A founder I was meeting with started going off on a tangent. We were maybe ten minutes into our agenda, and they were venting about something that wasn’t technically on it.
I didn’t pull them back.
If you watched that meeting, you might’ve thought I’d lost the thread. That I’m not great at keeping people on track. But I let it go there on purpose.
A tight agenda can feel safe, maybe calming. You know exactly what’s coming and are confident that you’ll cover everything you need to. But it can also be limiting.
Five minutes on this, timer goes off, move to the next thing. Very tidy. But you walk out having never heard what you actually needed to hear.
So sometimes I hold my talking points loosely. I know what we need to cover, and I’m tracking it mentally. But I’m confident enough in my ability to navigate a conversation that I let it go where it wants to go. Because the tangents are where I hear thoughts, stories, nuances, unfiltered opinions, and all the context.
And with a founder who’s fried, letting them vent or share what’s weighing on them can uncover the business pain points that need addressed that you’d never get if you just asked them a direct question.
One founder was frustrated and venting that everyone pings them for answers they could find on their own. Off the agenda, it sounds like a small complaint. But sit with it for a second. It tells me the team can’t operate independently. That they’ve become the bottleneck for every little thing. It even points me to the role that would actually take the weight off.
That one tangent led to key information that can help me improve their operations and keep the founder sane. And I only got it because I didn’t cut them off to stay on schedule.
That’s the game I’m playing. I’m not trying to run the perfectly ordered meeting. I’m trying to extract insights that help me uncover and solve operational issues.
Structure should make room for that, not shut it down.
I still cover everything on my list. I’m just not precious about the order. Some of the most useful things I’ve ever learned about a business came from the five minutes we “weren’t supposed to” spend there.
What’s a meeting you keep on a tight leash that might benefit from loosening up a little?
- Valentina
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"Emotions as Data, Not Directives" — Susan David (Article). David's entire framework lands on the exact idea this issue is built on. Emotions are data, not directives, one data point to mine for what you care about, and labeling them accurately is what lets you take the right next step. A founder venting that they're drowning isn't being unproductive. They're handing you the most accurate read you'll get on what's broken.
"Never Split the Difference" — Chris Voss (Podcast). Voss is the FBI-negotiator origin of "let them talk first." His tools, mirroring back their last few words and labeling the emotion out loud, are how you move someone from a vague complaint to the real thing underneath. The goal isn't agreement, it's getting them to say "that's right." Then you can actually help.
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