to speak about our projects and initiatives using a context the reflects our personal priorities – why we think it’s important. We get fixated on our own self-interest – what WE want to accomplish. And then we wonder why we can’t get anyone else to care about it.

If you want your boss (or anyone else for that matter) to care about a project you’re working on, start with what THEY feel is important, and work backwards to show how your project can help them. This is the complete inverse to what we see most of the time. Endless PowerPoint slides and conference calls that seem completely disconnected from what any audience member actually cares about.

My advice is to start by identifying the key outcomes and initiatives your boss cares about. Then map those to the potential benefits of whatever project you’re working on. Use language and metrics that can connect your priorities to your manager’s priorities. Show how paying attention to your initiative will help your boss achieve her goals. It will make all the difference in the world.

Tip #2 - Speak in outcomes, not activities

Too many of us speak about business activities instead of business outcomes. We talk about events and documents and processes instead of how those things deliver value to the company. And then we wonder why nobody cares about our work.

I can’t tell you how many presentations I see that skip over desired business outcomes entirely. People just jump straight to whatever activity they want attention on and never get to the point of it all. The impact is that activities become so derivative, so disconnected from what matters most. It can be hard to take seriously if you’re a busy manager or executive.

A good rule of thumb is to start every discussion about a project with the desired business outcome. What corporate initiative or goal or metric is this project in service of? Why are we here discussing this activity in the first place? What meaningful outcome is it connected to? How are they connected? How does focusing on this activity get us closer to achieving our highest-level objectives? If you build this context into your presentations – into how you talk about your projects – you will get more attention from your boss.

Tip #3 - Bring options and intentions, not problems

Your boss is likely a very busy person. More than busy, your boss likely has a wide variety of competing priorities that span functions, groups, even departments. That’s a different kind of busy from just having a high volume of work on one thing. It’s harder to focus. It’s hard sometimes even to remember all the issues and projects from one day to the next.

If your manager is anything like me, they have an endless line of people outside their office presenting various problems and issues for resolution. A large percentage of those people bring problems without solutions, without options, without anything. They bring problems. And then they are frustrated when they can’t get enough attention on whatever issue they are facing. They get frustrated that their projects can’t make progress. They talk about their manager as a bottleneck. This is a very common mistake. I see it more than once a day.

My advice, when you face an issue, is to communicate the problem to your boss and present options for resolving it. Options, you’ve thought through ahead of time. And if options don’t make sense in your situation, clearly express your intention for resolving the issue and give your boss the opportunity to align or adjust. One of my favorite books on leadership deals with this topic – Turn that Ship Around – a great book I highly recommend. My point is, you can’t just drop problems on your boss and expect he or she will have the time or mental capacity to do your thinking for you.

To make progress on your projects and initiatives, you must be able to make people care about them - your boss in particular. Too many of us get stuck in a mode of thinking and working that lead us to cast blame on others for the lack of attention we get on our projects. Don’t point fingers. There are things you can do, in the way you speak and present and design your projects, that will help get them the attention and priority they deserve. I hope these tips were helpful to you and as always, I’d love to hear your thoughts in the comments section.

The Weekly Reid: Do you need to be liked to be a leader?

Do you need to be liked to be an effective leader?

The answer to this question is not simple. I wish it were as easy as saying yes or no. It’s not. Although that would make for a very clear and concise blog, wouldn’t it?

The truth is, I have seen leaders who were incredibly effective and universally disliked.

I have seen incredibly well-liked people who were extremely ineffective leaders.

As you ponder your own career, my guess is you’ve seen something similar. It’s just not that simple.

What I can do is share my personal experiences with you. And hope that in so doing, I can offer a perspective you can use as you shape your own career strategy and mindset and plan. It’s entirely possible you won’t agree with me. I suppose some of it has to do with who each of us is as an individual, how we see the world, and others in it. Nevertheless, here we are, so let’s talk about it.

Do you need to be liked to be an effective leader?

My simple answer to this not so simple question is, “No, but it helps.”

Let’s start with what makes a great leader. Some things that come to my mind:

Can inspire and motivate a team.

Can develop and operationalize a strategy.

Are decisive and have integrity.

Can communicate clearly.

Can activate a group of people to work in unison towards a desired result.

Great leaders do these things well. But do they need to be liked to get it done?

The reality is, there are highly effective leaders who are not likeable. There are monsters and tyrants and bullies who are very successful, at least in their own definition of what success means. They direct teams (or entire companies) to achieve amazing results. They technically hit on all the points above. They do this through brute force, leverage and fear. It happens all the time and there is no sense in pretending it doesn’t.

I should say, these leaders – who are effective but not liked – seem to be rare. They’ve chosen, in my opinion, a harder path. Typically, they are very unique people in very unique scenarios. If a young leader came to me and asked what type of leader I thought they should strive to be, I certainly wouldn’t guide towards being a tyrant.

I have found, over the course of my career, it is much easier to be effective as a leader if you are liked. Note, I did not say “soft” – I said “liked”. If you build strong personal relationships with your team and your peers and your manager, the path to success is cleaner, with fewer obstacles. I imagine it also feels better on the inside. Being liked is not mandatory for a leader, but it’s easier.

But what do I mean exactly?

What does “being liked” mean in different contexts? For your peers? For your boss? For your team? Let me spend some time on each.

With your peers

Being liked by your peers is extremely important in my experience. Especially when we talk about peers from other departments in the company. Working with people, over whom you have no legitimate authority, requires diplomacy. It’s a constant negotiation to get things done. You need to influence these people. You can’t tell them what to do. They aren’t obligated to help you with anything. It helps if they like you.

When you don’t have positive relationships with your peers, they tend not to share information with you. They tend to avoid working with you. Sometimes they purposely oppose you just to take a stand. These are massive headwinds to your performance. By contrast, if your peers like you, they will share more information, earlier. They seek you out to work on projects. They search for reasons to support your projects and initiatives. These are all tailwinds to your performance. They make things easier.

My advice to leaders is to invest more time building positive relationships with your peers. Find ways to help them. Spend more time with them. Listen to them. It’s a much more pleasant way to operate, and it makes being successful a lot easier.

With your boss

There are people who say it’s not important to be liked by your boss. That you just need to deliver results. I have not found this to be the case in practice. In my experience, it’s extremely important to have a positive and personal relationship with your boss. You want your boss to see you as a partner. As someone they can trust. You want your boss to enjoy spending time with you.

Being liked by your boss provides a natural boost when things are going well i.e. you can be presented with more opportunities for success. It also provides some natural protection when things are not going well i.e. you’re more likely to be given the benefit of the doubt or assessed through a positive lens.

You often hear gossip around the office about a boss playing favorites. He’s never hard on this person. She loves everything that person does. This person always gets her budget requests accepted. My advice is to stop complaining about it and start building a more positive relationship with your boss. If, indeed, your boss plays favorites – try to become a favorite. You can only play the best you can with the cards you’re dealt.

By contrast, if you’re not liked by your boss, you will face a natural pullback on everything you do. It may be ok for a while, when you’re performing well. But the moment you slip up, or stumble or fail, that pull will grow exponentially.

My advice to leaders is to invest time and energy into building a positive personal relationship with your boss. You don’t need to be “friends”, but you do need to be in a good place.

With your team

This one is a bit trickier. That’s why I saved it for last. I’ve just told you it’s important to build a positive and personal relationship with your boss. Now I’m going to advise you not to be “friends” with your team members. On the surface these pieces of advice seem to be at odds with each other. And that has everything to do with my use of the term “friends”. There’s a lot of nuance in here and I’ll do my best to be clear.

Some managers fail because they have a deep seeded need to be “friends” with their employees. Some managers get into trouble because they don’t know the difference between being liked and respected, and being “friends”.

When you are friends with someone and they ask you for feedback, “do you like this?” Your priority is to make them feel good. Even when you need to give a friend some tough love, you still do it in the kindest way possible. Your top priority is for them to be happy – they’re your friend. This can’t be your mindset as a manager. Yes, you care about your employees. Yes, you want them to be great. But you can’t sugar coat feedback. You can’t package it. You need to be brutally honest. And you can’t do that if you’re trying to be “friends” with your team members. You wouldn’t fire your friend.

In my experience, to be an effective manager, your team members need to know that you care about their wellbeing, that you want them to be successful. This is mandatory to build a high-performance team. BUT … and this is a big BUT … you must be completely honest with them to accomplish this. And this is where we depart from the friend zone.

When it comes to the relationship a manager has with her team members, my advice is to focus more on being honest, than on being friends. When your team members see your honesty comes from a positive place, they will like you … just maybe not in the same way they like their friends.

The question of whether or not we need to be liked to be effective leaders is more complex than it appears on the surface. There are just too many examples of unlikeable leaders who are successful (at least in a business context). In my experience, it is not mandatory, but it certainly helps. Being liked provides a natural tailwind to everything you do, and it protects you when things don’t go well. I’d love to hear about your experiences in the comments section.

The Weekly Reid: 3 Critical Weaknesses that Often Disguise as Strengths

If you’re a regular reader, you already know how seriously I take interviewing. How much respect I have for the art and science of it. I will never proclaim to be a great interviewer, because as soon as I do, I’ll be proven wrong. But I do care about interviewing. I want to be a better interviewer, as I’m sure you do. And so, I try, with every interview, to get a little better.

I have noticed recently, some interviewers getting fooled by weaknesses that disguise themselves as strengths. On the surface, they seem to indicate confidence, experience, reliability, when in actual fact, they are red flags. I’m going to share them with you and give some advice on how to adjust your interview style to discover them sooner. I hope this is helpful to you.

Absolute Certainty

One thing I am 100% sure about is that you should never hire someone who operates with absolute certainty. (See what I did there 😊) Ok, this is a tricky one and possibly a little controversial, so let’s give it a go. With the benefit of 20 years’ experience, I have come to appreciate that we are never really certain about anything. We execute with best practices. We build models. We test solutions. We do research. We do these things to maximize our chances of success, but we never really know for certain. Sometimes, you think you know, but then you realize, you don’t. It happens over and over and over again. That’s just the nature of the game.

The world is changing. Rapidly. What worked yesterday, may not work tomorrow. The path you took to reach the level of success you have today, will not lead you to the successes you long for in the future.

