"How long? Who many?"
Jul 23, 2026
Last week, in an offsite with a leadership team, one of the team said something that struck a chord in the room:
"I want us to be a collaborative team. But we need to be okay with not bringing stuff to the table that doesn't need everyone here. We chew up too much time having conversations that really don't need our collective attention."
A few heads nodded. Then another leader added: "If I'm honest, I'm cautious about bringing some things to the room, because I'm scared that raising it will open up a conversation we simply don't need to be having."
That's the cost nobody talks about when leadership teams collaborate on everything by default: silence. Not the noisy kind of dysfunction. The quiet kind, where important stuff just stops getting raised.
So here's a pair of questions I've started offering leadership teams, so people can manage the things that get raised at the table with more confidence, not less:
"How long? Who many?"
"How long" is the easy one to explain but seemingly hard to do. Are we giving this five minutes? Fifteen? Forty? Time-boxing conversations forces you to be honest about what you're actually trying to achieve. And sometimes the honest answer is that today isn't the day... which is useful information, not a failure.
"Who many" - deliberately broken English - is really just asking: does this need everyone, or a few of us? Because the common problem in most leadership teams isn't too little collaboration, it's too much of it, by default. Someone quiet gets crowded out by a couple of louder, less-informed voices. People stop bringing things to the table at all, because they know the moment they do, everyone's hands are on it.
I catch myself in this too, even as the person whose job is to watch for it. A topic gets energy in the room and part of me wants to let them run with it. But that's exactly the trap I'm meant to be watching for in everyone else... by the time I've noticed, I've usually lost track of how long we've been in it. And so I jump in with: "Can we just pause for a second… How long? Who many?"
I wrote a while back that the real question for many leadership teams isn't "are we dysfunctional"; it's whether you're doing the work leadership teams are meant to do, or just boring each other with status updates. "How long, Who many?" is one way to force that question before anyone's said a word, and make sure the right few people are actually in the room to do it.
Go back to the leader who admitted they're scared to raise things that don't need everyone here. That's not a confidence problem. That's a deployment problem - a fear that we’ll use our time together in the wrong way. What if instead they said: “I’m sharing this with you as a 5 minute update, tops. This is a summary of a much more comprehensive debate happening in another forum, with select stakeholders.”
If you’re the one running a meeting: you can ask "How long? Who many?” before the topic gets airtime. If you're in the room: you don't need to be the leader to ask it - jump in as soon as you see the need to calibrate.
What’s the next opportunity you have to use the "How long? Who many?” questions to rightsize a conversation?
Until next time,
Simon
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