A Beginner's Life

The Player Coach Transition

4 min read
pete rose player coach

The last six months or so have been full of learning and transition. At the start of 2013, my time was mostly spent in our support inbox, communicating with dozens of customers every day.

Jordan, who joined our team in December, quickly took on the lion-share of the inbox, giving me more time to tackle tough technical issues and other projects.

Then in May, Mercer joined our merry band. As we were a bit more experienced bringing in new customer happiness team members, I’d like to think we did a half-way decent job. Mercer started answering customer questions on her first day, and never looked back.

I quickly began noticing Jordan and Mercer were doing a much better job in the inbox than I ever did – they were calm, empathetic, and clear in their emails. Customers were happy, even without me. It was time for me to hand over control of my beloved inbox.

I won’t lie, that was tough.


I’ve always enjoyed being a bench player around the company, helping Joe and Liat in design, or taking on small-but-necessary dev projects. I suddenly found myself with time for lots of new projects. The prospect of this sounded incredibly exciting!

But design and development projects were often slower-going. I would spend an entire day messing about with styles or troubleshooting a technical issue. While support emails are a grind, the instant gratification you get from solving customer problems is addictive and hard to transition away from. I couldn’t shake the nagging feeling I was now worth much less to the company.

Chris, his “employee struggling” spidey sense no doubt tingling, sat me down and helped me sort out my new role. I would act as a boots-on-the-ground contributor in some areas, and a mentor in others. He defined it as being a player-coach. This perspective has helped me categorize and prioritize my work, and has led to another awesomely productive period.

Here’s how I do it:

Categorize and Prioritize

At the start of each week, I lay out my goals. I organize them into player activities and coach activities. For example, last week I finished our implementation of the awesome MailView gem (player activity) and also worked with Max to better analyze our pre-sales communication activities (coach activity).

It can be easy to slot projects I can do alone above those that require organization and planning with others (I’m not as good with that). Thinking about each item in terms of priority, and whether I was acting as a bottleneck, helped me identify what to get done and when. It helps that our team is as obsessed with execution as I am. Once I got the ball rolling, I could trust the other team members would crush their individual parts and produce something of high quality for our customers.

It’s Mentoring, Not Managing

As a company organized with a very flat structure, the idea of managing people made me cringe. I go to great lengths to remind the Customer Champs that while I will try to lead them, and will always fight for them, it is not my role to manage their output.

Ben spent time helping me understand how to mentor, imparting my experience and sharing my opinions, without becoming an insufferable tyrant. I’m sure I have lots left to learn, but the feedback so far has been very positive.

To make sure I’m being clear, here is a real-life example: I started organizing a monthly customer happiness meeting for the four members of our Customer Happiness team (myself, Max, Jordan, Mercer). Last meeting, we spent a good amount of time discussing the future of our pre-sales process. My opinion wasn’t necessarily the winner (wouldn’t that be nice?) and my vote carries no more than anyone else. That being said, I could provide Max insight from my time in both the pre-sales and support, and I’d like to think that helped.

Take Time for Long-Term Thinking

When the inbox was a constant concern, I found it very difficult to take a few minutes to breathe and think about the future. While it is my natural tendency to identify inefficiencies and destroy them, taking the time to plan out more dramatic changes was not.

Chris was always pressuring me to think about the future of support and customer happiness – what it would look like it we had more resources. This was a struggle – I’d often find myself back in the inbox, answering emails “while I thought about it.”

I was also horribly allergic to meetings of any sort. I could feel the inbox queue growing with each passing minute of even the most productive conversation. This led to some poor communication and a real lack of collaboration. While this helped me alleviate inbox guilt in the short-term, it didn’t help elevate our customer experience at all.

A brilliant customer experience relies on customer happiness, development, marketing, and design working (and yes, meeting) together. We’ve got some awesome stuff planned for our customers in the coming months, and it wouldn’t be possible without better long-term thinking.


The dual role of player-coach isn’t just for me. In the right environment, everyone leads, and everyone follows. I’m hoping these tips will help lead you to an even more productive and happy place.

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