You Can't Fix What You Don't Understand

The Trap at the Top

There's a version of leadership that looks like this: you sit in the meetings, you review the dashboards, you manage the outcomes. You are, by every visible measure, in charge. And you have absolutely no idea what your team actually does all day.

I don't mean that as an insult. I mean it as a trap — one that's easy to fall into, especially the further up you go. The more senior the role, the more you're expected to operate at altitude. Strategy. Vision. Stakeholder management. And somewhere in the climb, a lot of leaders stop looking closely at the work. They start managing the results of problems they've never actually seen up close. That's how things stay broken.

Knowing About vs. Understanding

There's a distinction I think about a lot in leadership, and it's the difference between knowing about a problem and understanding it.

Knowing about a problem means you've seen it on a report. You've been briefed on it. Someone has summarized it for you in a slide or a Slack message, and you've acknowledged it exists. A lot of leaders stop there — and genuinely believe they've done enough to eventually fix it.

Understanding a problem means you've gotten close enough to see how it actually works. Where it starts. What feeds it. Who runs into it every day and what it costs them. What the downstream effects are that nobody put in the summary. Understanding requires proximity. It requires a willingness to go below the altitude and look at what's really happening at the level where real people are doing real work.

Most organizations are full of problems that are known and not understood. They show up in dashboards. They get named in planning cycles. People agree they should be fixed. And then they sit there — for months, sometimes years — because the leaders accountable for fixing them have only ever seen them from a distance.

"You cannot design a real solution for a problem you've only seen from above."

How Leaders Build Real Credibility

This is also, I'd argue, one of the most underrated ways to build trust with your team. When a leader takes the time to actually understand what their people do — not in theory, not from a job description, but in practice, at the level of daily friction and real workflow — something shifts. The team feels it. They see a leader who cared enough to look. Who didn't parachute in with a solution built from assumptions. Who asked questions before prescribing answers.

That's not a soft leadership concept. That's the foundation of credibility. Your team will follow someone who understands their world. They'll comply for someone who doesn't — and there's a significant performance gap between those two things.

Understanding the work is also how you protect your team. If you don't know what they're navigating, you can't remove the obstacles in front of them. You can't tell the difference between a people problem and a systems problem. You can't advocate for what they actually need. Leaders who don't understand the work often create more friction than they eliminate — not because they don't care, but because they're building solutions for a problem they've only seen on a slide.

The BeyondTrust Story

When I was at BeyondTrust, there was a known problem sitting right in the middle of the quote-to-cash process. Purchase orders were coming in — deals closed, customers ready — and a significant number of them were being put on hold. Something was wrong in the order, the quote, or the contract. And instead of catching it early, we were catching it at the end, right when the customer was expecting delivery. Everyone knew about it. Nobody had dug in.

I was in a position to dig in because six months earlier, I had built the deals desk from the ground up. I didn't learn how quoting worked — I wrote the playbook for it. I designed the workflows, defined what a clean deal looked like, built the team that would run it. So when I later took on order management, I already knew exactly what was coming out of the quoting side. What I was doing was connecting two ends of the same process — a brand new team I had built, and a tenured team that knew where every problem lived — and getting them to actually talk to each other.

What we found wasn't one problem. It was a system of small problems that had compounded because nobody had looked at them together: quoting errors that created downstream chaos, unclear authority levels that left team members waiting on decisions they should have been empowered to make, handoffs that were never confirmed clean, and no shared definition of what 'ready' looked like before a deal moved forward.

None of it was unfixable. All of it required understanding it first. We documented procedures, clarified authority, built structured checkpoints between teams, and fixed quoting issues at the source.

That result didn't come from a strategy session or a dashboard review. It came from getting close enough to actually see what was happening.

You Can't Fix What You Don't Understand

The problems that sit the longest in organizations are almost never unsolvable. They're underseen. They've been measured, reported on, and acknowledged — but nobody has gotten close enough to truly understand them.

Understanding the work isn't about losing yourself in the weeds or doing your team's job for them. It's about earning the right to lead the work. It's about knowing enough to ask the right questions, see the real friction, and build solutions that actually hold.

"If something in your organization has been broken and staying broken, ask yourself honestly: have you understood it, or have you only seen it from a distance?"

With passion, there is possibility.