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A conversation with Brandt Hanley brings 21+ years of executive search experience
In this powerful episode of CEOs Unscripted, host Jane Gentry sits down with Thomas Grealish, leader of Henderson Brothers, one of Pittsburgh’s most respected independent insurance and financial services firms with over 160 employees.
What You’ll Learn:
🔹 Culture as Competitive Advantage – How Henderson Brothers protects their independence and uses culture to naturally “weed out” bad fits while attracting top talent
🔹 The Stay Interview Strategy – Why Thomas asks employees two critical questions about leaving (before they ever consider it) and how this prevents turnover
🔹 Hiring Without Mistakes – The “messy but effective” referral-based hiring process that prioritizes cultural fit over impressive resumes
🔹 The Two-Minute Drill – Thomas’s crisis preparation exercise that helped his team navigate the 2008 financial crisis, tech bubble, and COVID without panic
🔹 Financial Transparency That Works – How sharing P&L statements weekly creates ownership mentality across the entire organization
🔹 Strategic Growth Done Right – Expanding to Columbus, Ohio organically while maintaining culture remotely
🔹 Community Giving as Leadership Development – Why Thomas encourages 30-year-olds to join nonprofit boards and how Henderson Brothers supports employee philanthropy
🔹 Family Business Survival – Navigating 40+ years in a family business with his brother while maintaining alignment on vision and values
KEY TIMESTAMPS:
00:00 – Introduction & Pittsburgh Culture
04:32 – Culture as Everything: Independence & Heroic Service
09:15 – The Stay Interview: Two Questions Every CEO Should Ask
14:20 – Hiring Process: Slow, Careful & Referral-Based
18:45 – The Two-Minute Crisis Drill That Prepares Teams
23:10 – Financial Transparency & Weekly P&L Sharing
28:30 – Operationalizing Culture as You Scale
33:15 – Community Philanthropy & Developing Young Leaders
38:40 – The Mario Lemieux Foundation Story
42:20 – Strategic Expansion to Columbus, Ohio
46:15 – Family Business: Alignment & Good Intent
51:30 – Rapid Fire: Books, Career Advice & Getting Unstuck
About Thomas Grealish:
Thomas has led Henderson Brothers for decades, growing it into a major regional insurance and financial services firm while maintaining private ownership and a culture-first approach. He serves on multiple nonprofit boards including the Mario Lemieux Foundation and is a Duquesne University graduate deeply committed to the Pittsburgh community.
