Get in the Weeds

There are two great, yet entirely avoidable, failings I see in executives. One is not taking time to speak one-to-one with people across the organization, especially those closer to the front lines. The other is becoming so distanced from the day-to-day work that they develop a blind spot to how things actually get done. The two go together.

The failing is understandable. Executives are busy. As businesses grow, it’s incumbent on leaders to delegate and count on people to run the business. A founder who can actually do this is showing a mark of quality. I regularly see founders and senior execs who cling to details they should let go of, failing to do their real jobs and frustrating their deputies in theirs.

And yet the separation can go too far, especially in times of stress or fast growth. In larger companies, executives may have come up through non-operational roles (like sales or finance) and never developed fluency in the nuts and bolts of delivery. Whatever the reason, there are real disadvantages to being non-conversant in operations. Whether you call it “operations” or “customer success” or “product support,” the way a business runs directly impacts customer retention and operating margin. When you’re not in tune with it, you can find yourself in deep water without knowing how you got there.

Why processes lag

As a business evolves, its ways of working need to evolve with it. But in most businesses I’ve encountered, this is rarely the case. Processes are, legitimately, hard to change once they take root.

Part of it is that operational improvement requires broad and deep command of technical, functional, and customer detail. Most companies don’t tackle operational improvements as they present themselves, but as “big bang” changes that require a lot of time and energy. In an ideal world, improvement doesn’t come from big bangs, but from small changes made every day—from marginal gains that are negligible in the short term but compound significantly over time. I’ve led functions that improved operating margin by three to five points over a year, but it took a solid year of effort to get there.

Part of it is that change is psychically taxing. It is hard enough to get people to start working one way; getting them to stop the old way and start the new way is doubly so. Then there are questions of agency and permission: who has the authority to decide what changes can be made? do I have that authority? Sometimes changes don’t happen because people have a vested personal interest in clinging on to the status quo.

Finally, nobody ever lets you stop the train to change the wheels. I don’t know a single business that can say “ok, let’s stop for a few months while we put these new processes in”.

The result is that outdated or broken processes become a common source of frustration up and down the organization. It’s not that people don’t believe things would be better if the broken stuff were fixed. It’s that nobody feels empowered to fix it.

Where you can step in

This is precisely where you, as a leader, can make a difference.

There is nobody better than the boss to say “this is really important, let’s do this.” Sometimes it takes executive intervention to break logjams or de-escalate turf wars that prevent progress. You don’t need to master the subject—you just need to show up, ask questions, and signal that this issue matters to the business.

And here’s the best part: it takes remarkably little time to get conversant. Walk around the office—literally or virtually—and ask people what are you working on right now? In my experience, within fifteen minutes you’ll learn what works well for them and what doesn’t. Watch how they work. Ask follow-up questions. Do two thirty-minute sessions a week. That’s one hour.

Something interesting happens when you start making rounds. People see you as more connected. Through genuine conversation, they see you as more human—perhaps even worthy of trust. You get a first-hand view of how the business is working, enough to make you conversant in its essential functioning. And where you lack detail, you’ll know exactly who to ask.

The payoff

When you stay connected to the coal face, you catch problems earlier. You spot inefficiencies before they calcify. You understand why certain changes are hard and where the real blockers live. You build trust with people who rarely see executives up close.

And you avoid the most dangerous trap of senior leadership: making decisions about a business you no longer understand.

One hour a week. Start this week.