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How do you judge whether someone can lead a business through changes nobody has been through before? Dan Ryan, global managing partner of client development and coverage at Heidrick & Struggles, has built his career placing senior executives at some of the world’s biggest financial institutions, and he later led the firm’s Americas region. He talks with So Many Questions host and Moses Singer CEO Rebecca Goodman-Stephens about how boards and companies are rethinking the way they find and assess top talent.

Dan explains why Heidrick built a forward-looking tool to sit alongside traditional assessments and references, which mostly show how someone performed in the past. With AI transformation becoming a bigger priority for boards, Dan sees more of them hiring CEOs from outside their companies, looking for leaders who can pivot and bring an organization with them. His own approach has changed over time. He used to want candidates whose backgrounds match the role exactly, and now he looks to adjacent industries for people he can mentor.

They also discuss the executives who choose interim and project-based work and how Dan leads his own teams, including the room he gives people to make mistakes.

In This Episode:

04:18 – Executives Who Choose Interim and Project-Based Work 
07:08 – Why CFO Searches Now Take Longer 
08:50 – Balancing Homegrown Leaders With Outside Hires 
13:32 – Moving Beyond Backward-Looking Leadership Assessment 
18:36 – Bringing the Team Along on a Decision 
20:39 – Giving Associates Room to Make Mistakes 
21:57 – Being More Open-Minded About Where Talent Comes From 
23:50 – Boards Turning to Outside CEOs More Often 
28:54 – The Capability Gap in Boardrooms and Executive Ranks 
33:41 – Stepping Into a Bigger Mentorship Role

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