I get worried, whenever I work with people who are overly certain about things. People who speak in absolutes.

There is only one way to do this.

We MUST choose this option.

I’m 100% sure this is the right course of action.

When I hear people talk like this, I get nervous. It looks like confidence, but it’s actually naivety. Or hubris. Or a lack of experience. It sounds great in an interview. Decisive. Clear. Enthusiastic. But is it real? Can you trust this level of certainty? In my experience, people who operate with absolute certainty can be dangerous to your team. They can very confidently lead you over a cliff.

My advice to hiring managers is to look for candidates who possess an appreciation for how uncertain business is. Look for candidates who have built decision making processes and models that allow for variance. Look for candidates who think in terms of probabilities instead of absolutes. They may not seem as confident in the interview, but their value will show through when tested in the uncertain realties of work life. I recommend adding questions to your interview repertoire designed to probe into how the candidate thinks about decision making.

Tell me about a tough decision you had to make recently?

How did you know it was the right one?

What would have had to happen for you to change your perspective?

What would you have done if you were wrong?

Process Possessing Intrinsic Value

All of us want to improve our processes. Our companies and teams are growing so quickly we feel starved for process. Our teams often operate in what seems like chaos, to produce and deliver amidst so much change and uncertainty. We are so desperate for a little control that we can be wooed by weaknesses masquerading as strengths during the interview process.

I’m going to overly simplify for a moment to illustrate a point – I realize the world is not quite this simple. Nevertheless, in my experience, there are two kinds of process oriented people in business. The first, are people who believe process is a valuable means to an end. They identify a valuable business outcome to pursue, and they build a process for attaining it. They can be excellent additions to your team as it grows. The second, are people who believe business process has its own intrinsic value. They believe the process itself, is the valuable outcome to pursue. They conflate process outcomes and business outcomes. They can be very determinantal to your team. Discerning between these two types of candidates can be trickier than it appears.

My advice to hiring managers is to ask questions designed to probe more deeply into a candidate’s view of process.

How much process is too much?

How do you measure the value of a process?

How do you know when a process is no longer effective?

How do you create alignment around a process?

By going one level deeper in your questioning, you’ll have more information to be able to determine whether or not you’re hiring someone who will help or hurt your team.

Binary Thinking

When I look back on the teams I have managed, the most valuable contributors were those who possessed the ability to perform integrative thinking. They were creative. They could look at two seemingly fixed options, and imagine a third possibility. Integrative thinkers can be game changers for your team and company. Finding them is the tricky part.

While there is value in being able to perform rigorous, logical analysis to make a well-judged decision between to options, you can run into problems when you build a team of people who can only think in black and white. A group of people whose thinking is constrained and rigid. Hiring a team of binary thinkers can limit the potential of your team to be creative.

My advice to hiring managers is to seek out integrative thinkers and be wary of hiring too many binary thinkers. You can have a mix of both on your team, but integrative thinkers are certainly scarcer. With that in mind, I recommend crafting interview questions designed to discern between the integrative thinkers and the more constrained, binary thinkers.

How do you decide between two seemingly equal choices?

Who would you assign to manage your highest performing product? Your best person or your weakest? (note – you are looking for the candidate to pose a third alternative)

Craft questions that force candidates to reveal how they think about problems. It will provide another data point you can use to make a solid hiring decision for your team.

Interviewing is hard – did I say that already? Sometimes, candidates who seem decisive are actually naïve. Sometimes, candidates who appear to be strong process oriented leaders are not focused enough on driving real business outcomes. Sometimes, logical decision makers are unable to be conceive of creative alternatives. It’s hard to tell the difference. I hope this blog will help make it a little easier.

The Weekly Reid: Delegating is way harder than it looks (3 tips to make it easier)

Picture a manager you know who is NOT a strong delegator. If I ask for your theory on why that is the case, you’re likely to say things like:

She never made the transition from individual contributor to manager.  

He doesn’t believe anyone else is as good as he is.

She just can’t let go of the details.

He’s a micromanager, and gets stuck in the weeds.

She’s a control freak.

As you may be anticipating, I don’t believe this is always true. A lot of these descriptions focus in on personal shortcomings. Personality issues. Hubris. Control. Obsession. I will admit there are some managers out there, whose inability to delegate stems from these personal flaws, but most do not. In fact, I would argue most managers are weak delegators, even those with all the personal qualities we respect and admire.

Most weak delegators I know, would LOVE to be better at it. They long for it. They admire leaders who can delegate. So, if it’s not about a flawed personality, what is it that prevents so many of us from delegating effectively?

A few possibilities come to mind.

Our teams aren’t strong enough … yet. Most of us are part way through a transformation of some kind. We don’t yet have all the pieces in place. We don’t yet trust our team members to take on the level of work we need them to.

We are under resourced. We don’t have the time or the people to delegate work to. If there is nobody to give the work to, how are we supposed to delegate?

We are under pressure. We worry about the consequences of delegating work and having it backfire. The risk seems too high. We’re scared of the potential repercussions. So, we promise to look for another opportunity in the future to delegate. And then we do it again.

If I could put you in the mind of most managers, these are the things you’d see; fear, risk aversion, stress. Not hubris or control or obsession.

Like most leaders, I’m somewhere along the delegator’s journey. I’m definitely better than I once was. But I’m certainly not all the way there yet. Here are three tips I’ve used to get a lot better at delegating work. More specifically, to build the environment wherein I can more confidently delegate work and have a reasonable expectation of success.

Build an apprentice culture

Every member of your team should simultaneously be an apprentice and mentor. You should have at least one apprentice. Rather than have team members work on projects and present them back to you for approval, you should work with them as a partner. This is how learning (and teaching) works. Many managers believe giving clear feedback is the magic bullet. They wait for work to be submitted and then critique. It is certainly important to give feedback, but this approach doesn’t go far enough. There is no substitute for working side by side with a team member on a tough project. That’s where the best learning takes place.

My advice to managers is to build an apprentice culture. Don’t worry so much about doubling up on a project. Don’t worry so much about being perceived as a micromanager. Get in there and work alongside your people and encourage them to do the same with their people. Building an apprentice model will protect you from unanticipated turnover and make you a more confident delegator.

Build procedural safety nets

One of the biggest reasons for not delegating (at least for me), is fear. What happens when I delegate and everything blows up? What happens when the work isn’t good, the employee is humiliated and I’m embarrassed, or worse? In my experience, you can delegate and de-risk at the same time. You can build processes that allow delegation to flourish but protect from the scary downside. It’s like pure delegation but with training wheels.

My advice to managers is to build in procedural check points, dry runs, and buffers to soften the edges of delegation. Create an environment where risks can be taken and hard lessons can be learned, without dire consequences. The impact will be a more empowered team, and better track record of success, and more effective delegation.

Build scale into your team

This may seem a bit harsh, but if you can’t find anyone to delegate work to, you probably don’t have the right team in place. At least not yet. Sometimes you need to have a hard conversation with yourself. If I can’t trust this person to execute, why are they on my team? Too often managers are reluctant to hire senior people - people as senior as they are. They find reasons not to; budget, levelling, salary boundaries, other team dynamics. As a result, they never achieve scale. They hire and hire and hire, but never get scale. In fact, some managers, lose scale through hiring. They hire people who need a ton of coaching and hand holding. So much so, it reduces their own level of contribution.

My advice to managers is to do whatever you can to hire people as experienced and talented as possible. Look at your team objectively. Are they skilled enough? If you could start over, what would your dream team look like? What would a team look like where you had to do no work whatsoever? Now make a plan to get there over the next few years.

Delegation is misunderstood. It might be the most misunderstood management attribute. It’s easy to sit on the sidelines and critique managers for being weak delegators. It’s easy to pass judgement on the personality flaws that must run underneath. It’s easy, until it’s you. Delegating is hard and its complex and I have a lot of respect for managers who are truly great at it. I hope the three tips I shared today will help you on your personal delegation journey.

The Weekly Reid: 4 tips to maintain your hiring standard … even when you’re desperate

It’s hard, seeing your team underwater, struggling under the weight of an ever-increasing workload, while you have 20 open positions to fill.

It’s painful, saying “no” to candidate after candidate when you know your team is falling further and further behind.

It hurts, to disappoint the managers on your team by pushing back on “ok” candidates, when you know how badly they want the position filled.

In times like these, when hiring is so tough, we need to add rigor to our recruitment process. If our emotions had their way, we’d hire anyone resembling a qualified candidate just to make some progress. So, we need to lean on structure and principles to help us make the right decisions in the face of such intense pressure.

Here are four tips that help me make solid hiring decisions, especially when I feel desperate. I rely on these to continue building a great team, even when the recruiting environment seems bleak. They help me double and triple check we’re hiring the right person, so we don’t inadvertently let emotions trick us into poor hiring decisions. I hope they are helpful to you.

Reward tough decisions

This one is critical if you manage other hiring managers. As much as you want to fill your open positions quickly, you cannot support hiring “so-so” candidates. There is nothing more important than building a high-quality team of amazing people. You can never let desperation trick you into hiring below your standard. As painful as it may feel to be short staffed, it is much more painful to be fully staffed with the wrong people. As leaders, we need to strike a fine balance between putting pressure on our team members to hire quickly, and insisting they hire only the highest quality candidates.

My advice to leaders is to constantly reinforce the need for high standards in hiring. Your team members need to know you support them, especially when they make a tough call to pass on an “ok” candidate. Your team members need your help to maintain the bar for quality. Whenever I get the chance, especially when I know managers on my team are feeling desperate, I make a point of recognizing them for upholding our high standard. It’s not always easy to do, when you’re feeling as desperate as they are, but your team and your company will thank you in the long run.

Add another check and balance

I often assign short projects to final stage candidates as a check and balance in my hiring process. It’s especially helpful when I know I’m feeling the pressure of a recruiting void. It’s an extra step that helps me gain a little more confidence in how a person will actually perform on the job. From a candidate’s perspective, this can sometimes feel like a burden – to be assigned work before even having the job, but I find it very effective to forecast how a personal will perform.

My recommendation to managers is to assign a 90-minute or two-hour project to all final stage candidates (usually no more than 2-3). Then invite the candidates to present their work to you as the last step in the hiring process. Most of the time, this extra step validates the decision you were already leaning towards. But sometimes, it will reveal a serious weakness you didn’t pick up on during the interview. It can save you (and the candidate) a lot of pain and heartache.

