Persistence, creativity, and at-bats

In this episode we discuss: Discovering Your Strengths and Living The Life That You Want. We are joined by Alicia Diamond, COO and Transformation Leader.

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We chat about the following with Alicia Diamond:

1. What happens when you stop waiting for “perfect clarity” and start sharing half-formed ideas with your team?
2. How much operational value is lost because your best thinking happens outside formal meetings?
3. Are your leadership decisions driven by energy and context — or by calendar availability?
4. What if the real bottleneck in your organisation isn’t process, but permission to think out loud?
5. How do you create space for strategic thinking when the operational noise never really stops?

References

1. https://www.linkedin.com/in/alicia-diamond/
2. https://aliciadiamond.substack.com/
3. https://www.aliciadiamond.com

Biography

Alicia has been the right-hand, “figure it out” partner to 5 CEOs as a 2x COO and 2x Chief of Staff. She's helped visionary CEOs across diverse industries to get their most transformative ideas unstuck and into action. Highlights include launching the Long-Term Stock Exchange and proving the bottom-line impact for listed clients and founding/managing the Chinese factory behind a portfolio of direct-to-consumer brands.

She sharpened her operational prowess under the scrutiny of top-tier investors including a16z, Founders Fund, Collaborative Fund, Obvious Ventures while working in the Lean Startup methodology, at Eric Ries' startup stock exchange.

Recently, Alicia expanded from working in tech into partnering with SMB owners. She helps visionary owners achieve their growth goals through scalable technology, best-in-class operating practices, and people-first leadership.

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Summary

05:45 — The power of unplanned conversations

06:55 — Why half-formed ideas are a leadership superpower

08:30 — Meetings vs momentum

11:00 — Energy as an operational constraint

14:15 — The danger of over-polished thinking

18:00 — Creating environments where ideas can be safely unfinished

22:10 — Leadership presence over process

26:30 — Rethinking how and when strategy happens

30:45 — What operators can do differently tomorrow

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