Host Julie Harris Oliver welcomes executive coach and two-time founder Connie Liu (CEO of Tandem) to discuss humor’s role in work, leadership, and coaching. Connie shares that her path to coaching began after hiring an executive coach during her transition out of her first company, valuing coaching as a place to be fully honest without “curating” for others. They explore humor as a release valve that extends emotional runway, reduces high-stakes pressure, and increases creativity—especially through improv’s “yes, and” approach and design-thinking environments that normalize risk and riffing on bad ideas. Connie describes using standup comedy as a counterbalance to founder seriousness and as a way to practice levity, while both reflect on when humor is welcomed or risky at work, including for women and in highly serious roles.

00:00 Welcome and Format

00:35 Meet Connie Liu

01:09 Connie’s Coaching Origin

02:31 Why Humor at Work

04:10 Standup as Counterbalance

06:09 Humor as Release Valve

07:15 Making Humor Feel Safe

09:07 Creativity and Yes And

13:40 Dog Interruption Reset

14:12 Lightening the Room Fast

16:03 Can You Teach Funny

16:23 Rule of Three Parenting

17:53 Sarcasm and Pranks Roots

18:36 Back to Executives

18:45 Personality on Calls

19:25 Creating vs Reporting

20:22 Finding the Right Balance

21:07 Sales Stories That Land

21:51 Standup Fear and Dares

22:49 Bombing and Getting Hooked

24:14 Comedy Style and Influences

24:57 Work Persona and Gender

28:41 Founder Seriousness vs Humor

30:18 Keeping Perspective at Work

31:37 Key Takeaways and Farewell