JackSkeels.com

Insights and ideas for leaders of agencies, consultancies, and complex project-driven organizations — on structure, AI, and how work actually works

Subscribe Now

Talking Machine #3: The AI Judgment Tax: How AI Slows Your Teams

Every time your team uses AI where the training data is thin, the output arrives fast and the tax follows: evaluating, correcting, reworking. Workday's 2026 research says 37–40% of the time AI saves gets eaten by checking its work. I think they're optimistic. Here's why.

Sam Altman’s Judgment Day

Altman’s judgment day came and went in a single interview. Yours arrives every morning, in the thousand small calls no machine can make for you. For the leaders willing to do the thinking, it’s the real opportunity.

The Client Paralysis Paradox

Your best clients can't make a decision right now, and you're misreading why. It isn't caution about budget. They're frozen, and they're waiting for the machine to hand them judgment it can't give. That's the paradox sitting under the paralysis.

Twenty Things Every Agency Leader Needs to Hear About AI

A social scientist posted twenty things academics need to hear about AI. Every one of them has a sharper version for agencies. So I wrote it.

AI Destroys What Clients Pay Agencies For

Most agencies that lose a long-standing client never see it coming. The work was solid. The relationship was warm. And then the client just… didn't need them anymore.

Feel like your business is borderline crazy, with people flying back and forth, priorities changing, work never done well enough, and…

Agency Insights

Part of what's so enticing about the agency business is its inherent mayhem. Chaos sounds bad, but for agencies it's unavoidable, even essential. How we deal with it largely determines how strong the agency is. Chaos comes because each assignment is different, demands come in…

Agency Insights

And can true leadership save it?

The hyperbolic sales pitch from quick-fix Agile providers misleads management into creating lackluster, forgettable Agile.

Agencies are filled with managers. We see ratios as high as 1:2 where for every two people who produce stuff, there is one person who…

Agency Insights

JackSkeels.com

Subscribe to our Newsletter and stay up to date!