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How Most Engineering Leaders Are Getting AI Wrong (And What to Do Instead)

ByJossie Haines

A podcast conversation on why engineering leaders misuse AI, the hidden cliff where women drop out of tech, and how coaching-first leadership drives real impact.

I had a candid conversation with Jeff Keyes from Allstacks last week on their new Stacked Sessions podcast that I think you’ll find fascinating.

We dove deep into something I’ve been seeing repeatedly with the engineering leaders I coach: They’re either not using AI at all, or they’re approaching it completely backward.

Here’s the pattern that got me started on this work: I was coaching someone who works on one of the largest LLMs for coding… and she wasn’t using AI herself. When I started asking around, this pattern was everywhere, even at companies with AI mandates.

Woman Working on a Laptop in the Garden - mindful productivity

In the episode, I share:

  • Why the “just experiment and see what works” approach is actually costing teams productivity (and what to do instead)
  • The real reason only 9% of engineering execs are women – and the specific “cliff” where we’re losing them
  • My “loving accountability” framework that helps high-achievers break through the “good girl” pattern
  • The technique I taught my husband that turned a 2-3 hour task into 5 minutes (yes, really)
  • Why cutting through overwhelm isn’t just about better tactics – it’s about nervous system regulation

One of the core principles we unpacked: coaching first, tech second. Starting with the problem instead of the tool is the difference between AI implementation that actually moves the needle and AI that just creates more work.

Check out the full episode:

Apple Podcasts: https://podcasts.apple.com/us/podcast/stacked-sessions/id1846908726?i=1000735242987​

And speaking of coaching…

I’m hosting a free drop-in Leadership Coaching Lab this Wednesday, November 12 at 1pm PT.

Bring your real leadership challenges. Get live coaching. And connect with a group of engineering leaders who get it.

I’m capping it at 20 people to keep it interactive.
👉 Save your spot: https://luma.com/vqwac51s

The types of topics people bring:

  • Rolling out AI with real adoption (not just buying tools)
  • Annual planning beyond just “doing more with less”
  • Tough performance conversations
  • Faster, clearer decisions with real buy-in

If you can’t make it, DM me on LinkedIn with your question, I’ll try to cover it and send the replay.

I’m running a handful of these free drop-in Leadership Coaching and AI Implementation Lab sessions in November and December, and honestly don’t know when they’ll be back next year. So if you want some free coaching support, be sure to attend.

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