The Ideal Manager Exercise — How to Choose and Communicate With Your Current or Future Manager
The reflection exercise that helped me find and cultivate a successful relationship with my manager.
Welcome to the Scarlet Ink newsletter. I'm Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers, and specific leadership advice. This week, I’m revisiting an article from 2019. I like to ensure all my articles are evergreen, and so I occasionally rewrite an older article to keep it at the highest quality. This article in particular is one of my favorites!
Quick FYI - This exercise used to be called the ideal boss exercise. I’m not a fan of the word boss. When we “boss” people around, that has a negative connotation. Good managers do things like “guide” or “coach” or “remove roadblocks” or “set expectations”. Manager feels like a better word for the relationship we’re discussing. I decided to rename the article to remove the boss word.
Your relationship with your manager is critical to your success or failure at work. A good relationship with your manager can help you love a boring job, but a bad relationship can make you hate an exciting job.
Your manager frequently influences what work you get, how you’re able to perform your tasks, and measures your success or failure. This relationship is really critical.
Clearly, if you can choose to work for someone who meshes well with your preferences and personality, that’s great! That’s one way this article can be used.
However, sometimes we can’t select who we’re working for. That’s fine. This article can still help with communication. It’s a roadmap for communicating our preferences, and our manager’s preferences. It can help us identify early where our preferences may clash, and we should probably address those areas up front before they become an issue.
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Step One: Welcome, and an explanation.
Welcome potential employee and/or potential manager! In my experience, this exercise will be useful for both of you. You’re welcome to forward this article to your manager (or potential employee) to get things started.
We’re going to walk through a few steps to outline how the manager and employee wish to interact with each other. At the end of those steps, we will hopefully have some clear talking points for where we agree, and where we disagree. Assuming two adults with halfway decent communication skills, this should enable us to iron out any potential issues before they become a serious problem.
In relationships, identifying a problem before it becomes a problem is a key to diffusing or resolving potential conflict. If you like to arrive at work at 10am, and your manager prefers people to show up at 8am, at least you both know you disagree. You can discuss this before day one. Worst case, you realize that you two probably won’t work together long. Best case, you two can discuss and arrive at a solution you’re both happy with. And even better, that you’ve both openly discussed and documented.
A few years ago, I was working within Amazon Web Services (AWS), and I decided I wanted to switch teams. To begin the process, I spoke to several potential managers. It was relatively easy to assess whether I would be interested in the product. I could generally figure out if the technology was something I would enjoy learning. It was challenging, however, to assess whether I would like my new manager. This was perhaps the most critical aspect of choosing a new team.
You can chat with someone for an hour or two over coffee and get a general impression. You can ask a pointed question or three. However, it’s impossible to identify all the areas where you may have a difference of opinion with a future manager. It’s not even that one manager is necessarily better than another. It’s more that what works for one person or team doesn’t work for another.
During my search, one leader asked me to do an exercise in which I would write statements regarding how I would interact with my ideal manager —that is, the perfect person to handle my quirks, appreciate my personality type, and mesh with my preferences. He walked me through this ideal manager exercise.
Below the steps, I have a copy of my personal ideal manager write-up from the first time the exercise was explained to me.
Step Two: Employee writes their version of the exercise.
The meat of the exercise is a brief document the employee writes up. What you are writing are statements of how your ideal manager would act or behave in certain situations, and then you add a bit of explanation to those statements. For example:
“My ideal manager lets me set my own hours.”
“As a software engineer, a flexible schedule is something I value. I’ll attend team standup, and any critical meetings, but I enjoy the ability to work late hours, or when inspiration strikes me. I’d like my performance to be measured on my output, not when I show up at work.”
These statements aren’t right or wrong, they’re simply how you feel about a situation. If you’re doing the exercise correctly, you should expect your future manager to disagree with some of them. That’s totally fine. The goal is to have an open line of communication around these issues, rather than having them cause problems down the road. If you write mushy statements you think your manager will agree with, then you’re missing out on the value of the exercise.
The written statements should be focused on controversial areas. These are the areas which have caused conflict in the past, or you believe have the potential to cause conflict. Things like how you interact with your manager, with your peers, when you’d like help, when you’d like independence, how you would like to complete your work, and so on.
I’d suggest writing 8 - 12 statements. Much fewer and you won’t have much to discuss. Many more, and your future manager might start to wonder if you’re high-maintenance.
Writing this exercise was enlightening by itself. It helped me internalize my own rough edges and the behaviors I was sensitive to. I took the opportunity to reflect on situations where my manager and I had not been on the same page, and I tried to determine the root cause of the friction.
As one example from my write-up below, my second ideal manager statement focuses on how I like humor at work. That was written because I had a specific manager who had repeatedly told me that managers needed “to be more serious”, and that my joking around wasn’t appropriate for a leader. After much consideration, I decided they were mistaken.