Doublecheck your forensic analysis

When I’m feeling the pressure to hire, I double down on the vetting of candidates. I review the resume like I’m a forensic detective. I search for red flags … anything that I might have missed through a cloud of desperation.

What companies have they worked for? Did they have great cultures or bad reputations?

How long have their tenures been? Do they hop from job to job? Did someone else value them enough to keep them for a long time?

Have they had promotions while at a company or have they only made vertical jumps by leaving?

Have they worked in a business model like yours? Will they give you scale or will you just have to spend more time managing them?

My advice to managers is to take one extra pass through resumes and perform some forensic analysis before hiring. It’s a great extra layer of security when hiring in desperate times.

Add a social encounter

When I’m hiring for a critical role, or if I’m not 100% sure about a candidate after the standard interview process has completed, I like to meet them socially. It’s an additional step in the hiring process but it can be exactly what you need to make a more confident hiring decision. I find a social encounter to be especially valuable when hiring senior level people, or anyone who will be a cultural leader in the organization.

We spend a lot of time testing for skills and competencies, and validating experience, but ultimately you need to enjoy working with a person for the relationship to be a success in the long run. A one-hour coffee or drink or meal, can give you one more window into the candidate, which can make all the difference in the world.

My advice to managers is to consider adding a social meeting to your process when you’re unsure about a candidate or feeling an unusual amount of pressure to fill a position. It will give you more confidence to make the right decision.

The war on talent has heated to unprecedented levels. Employers are pulling out all the stops to retain and engage their best people. The impact on hiring is being felt by all of us. Lately it feels harder than ever to find and hire amazing talent. You can go months and quarters without filling key positions. The team you have in place gets tired as you ask them to handle an unrealistic amount of work. The pressure we feel as hiring managers can lead us to make sub-optimal decisions because we’re desperate. When I’m feeling this way, I place additional rigor into my recruitment process to ensure I don’t let my emotions trick me into making bad hires. I hope these were helpful to you, and as always, I’d love to hear any tips that have worked for you.

The Weekly Reid: Getting a New Boss? 4 Tips to Make a Great Impression

Most people view a new boss as a risky situation … as a negative thing. And they act in a manner that reflects this perspective. They get worried. They start thinking and acting defensively. I see it happen all the time.

Let me know if any of these thoughts sound familiar:

I still have so many changes to make. What’s my new boss going to think when she reviews the performance of my team?  

What about all the issues we haven’t gotten to yet? Is he going to think I’m incompetent for not addressing them? 

What are my peers going to say about me? About my team? Are they going to throw me under the bus? Should I beat them to the punch?

 Is he going to make changes? Is he going to bring in his own people? How can I convince him I’m not the problem here?

Thoughts like these can attack when you find out you’re getting a new boss. They can make you act defensively, erratically. They can make you say and do things that are counterproductive. They can bring out the worst in you. They can trick you into doing things that don’t reflect your true skill and professionalism. If you’re not careful, they can cause you to manifest the very thing you’re most afraid of.

Most people fall into a defensive shell when faced with the prospect of a new manager. That’s exactly the wrong perspective. You need to see it as an opportunity, and act accordingly. As soon as I find out I’m getting a new boss, that’s exactly what I do. I prepare to make the most of the situation. I prepare to differentiate myself in a positive way. Today I’m going to share four tips to do just that. I hope they are helpful to you.

1.  Be the most prepared

When a new boss starts, the first thing she will do is meet with her direct reports and begin a process of assessment. She’ll want to understand your team and its performance. You might be surprised just how unprepared most people are for this process. They spend so much time worrying and gossiping that they neglect to actually prepare. Don’t fall into this trap. Instead of fretting about what changes your new manager might make, focus on being as prepared as you possibly can be.

I’ve found it extremely valuable, when faced with a new boss, to prepare an executive briefing package. Something clear and concise that will help make the assessment process as easy as possible for my new manager. In my first meeting, I can present a package that provides everything she needs to understand my team, our projects and our performance. I try to be as objective as I can in assessing strengths and areas for improvement. There is no sense in trying to hide or sugar coat anything. In my experience, people who try to hide issues or overstate performance ultimately reveal their incompetence.

My advice for anyone getting a new boss, is to prepare a briefing package that can be presented at your first meeting. Be objective and honest. Show that you have integrity. Every team has problems. Your new boss will understand that. What she won’t understand, is why you’re lying to her or hiding critical business issues.

2.  Master your metrics

One of the most important things you want to communicate to your new manager, is that you understand your business. You want to demonstrate a mastery of your team, performance, KPIs, and business model. There is nothing more important than this. Every mature, competent leader has a firm grasp over his or her operation. Having been a new boss several times, I can tell you nothing shakes my confidence more than discovering an employee doesn’t have a handle on their own performance. I don’t panic when a new employee describes their problems and plans for fixing them. I embrace that. I only get nervous when I discover an employee is lying to me or has no idea how they are performing.

Next time you find out you’re getting a new boss, start by mastering your key metrics. Prepare a dashboard or model or report that demonstrates you have a real command over your performance. The good and the bad. Your understanding and transparency is more important than the performance itself.

3.  Be helpful, not defensive

Most people act defensively when faced with the prospect of having a new manager. They get paranoid and act accordingly. Never do this. Your mindset, when you get a new boss, should be to be as helpful as possible. Your job is to help her be successful. If you are effective in doing that, your own success will take care of itself. No amount of politicking, sugar coating, or sucking up will save you if you haven’t done a good job. So, don’t bother trying. Just be helpful.

Part of being helpful to your new boss is being honest. Show her where the land mines are. Show him the skeletons in the closet. Help her be successful. Protect him from getting embarrassed. Imagine what it must be like to be in her shoes. A new team, a new company, high expectations. Be a trusted adviser and supporter to her, just as you would wish a new team member would be for you if roles were reversed.

4.  Don’t be political

One of the most common worries people have, when getting a new boss, is what their peers will say about them. We get paranoid. We imagine what our rivals will say. We worry about being thrown under the bus when we’re not in the room. I see this happen all the time. The fear of being painted in a negative light by others, makes people act that way themselves. They point fingers. They talk badly about their colleagues. They strike first before getting struck. Its ugly and it doesn’t work.

My advice is to rise above the politics. If you present yourself as a mature leader, with a command over your team and performance, you will distinguish yourself from others. You don’t need to play a political game if you are prepared and helpful.

Getting a new boss is a stressful thing. It carries uncertainty with it. You never know what you’re going to get. You can’t control it. Most people react defensively and politically and end up manifesting the very outcome they are most afraid of. My advice is to do the opposite. Prepare an executive briefing package. Master your metrics and business model. Focus on being helpful. And don’t get sucked into the backstabbing and politics. These tips have helped me navigate many new bosses and they’re exactly the way I wish new team members would behave if I was a new boss. I hope they’re helpful to you.

The Weekly Reid: My Tips to Avoid Getting Derailed by Short Term Frustrations

The more time you spend focused on your big wins, the faster they will come. The more time you spend executing on your mission, the faster you will accomplish it. It’s really that simple.

In my experience, the most productive people waste the least amount of time and energy on activities not directly related to their primary objectives. I realize that may sound like a truism to you, but it’s not as easy as it sounds.

Is there anyone at your workplace who always appears to be working hard but is completely unproductive? Someone who puts in long hours and always looks busy, but never actually gets anything done? I see these people all the time. To the casual observer, they appear to be doing all the right things. But on closer inspection, they are just highly inefficient. They waste time on nonessential activities. They chase non-critical problems. They react and obsess and spin in place. And when you add up all the hours they’ve “worked” in a given week, you see that they spent very little time focused on their mission. Their hard work was an illusion.

We are all victims of this behavior to a certain extent. None of us is perfectly productive. We all fall somewhere on the spectrum of efficiency. For me, the biggest detractor to productivity has been my tendency to obsess over conflicts and issues that, with a dose of hindsight, were always going to end up resolving themselves. When I look back on these issues I could see just how much energy I burned for no reason. I could see just how much time I wasted, when I could have spent it pursuing my mission.

Over the years, as I’ve observed this tendency in myself, I’ve developed some strategies for overcoming it. I don’t have it all figured out – that’s for sure. But these tips do help me quarantine short term problems to stay focused on my primary mission. I hope they are helpful to you too.

1. Time Travel

I engage in time travel more than you might think. I’ve gotten quite good at it actually. Whenever I’m upset or worried about a conflict or issue, I force myself to travel forward in time so I can have the benefit of hindsight while I’m still in the present moment.

I very purposefully play out the likely sequence of events and place myself in the highest probability future states. Most of the time - like 90% of the time - it becomes clear that whatever issue I’m dealing with, will inevitably be a tiny blip when viewed from the perspective of my entire career. It just won’t be that big of a deal. Most of the time, it will resolve itself. Sometimes, it will end better than it started. Other times it will end badly but even then, it won’t be THAT bad.

My point is, we need to be able to apply the benefits of hindsight in the present state. And whatever tricks you need to pull on yourself to be able to do this, it will help. Next time someone pisses you off, or you take some heat from your boss, apply some perspective, travel ahead in time, see that it’s likely not going to be that big of a deal when considered in the context of your entire career, and get back to focusing on your wins.

2.  Play out the worst case, and get comfortable in it

One useful exercise I frequently use when I’m at risk of being derailed by worry or anger, is to play out the worst-case scenario. This is a pretty common practice in Stoicism that I find very helpful. Rather than obsess and stew over a conflict or issue for hours and hours, I take 10 minutes and visualize the absolute worst-case scenario. Maybe my boss will reprimand me. Maybe I won’t get the promotion I was hoping for. Maybe a senior executive will be disappointed in me. Whatever the worst-case scenario is, I play it out fully in my head. I confront it. I put myself in that reality. I prepare mentally for it. I accept it.

By spending 10 minutes placing myself in the worst-case scenario, I normally get quite comfortable with it. I get less afraid. I get more prepared. I plan for what I’ll do if it comes to pass. And then I let it go. I stop worrying about an uncertain future state because I’ve already placed myself in the worst possible outcome and felt comfortable with it. It’s a very useful exercise.

