Interview your Boss

Selecting your boss is the most important decision that you can make in your career. Everyone has a boss, whether it’s in the form of a board of directors, first line manager, or a CEO. Most people believe they don’t have a choice. You do, and its the most important choice you make.

In your initial interview of your boss, and in the continuous evaluation, you should focus on four criteria:

1) Style

2) History

3) Goals

4) Values


Everyone has different styles, but the question is what kind of style you need in a boss to reach your potential. Some people need a constant kick-in-the-ass to achieve their potential. Others need to be inspired and motivated. Others need to be left alone. Your style dictates the type of style you need in a boss. Personally, I believe the best boss is a motivator, coach, and delegator. That’s what I look for.


This is most applicable the first time you interview your boss. You need to get to the essence of what they have done in their past. Are they a builder/creator? An operator? A talker/influencer? It is easy to be deceived by the talker/influencer. While they may have carried lofty titles, most of what they have done is ‘overlay’ or ‘influence’. If that’s the case, their ability to help you achieve your goals is dramatically reduced. The world is defined by operators, creators, and builders. That’s what you need in a boss, to achieve your goals.


The goals that your boss has, personally and professionally, directly impacts you, whether you realize it or not. Do they want to be a great spouse, parent, or friend? Or just successful in business? Or both? Is their goal in business to survive (in which case they will be cautious and political) or is it do something elite? I look for a boss that wants to succeed as a spouse/friend/parent, while having lofty goals professionally. Although it’s not always possible, I think you want your boss’ career goals to be equal to or higher than your own.


Integrity and empathy are table stakes. If you don’t sense that when interviewing your boss, run the other way. The more nuanced question is regarding what they value in terms of how they manage. Do they value process or performance? People that simply value process are not operators, creators, and builders. Their approach will stifle innovation, and ultimately demotivate the team. Process has a role, but only when performance is valued higher. Valuing performance means that you seek excellence, in everything you do, which sometimes means you have to violate process. That is a subtlety that many leaders struggle with. And, I’ve seen leaders move from a performance focus to a process focus, as they grow in a company. If you see this in your ongoing interviews of your boss, it’s time for a change.

Interviewing your boss is not a one-time event. While the first interview is critical, it must be continuous. While their history may not change, their values, goals, and style might. And, if they move in a direction that you are not comfortable with, then you need to fire your boss.

My personal goal is to lead, serve, and have fun. While I believe I am doing that right now, I expect constant interviews to see if I have deviated.

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Rob is the Author of The End of Tech Companies



Author of ‘The AI Ladder’, ‘The End of Tech Companies’ & ‘Big Data Revolution’

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Rob Thomas

Author of ‘The AI Ladder’, ‘The End of Tech Companies’ & ‘Big Data Revolution’