What nine years of field operations taught me about leading people

June 2026 · ~6 min read

Field operations leadership is one of the most under-romanticized jobs in business. Nobody writes books about it. There are no popular podcasts. The work is unglamorous on its face: rental counters, fleet ops, branch managers, KPIs measured in single percentage points. Most of the people who do it well will never write a LinkedIn post about it.

I spent nine years running field operations for a rental company. By the end I was responsible for up to $39.6M in annual revenue across multiple branches in the SF Bay Area. None of the lessons came from a book. They came from showing up at the same branches enough times that the people there stopped pretending when I walked in.

Here's what nine years taught me about leading the kind of team that does the actual work.

You can't manage what you won't walk through.

Dashboards are downstream. By the time the number shows up on a screen, the story behind it is two weeks stale. The fastest way to know how a branch is doing is to walk through it at 3pm on a Wednesday and watch the body language.

I've seen leaders try to run field operations from a desk. It works for a quarter. Then the team learns what you measure, optimizes for those specific metrics, and the actual operation rots underneath.

The job is to be in the field enough that the team doesn't have to tell you what's broken. You can see it.

Coach the manager, not the rep.

When something goes sideways at a branch, the instinct is to fix it yourself. The senior rep made a bad call, the manager didn't catch it, the customer leaves angry. You can walk in, smooth it over, save the day, drive home.

That's the wrong move. Every time you intervene directly, you teach the manager that you'll do their job. Now you have one fewer manager and one more direct report.

The harder move, and the only one that scales, is to coach the manager through how to handle it themselves, even when you could solve it faster. Especially when you could solve it faster.

The worst day reveals more than the best day.

Anyone can run a team when the truck shows up, the staffing is full, and the customer is happy. The actual test is the Friday afternoon when the truck is down, two people called in sick, and a corporate customer is on the phone wanting to know why their delivery isn't there.

Watch your managers on that Friday. The ones who get quiet and calm, who start making decisions instead of asking questions: those are the ones you promote. The ones who get loud, who blame, who deflect: those need more coaching, not more responsibility.

Numbers without context are noise.

A utilization drop is fourteen different things. So is a labor overrun. So is a customer complaint trend. The number tells you something is happening. It doesn't tell you what.

The temptation in operations is to react to the number. The discipline is to ask the manager closest to the work what's actually going on. Most of the time the answer is something a dashboard could never have shown you. Sometimes it's something simple you'd have spent two weeks unable to figure out on your own.

The boring discipline beats the bold initiative.

Every operations team I've seen that struggles is running too many initiatives. Every team I've seen that wins is doing a smaller set of things very consistently.

Hit the daily basics. Pre-shift huddles. Customer touch points. Branch walkthroughs. Closeout. Don't add anything new until those are clean. The team that does the basics consistently for a year will outperform the team running ten experiments by a wide margin, and the margin compounds.

Give people what they need, not what you'd need.

Different people need different things to do their job well. Some need autonomy and a check-in every quarter. Some need a check-in every week and detailed feedback. Some need direct coaching. Some need space.

The leader who imposes one style on everyone is solving a problem they invented. The harder skill is figuring out what each person actually needs, which is usually different from what they'd say they need, and giving them that.

The last thing.

None of this is original. None of it is rocket science. But the people who actually do it well, year after year, with the same kinds of teams, in the same kinds of operations: they're the ones running the actual economy. Trucking, logistics, retail, healthcare, hospitality, the rideshare fleet I run now.

When I moved from rental into rideshare fleet operations, I assumed the work would be different. It's not. The vehicles are different, the customers are different, the language is different. The leadership is the same.

If you're hiring for someone who's going to run a team that does real work, the question isn't whether they have the right vocabulary. The question is whether they've spent enough time on the floor to know what the floor sounds like when it's running well, and what it sounds like when something's wrong.

That's what nine years of field operations taught me. Everything I do now is built on top of that foundation: leading a fleet team, running side businesses, building tools for the operation.