I nearly accepted an executive role with a big company in Chicago several years ago.

I passed through the first round of interviews and enjoyed the time I spent with everyone, including the President who would be my direct manager.

I was asked to return to interview with the CEO. I prepared diligently and looked forward to meeting him.

Like most people in his position, he was direct and to the point. He wasted no time with pleasantries and dove right into my resume. He was a driver in every sense of the term, asking challenging questions with a brashness matching his title.

Every question felt like a right hook and my answers felt like counter punches just to get off the ropes. This was all fine and partly expected. I might be running a large business and he was putting me through the paces.

After 45 minutes of avoiding his knockout punch, he seemed satisfied and even started to smile. Up to this point, I liked his direct approach and actually enjoyed the challenge.

He opened up and asked what questions I still had. This is when my perception changed.

I asked him about the sales force.

“Our sales team is typical. Always complaining about something and incapable of independent thoughts. We haven’t figured out a way to get by without them so we live with what we’ve got.”

I asked him about how the organization used feedback from customers in product design.

“Customers are the worst place to get feedback. They don’t know what they want, especially our customers. Half of them are on the verge of bankruptcy so their feedback isn’t exactly helpful.”

I asked him about priorities and he quickly wrote down some words on paper and asked me to rank them. I did this strange exercise and he seemed pleased.

“That was actually an intelligence test. Most people fail it.”

Then he spent ten minutes telling me about all the bad decisions his Presidents make, including the one I would be reporting to. It was uncomfortable and clear that he didn’t care much for his management team either. Why he felt the need to share this with me is still a mystery.

So, he disliked his managers, sales team and customers.


The interview ended with him telling me that his company needs more people like me, a clear signal that I was getting his blessing.

I called my wife from the airport before my flight back home and she asked how it went.

“I think I did well but I can’t shake a bad feeling I have.”

“What’s that?”

“That CEO is an asshole.”

By all other accounts, this was a great opportunity. It was a growing company located in a city we wanted to move back to. The role was well suited to my background and the compensation package was generous.

I passed.

Six months later, the manager I would have reported to left that company. Free from the burden of covering up, he now confessed to me that my gut feeling was spot on.

“That guy was an asshole. We were all miserable.”

I have worked for many managers over the past 20 years. With each new boss, I adjust my approach, focus and communication style to match what they are looking for. In doing so, I have not found a manager I couldn’t work with.

But, I have only had a few truly great bosses.

To put it simply, I believe a great boss is likable and demanding. You can trust them and you respect them. They are fun to work with while also being someone who brings out the best in you.

You can see what kind of manager someone is just by paying attention during the interview. A likable boss is going to be likable in the interview. A demanding boss is going to be a demanding interviewer.

I taught managers how to interview for years and challenged them to think about how they wanted to be perceived. Job applicants have choices and evaluate interviewers as prospective managers. There are four types of interviewer and more often than not, interview-style matches their management style.

The Flake

This person seems distracted, unprepared and generally overwhelmed. They dive into the interview without building any rapport. They check their phone throughout the interview and let distractions get in the way. They were probably late in starting the interview. Their questions are bland and they rarely follow up on anything you say. They seem satisfied with asking a list of questions and dutifully jotting down notes throughout the conversation. Accepting a job with The Flake means entering a world of chaos, void of any organization. You’ll need to be a self-starter as they will not challenge you. They can barely keep up with their own tasks. You will want to make sure you have autonomy as responsiveness will be an issue if you can’t make your own decisions.

The Glad-Hander

This person loves to talk. They are talented rapport builders and make a great first impression. They smile often and provide a warm environment for the interviewee. The rapport building seems to go on for the entire interview and the Glad-Hander never seems to fully shift into interview mode, choosing banter over a specific line of questioning. Watching as an observer, you might not be able to tell who the interviewer is because they find themselves doing much of the talking. The Glad-Hander rarely gets into enough detail to know much about your effectiveness and track record. Working for the Glad-Hander can be fun as they have an outgoing personality and love to interact with their team. If you are a high achiever, you should be aware that you might not be challenged and will most likely work with others in the same boat. This manager values relationship over performance which can lead to a team filled with people who measure their worth by how much the boss likes them. This can also frustrate a high achiever as pay might not fluctuate based on performance.

The Jerk

This is a tough interview from start to finish. This interviewer takes pride in being known as “the toughest interviewer in the office”, as if that matters. They ask deliberately difficult questions to show you how smart they are and delight in watching someone stumble through the process. They share very little about themselves personally, rarely smile and pay more attention to their notes than you as a person. You have little time to ask questions of your own and don’t learn much when you do. Their inner cynic comes out and you catch glimpses of how they really feel about their team. Most of their insights are negative in general. You should expect little encouragement from this manager but ample criticism. Your conversations will always be about business and your peers will feel the same. If your interview was socially awkward, expect the office climate to be the same.

The Role Model

This interviewer is welcoming and makes a great first impression. They make you feel comfortable from the start and engage with you in friendly banter. The conversation feels easy as the two of you find areas you might have in common. A solid agenda is set and the interviewer is transparent in what they are looking for. Questions are specific and the interviewer follows up frequently to understand the full story. Questions are challenging and you feel like you get an opportunity to share your best accomplishments. It is obvious that someone who does not bring their A-game would struggle with this interviewer but they never seem to make you feel overly uncomfortable. The role model offers an opportunity for back and forth, though it is clear who is in control of the interview from beginning to end. You are offered a chance to ask questions and the interviewer answers those questions in an honest fashion, offering a real glimpse into the good and bad the candidate might be walking into. This interviewer is just as fun to work with as they were to interview with. Your peers will like this manager personally and work hard to deliver. The Role Model will constantly push you as your manager but offer all the support you need to win.

The next time you get out of an interview, pull up the graphic above and ask yourself two questions.

  1. Would I like and trust working for this person?
  2. Would I feel challenged and grow working for this person?

Answer yes to both or no to both and you have an easy decision. If your answers are somewhere in between, weigh out the pros and cons. Only you know what you need from a manager and everyone is different.

There is no definition for a “bad manager” but just like pornography, you will know it when you see it.

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