The Good Stuff

32 - Stewarding SMEs and AI with Bill Withers and Gabe Enslin

Nov 19, 2025
Bill Withers, a succession coach for SMEs, and Gabe Enslin, an AI entrepreneur, discuss the unique challenges small-medium enterprises face in adopting AI. They highlight the importance of stewardship, role clarity, and proactive leadership to ensure business resilience. The duo expresses how many founders lose their proactive touch as they grow, leading to a reactive management style. They argue for a mindset shift towards AI as a collaborative tool, not just a technology, emphasizing the need for incremental trust-building in AI adoption.
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INSIGHT

Stewardship Is A Distinct Leadership Layer

  • Stewardship is the non-operational decision layer: vision custody and organizational leadership.
  • Small and medium enterprises weaken stewardship as they scale because founders become reactive technicians.
ADVICE

Begin With Role Clarity

  • Start with role clarity: accept and define your owner, director and vision custodian roles.
  • Spend dedicated time crafting what you want and test whether the business is likely to deliver it.
ADVICE

Do The Hard Design Work Yourself

  • Commit uninterrupted time to design the business you want; there is no shortcut.
  • Work hard for a focused period (e.g., two years) and the returns compound exponentially.
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