Weekly Reid: Confronting Your Boss – When and How to Do it

Not surprisingly, the issues that cause us the most pain at work are the hardest ones to talk about. How do you approach your boss about this stuff?

I haven’t had a raise in three years and I deserve more.

My boss doesn’t seem to trust me and micromanages everything I do.

My manager yells and is aggressive and it’s starting to affect my confidence.

I got passed over for a promotion but I’m too afraid to ask why.

What I was hired to do and what I’m being asked to do are wildly different.

These are big problems. They affect the most basic tenets of motivation – purpose, autonomy, fairness. They are critical to get right but so often they are not. It’s hard to know how to broach these subjects because they are so loaded with consequence. To bring them up seems tantamount to accusation. Sure, you might be able to improve things by talking about them, but they could just as easily get worse. It’s easy to see why so many of us choose to grin and bear it instead of confronting our managers. I get it.

Today I’m going to share a few thoughts on when and how to approach these issues with your boss. I don’t have all the answers – it’s a hard one. I also don’t know the specifics of your situation. We’d need to do a coaching session for that. My hope is that by sharing my perspective, at a high level, you can have some of the tools you need to start building your own strategy for dealing with these tough issues.

WHEN should you confront your boss?

For most of us, the answer to this question <when to confront your boss?> is, “Never”. It always seems easier to defer, delay, turn the other cheek. For others of us, confrontation inevitably comes when we’ve reached the breaking point. A series of incidents boil up until we can’t take it anymore, and finally we blow up in spectacular fashion and try to pick up the pieces later. Neither is the right approach. Even though these are highly charged, emotional issues, we need to be smarter in how we resolve them.

When people ask me when they should confront their boss with a contentious issue, my advice is almost always, “once you’ve built some leverage”. The problem is, too many of us wait until we’re at our weakest to confront our bosses with the hard issues. After a huge mistake, after a big fight, when we just can’t take it anymore. That is the opposite of leverage. When we’re upset or damaged or struggling, we have everything working against us.

When my coaching clients ask me when to talk to their boss about a big issue, I recommend they start by creating leverage. Get a win, do something and get recognized for it … anything. Wait for a moment when things seem positive – from your boss’s perspective at least. That is the moment to have the tough conversation. Next time you feel like you’re boiling over, like the straw has broken the camel’s back, take a breath, make a plan, get some leverage back, and then confront your boss from a position of strength.

HOW should you confront your boss?

Most of us get these big conversations wrong. We approach them with emotion, without a plan. We don’t end up getting our points across. We come off as flaky and selfish and hypersensitive. Then we regret doing it in the first place. Before you have a hard conversation with your boss, consider the following:

What is the outcome you’re trying to achieve? Are you just venting or are you pursuing a specific result?

Are you considering all perspectives? Are you coming across as self-centered or are you thoughtfully acknowledging your boss’s position?

Are you presenting in a personal context or a business context? Do you know why?

Will you start by reaffirming your desire for a positive outcome or will you just launch into your complaints?

Do you plan on presenting ultimatums? Are you sure you want to do that? Can you live with the result? Are you bluffing? Do you have a backup plan if it goes badly?

My goal in posing these questions is not to dissuade you from having a tough conversation with your boss. You need to have them from time to time. Rather, I want to make sure you’ve thought your plan all the way through. In general, I try to avoid ultimatums unless I’m prepared to leave the company and torpedo the relationship. Ultimatums are rarely necessary in my experience. Knowing what outcome you’re pursuing is also critical to a positive result. If you haven’t visualized what a positive end to the conversation looks like, it’s very difficult to make it happen. If there is no positive end possible, ask yourself why you’re having the conversation in the first place.

My advice for these types of confrontational conversations is to start with a clear idea of the outcome you want, be sure to provide context and acknowledge your boss’ perspective, explicitly state your desire for a positive outcome, avoid ultimatums, and know what your back up plan is. Once you have a clear sense for these things, and you have leverage on your side, you can be confident in having the tough conversation.

