Karen Sergeant

I’m a font nerd too. Take great joy in finding the “perfect” one.

It looks like Arc on top of Brave (with Brave’s privacy). Nice!

…and then a heads-up display when I see them the next time. “This is Bob. He’s saved in your phone as BobwWhiteYorkie”

💯 agree, but it’s hard to convince some founders of this, though, and it’s hard to prove after the fact. “All the icebergs we never hit” never makes the KPI dashboard!

When I tell a client "Let's get you ready for AI" — I *don't* mean: Your team needs more training

It usually means:

- Your workflows aren’t visible
- Your delegation isn’t scoped
- Your judgment lives in your head

It’s not so much a skills gap, as it is a *systems* gap.

Same! And to give more clear feedback after the fact, too. All our loops are tightening up.

I feel like AI prompting is the ultimate "mirror test" of how well we delegate.

You know how we *think* we're clear? And have given someone "everything they need" to do a good job?? When really we're throwing half-scoped tasks over a wall.

AI just shows us where our leadership habits are brittle.

Retro image with text "The Top 7 Reasons AI Adoption Flops"

My first couple interactions with AI produced *garbage*.

AI didn’t feel like leverage.

It felt like rework. (And simmering resentment.)

I was rewriting AI outputs AND cleaning up the confusion it left behind.

So we can say I wrote this in self-defense.

karensergeant.substack.com/p/the-top-7-...

This happens to me so often that it’s now a habit. I push everything into my brain, then go walk the dog or go to bed and come back and solve it in one.