“Breaking Changes” Season 3: The Leadership Edition
Though it’s been years since I’ve coded full-time, I still identify as a hands-on builder. Like many developers out there, I was a reluctant leader.
Some years ago, I finally learned that you can build a lot bigger if you build together. And if I wanted to drive the direction of what got built, I would need to get comfortable in the driver’s seat. That brought me to start my own company and eventually to my current role at Postman leading the observability product.
I’m someone who learns best from mistakes: my own mistakes and the stories of others. Because of this, I often found public leadership advice a touch too censored to learn from. Instead, I devoured stories leaders told me in private of their mess-ups and subsequent insights. I also loved watching certain high-profile leaders from afar. It was great to cheer on their wins, but a blunder with a good postmortem was learning gold.
When I talked to the Postman team about hosting a leadership-focused Season 3 of the Breaking Changes podcast, I knew exactly what I wanted to do. I wanted to bring to our audience what had shaped my own views on leadership: authentic stories of mistakes and raw lessons learned—the “breaking changes” that shaped how people led.
For this season, the team and I were picky about the conversations we wanted to share with you. The goal was to fill a roster with engineering leaders who are builders, who have driven incredible engineering visions, who may not necessarily be people managers or self-identify as engineering leaders. When selecting who to invite, we valued the potential for good conversation over name recognition and insight over process.
A few themes this season:
- Breaking from tradition. We opened the season with a conversation with Mitchell Hashimoto, co-founder and former CTO of HashiCorp. For years, I’ve watched Mitchell and his co-founder from afar, with great curiosity and admiration for how they built a remote-first company before it was cool and pursued multiple product lines instead of focusing on a single one. Fun fact: I met Mitchell only after sending him a cold email about this podcast, so we had a great conversation where I asked him the questions I’ve been wondering about for years.
- Breaking from the past. Becoming a better leader requires growth, and growth often requires painful breaks from your past self. This season, I talked with my friend Tido Carriero, former VP of product and engineering at Segment, about lessons learned from his own mistakes in his first VP of engineering role. I talked with Steven Sinofsky, former president of Windows, about lessons learned from Windows 8.
- Changes that could break an organization. In every conversation, we address questions that keep engineering leaders up at night: pivots, reductions in force, stepping down as CEO, and other scenarios one does not wish upon their friends. (In fact, three of our 12 guests talk about stepping down as CEO of their own companies this season.) This week’s episode with Carta CTO Will Larson talks about a change that is affecting many organizations right now: the decreased budgets many tech companies are facing in the era of higher interest rates. I’m super grateful to our guests for opening up, making themselves vulnerable, and sharing lessons with us.
I learned so much from my conversations with these industry leaders and am excited to bring their insights to the broader software development community. You can find more details about each episode here. Follow and subscribe to Breaking Changes on Apple, Spotify, and YouTube to stay up-to-date on each new episode.
What do you think about this topic? Tell us in a comment below.