A Cautionary Tale for New Managers
By: Hannah Fleishman
Tags: Career Development, Management

It was shortly after a promotion that I had an epic #fail.

I’d been managing a small (but mighty) team for about three years when I was promoted to Senior Manager in 2019. Senior. A tiny word, but big enough to carry the weight of change. A change in title, a change in scope, and a change in expectations…or so I learned the hard way.

I knew that being a Senior Manager was different from being a Manager. But I assumed it meant doing what I’d been doing, just more of it. Like when you add guacamole at Chipotle. It’s extra, but it’s not a whole new dish.

So instead of reflecting on how my scope had changed, I took my snazzy new title and got back to work. I continued doing my best to set my direct reports up for success, to set a team vision, and to do great work myself. In fact, I invested more into doing great work myself. Extra great work, if you will.

That’s why my next performance review felt like a punch to the stomach.

Part of HubSpot’s performance review process is a one through five scale of how strongly you’re meeting expectations (or not). And I fell right off my Senior high horse when I saw my manager had given me a lower score than I’d given myself. It was the first time in our eight years of working together that we were on different pages about my performance.

I was angry, confused, and most of all, embarrassed.

How could she not think I was #crushingit? Since getting promoted, I’d been pushing myself for excellence. I thought I was serving up guac. Sure, she’d given me feedback over the past few months that I was still spending too much time on my individual work, and not enough time on building a scalable, high-performing team. But every time she said it, I’d make a note to read some more ‘manager books’ in the future and then get back to executing.

I had missed the critical memo that being a great manager isn’t about my work. When my title changed, the importance of my individual impact changed with it. Now, my team’s success was my success.

That might sound obvious to you. And I might sound silly for saying I learned it the hard way. But I didn’t internalize that shift in expectations at the time because my team was doing good work. Nothing was on fire. But that’s not the way management works — you need to invest just as much energy into your team when things are great as you do when they’re off the rails.

I should have been minimizing the time spent on my individual contributor work, and maximizing the time spent on team development. Things like hiring, passing down clarity, giving and getting feedback, opening doors to new opportunities, and creating psychological safety are hard and they don’t have a finish line. That scared me. So, I stuck to what I knew I was good at: getting shit done.

It wasn’t until that performance review that I learned why that was a mistake. My manager wasn’t saying I was failing, she was saying that I was failing my team in the long run. And she was right; I just hadn’t been hearing it. After that hard conversation (and a few glasses of wine), I saw my role through a new lens: a manager’s job is to serve their team, no matter how small or mighty.

I’d been thinking about this #fail a lot recently, trying to pinpoint why I had missed the bigger picture. Then someone spelled it out for me. I had the opportunity to do a coaching session last week with our former COO JD Sherman — who is full of good jokes and good wisdom. And when I asked him what I should keep in mind to not just be a good leader, but a great leader, he said: “You’ve earned this. And now, you need to keep earning it every day.”

I have a lot to learn about being a great manager, and about how to best serve my team. That will always be the case. But one thing I now know for sure, thanks to making mistakes, is that leaders need to earn the role every day.

And that it’s about a lot more than extra guac.