I’d love to hear about your experiences with these types of confrontations – good and bad. They’re extremely hard which is why so many of us avoid them. I hope my perspective has been helpful to you.

Weekly Reid: 3 Signs Your Candidate is Too Good to Be True

I participate in a lot of interviews. Many I do on my own, but frequently I do joint interviews with other managers. I’ve noticed many interviewers are not engaged enough during the interview itself. Yes, they’re asking questions and listening to the answers, but they’re often not watching or listening closely enough to notice some of the most important signals. It’s understandable. We’re busy people. I am a culprit too. We’ve often got multiple interviews on the same day. Interviews sandwiched between 6 other meetings. Sometimes we have no choice but to interview a candidate right in the middle of a critical project or a distracting crisis. It’s easy not to be completely present and active during an interview.

This week I’m going to share a few signs I actively search for in interviews. I make a point of looking for these signs even when I’m distracted and busy. By focusing on a few specific things vs. a universe of body language and subtle queues, I find it much easier to ascertain the evidence I need to make better hiring decisions.

Here are 3 signals I look for to know if my candidate is great or too good to be true:

1. Are they engaging or just presenting?

Sometimes candidates sound great even though they aren’t. Their words make sense, but there is little behind them. They seem well prepared but something just isn’t quite right. If you’re not actively listening, you can miss the subtle difference between a candidate who is engaging with you on a topic and a candidate who is presenting to you on a topic. The difference is critical.

The Internet makes it easy to prepare surface level messaging for just about any topic. An ambitious candidate can prepare canned answers to almost every question they’re likely to receive. You ask them something and they find an entry point into a prepared talk track or story. It’s a good strategy if you’re a candidate, but if you’re the hiring manager, you need much more. When you’re busy or distracted, it’s easy to confuse a canned answer with a thoughtful response.

My recommendation to interviewers is to pay more attention to how candidates answer questions. Listen for clues that will tell you if you’re getting a real response or prepared remarks. Ask follow up questions and engage in a conversation to test for depth of understanding. You’ll be surprised how often a great answer to the first level question is followed by a terrible answer to the second level question.

2. Did they actually answer the question?

If you’re not paying attention you can miss how often candidates don’t answer the actual question you’ve posed. You get distracted by what they’re saying and fail to notice they didn’t actually respond to what you asked. This is concerning for a couple of reasons. The first is when candidates don’t answer the question exactly how it was posed, its indicative that they may lack empathy and critical communication skills. In the interview, it may not seem like a huge deal but when you hire them and they still aren’t listening to you, it becomes a problem in a hurry. The second reason I get concerned when a candidate doesn’t answer the exact question I asked, is that it’s often an indicator they didn’t know the answer in the first place and have pivoted to a canned talk track in hopes I don’t notice. Sometimes I don’t.

My recommendation to hiring managers is to force candidates to answer the exact question you’ve posed. Don’t be afraid to restate the question or pull the candidate back to address exactly what you’ve asked.

3. Do they think and speak in a structured manner?

Some candidates sound great on the surface but are just rambling without structure or logic. Answers might be entertaining and contain some useful insights but meander aimlessly without a clear framework. As you start hiring more senior level candidates, this phenomenon occurs more frequently. Interesting, articulate answers that lack structure indicative of logical thinking and deep understanding. This is a red alert for me.

In my experience, the best candidates (for most jobs) are those who can think and communicate in a well-structured manner. This skill translates to how projects will be tackled, how communication with co-workers will be done, and how they’ll provide direction and leadership to a team. The problem is, it can be hard to tell the difference between a structured thinker and a rambling story teller if you’re not paying close attention.

My recommendation is to actively watch for signs of structure (and lack thereof). Look for bullets and lists and grouping. Pay attention for models and frameworks vs. anecdotes. Notice if they purposefully tie parts of their answers to parts of your original question. These are all signs you have a great candidate on your hands. When these things are missing, take caution.

As a manager, hiring great talent is everything. I don’t think I fully appreciated this truth early in my career even though it is repeated so often. The easier it becomes to prepare for interviews, the more you need to raise your interviewing game. I hope these tips will help you discern between the great and the too good to be true. Let me know about tips and tricks you’ve used in interviews. I’d love to hear them.

