How to Show Up with Brave Leadership - Wendy Harris

Super Powered: Leadership, Strategy, Decision Making & Peak Performance - Stories & Strategies from World-Class Performers for Executive Success

Ever wondered what true brave leadership looks like? Wendy Harris, former Goldman Sachs trader turned tech executive, knows it means putting aside personal comfort for the greater good. From transforming underperforming teams into global winners to making tough calls during COVID, she's mastered the delicate balance of driving excellence while staying human.

Named one of Fortune Magazine's most powerful women in business, Wendy scaled revenues to $25M at Gong, grew teams from 30 to 85 at CarGurus, and drove Dropbox's European sales past $100M. But what sets her apart isn't just the numbers – it's her radical commitment to authenticity in leadership, proving that vulnerability and fun aren't at odds with high performance.

Key Talking Points

• The "2-6-2 Rule" of team dynamics: why expecting everyone to like you is a leadership trap
• How one struggling sales team became top global performers by embracing change
• Why redundancies during COVID required both empathy and clear communication
• The "Flamingo Factor" - combining excellence, fun and vulnerability as leadership pillars
• Why Goldman Sachs' pressure cooker environment taught the value of workplace humour

Links & Resources:

• Wendy’s Website
• Wendy’s LinkedIn
• Book Recommendation: Radical Candor by Kim Scott
• Mentioned: Lewis Howes' Podcast

Today's Exercise: The Brave Conversation

This process helps leaders tackle difficult conversations they've been avoiding, combining directness with empathy to achieve better outcomes.

Steps to Apply:

1. Identify one conversation you've been putting off this week
2. Write down the core message that needs to be delivered
3. Focus on addressing behaviours/situations, not attacking the person
4. Deliver the message clearly and directly, with empathy
5. Allow space for the other person's response and perspective
6. Follow up to ensure mutual understanding and next steps