Earlier this year I spent ninety minutes with six people whose job, for the next year, is to help the senior executives of a large university use artificial intelligence properly. They are capable, they know the technology far better than the executives do, and every one of them was about to make the same mistake.
The session was called Who trains the trainers? and almost none of it was about AI.
The arithmetic of a senior leader’s diary
Start with what is actually true about the person you are about to meet. Someone running a substantial organisation has a diary carved into fifteen and thirty minute pieces, most of which were booked by someone else. They are carrying three or four problems that would each be a full-time job for anyone else. They will have had roughly four minutes between your meeting and the last one, and they will be going somewhere else immediately after.
They are not being rude when they seem distracted. They are triaging, continuously, because triage is the job.
In 1986, when I was training as an executive recruitment consultant, a sales manager named Mike Carroll gave me something I have used every working day since. In consulting, he said, every fifteen minutes matters. Stop at the end of each one and ask whether you spent it productively. The answer will not always be yes, and when it is no, you have the next fifteen to recover the value across the half hour. Eight hours is thirty-two of those, which is thirty-two chances a day to notice you are drifting.
Mike was talking about my own time. Forty years later I use the same unit for someone else’s, and it becomes a different rule. The first fifteen minutes you spend with a senior leader buy you the next fifteen. Nothing else does. Not your credentials, not your deck, not the fact that someone senior asked you to come.
What they are actually thinking about
They are not thinking about your technology. They are thinking about one of about four things, and if you cannot connect what you have brought to at least one of them, you will get a polite hearing and no second meeting.
They are thinking about risk: what could go wrong here that ends up in front of a board, a regulator or a journalist.
They are thinking about people: who is going to have to do this, whether they can, and what it does to the ones who cannot.
They are thinking about money and time: not the price of the thing, but what it displaces. Every yes is a no to something else, and they are the only person in the building who sees the whole ledger.
And they are thinking about whether they can trust you, which is a faster and more brutal assessment than most technical people realise, and which is largely settled in that first fifteen minutes.
What this means if you are the one arriving
Three things follow, and none of them are about your subject matter.
Lead with their problem, not your capability. The temptation, when you know a technology deeply, is to explain it. Resist it entirely. Start with something you know is on their desk, and let the technology arrive as a consequence.
Bring one thing, not six. A senior leader can take one new idea from a meeting and act on it. Six ideas is zero ideas, because the sorting cost exceeds the available attention. Decide in advance what the single thing is, and hold everything else in reserve for the meeting you have not earned yet.
Say the hard part early. If there is a limitation, a cost or a risk, name it in the first few minutes rather than the last. Counterintuitively this buys you more time, not less, because it signals that you are not selling. The fastest way to lose a room of experienced executives is to let them find the problem themselves after you have finished being enthusiastic about it.
The part I keep having to relearn
I spent thirty-seven years on the other side of that desk and I still get this wrong, though not in the way you would expect. My failure is not a lack of interest in the technology. It is too much of it.
I am genuinely excited by what this can do for people, and when I am excited I become an express train from London to Edinburgh that forgets to stop at the stations and pick up the passengers. The enthusiasm is real and it is also, from the other side of the desk, exhausting.
So I stop, and I ask Mike Carroll’s question with the sign reversed. Not did I use those fifteen minutes well, but did those fifteen minutes earn me the next fifteen.
Because the senior leader is not short of interesting. They are short of time, and short of people who will tell them the truth quickly. Be the second thing, and the fifteen minutes turn into a relationship.
I am researching what enables and disables senior leaders’ engagement with AI in their decision-making. The observation above is drawn from practice rather than from that research, and it is offered as such.