“Adventure Begins” by AndyWestface

Working Through Conflict With My Boss

… or how I completely failed to be a good leader

Tom Sommer
Redbubble
Published in
3 min readJul 7, 2019

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Like many others, I have written a Manager Readme. Among a few other things, I mention that I am constantly learning (slide 14 as of writing this). I claim to always try to become a better leader.

This article is about my learning, but also about my failure as a leader.

But let me start at the beginning…

I struggled earlier this year.

It has been the first time since I started at Redbubble — actually the first time in my career — where I felt I had a ‘bad boss’. (And I totally understand that this is a pretty awesome ratio, but that is not the focus of this article).

We did a mini restructure to align better to our business goals. This meant that the team I have been leading for a couple of years was moved to a different group. Which meant we got a different group lead.

On paper, things should have worked awesome between us. We have been here for roughly the same amount of time and known each other for years. We got along well early in our Redbubble life but then worked in different areas for the last few years.

So… what happened?

Moving to this new group and trying to take care of my team — their goals and happiness — I faced some major challenges. In short, the group lead and I were not quite seeing eye-to-eye.

Now that can happen, but for some reason, I took it quite badly.

I felt untrusted. Not being able to represent my team and care for them.

I felt unheard. Trying to get my points across without success.

I felt redundant. Being a token leader without any accountability or responsibility.

My Failures

I had plenty of failures here. There are obvious areas:

  • I could not shake the negative feelings off. Even though I knew much about the theory of these situations, I was not able to approach it constructively. Or at least not as constructive as I would have liked.
  • I was not able to accept a different leadership style. Even though — once again — I read quite a bit about it and even claim to be an advocate of Situational Leadership.

But the thing I am now most annoyed about is this:

My biggest failure was being hypocritical.

I was telling and mentoring others in these situations, all the while I was behaving quite opposite. I did not follow what I was preaching.

This for me is one of the biggest no-nos as a leader. I cannot expect folks to trust me if I am not true to my word.

My Lessons Learned

Most learning happens from mistakes and failure and this is no different. Here are my lessons to make sure I will not repeat the same mistakes next time:

  • No amount of theoretical knowledge can make up for the actual experience. Accept it, and relish those situations and treat them as true learning experiences.
  • Embrace other leadership styles. And not only accept them, but also try and learn from them.
  • Face-to-face time. Spend time with the person you have an issue with. Not just in a meeting room, but one-on-one. Talking about life outside of work.
  • Get help. Talk to someone who is not involved. It almost always works as a therapy session.

Although I had a few unpleasant months (to the point where I thought about throwing the towel in), I am now seeing it as a good — and necessary! — learning experience for me.

To be able to be on the other side of the problems I usually only hear about. To be able to reflect on it and learn a few lessons. And to ultimately become a better leader.

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Tom Sommer
Redbubble

Writing about Leadership and Personal Development. Director of Engineering @ Redbubble.