Lessons in Scaling: An evening with Stanford Professor Bob Sutton

Kalee Gardella
Trinity Ventures
Published in
4 min readNov 6, 2018


Insights from Trinity Ventures’ 2018 CEO Dinner

The early Fall sunset gave way to a giant moonrise over the San Francisco Bay as our Trinity CEOs, partners and friends enjoyed cocktails al fresco on the rooftop of The Pearl for our annual CEO Dinner.

Photos by David Dines of Dines & Co.

Most venture firms host a yearly CEO gathering, but I like to think ours is special. The group that assembles is a mix of friends old and new, companies large and small, and perspectives similar and different. Startup CEO’s are some of the busiest people on the planet, but at this event, we offer the opportunity to slow down, unplug, connect and be inspired.

After our guests made their way down the industrial staircase and took their seats for a delicious family-style meal, Trinity general partner Karan Mehandru took the stage to share highlights from the year for our #TrinityFamily. There was much to be celebrated: 15 new companies. 21 follow-on financings. 6 exits. A refreshed brand identity and website redesign (led by yours truly).

Karan also reiterated some of the beliefs that guide us as a firm:

We believe that winning takes heart.

We believe in the power of long-term relationships anchored in trust, empathy and mutual respect.

We believe that enduring franchises of mission-driven entrepreneurs are built on the foundation of culture.

We believe that being a good investor and a good person are not mutually exclusive.

Karan then welcomed our guest speaker Bob Sutton— Stanford professor, organizational psychologist and New York Times bestselling author— to the stage for an insightful (and very entertaining) fireside chat discussion about scaling companies.

Karan was a student of Bob’s at Stanford and to this day still has the textbook from his class (the only one he kept from grad school).

Top four takeaways

These are the insights that stuck with me most from the discussion.

1As your company scales, you will inevitably know less and less as a CEO about your company and its people. CEO’s should be wary of the fact that they may see a “cartoon oversimplification” of their organization which can lead to misguided decisions.

2 Structure and bureaucracy are critically important in scaling — the trick is finding the balance of just enough, but never too much.

3 Make sure the most intimate teams of your organization don’t get too big. When they do, productivity goes down and interpersonal conflict goes up.

4 In meetings, notice how much time you and your leadership team spend talking versus listening, and making statements versus asking questions. The research shows the more you can listen and ask questions, the more value you will contribute.

As evident in the lively Q&A and feedback from our CEO’s, our Trinity community was extremely grateful to Bob for sharing his insights with us. Check out his latest book Scaling Excellence, his podcast FRICTION, and follow him on Twitter at @work_matters. Until next year!

Special thanks to The Pearl SF, Paula LeDuc Fine Catering & Events and our photographer David Dines of Dines & Co. For more about Trinity Ventures, visit our website and follow us on Medium.



Kalee Gardella
Trinity Ventures

Founder of KMG Collective, supporting company builders and job creators who share my belief that work should be joyful.