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The Deetails · May 1, 2026

What successful AI implementations actually look like: 4 learnings from 150+ operators who attended our AI workshops last month

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Dee Kapila · The Deetails

Contrary to the latest “AI is going to eat your face” article, I thought I’d share what’s happening to teams on the other side of successful AI implementations. In the past month, my team and I have run AI workshops in person in Austin, Sydney and Paris with over 150+ operators who are currently implementing AI in their orgs. Here are the shifts I’m seeing:1. Leaders are re/inventing their own roles - deploying AI tools that show hardened metrics and real ROI immediately positions leaders as the AI experts in their org and many of them are rewriting their own job descriptions or creating net new roles and getting full backing from their orgs to transition into them.

2.

We are all perplexed by the “player/coaches are the future” talk track - The vast majority of leaders have been doing IC-style executional work on TOP of everything else they do for ages. “Let’s get rid of managers that only delegate work” is a tired old refrain that makes a comeback every 5-8 years or so when someone feels like cosplaying Frank Slootman. I’m reminded of when Valve released their employee handbook in the early 2010s and everyone thought it was some huge unlock but the cake, to borrow Valve’s own parlance, was a lie. We need leaders. They do many things. We need layers. Not too many. The end.

3.

Seasoned leaders are voluntarily opting for IC roles - I am noticing this trend in my peer group in particular. The people who came up building sites on Geocities, or making Flash (RIP) games. This crop of leaders crave uninterrupted, distraction-free time and space to do deep work. That deep focus/flow state when you’re in Claude or Lovable or whatever isn’t a new feeling for them. It’s nostalgia.

4.

Nobody wants big teams anymore
Well okay, some people do and always will. But AI-forward senior operators do not consider leading a large org to be a sign of success, and it’s not just because of the benefits of AI. It’s because they are tired of justification theatre at FY/headcount planning cycles, never-ending HR checkbox activities and no L&D budget. Instead, leaders want smaller teams with considered scope, unfettered or generous token spend, and streamlined HR processes. ICs want more challenge, more responsibility, and access to the best tools. Both groups want more autonomy.

5. I needed a 5th thing to have a nice round number of learnings so I’ll say that Sydney has the best coffee EVER in all the land. Nobody can top them.

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