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Finding Your Ideal Boss

The reflection exercise that helped me find and cultivate a successful relationship with my manager

Dave Anderson
Jan 2, 2019 · 7 min read
Illustration: Anna_Isaeva/iStock/Getty Images Plus

A few years ago, I was working in a particular group within Amazon Web Services, and I decided I wanted to switch teams. To begin the process, I spoke to a number of 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. And finding the best manager is essential to having a successful work environment.

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. It is not possible, though, to cover the full gamut of differences you may have with a future boss. It’s tough to roll the dice on such an important decision; your manager has a huge impact on your overall job satisfaction. What’s more, the management style that works best can vary from person to person and team to team.

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 boss—that is, the perfect person to handle my quirks, appreciate my personality type, and mesh with my preferences.

These statements focused on controversial areas and ones that had caused conflict in the past. In a process that sounds quintessentially Amazon, he would review the document independently and write a response. The response would clarify which of those statements would work for us and which required further discussion. We scheduled a final discussion of the document and response over lunch.

The exercise was enlightening. 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 try to determine the root cause of the friction.

Perhaps even more reassuring was our discussion around the points we didn’t agree on.

Reading and discussing the manager’s response was more valuable than a dozen informal lunch discussions. At Amazon, we rarely discuss without accompanying documents. This exercise is another example of why documents provide far more clarity than a solely verbal discussion.

I had a clear sense of relief around the aspects we agreed on, but perhaps even more reassuring was our discussion around the points we didn’t agree on. We were able to openly share our points of view, explain why we thought the way we did, and explore how we could deal with it going forward. Everything was out in the open, and we were able to have an honest conversation.

Because of the connection and trust we were able to build, I was comfortable taking the leap to join this new team. I have now been with my manager for more than three years. I am still impressed with how well this exercise identified our common values and the areas we needed to work on. It has provided a base framework for how we work together.

Below is a copy of the exercise, which describes the ideal boss in the type of role I was seeking. I was a senior manager at Amazon (I am now a director), and I was looking for a specific type of autonomy and purpose. My ideal boss may have been a nightmare for someone else.

This is not a complete list of everything I might need from a boss. Rather, it is the result of thinking through the ways I haven’t completely meshed with my previous managers (or peers) and articulating how my ideal boss would handle those situations.

1. My Ideal Boss Will Recognize That I Get Passionate and Take Action Quickly

I enjoy solving problems and moving fast. This is why I’m responding to the ideal boss exercise on the same day it was proposed. My ideal boss and I need to ensure we’re on the same page when making a decision, as I’m likely to take action immediately when our discussion is over. I prefer to take action rather than agonize over decisions, which means I do important things quickly, and occasionally, I make sloppy mistakes. If I don’t take action immediately on something, I often don’t do it. I apologize in advance that you had to remind me.

2. My Ideal Boss Will Recognize That Our Work Can Be Fun and Humorous

I’m a fan of reminding people that we’re not doctors; no one dies if we make a mistake. I need to enjoy my job and laugh while I’m at work. I enjoy humor in emails. I enjoy sarcasm and dry humor, and I sometimes need feedback when I go too far. I enjoy this specific writing exercise because it feels lighthearted. I want my boss to be able to enjoy these things with me. I don’t want to hide my enthusiasm and pretend to act more professional than I naturally am.

3. My Ideal Boss Will Let Me Fail When Appropriate

I want the opportunity to make mistakes because it is also an opportunity to take ownership for my success. I want to learn from acceptable mistakes that won’t damage my career. I want my boss to recognize when my decisions need scrutiny because potential mistakes are unacceptable or one-way doors. My boss should also know when it is safe to let me succeed or fail on my own.

4. My Ideal Boss Will Coach Me Through Interactions With Peers, Stakeholders, Customers, Etc.

This is particularly important because I’ll be joining a new domain with new peers and partners. I would like my boss to help me build relationships by explaining what others want and how they prefer to communicate, then coaching my behavior. My ideal boss will help me build long-term partnerships. Building strong relationships with my peers is not my superpower. I don’t enjoy it, but I know it’s important. I’d like assistance. My ideal boss will let me own these relationships, but will help me and encourage me to build them properly. I want context and coaching so I can own my space in the long run.

5. My Ideal Boss Will Respect the Management Chain

This is particularly true regarding allocating resources (engineers), hiring, performance management, setting priorities, general engineering related decisions, work scheduling, deciding who works on what project, and operations focus. I like to be fully responsible for the team being run well, so I want to be an owner in the decision tree. I will own the engineering organization, so I need to feel responsible for the team’s outcomes. This means clear ownership over what the team does and how it works.

6. My Ideal Boss Will Have a Personal Connection With My Team and Me

Our team will feel like we’re working for a human, not a boss. I’d like to respect and like my boss as a person and have a social relationship outside of work. I’m an introvert, but I would like to have a human connection with my manager, peers, and team.

7. My Ideal Boss Will Help Fill In Gaps Where I Feel Weak or Don’t Enjoy the Needed Work

For example, I’ve never enjoyed organizing social events for my team. I would like help from my boss regarding social planning and organization—or permission to delegate—to ensure those important tasks are done well. I also don’t shine doing repetitious detail work. I will often forget, do a poor job, or become bored. Preferably my boss will be supportive of me playing to my strengths and helping me find others to play to theirs.

8. My Ideal Boss Will Let Me Shine Where I Feel I’m Strong or in Areas I’m Passionate About

I love recruiting, managing, improving company-wide processes, and promoting people. I love strategic long-term planning, brainstorming on new products, and filing patents. I love building large-scale architectures, figuring out the root cause of operational problems, and handling high-severity events and brainstorming ways to avoid them in the future. I love writing six-pagers and three-year vision documents and helping others deliver their own documents. I’d like support in these things I enjoy and for my boss to recognize and take advantage of my interests and skills.

9. My Ideal Boss Would Support My Amazon Extracurricular Activities

I like to stick my nose into areas of Amazon where I feel I can add value. I am a bar-raiser, and I regularly participate in local and remote interview events. I volunteer for Amazon Women in Engineering and related diversity events, and I write white papers on internal HR processes. I like to volunteer when I feel I can add value to Amazon. I’d like my boss to support activities outside our team as long as I’m delivering on the team’s commitments.

10. My Ideal Boss Will Make My Team a Safe Place for Me to Work and Take Risks

I want to feel protected and supported by my manager. I’d like my manager to support my decisions as much as possible publicly. I’d like to take risks without looking over my shoulder. I’m not afraid of failure, but I’m afraid of people who are not tolerant of occasional failure.

11. My Ideal Boss Will Have an Open Door

If I am concerned or unhappy about something, I want to feel like I can speak openly to my boss. I want to feel like we’re on the same side. When we’re in a one-on-one situation, I’d like to feel like I can be 100 percent me and speak my mind.

12. My Ideal Boss Will Give Me Positive Feedback When I Deserve It

I know my personality, and my mood is affected heavily by the feedback of my management chain. I find it important for my own job satisfaction to feel my work is appreciated when I do a good job.

Disclaimer: I’m not representing Amazon in any way with my posts. Opinions written here are strictly my own.

Written by

Head of Technology at Bezos Academy. Former Director/GM at Amazon. Husband, and Father. Find me professionally at https://www.linkedin.com/in/scarletink/

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