The Beautiful Mess · Free post · Building AI products · Leadership & management

TBM 425: AI and Agency

John CutlerJun 7, 2026♥ 83
SourceThe Beautiful Mess
KindFree post
PublishedJun 7, 2026
Readers♥ 83
Originalcutlefish.substack.com ↗
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The piece argues that organizations asking their teams to find ways to use AI for company benefit are undermining that goal by stripping away the agency people need to experiment and decide. The core claim is that meaningful AI adoption depends on giving practitioners room to explore, not just mandating outcomes. Because teams closest to the work hold the most context about where AI can help, constraining their autonomy works against the very results leaders want. The point matters for product leaders who are pushing AI initiatives top-down while expecting bottom-up ingenuity.

01Key takeaways

  • Asking teams to find AI value while restricting their autonomy works against the goal.
  • Experimentation needs real freedom to try and fail, not just permission on paper.
  • Teams closest to the work hold context leaders lack about where AI helps.
  • Set clear outcomes and boundaries, then let teams choose how to pursue them.

02Key sections

The contradiction in AI mandates
Leaders often ask teams to discover valuable AI applications while simultaneously restricting how those teams can work. The tension between the request and the constraints is the central problem.
Why agency matters for discovery
Finding useful AI uses requires experimentation, which requires the freedom to try, fail, and adjust. Without that agency, teams cannot learn where AI actually fits.
What leaders should do instead
Leaders should loosen prescriptive controls and create safe conditions for experimentation rather than demanding predetermined results. The implication is to trust teams with the decisions they are best positioned to make.

03From the post

“So you want your team to figure out how to use AI for the benefit of your company? Then stop stripping them of the agency to do it.”

“So you want your team to figure out how to use AI for the benefit of your company? Then stop stripping them of the agency…”John Cutler · The Beautiful Mess

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.