The Colander.
When you get the rare clean break of a new role, three moves pay off together: adopt an operating rhythm your organization already recognizes as its own; introduce a few highly visible new behaviors that ride momentum the company already wants; and wire AI into the cumbersome management work — orchestration against your steady documents, prepared one-on-ones, generated updates — with human gates left deliberately in. The old lesson underneath: hold people accountable for the what, and let them own the how.
01A clean break
Since the second quarter of this year, I've been in a new job. My old job ceased to exist, and a new one opened up — and if you're ever allowed to make a career switch with a little drama and a clean break, take it.
It hands you a choice: take the new role, or, after a long stretch at the same company, do something entirely different. It wasn't a trivial question, because I've spent my whole working life in the seams — the places where new technology slowly, then certainly, lets people think and work differently. It started with music: I went from playing an instrument to discovering that a computer could make me the whole band. From instrumentalist to composer to producer — still music, completely different role. I loved that shift. I also watched, up close, how much some people did not.
I've watched the same movie on repeat ever since: in a weekend job at a retailer running its shop on a disconnected database next to a website that was outgrowing it, in marketing departments learning to measure, in IT departments suddenly asked for pixels and tags four times a year, in video, and now in AI. Every time, the people anchored to the least adjusted the fastest, and the technology was the easy part.
So when the choice came, the interview process itself did something valuable. Getting ready to decide on a new job is exactly the moment you build up resolve as well as confidence: this time I'm going to start differently. This piece is about what that looked like — because I think the moves are worth considering for any executive handed a clean start.
02The colander
First, the old lesson — the one everything else in this piece leans on.
When I was twenty or so, someone trying to sell me something said a thing I still believe, and that I think most professionals don't get right until they're very senior: you can hold me accountable for the what — but then I determine the how.
As you grow, you really are held accountable for the what. It shows up in your grading, your rewards; ultimately the very existence of your position is a consequence of a deliverable the business needs. But if you put someone on a what, and then the how becomes the unspoken expectation, the organization can no longer fairly hold that person accountable for anything.
The picture I use: suppose I reward you for every liter of water you carry from A to B. You agree — you're already thinking about buckets. Then I tell you: actually, I want you to carry it in a colander. Walking backwards. Doing somersaults.
Don't take my word for it. Run the water yourself:
You are paid per liter of water carried from A to B. That is the whole job. Carry — and mind the memos.
Carry water from A to B.
Five taps of CARRY WATER move one delivery of ten liters from A to B. You are paid per liter. That is the whole job — for now.
Organizations do this constantly. They put someone in a clear, high-outcome position — and then throw handicaps into the how: constraints invented by people who've never done the job but want to see it done a certain way. And at some point the person holding the colander says: either the how becomes the what — in which case it is my deliverable, and we should agree on it as such — or I deliver the what, and I determine the how.
There are degrees, of course. If the job is sales, arguing against seeing customers is silly. And some hows are the point: if what you sell carries a quality bar that protects the customer, that's a how worth defending. But there is a line where the how becomes so restrictive, and so arbitrary, that the what can no longer be delivered. Knowing where that line sits, and saying it out loud early, was step one of the new job. The new team's work runs on longer arcs and more milestones than a standard sales motion — exactly the kind of work where hows pile up unnoticed. Getting the what right, and protecting the how, decided whether the team could deliver at all.
03Three moves
So we went to work. Three moves, in order.
First: borrow the operating system — don't import one. After years at the same company, my first question was which methods were already proven in-house, because the last thing you want is to become an innovation island. Any large organization has two places to look: the teams that think in decades, and the teams that ship on cadence. If you want a commercial team to think long-term, borrow from the first; if you need short-term deliverables against a long horizon, borrow from the second. It helped that I'd worked with Verne Harnish's Rockefeller Habits at earlier companies — a method that sits comfortably on top of the OKRs and quarters most big companies already run on. And the quarterly focus matters more than it looks: everyone can paint the twenty-five-year vision, and everyone knows this week's deliverable. It's the five-to-ten-year middle distance where abstraction takes over. So: an operating rhythm the organization already recognized as its own, twelve-week sprints and all.
Second: introduce visible behaviors that ride existing momentum. We were vocal about the team's new what and deliberately quiet about the how. The daily standup got a name the wider organization already liked the sound of — and when you attach a new ritual to words a company already wants to hear, it spreads on its own. Before long, neighbouring teams were asking why they weren't doing it. That's momentum you didn't have to buy. Then comes the familiar decay: the daily ritual loosens into morning coffee chats, because you've built the daily muscle but haven't anchored it to the sprints yet. Which raises the question: how do you run twelve-week sprints and a daily rhythm taking AI into account?
Third: wire AI into the cumbersome work — with the gates left in. Rhythms like agile are good ideas that eat enormous time to run well. Consistent communication is hard. Cascading — action, not just information — is hard. Keeping an org on priority is time-consuming, because priorities are always being challenged. Where AI helps a leader most is in getting through exactly that cumbersome work — the things that would visibly move the business if only you had time to do them properly. Three uses, running today:
An orchestration layer on the steady documents. OKRs, sprint priorities, role expectations — on a schedule, an agent revisits whether they're still on track and on point. A chief of staff and a strategy consultant that is always on, nudging when communication or prioritization drifts from what we agreed.
Prepared one-on-ones. Every team member has goals, feedback, a development plan, and expectations. That's the category of management work that always improves with more preparation time — and never gets it. We moved from loosely structured bi-weeklies that only ever covered “the now” to dedicated, prepared hours: one guiding document per conversation, drafted from the notes we already keep and read by a human before anyone sits down.
Generated updates. The weekly update upward, drafted against a standing rubric of what the role is expected to deliver — so the writing takes minutes and the thinking gets the time instead.
All three are doable with whichever assistant your company has approved; the model matters less than the files. Build them as skill prompts, and keep the human-gate moments in on purpose. The mechanism underneath — the files, the clerks, the register — I've written up separately in The Only-Me List. The secret to scaling it is the same in both pieces: build and maintain the library of source documents. That part is bespoke to your organization, and it's the part worth doing yourself.
04Starting differently
So, to close where I started. There are things you can do personally any day — but when you get that rare moment of shaping new work or a new team, use it for the three moves above. The third can start today: on the cumbersome work, with the gates left in.
Because the moment you take a new job is the moment you get to decide whether this is the time you really do it differently.
