Founders Series: the questions that keep you up
I’ve spent the last few months speaking with founders and CEOs, and I keep having the same conversation.
Nobody quite names it, but AI is the thing underneath all of it. It rarely arrives as a tidy question about AI. It arrives as everything that used to feel settled suddenly being up for grabs.
Here’s what I mean. “Every tech company needs a CTO” used to be a given. It isn’t anymore. In one week I spoke to two founders who’d split the CTO role in two, and were weighing up a third. The questions founders thought they’d answered are open again.
Here’s the honest part. I haven’t got all of these fully worked out either, because nobody has yet. We’re all learning on the fly. I told a founder just today that they shouldn’t have to pay me to figure this stuff out, because we’re figuring it out together. Same boat, same weather.
So that’s what this series is for: the questions founders raise with me at all hours, split the way they actually fall. The new ones AI has set off, and the ones that never left.
The new questions
The things founders thought were settled, suddenly back on the table:
- The CTO role is splitting. One job, two, or three, and who owns what?
- How much time should engineers actually spend in these tools?
- Do we budget for people now, or for tokens?
- We used to put ten on a sprint. Could it be three?
The questions that never left
AI is not touching these. They’re still here, still unglamorous, still expensive to get wrong:
- How do I run probation properly under UK employment law?
- How do I hire someone in Spain without tripping up: employer of record, our own entity, or a contractor?
- Am I misclassifying the contractors I already have?
- I want to promote someone, but there is no structure to promote them into. Now what?
- What does career development even look like in this new world?
- What are we actually hiring for now, and why is the market saturated in some places and bare in others?
So that’s the plan. Each week, one of these, new or never-going-away. First up, the one I can’t stop thinking about: the role of the CTO. What it was, and what it’s turning into.
If there’s a question keeping you up, send it through the contact form. I’ll work through the ones that come up most. No names, no judgement.
That’s the diary open. Let’s get into it.
Enjoyed reading this article? What would you like to see next? Leave a comment below.
The series so far: Vol 1: Rethinking the CTO, Vol 2: Why the goal of fractional HR is to make yourself redundant and Vol 3: Suddenly a Manager.