4 Keys to Advance from Director Level to VP Level

I should tell you before I get started, that getting to the Vice President level in your career is not easy. I’m sure most of you already know that. Either you’ve reached that level through hard work and sacrifice or you’re not their yet and the task of getting there seems daunting. The reality is, there just aren’t that many VP roles available. Organizations are shaped like pyramids and the further you go vertically the fewer opportunities there are.

In my previous blog I mentioned, that in my experience, the move from Manager to Director is the hardest jump we have to make it our careers. It demands such a fundamental shift in mindset and skillset, many of us struggle to ever make the leap. The move from Director to Vice President is a close second. Not so much for the mindset shift or functional skills gaps, but for the new levels of strength and toughness it requires. I’ve seen many first time VPs struggle under the weight of it all. To be honest, I was one of those people.

The biggest difference between the VP and Director level is the scope of responsibility and the complexity that comes with it. At the VP level, you typically manage multiple teams with priorities that are often not totally aligned. This dynamic makes everything harder … messier. It becomes less obvious how to make decisions. More often than not, you find yourself choosing between several suboptimal paths – nothing is clean. It feels like you can’t make a decision to favor one thing without hurting another. There are always many different perspectives to consider, instead of just a few. You aren’t just leading a team any more, you’re leading on behalf of the company. The stakes seem higher and your impact - positive and negative - seems so much more poignant.

To be ready for the Vice President level you need all of the skills you needed at the Director level plus a new level of strength, conviction and perspective.

Here are my 4 keys to advance from Director level to Vice President level

1. Find Common Purpose for Disparate Teams

One of the first awakenings I had when I finally reached the Vice President level was how hard it was to get my entire staff aligned to the same mission. You hear that from people and in books but this is where it became real for me. I didn’t have this problem when I managed a single team or a couple of teams that were more naturally aligned. But when I started managing numerous teams with widely varying functions, things got tricky. I remember being frustrated and asking myself:

Why can’t these teams work together?

Why are we doing so many activities that seem so disconnected?

Why is one team celebrating success and others aren’t?

Why do I know our mission and nobody else seems to?

Like most things in my career, I went through a classic cycle – from denial, to frustration, to blame, to self-discovery. Ultimately, what I learned, is that the larger and more diverse your team is, the most important it is to help each person identify and understand their role in a common purpose. When you can help people find personal meaning in the mission of the greater team, good things happen. When that doesn’t exist, people tend to revert back to pursuing their own self-interests, whether or not those interests are aligned with the mission of the team.

My recommendation for would-be Vice Presidents, is to find ways to create a common purpose for a multi-functional team. Something that isn’t tied directly to the team’s functional disciplines themselves. For example, in Marketing, I try to avoid setting goals for the Web Site or for Public Relations or for Social Media. Instead, I try to find a purpose that spans all of these functions – something everyone can find meaning in. Rather than set goals at the functional level e.g. Web site traffic, I might set a goal at the market performance level e.g. Take 2% market share from our top competitor. Then I’ll help each of the functional teams and the individuals on those teams to identify what their role can be in helping us achieve this higher level outcome.

2.  The Courage to Prioritize Ruthlessly

The next thing I discovered in my early tenure at the Vice President level was how easy it is to get buried under the weight of low impact activities. I don’t care what department you’re in - Development, Product Management, Marketing, IT - it’s all the same. There are an unlimited number of activities you could do. There are an unlimited number of incoming requests your team could take on. That’s the nature of corporate life – there are an unlimited number of things you could do.

We all want to be helpful and none of us likes to say no. We worry about what people will think of us if we do. And so for a while, we try to say “yes” to everything. But the challenge we all have to face, at one point or another, is that our capacity will always be outpaced by the demands on our time and resources. And, if you’re like me, you’ll wake up one day wondering how it’s possible your team is working 24-7 and yet it seems like nothing of significance is getting delivered. Sound familiar?