3. Add more positives

If I’ve gotten myself into trouble or into conflict, or otherwise done something that may ding my reputation, I immediately try to find a win. Rather than expend energy regretting what I’ve done, or worrying about how my career has been hurt, I try to get back in the win column quickly. Ultimately, the scorecard of your career will have many wins and losses. It’s inevitable. None of us are perfect. You can make quite a few mistakes and have an extremely successful career, if you accumulate enough wins to offset them. Some of the most successful executives I know have made huge blunders – but they have tons of wins too.

Rather than dwell on short term problems, that may or may not prove to be losses on your record, its far more productive to focus on pursuing your next big win. Next time you catch yourself worrying about a mistake or conflict or problem, stop yourself, reset, and start pursuing something positive.

The most productive and successful people I know are the ones who maximize energy spent on positive pursuits and wins. They don’t allow themselves to be derailed by conflicts or frustrations that are inherently short term in nature. They have the ability to quarantine their productive energy from time wasting behaviors. I was a victim of this for many years, even though I probably appeared quite calm on the outside. I hope these tips were helpful to you.

3 Tips to Reduce Pre-vacation Anxiety

I’m not proud to admit I get anxiety before I take time off from work. It feels like a sign of weakness. It’s definitely a sign I have not yet reached work life harmony. For me, the anxiety manifests mostly as a fear of missing important things. Big decisions, private conversations, strategy shaping moments. Also, a fear of forgetting to take care of something and having it explode when I’m not there to help. And if I’m brutally honest, a fear of being forgotten. There’s no sense in pretending the anxiety isn’t there, as silly as it may sound. It is there. The question is, how to manage it.

Here are three tips I’ve used over the years to control my pre-vacation anxiety. They help me de-stress before I leave and reduce the worry I often feel when I get back to work.

1. Prepare a pre-vacation briefing package

Many managers do not do this effectively. In fact, most managers don’t do it at all. Before you leave for vacation, you should prepare a briefing package for your manager and for key leaders on your team. If you’re just bailing with little or no preparation, and hoping things don’t die while you’re sunning yourself at the beach, you’re not being a responsible manager.

Before I leave for vacation, I take a couple of hours and prepare a briefing document for my manager that outlines all the major issues I have ongoing, as well as a list of specific actions I need her to take on my behalf when I’m out of office. I try to be as detailed as I can since I really don’t want things to pop up and surprise her when I’m away. I also don’t want it to appear like I don’t have a handle on my business when something I didn’t prep her for becomes a problem while I’m sipping margaritas.

I also create shorter packages for the key leaders on my team. Priority items for them to focus on, clear expectations for progress that needs to be made while I’m away. By doing this, we can all be on the same page with what the objectives are for the period and how they will be able to make decisions in when I’m not present to weigh in. The last thing you want is for momentum to stall out because you’re on holiday. You goal, in preparing for your vacation, is to arm your team with enough direction and authority so they can push forward confidently without you.

My advice to managers is to spend a little more time preparing pre-vacation briefing packages for your boss and team members. It will ensure progress is made when you’re away and it will set your mind at ease so you can relax and enjoy your well-deserved holiday.

2.  Check in with your key stakeholders and influencers

Before I take off, I try to connect with the most important stakeholders and influencers in my work life. I’m talking about key people in the organization, peers, people you’d normally be meeting with but won’t be. I don’t think it’s enough to just switch on your out of office reply and hope for the best. I like to have a quick friendly conversation to let them know I’m taking off for a while. I have found these quick pre-vacation check-ins make things go a lot smoother when I’m out. Nobody panics when they have an issue and realize I’m not around to help. And we can get alignment on key issues that might occur during my time off. It helps.

My advice to managers is to make a quick list of the most important people in your work life, and give them a call before you take off on vacation. There is no downside to doing this and it can help maintain momentum and alignment on key issues while you’re away.

3. Take some perspective

This one probably should have come first. Clearly, I need this perspective as much as any of us by virtue of the fact I felt compelled to write this blog in the first place. I try to remind myself that the world doesn’t revolve around me. That, my career will be played out over many years and decades, and that a couple weeks off is a mere blip on that timeline. In the grand scheme, this vacation will have zero impact on my reputation or career trajectory. Its pure hubris to think that somehow me being away will send the department or company into a tail spin. I get quite embarrassed whenever I catch myself in this mode of thinking.

My advice to managers is to take some healthy perspective the next time you feel anxiety about taking vacation. Remind yourself that you are just not THAT important. The world, the company, your team will go on without you. At the scale of your career, this two-week period – any two-week period - is nothing. The energy you will take from unwinding will greatly outweigh any drawdown in productivity that could occur in your absence. Take your vacation, enjoy your time off, come back and start doing your best at work again.

Some of you, I suspect, will be able to relate very personally to the issues I’ve raised in this blog. Some of you may not. It’s certainly not something we should simply accept as a normal way of being. My hope is that by sharing some of my own anxieties and tips for managing them, you’ll be able to face your own pre-vacation angst. I’d love to hear your thoughts in the comments section – if for nothing more than to let me know I’m not alone 😊

The Weekly Reid: Sink or swim or something in between?

Before I argue against the sink or swim philosophy of management, let me make clear I do not advocate the opposite approach either. There are some managers who, for various reasons, are completely unwilling to give their employees a shot at anything. They protect them and shelter them and effectively block them from growth. I would never support this. We need to help our people develop – that’s the duty of a manager. We need to push them. The question is, how best to do that? Is the sink or swim approach optimal or is there some other, better way?

My experience tells me, there is no substitute for winning. Winning begets more winning. Winning creates momentum, and momentum can take you places you didn’t think possible. My fundamental philosophy as a manager is to create as many winning situations as possible for my team and the members of it. I look for potential wins, I focus my energy on winning opportunities, I celebrate and reward and recognize wins as much as I possibly can. A culture of winning is hard to beat.

The counter argument to this is if you never place team members in situations that will test them – where they will likely fail – they’ll never be able to win at the highest levels of the game. That if you create artificial winning scenarios for people, they’ll eventually have to learn the hard lessons anyway, and by that time it will be too late. I see merit in this argument too.

The right question, in my opinion, is how do we strike a balance between building a culture (and habit) of winning while also challenging our people enough so they keep developing and can ultimately reach the highest levels of performance?

Here are 3 tactics I use to strike that magic balance between winning and development.

1.  Fail in practice, win in the game

In martial arts there is a saying – train hard, fight easy. I think there is a lot of wisdom here that can be applied to the workplace. The essential point is you should challenge and test yourself relentlessly within the relatively safe confines of training, so when you’re on the big stage you can be confident and shine. You lose a hundred times in practice so you can win when it really counts.

As much as I can, I try to create this environment at work. I try to build a safe training space where team members can be challenged and fail without suffering the repercussions of failing on the big stage. This way they can develop and grow and adapt AND create a habit of winning.

A good example of this is when team members have big presentations like an executive briefing or a customer presentation or some other high-pressure event. In these situations, I get deeply invested in helping prepare my team members. Probably more than just about any manager I know. I review presentations and talk strategy and ask hard questions and give extremely critical feedback. I push and push and push during the preparation phase. I create a safe space to fail so they will be ready to win when its show time.

At first, it can seem like micromanagement. Like I’m getting all up in their business or like I don’t trust them to deliver. But over time, as team members win and get recognized and rewarded, and as they build stronger and stronger reputations, they come to embrace the process, they seek out opportunities to learn hard lessons in private so they can win big in public.

My advice to managers is to create safe learning environments for your team members. Create opportunities for them to learn tough lessons and get difficult feedback in an environment that doesn’t carry the same consequence as failing in public. I have found this approach helps build deeper levels of trust between you and your team members as they come to realize your harsh criticism and feedback is designed to help them succeed under the bright lights.

2. Tough love in private, praise in public

I have found the best way to build trust with team members is to praise them in public while being tough on them in private. At first this may seem like a truism but I don’t think it’s as self-evident as you might think. Some managers are hard on their people 24-7 - in private and public. They push and they push some more. Other managers are way too soft on their people. They praise and praise and praise and don’t have the stomach to provide honest, critical feedback to their teams. Neither of these approaches work.

I want to be able to be hard on my team members so they can push themselves to new levels. I want to be able to be very direct and honest with my feedback. I want to be able to continuously raise the standard of excellence. But if you’re constantly criticizing your team, they’ll eventually give up on you, and then everyone loses.

My experience tells me there is a balance to be struck between praising and pushing. I want team members to know I will support and praise them in public when they’ve won. I want them to know I’m their biggest fan and that I’m personally invested in their success. But in exchange for that, when the lights go down and we’re back in a safe space, I will be quite hard on them. I will push them. That’s the bargain.

3. Find the win in failing

Win or learn. Another great philosophy that applies well to leading a team. No matter how much you support your team members in the preparation for big moments, they will fail from time to time. It’s a reality of life and work. The question is, how do we maintain a winning culture in moments of failure?

Great managers help their team members be as prepared as possible for big moments. Great managers are also supportive when that preparation isn’t met with a win. Sometimes we lose. Winners lose all the time. Our job as managers is to give our people the highest probability of winning and then help them find a win even in defeat. The worst managers bail on their people when they fail. They avoid talking about it. They lay blame. They shirk responsibility. Never do this.

The bargain you strike with your team members is to do everything possible to put them in a position to win and then accept whatever result happens. Your team members need to believe you won’t give up on them when they’ve prepared well but still fail.  

My advice to managers is to talk openly about failure. Don’t pretend it doesn’t exist. Don’t hide from it. If a member of your team gives maximum effort and still fails, help them find a win in the lessons learned. That way you can continue building a culture of winning even in defeat.

The sink or swim mentality has some merit to it, but I don’t think it’s always applied correctly in the workplace. Too many managers place their team members in unwinnable situations under the auspices of sink or swim. I reality, they’re just creating a losing culture. My experience tells me we can push and test our people AND create a culture of winning. I’d love to hear about your experiences in the comments section

The Weekly Reid: Are Your Team Members Lying to You?

As I’ve progressed in my career, from my first management jobs to running a large team, I’ve had to face a difficult reality. As you move higher in an organization, people (some people), find it harder to tell you the truth. They don’t want to disappoint you. They fear repercussions – real and imagined. They infer a certain power dynamic whether or not you believe it exists. And so, they package their messages, they qualify their statements, they seek out ways to agree with you.

