There are few people who understand leadership more than Dan Ryan, global managing partner of client development and coverage at Heidrick & Struggles. He built his career in executive search, placing financial leaders and board members in some of the world’s leading financial institutions, and also ran Heidrick’s Americas region. With business models changing as fast as they are, he believes companies need leaders who can pivot and bring their organizations along with them.

Dan tells So Many Questions host and Moses Singer CEO Rebecca Goodman-Stephens how the search for senior leaders has changed, including why Heidrick now assesses leaders for what comes next instead of relying only on their track record, and why more boards are looking outside their companies for CEOs.

The two also go back and forth on hiring leaders from outside an industry and executives who prefer interim work. Dan also shares how he leads his own teams.

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

Relevant Links

• Moses Singer: www.mosessinger.com
• Heidrick & Struggles: https://www.heidrick.com
• Connect with Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/
• Connect with Dan Ryan on LinkedIn: https://www.linkedin.com/in/dan-ryan-689b06/

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As managing director of business development at Oaklins DeSilva+Phillips, Marci Weisler works mostly with founder-led media and technology companies. Her superpower comes in two parts: a deep curiosity and a knack for connecting people who should know one another.

She tells host Rebecca Goodman-Stephens how a winding career commercializing emerging technology brought her to M&A, and why today's leaders can't afford to stay behind the scenes.

The two also go back and forth on focus and serendipity. Marci is trying to shake the startup habit of doing everything for everyone, while Rebecca makes the case for the lunch that doesn't look essential on paper. Stick around for Marci's work supporting women founders and the advice she'd give her younger self.

In this Episode

01:06 – A nonlinear career in emerging tech 06:59 – Falling into technology and learning from mentors 12:48 – How the creator economy pushes leaders to build an audience 19:26 – Reading the fine print before giving away rights 25:51 – Building relationships years before a sale 29:56 – Introducing people who should know one another 32:33 – Prioritizing as a horizontal player in a vertical organization 35:29 – Focus vs. serendipity and the 20% rule 37:47 – Being the only woman in the room and talking salary 45:09 – Advice to a younger self on being bold01:06 – A nonlinear career in emerging tech

Relevant Links

▪ Moses Singer: www.mosessinger.com

▪ Oaklins DeSilva+Phillips: https://www.oaklins.com/dp/en/

▪ Connect with Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/

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Thomson Reuters’ Head of Product of CoCounsel Transactional & GCOs, Rawia Ashraf, builds AI products for lawyers, accountants, and auditors, and moves fast without sacrificing accuracy. Rawia started her career as a lawyer at Simpson Thacher before moving into product management at Thomson Reuters.

On this episode of So Many Questions, Rawia tells host Rebecca Goodman-Stephens, CEO of Moses Singer, how a piece of advice from a Big Law partner, don’t let perfect be the enemy of good, shaped the way she runs product today. They discuss how Rawia and her team rebuilt CoCounsel as an agentic AI platform, why she looks to hire a mix of detail-oriented “spreadsheet people” and big-picture “whiteboard people,” and why she believes law firms need to rethink the billable hour as AI changes how junior lawyers learn.

In This Episode

00:29 — Rebecca Goodman-Stephens welcomes her guest from Thomson Reuters.

04:26 — Why a 175-year-old content company now calls itself an AI company.

05:59 — Hiring for a mix of detail-driven executors and big-picture thinkers.

08:52 — The advice a Big Law partner gave during late-night deposition prep. 1

0:12 — How Liz Wiseman's book "Multipliers" shaped a habit of asking questions instead of making statements.

12:12 — Why law firms should charge for outcomes rather than inputs.

17:35 — Advice to a younger self about not needing the path figured out.

19:59 — Inside the "brain transplant" that rebuilt CoCounsel on the Claude Agent SDK.

23:35 — What changes in an organization when women hold the leadership seats.

25:58 — Testing ideas fast while accuracy for lawyers stays non-negotiable.

Relevant Links:

• Moses Singer: www.mosessinger.com

• Thomson Reuters: https://www.thomsonreuters.com

• Connect with Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/

• CoCounsel: https://www.thomsonreuters.com/en/cocounsel

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