The Leader Interview Series...So Far
An archive of January - May 2022 conversations
At the end of 2021, I decided to create an interview series as a way to capture the real stories of leaders. I wasn’t looking for highly filtered or philosophical thoughts on leadership. I longed to hear how these folks navigated some tough situations. From inception to the end of May, there were 14 published conversations with leaders. Talking with these folks has become one of my favorite things I do. The interviews are mixed in with other content so I thought an archive would make them easier to find.
A small fact about me: I adore a good behind-the-scenes sneak peek. When I buy movies online I always buy the version with bonus features. I spend hours learning how films got made and how they over came technical, creative, budget and people problems. Finding Nemo, The Matrix and Free Guy are among some of my favorites. In honor of my adoration for these sneak peeks, I’ve included a little note on how I connected with each of these folks to give you a behind-the-scenes look at the series.
#1 Leading a FinTech Startup Pre-Launch
Maria Campbell, VP of People, Griffin
Maria and I met on Twitter three years ago. After one conversation we became fast friends. She’s so insightful I leave a conversation with her feeling like I understand the world a bit better. When I started the series she was the first person I asked. We talked about the challenges of building a company and a robust exec team before you have product market fit. The team faced an interesting scaling challenge, how they handled it is so instructive.
#2 Pivoting During a Pandemic
Rob Smith, Head of Content, LeadDev
As the host of LeadDev’s Bookmarked, I’ve worked closely with Rob Smith for the past two years. He’s been an invaluable sounding board as I created workshops, Leadership Archetypes and a leadership competencies framework. We started working together just as the pandemic was hitting so I got a real-time view of the work he and the team did to pivot the business. I knew was a story that needed to be on the series. During our conversation we also talked about what it was like to scale himself as a new leader.
#3 Being a First Time Exec at an Early Stage Startup
Jean Hsu, VP of Engineering, Range
I met Jean when we spoke on a panel about how to transform traditional performance management. Her answers were thoughtful so I’d been looking for a way to collaborate again. Jean became a VP of Engineering for the first time in the midst of the pandemic. It was a delight to hear how she navigated being a mother and what it’s like being a first time exec at a startup. She was kind to invite me on to Lead Time Chat to talk about navigating conflict on remote teams.
#4 Transforming a 300 year-old Organization in Four Weeks
Matt Stutely, former Director of Engineering, British Parliament
Twitter is a place where I’ve met many colleagues, friends and even my husband. I’m grateful I met Matt there was well because he had an amazing story to share. We talked about how he headed an initiative to create a new set of products to deploy a secure voting platform for 650 member of the British parliament. This project, which allowed Members of Parliament to vote remotely for the first time, was conceived and delivered in four weeks!
#5 Being Open and Vulnerable as a CEO
Beth Smith, CEO, StickerGiant
Beth is a dear friend so I’ve been watching their career for a while. They are one of the wisest folks I know. When the series started I wanted to share their wisdom with others. I was thrilled when they agreed to talk about how their background as a mindfulness teacher helps them as a leader and what it was like to come out as non-binary while CEO. It’s difficult to be vulnerable when CEO. Beth handles it with aplomb. This is must-read for any leader wondering about vulnerability.
#6 Creating a New Program at a High Profile Scaling Startup
Mindaugas Petrutis, Program Director, On Deck Design
I went through the first version of On Deck Writers where I met David Hoang, the head of Product Design at Webflow. He introduced me to Mindaugas. We had such fun developing a workshop for his On Deck Design program. I wanted to share his experience building a global program at a highly visible scaling startup. His indomitable spirit really comes through in this conversation.
#7 Helping Tech Companies Look Like the World
Sidney Miller, Strategic Sourcing Lead, Equinix
Sidney is another Twitter friend. We have a whole bunch of real world friends too so it seems inevitable our paths would cross. After watching her talk about her work, she became an obvoius choice for the series. Sidney has a clear mission around hiring in technology. She’s one of those people who has a vision and is going to see it through, no matter the obstacles. Packet was acquired by Equinix just as she was joining. This could have been an obstacle but instead Sidney helped them transform their hiring.
#8 Riding the Roller Coaster as an Early Stage Startup Founder
Sam DeBrule, Co-founder, Heyday
Sam popped in my DMs asking if I’d be interested in beta testing the app. I said yes and then immediately asked him to be a part of the series. Sam was just about to get married when we did our interview. I’m so glad he made time to chat with me about his experiences as a early stage startup founder. Trying to find product-market fit can be exhausting and mentally draining. Sam’s insights into how he gets support and manages his well-being is useful for other founders and leaders, especially during tough business cycles.
#9 Finding Balance in the Midst of Constant Change
Ashley Hunsberger, Director of Developer Advocacy, Blackboard
Another Twitter friend, though I can’t remember when we connected. I’ve always admired the way she seems to flow with change. When I discovered Ashley was in grad school while holding a leadership role, I headed directly for her DMs with an invitation. It was such fun to talk about the field of I/O psychology. In addition to sharing how she manages constant change, you’ll find her thoughts on the psychology of work fascinating.
#10 Leading Engineers at a Remote-First Scaling Startup
Kainar Kamalov, Director of Engineering, Pipe
Rob Smith of LeadDev introduced me to Kainar. He was so thoughtful throughout the process. It’s no surprise he’s such an intentional leader. I enjoyed how open he was in our conversation about his leadership experience. We talked about how to be intentional with your culture, picking up on and handling emotions in a remote-first culture, and how to make sure the team stays aligned.
#11 Being a First Time CEO at a Startup in a Highly Regulated Industry
David Jarvis, CEO, Griffin
David and I were introduced by Maria Campbell to talk about my Leadership Archetypes framework. Discovering we hold similar views on leadership, he’s become one of my favorite collaborators. He and his co-founder were intentional with values and culture, something I suspect has helped them build a startup in a highly regulated industry. In this conversation he also goes into detail about how they created a purposeful culture interview.
#12 Being an Accidental Startup CEO
Lilly Chen, CEO, Contenda
Lilly came across my timeline when I tweeted about wanting to feature more under-represented leaders on the series. I’m so glad she raised her hand. It was such a delightful interview that included a bit of conversational scat. She spoke eloquently about her past as a Buddhist monk, how she accidentally created a startup (and became its CEO), and made a conscious decision to change the culture of the company. This young leader is one to watch out for.
#13 Leading a Company Through Acquisition
Jacob and Zac Smith, founders of Packet
I met Zac just after leaving Travis CI. We met in a midtown hotel to talk about organizational strategy and scaling startups. Finding similar mindsets, we’ve kept in touch ever since. I’ve wanted to share an acquisition story and was thrilled when he said yes and invited his twin brother Jacob to come along. They’re smart, thoughtful leaders and so much fun. We talked about their mission, the role their background as musicians played, how to bring the team along after an acquisition, melding cultures, and the mistakes they made along the way.
#14 Leading a Team of Internal and Open Source Software Engineers
Madleina Scheidegger, Engineering Manager, Google
Sarah Drasner, Director of Eng, Web at Google introduced us. She thought Madleina would have a good story to share. She was so right. Ambiguity, unknowns and interrelated variables make leadership a complex task. Leading leading the Angular team of both Google and open source engineers adds complexity to Madleina’s role. She gave a great behind-the-scenes look at how she manages this challenge and how the team reduced their open PRs from 650 to under 100.
Are you a leader with a story to share about a change or challenge you’ve navigated? Please get in touch, I’d love to know more.