I see this dynamic just about every day. Team members find it hard to be honest with senior leaders, managers and executives. Whenever possible, they try to find a way to be supportive, agreeable. They want to make the leader happy. They want to find common ground. It is a very logical behavior quite honestly. If that’s not the optimal career strategy, you could see how it would seem like a pretty safe one. Aligning with your boss on everything seems like a path to job security, doesn’t it?

It’s easy to sit there, as you read this, and be critical of this approach i.e. agreeing with senior leaders whether or not that means you have to tell half-truths every once in a while. But ask yourself honestly, what are you doing as a leader to create an environment where being honest is a better career move than being agreeable? What are you doing to make honesty a policy that pays off for your team members?

Do you have a tendency to overreact to bad news? Do you ever blame the messenger? Do you ever fly off then handle when you learn of some indiscretion and then explode a bunch of relationships your team members have worked hard to build? Whether you realize it or not, you may be creating an environment where your team feels you can’t handle hearing the truth.

Here are 4 specific behaviors managers can adopt that will help them create an environment where team members feel comfortable (and compelled) to tell the truth, no matter how hard those truths may be to hear.

1. Build a culture of calmness

With every passing year, as our companies move faster, the number of decisions a manager needs to make is growing rapidly. Every day it seems there is a new big issue or challenge or problem to deal with. If I overreacted to every piece of difficult news I got, my life would be a mess and my team would be anxious and stressed.

Unfortunately, some managers still react too strongly to every little problem they encounter. A campaign bombed, a new hire isn’t working out, someone did something stupid, a competitor made a big announcement. If you’re not careful, you can run around screaming from one thing to the next and leave a wake of anxiety behind you. This is not how you build a winning team.

My advice to managers is to focus on building a culture of calmness. This culture shift starts with you. Set the example. Learn to control yourself when you hear difficult news. Act logically and unemotionally when you are faced with problems. Show your team members how a leader faces challenges. Your poise will be infectious. It will trickle down. This doesn’t take years either. Start presenting a picture of calmness to your team and you’ll witness a noticeable and collective sigh of relief. The impact will be a team that can be honest with you and a team with the confidence to face difficult challenges with control and objectivity.

2. Focus on what do we do next vs. whose fault was it

I’m sorry to say there are still many managers out there who tend to shoot the messenger. They give such visceral, emotional reactions whenever faced with unfortunate news, their team members become too afraid to tell them the truth. Team members fear getting penalized just for being associated with something bad. God forbid they commit some mistake or indiscretion themselves – hiding the truth would seem like a more prudent move than being honest.

You may say, employees who can’t be honest are just not good employees. They lack a certain moral code. I say, look in the mirror. The one thing we know about companies is they are made up of people, and people are inherently flawed. We all are. If you’re operating as a manager with some misguided expectation that people will be anything other than human, you’re fooling yourself.

The best managers, in my experience, immediately jump to “so what do we do now?” when employees share tough news. They don’t dwell on whose fault it was or immediately jump to laying blame. They take the new information calmly, make a good decision and move forward. If further reflection is required, they do so constructively and only after the crisis is over.

My advice to managers is to make yourself an easy target for bad news. Don’t shoot the messenger. Don’t make the consequence of communicating failure so high people feel they can’t be honest with you. That isn’t to say you don’t hold people to account. You do. And you give feedback and make changes when you have to. But, you cannot create an environment where the cost of telling you the truth is so high that lying and withholding become attractive options. Don’t create an environment where the “yes” men and women get ahead and the honest people get left behind.

3. Get over things quickly and give second chances

Managers who hold grudges tend to get lied to a lot. The higher the price for disappointing you, the fewer people on your team that will own up to mistakes. I’ve seen some leaders who hold grudges for so long and so publicly, they create a culture of fear. They attract political animals and morally corrupt individuals around them. They’ve made the price for disagreeing with them or disappointing them so high, team members see no choice but to lie, withhold, and package information.

The best managers I know, can bounce back quickly from bad news and failures. They give people second chances so long as they still have reason to believe in the person. They tend to focus on the future and don’t dwell on the past. Team members see this. They grow more confident. They become willing to take calculated risks. They become comfortable sharing their mistakes and failures with you. This leads to better performance, a developing team, and a culture of honesty. This is what we want.

My advice to managers is to give feedback, hold people accountable, but get over things. If you find yourself holding a grudge over someone for a long time, ask yourself if you should just fire them instead. It’s not constructive, for anyone, to have someone on your team you can’t trust. When people make mistakes, but they used reasonable judgement, give them a second chance. Give them a third chance. Let people see that it pays to be honest in your organization.

4. Take and give feedback easily

It hurts when a team member gives you tough love. It always stings a little, to hear you’ve done something to upset people. Some managers react very poorly when criticism is given to them by team members. They get defensive. Their natural reaction is to justify or bite back. I know this because every time it happens to me, I can feel that reaction swelling inside me for a split section before I remind myself to be calm and embrace the feedback.

The fact is, you want your team members to be able to give you criticism. You are making mistakes, I can promise you that. And sometimes, when you’re moving so fast, it’s hard to see the real impact your statements and actions have. Sometimes your actions have unintended consequences. It happens. You need to build a team of people who feel they can be honest with you when you’ve done something to upset them. Likewise, you want to build a team of people who are willing to hear the same criticism from you.

My advice to managers is to focus on building a culture of feedback. Where all members of your team (including you) can give and take feedback easily. Where every ounce of criticism doesn’t carry existential consequence. Constant feedback and adjustment leads to higher performance. Building this culture starts with you. Learn to accept feedback well and give feedback fairly and with compassion.

When I ask leaders if their teams lie to them, the first reaction is always a visceral “no”. But then, as we probe a little further, we discover that like most things in your career, it’s just not that simple. What we do know, is that to be effective as a manager in the long term, you need to build a culture where team members feel compelled to be honest with you. They want to come to you with problems. They tell you when you’ve done something silly. Their first thought when a mistake happens, is to tell you about it. Honesty, like this, is a key building block of a performance culture. I’d love to hear any tips or advice you have for building honesty into your team culture.

The Weekly Reid: Why I worked 20 hours straight and threw it all away

Can you work your butt off for hours and days and weeks and months and have the strength to throw it all away?

Can you look at your own work and have the courage to admit it’s not good enough?

If you can’t honestly answer “yes” to these questions, don’t beat yourself up too hard. It wasn’t long ago I couldn’t do it either. But it’s important. To be self-aware. To be able to look at yourself and your work objectively. It’s one of the top attributes I look for when I’m hiring.

To move fast, we need to be agile, we need to correct course quickly. We can’t afford to dwell on sunk efforts. We can’t afford to invest good money (or time) after bad.

I worked all weekend on a project I was sure was going to be a homerun. I had it all figured out. I stayed up late. I cancelled plans. It was sunny and warm outside and I stayed inside and worked. And then, 20 hours later, when the work was done, I had to admit to myself that it wasn’t anywhere near as good as I hoped it would be. It wasn’t up to my standard. There were holes in my logic all along. The right move was to throw it all in the garbage. To cut my losses.

But was it really?

Maybe it wasn’t that bad. Maybe I could salvage a piece of it. Maybe with a little more work I could turn it into something good.

Maybe not.

I caught myself in this line of thinking after about an hour. I wasn’t thinking right. I was upset about wasted time and effort and money. I was no longer making an optimal decision with the information at hand. I was emotional. I was grasping for anything that would mean I didn’t burn an entire weekend for nothing.

Put up your hand if you know the exquisite pain that comes from having to throw out something you’ve worked your ass off on. It hurts. But you have to do it. And I’m proud that I did.

Here are four mindset tricks I’ve adopted over the years, that make it easier to do this.

1.  Take pride in being objective

I’ve written extensively on the power of objectivity. It’s one of the most powerful qualities I look for in leaders. It’s something I’ve worked hard to develop in myself. Self-awareness and objectivity will keep you on the right path no matter where your emotions try to steer you. To be successful in the long term, you need to be able to see yourself and your work for what it really is, not for how you wish it would be. Just because you worked hard on something does not mean it is any good. In fact, many of the projects I’ve worked hardest on were total crap. Many of the projects that came out easy, were my best work.

My advice to managers and career-minded people is to force yourself to be objective. Pride yourself on self-awareness. Nurture this skill in yourself and your teams. Objectivity begets credibility. Credibility begets trust. And trust, brings new opportunities for growth and expansion.

2.  Focus on making an optimal decision right now

All you can do is make the best decision with the information you have at any given moment in time. This is my mindset whenever I’m making decisions. Am I confident that when I look back on this decision at some later time, that I’ve made the best decision possible with the information at hand? Am I using good judgement? If you can answer “yes” to these questions, it will give you the courage to make a tough call.

Even though, as the months and years pass, some of your decisions may prove to have been wrong, you can still be confident so long as you made a solid decision with the information you had. In my case, I’m very comfortable with my decision to invest an entire weekend on a project that landed in the garbage can. Based on what I knew at the time, my approach made a lot of sense. It just didn’t work out. Things happened that were impossible for me to foresee at the outset. And that’s ok. I made an optimal decision to start the project based on what I knew, and then I made an optimal decision to trash it when I discovered new information that changed the dynamics of the game.

My advice is to leaders is to focus only on making optimal decisions based on the information at hand. It’s rare we have perfect information to work from. And waiting for more information will slow you down and make you less competitive. Make good decisions and then make new good decisions when the information landscape changes. Then be satisfied with all the optimal decisions you’ve made.

3.  Never compromise your high standard

Every time I compromise my personal standard, I regret it. Every time I let something squeak through, or give something a pass when I know it deserves a fail, it comes back to haunt me. I can’t think of any time where I compromised my standards for quality, that ultimately helped me progress in my career.

It’s easy to be tempted to compromise your high standard. I nearly was today. I made several arguments (to myself) for why I should just go ahead and publish my crappy work. But ultimately, I couldn’t do it. It takes years to build a reputation and minutes to blow it all away.

My advice is to figure out what your standard is and hold to it. Hold your team to it. Don’t take short cuts. Do great work. And when your work isn’t as great as you thought it was going to be, fix it or do something else.

