The most expensive conversation you’re not having
There’s a moment I’ve seen play out more than once. I’m sitting with a leadership team. Confident people, genuinely smart, with a strategy they’ve spent months shaping. They walk me through the plan. It’s coherent. It’s well-presented. And somewhere in it is an assumption about how the business operates that I’m fairly sure isn’t true.
So, I go and talk to the people doing the work.
It doesn’t take long. Usually, one or two conversations are enough to find it. A process that works on paper but has had an unofficial workaround in place for 2 years. A customer complaint pattern that everyone on the front line knows about, and nobody has escalated because it doesn’t feel like their place to. A product feature the team has been quietly steering customers away from because it causes more problems than it solves.
When I bring this back to the group, the response is almost always the same. There’s a pause. Then someone says something like “yes, we’re aware of that”, and the conversation moves on.
That’s the moment that interests me most.
The open-door myth
Ask most leaders whether their team can come to them with problems, and they’ll say yes without hesitation. And most of them mean it. The door really is open. The issue is that an open door doesn’t create a safe conversation. It just removes one physical barrier.
The person on the front line is doing a calculation every time something goes wrong. Is this worth raising? Will it change anything? Will I look like I’m complaining, or worse, like I’m criticising a decision someone senior made? Most of the time, the rational answer to all three questions is no. So, they don’t raise it. The insight stays where it is.
Leadership interprets the silence as confirmation. Everything must be fine. If it weren’t, someone would have said something.
What happens to intelligence on its way up
When frontline insight travels upward, it passes through layers. A team leader hears it, filters it, decides what’s relevant, and passes on a version. A manager does the same. By the time a pattern reaches the boardroom, it’s been translated so many times that it barely resembles the original observation.
Some of this filtering is reasonable. After all, you can’t surface every operational detail to every level. But a lot of it is cultural. People learn quickly what kind of information their organisation rewards and what kind it tolerates. Bad news, complexity, and contradiction…these tend not to travel well.
What travels well is information that confirms the direction of travel. Positive data. Progress reports. Evidence that the strategy is working.
The real barrier is prior commitment
Here’s the thing I keep coming back to. Most leadership teams don’t ignore frontline intelligence because they’re arrogant or incurious. They ignore it because they’ve already decided.
Once a strategy is in motion, the budget is allocated, the team is aligned, and communications are sent, the cognitive work has been done. The plan is the answer. Incoming information gets evaluated against that answer, not alongside it. Evidence that supports the strategy is useful. Evidence that contradicts it is a problem to be managed.
I sat with a senior team once who’d been running a customer experience programme for the better part of a year. Significant investment. Real effort. The metrics they were tracking looked encouraging. But when I talked to the people delivering it, a different picture emerged. Customers were responding well to the parts of the programme that were already working before the initiative launched. The new elements were causing friction. Nobody was saying this upstairs because the programme was a leadership priority and the quarterly review was coming up.
The team wasn’t hiding anything malicious. They didn’t want to be the person who complicated a success story.
The cost stays invisible until it doesn’t
The uncomfortable thing about this pattern is that it doesn’t feel like failure in the moment. The business keeps moving. Reports are produced. Targets are hit or narrowly missed. The gap between what leadership believes and what’s actually happening compounds quietly.
It shows up eventually. In customer churn, nobody can fully explain, in a competitor who somehow understood your customers better than you did, in good people leaving and saying they felt like they weren’t heard. By the time it’s visible, the gap has been there for years. And the question of when it started is usually unanswerable, because the information that would have pointed to it was there; it just never made it into the right room.
The question I’d leave you with
Think about the last time someone on your team who is closer to the customer than you are told you something that complicated a decision you’d already made.
What did you do with it?
If you have a clear answer, that’s useful information. If you’re not sure, that might be even more useful.
The insight isn’t usually missing. The question is what happens to it upon arrival at your door.
Have a brilliant week!
Dave Rogers, The Business Explorer
If this struck a chord, my Substack goes further on the same questions. Want help applying any of it to your business?
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