Though it doesn’t make me a cent, leader series is some of the most important work I do. It’s also one of my favorite things. I’ve learned so much talking with a wide variety of folks across roles and experiences. These interviews are scattered between my own editions so I created an archive for the first half of 2022. This edition chronicles the second half of 2022 which featured important stories about handling health challenges (both physical and mental) as a leader, being an under-represented leader, as well as handling big transitions.
More fantastic stories are coming. I’m also in the process of turning the series into a proper podcast. Look out for that in 2023!
#15 Leading While Managing a Chronic Health Condition
Dizzy Smith, VP of Engineering, Edge & Node
Leaders are often expected to be tough and strong but they’re also human which means they get sick too. As someone who managed a chronic health condition while leading, I wanted to talk with someone else who has navigated this particular challenge. We talked about why he went into management (despite swearing he never wanted to do it), his transition into leadership, and what keeps him up at night.
#16 Overcoming Leader Burnout
Vaidehi Joshi, Engineering Manager, Vimeo
I found Vaidehi incredibly insightful when I had her on my first podcast, Indiedotes, which featured creators. After hearing her tweets about how she handled burnout, I asked her to come on the series. Our conversation covered how she became a manager, how she’s battled with perfectionism and over-committing, how she burnt out and eventually came back to a leadership role.
#17 Being a Startup CEO as a Non-Founder
Henrik Mattson, CEO, Lookback
Many CEOs of startups are often co-founders. Henrik was neither of those when he became the CEO of Lookback. The story of how he came to the role is fascinating. We spoke about how his life changed in the span of an hour, handling change, shifting company culture after taking the role, and his philosophy of distributed leadership.
#18 From VP of People to COO
Jessica Zwaan, COO, Whereby
There’s often an impression that People Ops folks aren’t especially business savvy. I disagree with this notion and was happy to talk with another leader who’d made the move from people to COO. We spoke about why People leaders can make great COOs, the multi-faceted role of COO, the risks execs have to take, what it was like bringing the Whereby team along after a pivot, and treating your culture like a subscription product.
#19 How a Leader Made the Interview Process More Collaborative
Angela Riggs, SDET Manager, Cloud Platform, Sonos
The technical interviewing process often feels more combative than collaborative so I was interested to hear how Angela Riggs made the process less stressful. We talked about how she accomplished this, how her background as a teacher helped her and how to make interviews more collaborative and less like a test.
#20 Being an Under-Represented Voice in the CTO chair
Tramale Turner, CTO, Taxbit
Part of why I started this series was to show the variety of leaders that exist, outside of those presented in traditional media. When Tramale was open to talking about his experience being an under-represented voice as a CTO, I was thrilled. We talked about how growing up in Detroit influenced his career, investing in himself, and why he decided to join TaxBit as the CTO.
#21 Building Trust as a First-Time VP at a New Company
Michael Stahnke, VP Platform, CircleCI
Spending many years at one company can be fulfilling, it can also feel daunting especially when moving into a leadership role at a new company. After eight years at his previous company, Puppet Mike found the transition to VP at a new company jarring. We talked about why he took the role, what he found most difficult, and how he built trust with different parts of the org — the engineers, his engineering peers, and the rest of the exec team.
#22 Being the First People Leader at the Company
Christie Williams, VP Employee Success, Softdocs
At startups the people function is often under-invested. Christie Williams has been the first people leader at several companies so she’s gained insights on this. Our conversation covered her motivation for doing people work, what it’s like being the first people leader on the team, how she thinks about the technology stack that runs the company, and her advice for other “first” people leaders.
#23 Leading a Startup While Navigating Personal Strife
Kirk Fernandes, Co-Founder, Merit
We often expect leaders, especially those in startups to be all business all the time. What happens when their personal life falters? I was happy when Kirk wanted to talk about how he handled this when three family members got sick within a year. Our conversation covered why he started Merit, what he learned about asking for help, the importance of self-talk and why he recommends therapy to everyone. It’s an incredibly moving story.
#24 A First-Time CEO Navigates an Economic Downturn
Aline Lerner, CEO, Interviewing.io
Leaders often make big promises, gaining the trust of the team and clients in the process. Sometimes the business landscape changes and we can’t honor those promises like we have in the past. Aline faced this when like many, the company found itself facing a steep revenue cliff in 2020 during the heart of the pandemic. We talked about leading the team through a downturn, feeling like a wartime CEO, and raising a Series A while pregnant.
#25 Starting a Family and a Company at the Same Time
Natasha Vernier, CEO, Cable
Starting a family and starting a company are considered top stressors. What happens when you do both at the same time? I was keen to find out in my conversation with Natasha. During our conversation, we talked about leaders' role as stress absorbers, the difference between being a leader and a CEO/founder, and what it’s like starting a family and founding a company…at the same time. Her mission for founding the company is inspiring.
#26 A Blind CEO on a Mission to Help Companies Prioritize Disability Inclusion
John Samuel, CEO, Ablr 360
My goal is to have leaders of all shapes and sizes on the series. I was thrilled when Christie Williams introduced me to John Samuel, the CEO of Ablr who happens to be blind. We talked about how he struggled to advocate for himself, how he went from thinking his career was over to becoming a CEO, what keeps him up at night, and his mission to help companies prioritize disability inclusion.
#27 From Founder CEO to VC
Ellen Chisa, Parner, boldstart Ventures
Being an operator is quite different from being a person who makes investment decisions. I talked with Ellen about her startup leadership experiences and how she became a partner at a VC firm. Though this challenge is slightly different from others, I wanted to cover it because we don’t talk enough about the transition from a leadership role, especially one like CEO. I think you’ll find Ellen wise and her story enlightening.
#28 A CEO Pivots From Events to Digital Publishing During the Pandemic
Ruth Yarnit, CEO, LeadDev
I’ve worked with LeadDev for several years as the host of Bookmarked which interviews authors and as a workshop facilitator. This gave me a front-row seat to watch the company handle the sudden shift in the market after the world shut down in March 2020. I’m thrilled LeadDev CEO Ruth Yarnit was willing to share her story with me. We talked about Ruth’s unexpected path to CEO, how she thinks about the balance between being internal and external facing, and her advice for other leaders facing a sudden market shift.
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