When someone asks me if they’re ready for the VP level, one of the first things I look at is their ability to prioritize ruthlessly. Can you focus a team on the most important things? Can you communicate a vision that is compelling enough so your boss and other leaders will trust you to say “no” to activities in favor of the initiatives you’ve defined as top priority? Can you build relationships that are strong enough to allow you to say “no” or “not yet”?

My recommendation for future Vice Presidents is not necessarily to work on your ability to say “no” – although that is part of it. Rather, my advice is to be more proactive at sharing your mission with others around you so they can get invested in your priorities. When you fail to get others excited about your priorities, they naturally start to project their priorities onto you and your team. The more visible your mission is to the company, the fewer incoming requests and distractions you will have.

3. Remain Objective at All Cost

If you’ve read my book, Stealing the Corner Office, you already know how important objectivity is to me.  In my experience, creating an image of objectivity is one of the most valuable things you can do to advance your career. One very common problem in most organizations is that individuals and teams tend to be overly passionate about their own ideas, their own projects. Do you ever find yourself in meetings with someone who seems unable to even entertain a different perspective? Do you have colleagues who just can’t seem to let go of a project that is clearly a losing proposition? Do you see leaders around you focusing only on the interest of their teams at the expense of what’s best for the company? Are you ever that person?

Many years ago I made a conscious choice to develop a reputation as an objective leader. I try very hard to look at all business situations dispassionately. I pretend I am analyzing a business case. I want to be able to put my heard into a project for a year and be able to pull the plug on it in an instant when it doesn’t make sense anymore. I want my team to be able to work all week on something and take a 180 degree turn because a better option emerges. I want other leaders to know that I will make sacrifices to my team and my budget if it makes sense for the business at large.

Cultivating an image for objectivity pays off. It’s valuable for building relationships. It demonstrates maturity and good judgement … and its surprising scarce amongst executives. My recommendation to future VPs is to work on your ability to make objective decisions even when it might damage you in the short term. It can be tough at times, especially when you have to make a hard call that hurts a team member or dings your record a bit, but it will pay you back in the long run.

4.   Be a Cultural and Ethical Leader

To be successful at the Vice President level and above, you need to be a strong cultural leader. At the Manager and Director levels, you typically take your cultural queues from your department head. But once you reach the VP level, that responsibility rests with you. Your team is typically quite large and diverse. You are responsible for bringing people into the organization and occasionally you have to ask people to leave. You set the cultural tone for your team.

In my experience, your moral compass gets tested at the VP level. The pressure rises. The influence you have on others becomes significant. Your impact on people’s lives gets real. If there are cracks in your core values, they will be exposed under the weight of VP level responsibility. If your integrity isn’t solid, it will show. And worse, it will multiply if you set a poor example for the team you lead.

When I evaluate would-be Vice Presidents I pay particularly close attention to their moral fortitude. I look for evidence they can maintain strong values and ethics in chaotic circumstances. Will they sell out a team member when the heat is on? Do they avoid hard conversations even when they’re necessary? Can they look a person in the eye and give them bad news or hard feedback and do it with compassion?

My recommendation to those of you who have desires on reaching and succeeding at the VP level is to spend more time actively thinking about your core values. Put them to the test. Don’t shy away from the hard conversations and tough decisions even though that often seems so much easier. Keep training yourself to operate with integrity and compassion when its hardest to do that. That’s the sign of a great leader and successful Vice President.

Every level of your career presents new challenges. The approach you took to find success at the Manager level probably won’t work at the Director level. And that approach won’t get you all the way at the VP level. To find success at every level, you need to constantly evolve and develop. I hope these tips are helpful to you as you plan your path to the Vice President level and above.

Weekly Reid: 2 Ways to Make Your 30 60 90 Day Plan Even Better

The fundamental premise behind the 30 60 90 Day Plan does not change no matter what role you’re in or hoping to be in. The purpose of the 30 60 90 Day Plan is widely misunderstood. It has nothing to do with helping you “get up to speed” or “hit the ground running” and everything to do with aligning your boss and management team to a definition and framework for success.