4.  Take “learning” as a win

In the moment, when you’ve just “wasted” 20 hours working on a project that will never see the light of day, the value in learning a lesson is hard to swallow. But I do find, with enough time, I can point to the value in the hard lessons I’ve learned. If you can force yourself to step back, and view things with a wider perspective, you can take solace in learning from your fruitless efforts.

I will admit, if someone had told me to “take learning as a win” about three hours ago, I wouldn’t have responded as positively as I should have. But that doesn’t mean it’s not true. Most of my success (and ironically, most of what I write about) comes directly from my mistakes and lessons learned.

My advice is to search for the wins in admitting defeat and moving forward. They’re not always easy to find in the moment, but they are real and they will help you in the long run.

It takes great discipline and strength to be able to look at your own work, after hours and days of effort, and admit it isn’t good enough. The courage and objectivity to do this are qualities I look for in every candidate I hire. I may have wasted my weekend on a project that will never see the light, but my hope is by sharing my lesson, I’ll have created some value for you in the process.

The Weekly Reid: 3 Big Moments Most Managers FAIL to Capitalize on

Let me set a tiny bit more context before we jump into examples. Whether we want to admit it or not, career progression is a competitive game. Everything is relative. Everything is comparative. If you’re a manager – you get compared with other managers. If you’re a Director – you get compared with other Directors. The same holds true until you’re CEO and then you get compared with CEOs from other companies. This is a reality of corporate life. Your value is always measured in relative terms.

She’s one of our brightest executives

He’s been placed on a management fast track

She’s high potential employee

He’s a key manager we need to retain

The entire dialogue about careers in the workplace is comparative. And that makes sense. The higher you go in an organization, the fewer spots there are. Organizational structures, for the most part, are smaller at the top than they are at the bottom. This means we are all competing for advancement opportunities, whether we like it or not.

This doesn’t mean you need to turn into a blood thirsty shark at work tomorrow.  I’m not advocating for that. But it does help to take an accurate view of the playing field you’re on. It does help to appreciate the real dynamics at play so you can play your optimal game and maximize your chances of success.

I’m often surprised by the poor career choices I see managers make. Where they invest their time. Where they choose to focus. What upsets them. What opportunities they ignore completely. The good news is, with so many managers making suboptimal career decisions, you can find an edge. You can take advantage of the opportunities they pass up.

Here are three moments I see managers consistency fail to capitalize on. They don’t give them enough attention or energy. They mail it in when they should be leaning in. My advice, when you’re next faced with one of these, is to double your efforts, make it a priority, differentiate yourself from your peers. Your career will thank you.

1.  Your Presentation at Annual Kickoff

Most of us have some forum at the beginning of the year to present something. For some of us, it’s in front of the entire company. For others, it’s in front of a smaller team. Whatever your moment is, my advice is to quadruple your efforts to make it great.

Your annual meeting is one of the few times people will see presentations from a bunch of managers in a row. Whether we are conscious to it or not, we are rating, ranking and positioning managers in this moment.

Whose presentation was amazing?

Who was funny?

Who looked unprepared?

Who energized the audience?

Who has mad presentation skills?

Who seemed authentic?

Who was full of crap?

These are the questions racing through the minds of audience members during annual kickoff. Your boss, the CEO, other executives, your peers, your team members. It’s a huge moment.

It’s a huge moment, but also one that way too many managers squander. It never ceases to amaze me how weak most of the presentations are at annual kickoff. People just don’t try that hard. They aren’t polished or prepared. The tragedy is, many managers work tirelessly to build great plans and execute them all year, only to mail it in when presenting at the annual kickoff.

I never do this. For me, the presentation about what I’m going to do, or about what I have done, is equally as important as doing it in the first place. You’d be shocked at how much effort I will put into my presentation at a kickoff. It’s THE moment to distinguish yourself from everyone else. Even if your actual contributions were only on par with your peers, this is a moment where you can separate yourself from the pack. This is a moment where you can energize the company (or department) about your initiatives such that it will provide a tailwind for your efforts for the rest of the year.

My advice to managers is to triple or quadruple the amount of effort you expend preparing for your presentation at annual kickoff. Make it amazing. Focus on making a presentation that will set you apart from everyone else. Don’t just be good. Be amazing.

Now, you may say – I’m not a great public speaker, so what about me? – that’s fine. Be the person who has clearly put in the most effort. Have amazing materials, polished slides, great data, concise points. You don’t need to the best speaker to advance your career in a material way at your annual kickoff.

2.  Any time Your Team Members Present

One thing that might surprise you, is how much time I spend helping my team members prepare for their own presentations. Reviews with executives, team meetings, anything with an audience of significance. My job as a leader is to help my people maximize their potential and realize success. So that’s what I do. I never let a manager on my team present in front of a large group or senior leaders without helping them prepare. At first, this might sound to you like a control mechanism. Like I’m a micromanager. Like this is all about me. It’s not. The deal I make with managers on my team is that I will do everything in my power to make them successful, to make them look great. And that means getting personally invested in their big moments as well as mine.

I’m often shocked when I see people deliver poorly prepared or unpolished presentations in large groups while their manager looks on in horror. I would never allow this to happen. When my team members present, I want them to be the best. I want them to be confident and proud. I want them to know, no matter how the presentation goes, that we’ve worked on it together and I’ve got their backs. Even if it doesn’t go well - if they struggle in the moment, that we’ve done everything we could to make it great.

It should go without saying, your team members are a reflection on your management competency. Which is why I’m often shocked at how many managers leave their team members to fend for themselves when preparing for a big presentation. It’s possible they think it too controlling or micromanaging to review their team members’ presentations. I obviously disagree with that perspective. In my experience, the kindest thing you can do for your team members is to help them be great.

My advice to managers is to get more involved in helping your team members prepare for big presentations and meetings. Get in there. If they know you’re doing it because you genuinely want them to look good, they’ll appreciate it. And once they knock a few out of the park and separate themselves from their peers, they’ll embrace the process.

3. Your Quarterly Business Review (QBR)

This is another moment most managers don’t expend enough effort on. They take quarterly business reviews for granted. They view them as necessary evils – an event that gets in the way of what’s really important. This is a misguided perspective. How you present your progress and results is as important as the results themselves. I realize that sounds like quite a statement. Can that really be true? Is this one presentation every three months really as important as all the work expended the other 99 percent of the quarter? Yes.

Put yourself in your boss’s shoes. The QBR (or whatever the equivalent is at your company) is the one moment she gets to compare all the managers on her team. To see them perform on an equal playing field. In a matter of hours or days, she gets to see your management prowess on display, one after another. If you think she’s not evaluating, making judgement, mentally positioning you, you’re naïve. 

Of course, you need good results. If you’ve bombed the quarter, no QBR presentation in the world is going to save you. But if you’ve done reasonably well, this moment can differentiate you from everyone else. If your results are slightly below average, a great QBR presentation can make people believe in your potential. If your results are great, it can catapult you into consideration for promotion or expansion. The QBR presentation is your showcase opportunity, and you need to NAIL it.

Let me give you a window into how your competition might be thinking (by sharing my own mindset). When I am preparing for a QBR (or when I help my team members prepare) I am 100% committed to building what I believe will be the number one presentation my boss sees that week. I commit to spending more time preparing. I commit to polishing and practicing. No matter what happens, no matter what results I’m sharing, I make certain my presentation will be the best. Unlike the results, which have already happened, the quality of my QBR presentation is something that is fully under my control. And so, I nail it. I help managers on my team nail theirs. If you’re not doing the same, your competition is lapping you.

My advice to managers is to invest more energy in your QBRs. Commit to be the best. Presentation quality, slide design, data accuracy. Be compelling. Even if you think every other manager is just going to follow some standard template, go three steps further. Take unnatural efforts to be great in this moment.

I’m often confused by the moments managers choose to focus on (and ignore). In my experience, we spend too much time fixating on creating and executing our plans, and not nearly enough time preparing to tell people about them. I’d love to hear your experiences and perspective on the issue in the comments section.

The Weekly Reid: 4 Times When The Best Move is to Do Nothing

Most managers are action oriented. They see a problem and try to solve it. They meet a roadblock and they try to push through it. I believe you need to have more depth in your game than this. You need to know when taking no action is the best action to take.

Here are a handful of scenarios where doing nothing is usually the best approach.

1. Flaming Emails

The first instinct for many managers, when on the receiving end of a flame email or criticism, is to hit back. Many of us hit back twice as hard. We meet aggression with aggression. We stand up to the bully. We can’t stand the thought of losing. And so, we fight. There is certainly a school of thought that advocates for this level of aggression in business, I just haven’t found that it works over the long term.

Early in my career, if I received an A$$H#&E email from someone, I would instantaneously react. I would respond with at least as much aggression as was targeted at me. Usually a lot more. I reacted emotionally. I reacted quickly and without thinking. Even though it was often therapeutic to bite back, and even though I managed to “win” some battles along the way, my reputation in the long term took a hit. I became known as aggressive, immature … volatile even. It became painfully clear to me a few years in, when I got passed over for a leadership role because the executive team didn’t think I was ready yet. And then it happened again.

As I’ve matured in my career, I’ve learned to not react. To do nothing. I have built great self-control. I have learned to act with purpose. If you send me a flaming email, the chances of receiving an angry response back from me is almost zero. I will let it sit. I will let you sit and wait for me to respond. I’ll let you get impatient. I’ll let you wonder if I’ve even received it. I’ll let you contemplate what you’ve done. And as the hours pass and your emotions shift, you’ll start second guessing yourself. You’ll start wondering if you were inappropriate or unfair. You’ll wonder who I may have shared your email with, and what they may be thinking or doing. I’ll let you sit for a long time. And then, in a day or two or more, when your emotions have calmed and you’re questioning your approach, I’ll call you and very calmly address the issue, make my argument and you’ll apologize to me for being a dickhead.

Who is the leader in this scenario?

Who won this battle?

My advice to managers is to press pause every time you’re tempted to bite back at someone for an angry email or call. Just stop and do nothing. Let it simmer. And when you finally act, do so with purpose and poise. I’m not advocating that you roll over every time someone attacks you – far from it. I’m advocating to act strategically. It will do wonders for your reputation and relationships.

