Ground Decisions

Often, when we talk about automation, we talk about planes. We say they fly themselves, which, sure – and technically the largest planes can even land themselves, if the airport has the equipment (it’s mainly used for bad weather). However most takeoffs and landings remain manual. My pilot friend also points out that many decisions (fuel is a big one) get made on the ground.

The other thing my pilot friend pointed out is that pilots are in for any decisions they make. They are not just flying the plane; they are in the plane. Contrast this with the surgeon, who performs the surgery, and walks out of the operating room afterwards, regardless of the patient outcome.

In this analogy, VCs are surgeons. Developers are pilots. And the hype-men… travel agents selling plane tickets, mainly.

The problem with much of the hype around AI is that it’s not meeting the people who actually do the work where they are at. We’re not being clear about what’s takeoff, what’s landing, and what the ground decisions are.

The cracks are starting to show. I’ve seen various bits and pieces, but nothing captures it better than Luca Rossi’s summary of CircleCI’s State of Software Delivery 2026 data: elite teams nearly doubled throughput YoY, median barely moved. 81% use AI, so the differentiator is not the tooling; it’s infrastructure. Teams with CI pipelines under 15 minutes in 2023 are 5x more likely to be top performers today.

I am fascinated by the software factory model — Dan Shapiro’s Level 4, where programmers are less programmers and more managers of AI agents and tasks — and the challenges of retro-fitting it onto an existing engineering organisation. It’s been a lightbulb moment for me – I feel like I finally get why the layoffs happened first, and why the productivity gains have failed to materialise.

I think the answer lies in the ground decisions, or the open questions from an organisational perspective.

How does the developer tooling calculus change?

With teams of developers, we used to know the things that were useful for a team of 20 but not 2, and the things that made sense at 200 but not 20. That calculus seems to have changed fundamentally for two reasons. First, headcount is not (or shouldn’t be) a good proxy for productivity. Second, tooling itself is easier to build.

Concrete example: every organisation eventually evolves to have a design system. Few start with one. But if you were building a web app today, would it make sense to start with a design system from day one? The answer might be yes.

How do budgets need to evolve?

Historically, dev team budgets are mainly salaries and some tooling. But StrongDM, who built one of the first real software factories, use $1K/engineer/day in token spend as their benchmark for whether you’re doing it seriously.

Firstly, how do you factor that kind of ongoing cost in? Secondly, is managing more complex budgets and ROI going to become a bigger expectation of engineering managers? And what does it take to get good at that?

What does skill definition look like now?

It’s clear that a different skill composition will be more valuable in this model. My predictions are that judgement – understanding what to build and why, what is good to ship (aka takeoff and landing) – and feedback – providing clear direction and iterating well – will be bigger differentiators, and earlier in someone’s career than before. What people call prompt engineering is just problem definition and refinement – skills that have always mattered, now moved to the front.

What does this mean for hiring and onboarding?

Skill definition leads neatly into these two problems: what do you evaluate, and how do you onboard?

In hiring, most of the conversation has been about the ways AI generates noise from candidates and heartless automated rejections from companies. Which is a real problem, but not the most interesting one. Beyond that: once there’s a human in the process, are the skills being evaluated the best predictors of success in this new model?

Similarly with onboarding: having hired many people over the years, I used to have dialled in what good looked like at key intervals — 30, 60, 90 days. But in this model, what does a good trajectory look like when AI can both accelerate and abstract from understanding the systems?

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I have my own concerns about AI, I’m not going to pretend otherwise. But I also think the adoption curve is inevitable, and I’d rather help engineering leaders navigate the reality in front of them than relitigate whether we should be here at all.

Coming back to the pilot analogy:

• Takeoff – what we build and why
• Landing – shipping and the decisions around it – what’s actually good enough to meet the definition of done?
• Ground decisions – the open questions above.

What am I missing? What’s your definition of take off and landing, and what are the ground decisions that are changing in real time?