7 leadership lessons over 2.5 years

Over the past 2.5 years, I’ve interviewed 49 leaders for our podcast on leadership, The Heartbeat. These are the leadership lessons that have influenced me the most, personally.

“What are the biggest leadership lessons you’ve learned from others, that have changed or affected your own management style?”

No one had ever asked me this question before – let alone on my own podcast show – until recently.

Who asked me this? None other than Jason Fried, CEO and co-founder of Basecamp. I’d invited Jason back on The Heartbeat, our podcast on leadership, for our 50th episode. He’d been our very first guest back in 2017 when I started the show. (Jason also sits on our board and originally spun out Know Your Team back when it was a part of Basecamp).

For this 50th anniversary episode, I thought I’d turn the tables: I asked Jason if he might interview me. And so, Jason asked me this never-before-asked question, “What are the biggest leadership lessons you’ve learned from others, that’s changed or affected your own management style?”

At the time, I answered this question unsatisfactorily. When asked live on the podcast, I shared only one lesson. Maybe two. 

However, when I deeply reflect on the past 2.5 years of interviewing leaders who I respect and admire, I’ve learned many tremendous insights. I’ve asked each leader the same question – “What’s the biggest leadership lesson you wish you would’ve learned earlier?” – but no two answers have been the same. From the Contributing Editor of Harvard Business Review to the CEO of Lonely Planet, this has held true.

Yet there are a handful of interviews – seven in particular – that have affected me, the most. I’ve changed how I think or how I behave as a leader, because of them.

Here are the seven leadership lessons over 2.5 years I’ve learned from running The Heartbeat podcast that have had the biggest influence on my own management style:

#1:  Stop doing what you’re good at. 

Sometimes, the most counterintuitive leadership lessons are the most helpful. This is one of them. Peldi Guilizzoni, CEO of Balsamiq, shared the most counterintuitive insight with me on The Heartbeat, when he espoused: “Doing what you’re good at hurts the team.” Huh? He explained how when you’re the one always doing the thing that you’re good at, you create a dependency within your team. They can never be self-sustainable or perform at the highest level if you’re the one always doing the things you’re good at. Because of Peldi, when I find myself leaning into a task I’m good at, I now actively ask myself: “Are my actions feeding your team, or my ego?” (You can catch the full podcast episode here.)

#2: Step back. Take stock.

Intuitively, we all know it’s important to take a step back and reflect, as a leader. But for me, it took Natalie Nagele, CEO and co-founder of Wildbit, driving this point home in our Heartbeat interview, for me to act on this wisdom. Natalie admitted how this advice to “work on the business, not in the business” is seemingly cliché. But she emphasized how regularly distancing yourself from problems can in fact help you solve them better, later on. Inspired by her conviction, I started investing more in our own leadership strategy sessions with my business partner and CTO, Daniel Lopes. Now every month, at minimum, we take a day away from the business to step back, and take stock. Big thank you to Natalie, for this. (You can catch the full podcast episode here.)

#3:  Screw the Golden Rule.

“Treat others the way you want to be treated.” This is the Golden Rule we’re all taught growing up. When I chatted with David Heinemeier Hansson (DHH), the Creator of the popular web framework Ruby on Rails and Chief Technology Officer at Basecamp, I realized how backwards this precept was in the context of leadership. David shared with me how you shouldn’t treat other people the way you want to be treated because the other person isn’t you. It’s a poor definition of empathy, if that’s indeed what we do as leaders. Instead, in large part to David, I’m more rigorous than ever about making sure I’m treating others on my team how each individual wants to be treated. (You can catch the full podcast episode here.)

#4:  Good leadership is pruning.

There are no shortage of analogies made about leadership. A leader can be seen as a “coach” or “captain.” But David Cancel, CEO of Drift made an unlikely comparison about leadership in our podcast conversation:  He said that good leadership was like pruning an English garden. It requires small, incremental actions, not big sweeping actions. It focuses on clearing away what’s stifling growth. And, it’s only done periodically – research reveals how managers who are “constantly coaching” overwhelm and exhaust their team. Constant coaching, like constant pruning, can do more harm than good. For me personally, as a leader, this was an important reminder to calibrate my touch points with my team. I’m pruning, not uprooting. (You can catch the full podcast episode here.)

#5:  Transparency requires context, and is on a spectrum.

“How transparent should I be with my team?” As leaders, we’re often faced with this question. We know transparency is supposed to be positive… But to what extent? I so appreciated how Des Traynor, Co-Founder of Intercom, decides what his answer should be. Des revealed to me how transparency “is not about opening up the Google Drive and making sure that everyone can read everything.” It’s about ensuring that people have transparency of context – and that it’s not all or nothing, either. Today, when I consider what and how I should share information with my own team at Know Your Team, I reflect on how well I’m considering Des’ advice. (You can catch the full podcast episode here.)

#6:  Don’t solve the problems yourself.

Leadership is stewardship. We so often forget this. Wade Foster, CEO of Zapier, reminded me of this essential notion. In our Heartbeat podcast interview, Wade acknowledged how in his early days as a leader, he would be eager to roll up his sleeves and solve all the problems for his team. However, this would backfire. It meant his team would always come to Wade with their problems. He became a bottleneck. Now, Wade sees how his role as a leader is to help a team think for themselves – not to solve everything for them. Because of this, I consciously check-in with myself and with my team to make sure I’m practicing this. My measure of success as a leader is how well I’m helping others solve problems. (You can catch the full podcast episode here.)

#7:  If you’re busy as a leader, you’re doing it wrong.

I remember when I interviewed Michael Lopp, VP of Engineering at Slack, his observations around leadership lessons was immediate:  “If you’re too busy doing the actual work, as a manager, that’s a huge mistake.” Michael shared how you can’t truly anticipate nor respond to the needs of your team if you’re in the weeds of the work. You can’t clarify a decision or help sort out interpersonal dynamics. I now remind myself of this constantly, if I find myself too busy, as leader. I ask myself, “How am I making space to listen, respond, and be available to my team, instead of executing the work itself?” (You can catch the full podcast episode here.)

I come back to these seven leadership lessons, almost every week, if not every day. I hope they were as formative for you, as they were for me.

Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

2 thoughts on “7 leadership lessons over 2.5 years

  1. That’s a fantastic list. One of the most important leadership lessons I have learned is this yin/yang approach – practicing non-judgment/taking full accountability – with staff. It is a lesson that has to translate into your personal life, but when I was able to put that in practice with my staff, things changed dramatically.

  2. Hi,

    Thanks a lot for the nice article on leadership lessons.
    I can’t believe I am already following these 7 steps but didn’t know that they were related to leadership!!
    Keep up the nice work.

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