Building teams and culture to navigate catastrophe w/ Ken Pickering #151
The Engineering Leadership Podcast
Failing as cheaply as possible and navigating uncertainty
Exploring the significance of failing cheaply and overcoming internal self-talk, along with a sponsor break featuring Jellyfish. The tension between an uncertain future and execution in the present is also discussed, emphasizing focus, resiliency, and acceptance.
Navigating catastrophes is never easy for eng leaders, but it’s an essential leadership skill in the startup world. Ken Pickering, SVP of Engineering @ Starburst Data, discusses navigating catastrophe, and uncertainty and building a culture of resiliency within startups & eng teams. We cover how to embrace challenges / failure, and cultivate centralized beliefs within your org. Plus the challenges behind finding PMF for a second product, and how to leverage first-principles to avoid a failed second product.
ABOUT KEN PICKERING
Ken Pickering is the SVP of Engineering at Starburst Data, where he is privileged to work alongside some of the best product and engineering humans in the world. Prior to his role here, he held leadership roles at large-scale consumer SaaS and enterprise security companies.
"Communication and context are some of the things that are most successful in feeding an engineering organization because engineers are generalized problem solvers. We all want to be engaged with the problem and then apply a methodology to that problem. Even in high stakes situations, articulate the problem clearly, give people the timeline, give people the constraints, and let them rip. The people that can do that and perform in different kinds of environments and be flexible and adaptable are really key to driving that kind of culture.”
- Ken Pickering
We’re hosting the first ELC Annual Watch Party on 11/8!
We’re livestreaming the most popular sessions from the ELC Annual 2023 conference + hosting virtual roundtable discussions to connect you with eng leaders around the globe AND in your city.
Our first topic covers Generative AI & engineering leadership with Wade Chambers… no this isn’t about the tech - it’s about the leadership skills and competencies you need to evolve and adapt to lead in this next generation!
We have different events for Europe, East Coast & West Coast! To RSVP, find your location HERE:
SHOW NOTES:
- Why the right team / culture can successfully navigate catastrophes (2:30)
- Ken’s leadership approach to tackling challenges & embracing risk (3:52)
- How Ken navigated an unexpected catastrophe @ Rue La La (5:58)
- Practices that can prepare a team for handling obstacles well (8:12)
- The “Travel Deal Tuesday” story @ Hopper (10:24)
- Hiring leaders & creating teams built to endure challenges (12:58)
- How a startup’s centralized beliefs impact leadership styles / decision-making (15:09)
- Ken’s perspective on cultivating shared beliefs within eng teams (17:01)
- Tips for preparing people to better endure catastrophe during downtime (19:10)
- Key takeaways / follow-ups from practice disaster drills (21:14)
- Strategies for coaching people through their first failure (22:38)
- Sharing examples of resilient eng leadership (24:44)
- Balancing the reality of an unknown future vs. the demand to execute now (27:05)
- Why communication & context are key for navigating uncertainty (30:11)
- Challenges that come with finding PMF for a second product (33:34)
- Ken’s examples of enduring through repeated failures / iterations (35:46)
- Facilitating conversation on first principles while working on a second product (38:09)
- Rapid fire questions (39:53)
LINKS AND RESOURCES
- The Destroyer of Worlds: A Return to Lovecraft Country - In this thrilling adventure, a blend of enthralling historical fiction and fantastical horror, Matt Ruff returns to the world of Lovecraft Country and explores the meaning of death, the hold of the past on the present, and the power of hope in the face of uncertainty.
This episode wouldn’t have been possible without the help of our incredible production team:
Patrick Gallagher - Producer & Co-Host
Jerry Li - Co-Host
Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/
Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/
Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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