Behind the Scenes of Navigating the AI Shift
How Cate Huston and I built a course on navigating the AI shift, while navigating the AI shift.
Navigating the AI Shift is starting soon on May 11th! An async course for engineers and engineering managers. Sign up here.
Cate and I almost didn’t build this course.
A few months ago, we had a spurt of AI learning and were feeling confident about our progress. Then we spent a few weeks focused on our first DRI Your Career cohort and resurfaced suddenly feeling behind. The tools are changing every week, sometimes every day.
That feeling of being behind (and also Cate’s reminder that on top of being engineering leaders, we are also experienced coaches who have helped tons of people navigate mindset shifts) became fuel for the course. Turns out, a lot of people are wondering the same thing: whether they’re behind, and whether the years they poured into their engineering career still matter.
This post is a little peek behind the scenes of what it was like for Cate and I to build a Navigating the AI Shift course while continuing to navigate this shift ourselves.
Building our course platform
My own building with AI journey has been one of awe and also often frustration. In my last post about being a human engineer in an AI era, I shared some of my earlier projects, and as my own confidence grows with each project, so does my intuition about what I can build and how I can most easily build it.
Late last year, Cate and I had been collaborating on the content of our first course, and I had taken on the task of researching a few different course platforms to figure out where we’d want to host the course.
I happened to have a few precious hours at a coffee shop. Tired of copy/pasting our course content from Google Docs into chatgpt for feedback, I moved it all into local files and opened up Claude Code to iterate on the with full context. Wait a sec, I thought, since all the content is all here, why can’t I just build the platform to host the course? We had very basic needs — login, modules with written content, an audio file, and the ability to submit exercises. “I think I’m going to try to build a basic platform for our course,” I texted Cate, and within a few hours, while Cate was asleep in Ireland, I had basic functionality up and running.
Since then, Cate has joined me in the github repository, and we’ve had our fair share of breaking production, botched database migrations, and oh-shit moments. After a middleware refactor a few months ago, we realized a week or so later that our course landing pages (where people BUY the course) weren’t accessible to logged-out users, so basically everyone. Whoops.
Through it all, we’ve been figuring out what it actually takes to work together with AI as a third collaborator. The async rhythm across an 8-hour time zone gap, where Cate’s evenings overlap my mornings. The social media manager tool that Cate built to analyze our shares and tell us what’s working and what’s not. The places AI dramatically accelerates us, and the places it’ll happily lead us into a pile of slop, and our experience and judgement are so valuable.
We’ve also seen how important it is to have a space to share half-baked ideas with each other without judgment. I get lots of “Ok I have an unhinged idea” texts from Cate and then shortly after, invitations to new github repos.
From skeptic to enthusiast
Six months ago, Cate’s relationship to AI looked quite different. We were collaborating on our first course, DRI Your Career, when she asked: “Should we have a disclaimer about how we used AI to build this?”
Her question reflected where a lot of thoughtful people were six months ago — dipping their toes into using the tools, but unsure about the optics and the expectations. It also reflected her own situation as a busy engineering director dealing with a huge influx of AI-generated docs to review, and not wanting to inadvertently do that to others.
Fast forward to last month: Cate sent me a present, a custom Chief of Staff repository — a tool she built with Claude Code to help me manage the growing chaos of my many projects. She’d seen me juggling fractional work, course development, content, other side projects, and just... built me something to help me stay on top of everything.
That arc from hesitance to fluency mirrors the journey we’re wanting to support others in taking. You might be cautious of AI because of the slop that you’ve no doubt been subject to at work. Or you might have some subconscious fear about what it all means for your job and the type of work you love doing. You’ll start with something small to get over that initial hump and be well on your way to a kind of fluency where the tools just become part of how you work.
Navigating the shift ourselves
For weeks, we agonized over whether we had the credibility to build an AI course. And how we could build something that wouldn’t be outdated the moment we announced it. But it turns out that as coaches and engineering leaders actively navigating this transition and all the feelings that come up, we are uniquely well-suited to help others on this journey.
Every module in this course reflects something we worked through ourselves and continue to work through.
We built this course because the most valuable thing in our own AI journey was having a space to experiment, be a beginner, and develop real opinions based on the work we actually needed to get done. A space where it was safe to be bad at something new.
And from that space of exploration and learning together, we’ve been able to figure out how to build in a way that is delightful, joyful, and more powerful that we could have ever imagined over a year ago when we first started working together.
A lot of people feel behind. But that feeling is not supportive to actual learning — it pushes you toward avoidance and shame at the moment you’d benefit most from leaning into curiosity and joy. This technology is genuinely new for everyone. So start trying things, share what you don’t know, and build your own confidence in the skills you’ve already developed and the ones you’ll build next.
And if you’d love a little coaching support and scaffolding, you know where to find us.
Sign up for Navigating the AI Shift.
Also, Cate and I recently chatted with Luca over at Refactoring. We discussed all things DRI Your Career, from exploring what you want from your career, how to be intentional about it, how to use feedback to assess how you're doing, to how AI is changing and not changing the picture. We hope you enjoy it!