2. Low Priority Work

This is a very different example from the first one, but no less important. Many of us fall victim to the constant onslaught of emails, meetings, calls, minor issues. If you’re not careful, taking action on these can stagnate real progress. In my job, I could easily burn 40 hours a week responding to emails, attending second tier meetings, and answering the phone. I could spend 40 hours a week and make zero progress. I see other managers do this all the time. They just don’t seem to have enough hours in the week. They just can’t seem to move the ball forward on key initiatives.

This is another scenario where the optimal move, in my opinion, is to do nothing. I never answer emails as they come in. I only answer the phone if I know the caller and I have reason to believe the issue is a priority. I decline all non-essential meetings. I almost never schedule meetings for more than 30 minutes even when they are essential. My default response to incoming activity is to do nothing. To let it sit and simmer while I make progress on my big wins.

My observation is that many managers overvalue responsiveness as a management virtue. They respond and respond and respond and at the end of the year, have nothing to show for their work. And when they are being considered for a promotion or expansion, they struggle to show enough progress to support their case.

My advice to managers: When you see the emails flooding your inbox and the calls coming in and meetings piling up – do nothing. Focus on your wins, make progress.

3. Losing Small to Win Big

Managers need to keep their eyes on the prize. You need to know what your big goals are at all times. The decisions you make, on what to give attention and energy to, must be directed by your target wins. One of the biggest mistakes I see managers make is winning small only to lose big. This is true in relationships as well as projects and programs.

To be successful in the long game, you need to build a network of strong relationships. And those strong relationships can’t only be with people you like. The most successful leaders have productive relationships with people they don’t particularly care for. The only way this is possible is if you can keep from getting sucked into petty conflicts that turn into feuds and impasses. You might be surprised at how often I will intentionally lose an argument. You might be surprised at how often I’ll let something slide by that upsets me, that I know is wrong.

I lose small all the time. Some people will scratch their heads and wonder if I’ve gone soft or if I’m not paying attention. That’s not what’s happening. I choose to lose small in order to win big. I choose to accumulate goodwill by sacrificing for other leaders, so when something big comes up, I can cash in my chips.

My advice to managers is to look for more opportunities to lose small so you can win big later. Look for opportunities to turn the other cheek, to do nothing. My experience tells me this approach strengthens relationships, accumulates capital in your network, and strengthens your position when you ultimately do fight for an issue.

4. Unclear Risk vs. Reward

The last scenario I should mention is when you’re unable to approximate the risk/reward for a decision with a reasonable degree of confidence. This is a tricky one and should not be mistaken for tacit permission to punt every tricky call you need to make. The best managers need to be able to act with imperfect information – that is not up for debate. But even without perfect information, you should be able to assess the risk/reward dynamics of a situation before acting.

Is there a big win for me if I do this?

How big is the downside if I mess this up?

If this goes bad, am I comfortable with my decision based on the information I have?

My advice to managers is that if you can’t answer these simple risk/reward questions, it’s usually a good idea to do nothing. Wait. Pass. Take a breath. Like in investing, sometimes the smartest moves are the investments you didn’t make.

Sometimes it pays to take no action at all. This doesn’t come naturally to most managers. We are bred to execute with aggression. Most of us have realized some measure of success by being action-oriented. To do nothing, seems weak, indecisive. Don’t let yourself fall into this line of thinking. Your goal is to make the optimal move in every business scenario you encounter. And many times, in my experience, the optimal move is no movement at all. I’d love to hear your thoughts and feedback in the comments section below.

The Weekly Reid: The one question you should ask yourself every day

“Where is the win?”

“Where is the win?”

“Where is the win?”

This is one of the most important career questions you can ask yourself.

It has endless applications. It never gets old or irrelevant. It is the secret to any measure of success I have enjoyed. It seems simple, but its immeasurably powerful in my opinion. So many of us get stuck in situations where a win is impossible or we aren’t clear what win we should be pursuing in the first place.

So many of us take on projects that are not winnable. So many of us focus our energy on time-consuming activities instead of concrete wins. Some of us used to win, but now we’ve taken on more, and we aren’t winning any longer. We traded winning in exchange for money or role expansion or title. It’s a bad trade every time.

The most important career advice I give to clients and team members is to focus on winning. I tell people to seek out wins, to build a reputation of winning. Even if that means taking a step back, changing jobs, reducing responsibility. The most important thing you can do for your career is to build a reputation as a winner. You are better served being a winner on a small scale than being loser on a large scale. Winning is how you build the forward momentum you need to progress in your career. Winning also builds spiritual momentum and energy and confidence which beget even more winning.

One obvious question you must have is, “what exactly is a win?”

Here’s how I think about wins:

Is the reward I can expect for my activity commensurate with the effort I’m exerting?

Are the potential rewards disproportionately high relative to my efforts?

If I’m successful, will anyone know or care?

Does this effort advance me on the path to my larger purpose in life?

Do I find intrinsic fulfillment in doing this irrespective of any discrete reward at the end?

On the surface, this lecture on winning may sound self-evident. Simple even. If it were simple and self-evident, I wouldn’t have to remind myself and others about it nearly every day. I wouldn’t observe so much wasted energy in the workplace. Let’s look at some pragmatic examples of its application to get a little deeper into it.

To leave or to stay?

It’s very hard to leave a job, a boss, a company. Even when your current situation is bad, there is no guarantee the next opportunity will be better. The grass isn’t always greener. Many of us have learned that the hard way. In fact I wrote a blog last year that documents my own thought process when I left my last company. You can read it here.

Too many of us stay in unwinnable situations. In unwinnable jobs. With companies that can’t win. We get lost in the routine, comfortable in the environment, even numb to abuse. I stayed in a job, which by any objective measure was destructive, for four years when I knew after four months there was no reasonable expectation of a win. Believe me, I get it.

But then you wake up one day, as I did, and you’ve accomplished nothing. You’ve become a fragment of your former self, you’ve gone from being a winner to being a loser. You tricked yourself into believing you could win when you couldn’t.

My advice is to ask yourself every day or week or month, “Is this a winnable situation?” If I keep working hard in this job, is there a win in it for me? If you can’t answer “yes” with conviction, you need to find a new path, a new company, a new job.

Going backwards to go forwards

There are many situations where we find ourselves in unwinnable positions. Sometimes we’ve taken on more than we can reasonably expect to succeed at. Other times we’ve taken a job that, by its very nature, can’t result in a win. Sometimes we take on challenges that, even if we were to win in some way, nobody else would care.

Sometimes it makes sense to go backwards to move forwards. I see this a lot with inexperienced managers who get prematurely promoted to run large teams. They can go from being a recognized winner at a smaller scale to a clear loser on a larger scale. It can happen in an instant. When I observe this to be happening to me or to people I manage, I immediately try to find ways to help bring the person back to winning. It’s a tragedy to see a career stall out or falter for no reason other than we’ve placed a winner in an unwinnable situation.

My advice to leaders is to purposely place your top performers in positions that are designed to help them win. The best gift you can give a team member is the opportunity to consistently win. Winning begets winning. If you see someone who was a star, now struggling, pull them back into a winning situation, retool, recharge, and then start moving forward again. Keeping someone in a losing role when they could be winning at something else, is to do them a disservice. It may feel awkward to have this type of conversation with a team member, but in the long run they will thank you.

A path to prioritization

The larger your mandate, the more priorities you must juggle. Most days when I look at my list of things I could do, its daunting to say the least. In fact, if I tried to pursue my full list every day, I’d never win at anything.

When I look at my list in the morning, I do so through the lens of winning. I ask myself, and my team members, which of these tasks are most likely to lead us to a big win. Which of these tasks are going to propel us forward? Which of these activities presents the opportunity for a win that is disproportionate to the effort we would expend pursuing it? I let these activities take priority every time.

You may be asking yourself, well that sounds nice, but what about all the other stuff we have to do but aren’t winnable? My advice to is pursue big wins when you have maximum energy and pursue your table stakes activities when you don’t. I try to pursue wins first thing in the morning and early in the week. Later in the day or week I’ll catch up on the routine things that don’t present me or my team an opportunity for a win.

Outcomes vs. activities

The dialogue I have with my team is always about wins. I don’t speak in terms of activities. I try not to reward efforts that cannot be directly correlated to a win. To do so, would be to reward the exact behavior we want to avoid. I try to find examples of highly efficient wins – where disproportionately small efforts result in disproportionately large wins. I’m even happy recognizing failed efforts that were rooted in the pursuit of a disproportionately large outcome. It’s about building a winning mindset in your team culture.

My advice to managers is to focus on building a winning culture. Ask yourself and your team the question, “where is the win?”. I think you’ll like the answers you get back.

The Weekly Reid: How do you manage "ok" performers?

Most good managers act in basically the same way and with basically the same mindset when it comes to top and bottom tier performers. That’s a bit of a generalization, but true for the most part. The wider variance in management focus and approach can be found in that middle performance tier, the average and slightly below average team members. I don’t think we all approach them the same way. It stands to reason, if this variance does exist, that there is a lot of ground to be won vs. your competition by making better decisions about the middle group – the “ok” performers.

Why do I describe the issue in this way?

My mindset is always to strive for “best in the world.” In fact, the number one attribute I look for when hiring new people is a genuine desire to be great. Truly great. Irrespective of where your team may be today, you should be working towards being the best in the world at what you do. It may take 20 years. You may never have the budget to do it. Your company many be in a tough industry. I get that. But what matters to me is the mindset – the commitment to a process that ultimately (even on an infinite timescale) gets your team to best in the world status.

If your team is striving to reach best in the world status, you need to find every edge you can get. In my experience, how you manage your middle tier, or “ok” performers present a real opportunity to find that edge. Most managers tend to ignore this group. It’s easy to do that. And sometimes, frankly, it’s the right thing to do if you have many other burning priorities. It’s easy to place all your attention and investment on motivating your top performers and managing your low performers. Part of the reason for that is it’s just so much more obvious to know what to do with them. The optimal approach for managing average or slightly below average team members if a much more complex problem. As a result, most of us do nothing. And therein lies the opportunity for competitive advantage.

If similar departments in other companies in my industry are ignoring their middle performers, I want to exploit that weakness. I want to outplay them in this area of management. Over the long run, as my middle performers become stronger and their middle performers stay flat, my team becomes better and my company has a new edge in the market. That’s the point of this article.