The 30 60 90 Day Plan is designed so your hiring will be declared an unequivocal success after 3 months by the people who matter most to your career. It’s designed to guarantee the success of the major projects you take on. It’s not about making sure you focus on learning or training or any of the other misinformation out there. No one cares about that. The purpose of the 30 60 90 Day Plan is to set the foundation for your career advancement.

While the basic goal of all 30 60 90 Day Plans is the same, you can and should customize your approach based on the situation you’re in and the role you hold or would like to hold. I’ve given some advice below on how to customize your plan for Sales positions and Management roles. If either of these sounds like you, keep reading.

The 30 60 90 Day Plan for Sales

The 30 60 90 Day Plan is critical for sales. In the interview process it can help you land the job. And once you have the job it can help you build a reputation as a smart and savvy sales executive. It’s about demonstrating that you understand how to build and execute a sales plan for a territory.

Here are three quick tips to help you build a great 30 60 90 Day Plan for Sales:

Define the Target

If you want to differentiate yourself from other candidates applying for a sales job, or just to impress your boss with your approach to planning a sales territory, you must start by defining your target with precision. Most reps and sales managers don’t take this seriously enough and aren’t scientific in their approach to identifying the “perfect customer”. My recommendation is to spend the first phase of your sales 30 60 90 Day Plan on defining your highest value target customers.

Show the Model

The difference between average sales professionals and exceptional ones is often the model they use to attack a territory or quota. Many people take a “best effort” approach. They rely on salesmanship and intuition to hit a number. While that may work some of the time, it’s not a strategy that is going to set you apart from others. My recommendation is to spend the second phase of your 30 60 90 Day Plan on dissecting your quota and building a model that shows exactly how you’re going to hit it.

Demonstrate your Approach

This is where you need to combine the art and science of sales. Now that you’ve show you can quantify your target and model your business, you need to demonstrate you the art form of sales. My recommendation is to spend the last phase of your 30 60 90 Day Plan showing the tactics you’re going to use to build pipeline and develop customers. If you do this effectively, your boss or future boss will know you have everything it takes to be an effective sales professional.

If you want my ready-to-use 30 60 90 Day Plan Template designed specifically for sales, you can download it here.

The 30 60 90 Day Plan for Managers and Executives

It’s very difficult to be successful as a manager if you haven’t mastered the 30 60 90 Day Plan. In the interview process it will differentiate you from other candidates. And once you have the job it can help you build a reputation as a seasoned, thoughtful executive. When done correctly it will demonstrate that you can think logically about how to build a team and attack a management problem.

Here are three quick tips to help you build a great 30 60 90 Day Plan for Management roles:

The Situational Assessment

All great manager’s start by performing a situational audit or assessment. The 30 60 90 Day Plan is no different. Without this context, you run the risk of being perceived as an activity based, immature manager. My recommendation in the first phase of the plan is to focus on demonstrating how you’ll gain a solid understanding of the business situation and competencies of your team.

The Strategic Initiatives Plan

Now that you’ve completed a situational assessment, you need showcase your ability to build a focused plan that addresses top tier initiatives. One thing that distinguishes average managers and great managers is the ability to focus on the most important issues only. My recommendation is to spend the second part of your plan describing how you’ll build a plan that addresses the most prominent opportunities and gaps.

The Management Dashboard

The last thing you must focus on in your 30 60 90 Day Plan as a manager or executive is the management and measurement framework. There is no point in describing a strategic initiatives plan if you aren’t able to measure it. My recommendation is to focus the final phase of your 30 60 90 Day Plan on providing a KPI dashboard or performance scorecard to measure the success of your strategic initiatives.

My ready-to-use 30 60 90 Day Plan Template designed for managers and executives has all of this built already with tons of extra content from my generic plan template. You can download it here.

>>> As a subscriber, you can use the promo code “WEEKLYREID” and get 25% off the prices listed above until February 12th.

I hope my templates are helpful for you. And if you don’t feel like grabbing one, I hope these tips will make it a bit easier next time you need to build a 30 60 90 Day Plan.