Inside the Search: What Executive Hiring Actually Looks Like (EP.91)
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Updated: April 27, 2026
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 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 network of relationships with nonprofit leaders, a deep understanding of the skills and experiences that make candidates successful, and knowledge of the institutional conditions necessary for supporting that success. She is particularly adept at understanding the culture of a client organization and identifying people who will thrive there. She has a BA in English from Brown University and an MFA in Fiction Writing from New York University.
Deeksha Gaur is Executive Director at Theatre Development Fund (TDF), a non-profit that is building the future audience for the performing arts by removing financial, physical, and invisible barriers to attendance. Prior to this, Deeksha spent eight years at the nexus of theatre and tech at Show-Score, a consumer reviews platform that she co-founded. Following its acquisition in 2020, she ran the incubated brand for TodayTix Group. With TDF, she returns to the non-profit arts world, where she has previously held senior marketing and PR positions at Woolly Mammoth Theatre Company, Two River Theater Company, and Long Wharf Theatre. She serves as Treasurer and a founding board member of Kaleidoscope Dreams Foundation, chaired by Alicia Keys, and has previously served on the boards of the award-winning Second Stage Theater, Ars Nova, and Space on Ryder Farm, where she was also Treasurer. She is an adjunct professor at Fordham University and guest lecturer at Yale University's David Geffen School of Drama. Deeksha is also a Tony Nominator and a published crossword constructor.
Tim Cynova is the host of the Work Shouldn’t Suck podcast, where he and guests explore bold ideas and practical strategies for creating workplaces where people thrive. At the consulting firm WSS HR Labs, he draws on deep experience leading and advising mission-driven organizations through growth, change, and complexity to help them dust off outdated policies, challenge default approaches, and design values-centered workplaces that align people strategy, organizational culture, and operational infrastructure. A certified Senior Professional in Human Resources (SPHR) and trained mediator, Tim’s path has taken him from orchestral trombonist to C-level roles in multiple $25M+ nonprofits around the globe. Whether consulting, teaching, or recording, he brings curiosity, candor, and a knack for making workplace design engaging and actionable. More at timcynova.com.
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