Episode Details

What does an executive search actually look like from the inside?

This episode brings together two people who know the process from different vantage points: Pamela Bol Riess, CEO of PBR Executive Search, and Deeksha Gaur, Executive Director of Theater Development Fund, who was a candidate in a search Pamela led in 2023.

Together, we discuss how executive hiring really works right now — what search committees are actually evaluating, why the boldest candidates tend to win, and how to show up in a competitive market without losing yourself in the process.

In this conversation:

• Why you usually can't get everything in one hire, and how smart organizations identify their true must-haves before the search begins.
• How candidates are being evaluated from the first email they send, not just in the interview room.
• Why "the answers are in the position description" and what it looks like when candidates use them.
• Deeksha's approach to her own search: researching every search committee member, preparing a strategic deck, and giving herself the freedom to show up authentically.
• Why the boldest candidates tend to win and what "leading in the room" actually looks like.
• How post-pandemic uncertainty has shifted what organizations are really hiring for: pattern recognition, comfort with failure, and judgment over credentials alone.
• How to stay resilient as a finalist who doesn't get the offer.

Whether you're navigating a search, hiring into complexity, or doing search work yourself, this one's full of practical insight and rare candor from both sides of the table.

Highlights:

• 01:40 Meet Pamela and Deeksha
• 02:34 Career Origins and Paths
• 03:50 What Hiring Gets Wrong
• 06:11 Judgment and Fit at Exec Level
• 07:42 Defining the Right Leader
• 10:04 Showing Up as a Candidate
• 12:28 Bold Interviews That Win
• 14:45 Testing Thinking and Ego
• 17:36 Practical Interview Prep
• 19:51 Signal Commitment and Research
• 23:49 Authenticity and the Current Job Market
• 27:04 Cover Letters and Owning Your Gaps
• 29:24 Everything Is Data
• 33:28 Bravery and Joyful Leadership
• 37:17 Networks and References
• 38:34 Encouragement and Relationships

Links & Resources

• PBR Executive Search including their Active Searches and Recent Placements
• PBR's Job Search Guide
• Pamela's Succession Planning Series
• Theatre Development Fund (TDF)

About the Guests

Pamela Bol Riess has been in the search business for more than 25 years, focusing exclusively on the nonprofit sector. During her career, she has led hundreds of leadership searches for a wide variety of nonprofit clients based in the US and abroad. Through this work, she has developed an extensive