You may not often think of your team in this way. But what else is there? You’d compare sports teams on the strength of their starting lineups and the strength of their bench. Look at my beloved Toronto Raptors. The had a great season, by in large a result of their middle tier team members. Rather than ignore this group and attend only to the top and bottom players, they focused on building a stronger middle contingent, and it led to a competitive edge (for the regular season at least ☹)

Hopefully, I’ve made a decent argument for why you need to spend more time actively thinking about the development of your “ok” performers. Here are a few tips for how I do it:

Differentiate between “ok now” and “ok forever”

I pay very close attention to forward momentum when evaluating middle tier performers. If I can spot progress, even if it comes at a slow pace, I will happily continue investing in development. As much as I can, I take a pretty long-term view when it comes to team management. I don’t want to be trading people around like baseball cards. It’s important for me to develop long terms relationships with strong performers so we can build great teams together for many years and across many companies. This is not to say I would keep someone in a specific role if they aren’t competent – I wouldn’t. But I won’t give up on a team member if I see some evidence of forward momentum. That is, if I believe there is a reasonable probability the person will someday be great.

On the other hand, when I don’t see evidence of progress in a team member, I immediately start managing in the same way I’d manage a low performer. Either find a role that is a better fit or aggressively performance manage. That may sound harsh to some people. If the person is doing ok, why treat them like a low performer? And my answer is, because I want to be the best in the world.

My advice to managers is to look more closely at your “ok” performers. Specifically, I recommend looking for signs of momentum. If you find it, great, keep challenging them and don’t give up. If you can’t find it, I recommend managing them more as you would a low performer.

Aggressively move people to where they can be great

I need to be a bit careful on this one. I am not really a supporter of moving people around the organization from one role to another when they have not been successful anywhere. You see this happen in a lot of companies. Moderate performers moving from one group to another, ostensibly for their experience, but really because it seems easier than letting them go or hiring an unknown from outside the organization. I call this group, “serial movers”, and advocate against doing this.

With that said, there are cases where otherwise talented, high potential team members are just misplaced in the company. Strong individual contributors who moved hastily to management is probably the best example. Another example are team members who were very effective when the company was small, but now that it’s much bigger, seem a bit lost.

Many managers are reluctant to take action on this group. For the reasons I mentioned above or out of a sense of loyalty to long time team members who were once successful. I think this is a mistake. In my experience, team members are happiest when they are winning. It can be demoralizing for a habitual winner to start losing for a prolonged period of time. So, while you may be reluctant to have a tough conversation about a role change with someone on your team, they may well be silently wishing for it.

My advice to managers is to study your middle tier performers and identify those who could be great if placed in a different role. But really hold yourself to that standard – could this person be great if placed in a new role? If the answer is “yes,” then I recommend moving aggressively. If the answer is “no,” then I would immediately start managing them like you would a low performer.

Hire for the desire to be great

I won’t belabor this one since I kind of already made the point. In my interviews, I actively search for signs that the person I’m talking to has a deep seeded desire to be great. I look for people who are obsessed with best practices, and are well versed in what the best companies in the world are doing. When I find these qualities, I hire. It’s very rare, that a person who genuinely needs to be great will disappoint you. They may struggle here and there, but ultimately their drive and ambition for greatness will overcome.

Note, there is a big difference between wanting to be truly great in the purest sense, and wanting the trappings of success. You need to learn to tell the difference between the two. I’m looking for people who want to be true masters of their craft – to be great ... intrinsically. That’s the kind of magic that can transform a middle performer into a future star.

It’s not always clear how to manage average performers. It’s very easy to do nothing. To ignore them and place your all your energy on top and bottom performers. My contention is there is a competitive edge to be found in out-managing your competition in this middle realm. By raising the level of your “ok” performers, you could well become the Toronto Raptors of your industry (except hopefully you won’t’ collapse in the playoffs). Have a great week.

Want to Lose Your Top Performers? Do these Four Things

I have been critical in the past about managers and media speaking about engagement as an abstraction. As some high-level program or company-wide initiative that lumps everyone together. You’ve read the stat that more than 50% of us have quit a job because of a bad manager. You’ve heard the saying, people quit managers, not companies. This completely lines up with my experience. My observation is that employee engagement is the biproduct of a very personal relationship between an employee and a manager. It’s the result of a partnership based on fairness, opportunity, challenge, and development. I get frustrated when I hear people speak about engagement at the surface level only. As though some system or program or policy is actually going to change how engaged a high performer is.

I spent some time thinking this weekend about the periods where I have felt unengaged at work. They weren’t during the most challenging times, or the times when the company was struggling. They weren’t when I had a crappy vacation plan or a when I couldn’t wear jeans to work. My lowest periods of engagement came when I felt I was being treated unfairly. My engagement withered when I felt the game was rigged, when I couldn’t win. My great efforts no longer resulted in great outcomes.

If you want to retain and engage your top performers, you should never do the four things below. You may find these to be extremely specific and tactical. They are. They are directly related to creating and maintaining a fair playing field at work. I’m sharing with you because after 20 years of career, these are the four things tattooed into my subconscious as guaranteed engagement suckers for top performers. They caused me to leave companies which tells me they’re likely to have the same effect on others.

1.       Friday-night Flames

I used to work with a leader who made a point of sending incredibly harsh emails every Friday afternoon. At first, I thought it was unintentional, but as the months and years went by I became quite certain it was purposeful. Every Friday afternoon around 3 or 4 o’clock, this manager would send a nasty, pointed, critical email seemingly designed to create chaos and anxiety. He would target key members of his team and stakeholders from groups he worked closely with. For about three years, I went home just about every Friday, thinking about or worrying about some critical message this guy had sent.

This was obviously an extremely divisive and frankly, sadistic management technique. And, as I reflect on it now, it was clearly an attempt at exerting control. We’re all nodding our heads as we read this – what a jerk – but ask yourself, do you have any habits like this?

I make a point now, of saving my harshest criticism for a time when we will have the chance to actually talk it through. This may sound like a truism, but I try not to ruin people’s evenings and weekends whenever possible. Even when something really upsets me, and I feel compelled to admonish a person, I’ll hang on to it until Monday and deal with it in a 1-1.

My advice to managers is to dial up your level of self-control. Stop sending flame emails or harsh criticism on Friday afternoons or weekends or evenings when the target of your admonishment isn’t able to talk to you and resolve it. If I’m still painfully recalling those Fridays and Saturdays I spent stewing over flame emails, you can bet your top performers feel the same way about yours.

2.       Copy Staff Members on a Critical Email to their Manager

Don’t undermine your leaders in front of their team members. There is little worse as a manager, than getting crushed on an email or in a meeting in front of your team. If I’m honest with myself, I’m sure I’ve done this more than I should. You tell yourself you want to send a message to the team, or you come up with some other justification for why a hard, public reprimand makes sense. The problem is, when you admonish a manager in front of her team, you create an amplification effect that may have unintended consequences.

When you de-pants a leader in front of the team, you give the team members tacit permission to question his or her competency. You send a clear message to the team that you’ve lost confidence in their leader. It’s easy to imagine the trickle-down effects of this. You crush the manager, the team sees this, they question the leader’s skill and career prospects, they start second guessing direction given to them by the manager, projects start suffering, the member and team perform poorly as a result. Your “message” accomplished exactly the opposite of what you wanted it to.

My advice to leaders is to give hard, critical feedback directly to managers. If you want to send a message to the larger team, I suggest first engaging with the manager and then delivering a purposeful message to the team together. That way you preserve the manager’s ability to lead the team, you have the opportunity to voice your criticism, and you get to deliver a larger message to the team.

3.       Harsh Criticism Too Soon After a Big Effort

I’ll never forget this one time my team and I pushed hard for two months on a massive project – really went above and beyond – the team was completely fried by the end of it. By all accounts it was a success. And then, not even eight hours after it was over, when we were still basking in the glow of our crazy hard effort, we received a flaming email about a mistake we’d made on some other, unrelated project.

If you want to take engagement from 100 to 0 in 5 seconds, this is how you do it.

As a manager, you must pick and choose when and how you criticize. I’m the first person to point out we need to be more critical of our teams. I wrote an entire blog on the subject. But be smart about it. If your team has just worked hard on a tough project, give them a minute to enjoy the success. Have the self-control to hold your criticism for a few days.

In the same vein, if your team is in the heat of the moment – during a big event, in a big customer meeting, about to do something pressure packed, hold your feedback until its done. I’ve never understood managers who insist on crushing their people in the heat of the moment. If they were unprepared, nothing you will say now can fix that. All you will do, by admonishing them in the moment, is make things worse. Performance and engagement will suffer. Wait until it’s over and set up a productive feedback session to share your criticism and advice.

My advice to managers is to be more purposeful in your delivery of feedback and criticism. Too many leaders operate from emotion instead of purpose. Yes, you may be pissed. Yes, your team may have screwed up. But that doesn’t mean you have to react recklessly to satisfy your emotional needs. That is short sighted. Stop reacting. Think through how you want to deliver criticism. Act from purpose, not from anger.

4.       Coddle Underperformers

I wrote about this one in my blog, How to Lose a Team in 10 Days. I won’t dwell on it. Except to say, a guaranteed way of losing your top performers is to be seen coddling or favoring underperformers. Some managers, who aren’t comfortable delivering pointed, critical feedback, or who are unwilling to make hard changes on their teams, can get sucked into a habit of lowering the bar for low performers. You must never do this. I realize it can get exhausting having to constantly provide performance feedback to low performers. It can be tempting to give them a pass just to save the energy. The problem is this behavior sends a clear message to your higher performers. It says the game is not fair.

The worst thing we can do as managers is to sacrifice the engagement of our top performers to coddle our low performers. My advice to leaders is to set a consistent standard for performance and stick to it. Your high performers need to see you pushing lower performers, otherwise you risk losing them.

I think we speak about employee engagement too generically. We rarely get past the surface level in our discussion of it. If we’re not careful, we risk missing the real point. Our goal as managers is to behave in a way that motivates, engages and retains our top performers. I’ve shared a handful of behaviors I’ve seen over the years that do the exact opposite of that. I try really hard not to do these things. I’d love to hear from you about other behaviors you’ve seen that are sure fire ways to suck the engagement from high performers.