His board had asked him to dream bigger. The market had given the business headroom, things were going well, and they wanted to know where he actually wanted to take it.
He brought me his 12-month plan instead. He laid it out, line by line, and when he'd finished I asked him how ambitious he thought it was.
"Very ambitious," he said. "I think it's very aggressive."
"Based on what?"
He took me through the market conditions, why they made the plan hard, and why the numbers he'd written down were already a stretch. He was fluent and he was prepared, and every sentence was a reason.
So I asked him what it would look like if we took that plan and made it ten times bigger, over three years instead of twelve months.
"That's not possible."
He said it before he'd thought about it, which told me more than the plan did.
You might recognise the move. Somebody hands you room, and you hand them back a plan that fits the room you had last year. You call it realism, and the people around you nod, because a leader who knows the limits of the market looks like a leader in control.
Nobody forced the ceiling on him. His board had lifted it and the market had lifted it. The only person still holding it in place was the one who'd been asked to take it down.
Most leadership advice assumes you're being held back: not enough money, not enough people, a board that won't back you. Almost nobody tells a CEO that sometimes you have all of it, and you still write the small plan.
When he said it wasn't possible, I asked him why not.
"I don't think we have the resources."
So I pointed him back at his own plan. If he delivered the twelve months he'd just shown me, he'd have capacity to build on. He wasn't being asked to find ten times the resources tomorrow; he'd be building towards them. His board had already told him they'd back him with extra investment if he needed it.
Then I asked the question I actually cared about. Is it that you don't have the resources, or have you decided what's possible before you've looked?
He didn't answer that one straight away.
We did the exercise instead. Assume everything you've just told me isn't true. Assume the resources are there. What happens next? He'd name a problem, we'd take it apart, and he'd name the next one. Bit by bit the objections went, until he could see the bigger version of his business in front of him.
Underneath the last objection there was no market condition at all. Things were going well, and he didn't want to risk that.
We talked about the difference between smart risks and dumb ones. This wasn't a dumb one. There were reserves, the protection was in place, and his board had walked through all of it with him before they ever asked him to think bigger. The safety net he was afraid of not having had already been built for him, and he still wouldn't step out onto the wire.
A well-cited 2011 paper on stretch goals by Sim Sitkin and colleagues at Duke lands on an odd finding: the organisations most drawn to extreme goals tend to be the ones least able to afford the risks, while successful companies with plenty of spare resources can turn cautious because of that success, and avoid stretch goals they could easily afford. He was the second kind. That's much harder to see from the inside, because caution after success feels like good judgement.
This is what the Intention Gap looks like at the top. It rarely shows up as a leader who doesn't know what they want. It shows up as a leader quietly protecting what they've already built, dressed up in market analysis so nobody, including them, has to call it fear.
You can run like that for years without it costing you anything visible. The business keeps performing and the plan keeps getting hit. Eventually the board stops asking, because they've learned what you'll say. The cost is the company you never found out you could build, and there's no line for that in any report you'll read.
If you read his objections and heard your own voice, you know what the problem is. Nobody in your building is going to take those reasons apart one at a time, because nobody in your building is paid to. That's the conversation I have with CEOs, the one where the reasons run out and you finally see what was sitting underneath them.
This week, put your current plan on one side of a page and write the ten-times version, over three years, on the other. Don't make it sensible. Underneath it, list every reason it can't happen, and next to each one write whether you've checked it or assumed it. Count the assumed ones, and don't do anything with that number yet.
- When did you last call a plan aggressive, and who actually told you it was?
- If your board offered you more investment tomorrow, what reason would you give for not taking it, and would that reason survive one honest question?
- What are you protecting that was never really at risk?