The One Question That Reveals Your Real Capability Gap with CEO Tom Monahan

Why hasn't AI showed up in the P&L yet?

Heidrick & Struggles CEO Tom Monahan joins Meg and Amy. His one question that reveals your real capability gap: If you just told your team to go do that, what wouldn't happen? Tom unpacks why the CEO job is now a two-way ambassador role, and why moving AI from the CEO story to the CFO numbers is the real test.

He also makes the case for managers in an age of flat org charts, and why AI should mean better work sooner — especially for junior talent.

Featuring Tom Monahan, CEO of Heidrick & Struggles, in conversation with Meg Bear and Amy Wilson.

TIMESTAMPS

00:15 - Meet Tom Monahan, CEO of Heidrick & Struggles

01:19 - Lessons from a family carnival business

02:42 - Most businesses are all about the people

04:20 - Why the CEO job is getting more complex

05:49 - The CEO as two-way ambassador

12:18 - The one question that reveals capability gaps

17:51 - Move AI from the CEO script to the CFO numbers

19:02 - Using AI for immersive candidate scenarios

25:39 - Why demanagerizing has not worked

31:06 - When build costs go to zero, advisory value rises

35:52 - Better work sooner for junior talent

39:19 - 4 qualities of leaders who win now

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📚 RESOURCES:

Show Up to Win by Jeff Sanders and Kelly O. Kay (Heidrick & Struggles): https://www.heidrick.com/en/pages/show-up-to-win-book

"Finding the Human Core of Competitive Advantage in the AI Era: Avoiding the Pygmalion Trap" by Tom Monahan and Les Csorba: https://www.heidrick.com/en/insights/frontier-tech/finding-the-human-core-in-ai-era

Route to the Top 2025 (Heidrick & Struggles research): https://www.heidrick.com/en/insights/chief-executive-officer/route-to-the-top-2025-the-ascent-redefined

"From Hierarchy to Intelligence" by Jack Dorsey and Roelof Botha (Block): https://block.xyz/inside/from-hierarchy-to-intelligence

Level 5 Leadership (Jim Collins): https://www.jimcollins.com/concepts/level-five-leadership.html

Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox

Generally Accepted Accounting Principles (GAAP): https://en.wikipedia.org/wiki/Generally_Accepted_Accounting_Principles_(United_States)

Survivorship bias: https://en.wikipedia.org/wiki/Survivorship_bias

"The Future Is Interdisciplinary" by Meg Bear: https://www.megbear.com/post/the-future-is-interdisciplinary

Heidrick & Struggles: https://www.heidrick.com/

🔗 CONNECT:

Tom Monahan: https://www.linkedin.com/in/tlmonahan/

Jeff Sanders: https://www.linkedin.com/in/jeffsanders2/

Kelly O. Kay: https://www.linkedin.com/in/kokay/

Tobi Lütke: https://x.com/tobi

Website: https://www.themegandamyshow.com/

Instagram: https://www.instagram.com/megandamyshow/

LinkedIn: https://www.linkedin.com/company/the-meg-amy-show

https://www.linkedin.com/in/megbear/

https://www.linkedin.com/in/amy-wilson-insight/

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