Boulders and Trails
Is there an employee problem in your company that everybody knows about and nobody touches? Maybe it's a manager who's brilliant with clients and quietly brutal with their team. Maybe it's two departments that have been at war so long the war is just the weather now. Maybe it's one employee whose performance fell off a year ago and everyone has silently agreed to work around. Whatever it is, it's been there long enough that the company has organized itself around its existence.
I think of these as boulders. It’s part of my work. I notice the big rock sitting in the middle of the path. And here's what employees do with boulders. They don't move them. Moving them is hard, unpleasant, and might involve a conflict they prefer to avoid. So instead they build little trails around them. A workaround here, a side channel there, an unspoken rule that you just don't put those two employees in a room together. Over time the trails get worn smooth, and the boulder becomes invisible, just part of the landscape, until a new employee shows up and asks the obvious question: Why is there a giant rock in the middle of this particular path? And everyone looks at them like they “just don't understand how things work around here”…followed by an eyeroll.
The trails can feel like wisdom. They feel like being practical, like picking your battles, like not making waves. But add them up and they're enormously expensive. Every workaround is a small tax you pay forever. The brilliant-but-brutal manager costs you a quiet stream of good employees who leave rather than be managed by them. And, you never connect the resignations to the cause because the manager hits their numbers. The two warring departments cost you every handoff, every duplicated effort, every project that takes twice as long because the two halves won't talk. You've decided the boulders are cheaper to live with than to move. I’ll bet you’ve never actually done that math.
Here's the thing about the math, and the thing most leaders never stop to consider. The difficult conversation everyone is avoiding usually carries a finite cost. It may create tension for an afternoon, a difficult week, or even a challenging month. But eventually, it is resolved. The workaround is different. It continues to extract a price long after the discomfort of the conversation would have passed. It shows up in turnover, delays, duplicated effort, strained relationships, and opportunities that never quite materialize because employees have learned to work around the problem instead of addressing it. Over time, organizations convince themselves the boulders are cheaper to live with that to move. In reality, they often choose the more expensive option simply because the cost arrives in small, easy-to-ignore installments rather than all at once.
I'm not going to pretend the difficult conversation is easy, because it isn't. And anyone who tells you it is hasn't experienced enough of them. Confronting the high-performing manager about how they treat employees is genuinely hard. Telling two senior leaders their feud is costing the company real money is genuinely hard. But hard isn’t the same as expensive, and companies confuse the two constantly. The conversation is hard. The boulders are expensive. Those are different currencies, and we keep paying the expensive one to avoid spending the hard one.
So the next time you catch yourself building a trail, stop and look at what you're walking around. Name the boulder out loud, even just to yourself. Then do the small brave math. What is this workaround actually costing me every week in employees, time, and the slow erosion of everyone watching me not deal with it?
Because they are watching. Every boulder you refuse to move teaches your best employees exactly what gets tolerated here, and that lesson costs you more than any single conversation ever could.
You don't have to move every rock today. But you have to stop pretending that traveling those trails is cost-free. It isn’t. It never was.