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Lesson 2: Ride Along Operations Leadership Habit

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Stop Reading Reports. Start Watching the Work. (A COO’s Most Underrated Habit)

 

If you really want to know what’s breaking your operations, skip the meeting. Grab a chair and sit beside the person/people actually doing the job.

 

There’s a kind of leadership that stays locked inside dashboards, PowerPoints, and endless boardroom talks. Executives debate strategies. They scrutinize reports. Big decisions happen upstairs. Yet, way below all that, the real work is going on – messy, unpredictable, and never quite matching the nice, neat stories the reports tell.

 

I made the classic mistake early on as COO: I put too much faith in summaries. I’d pore over a report, spot what looked like the issue, and immediately start fixing it – basing all my decisions on data that, honestly, was just a polished version of what was really happening.

 

Then I started doing ride-alongs, actually shadowing people on the floor. And surprise!!! Almost everything I thought I knew turned out to be wrong.

 

Here’s the core idea: 

If you want to find the truth about your operations, talk to the people doing the actual work.

 

As execs, we’re used to talking about problems from a thousand feet up. That’s part of the job. But the real feel of an operational issue is the workarounds, the things left unsaid, the stuff that never makes a report but lives with the folks on the ground. It’s there with the support rep handling a tricky ticket. The operator working through a clunky process. The manager quietly patching up problems that should’ve been fixed last year.

 

The most valuable habit I picked up was embarrassingly basic: just sit with the people doing the work.

 

No conference room, no detailed agenda, none of that performance review tension. Just me, watching – asking questions only when invited. You’d be shocked at what a single hour of real observation can show you that six months of reports never do.

 

A Story That Stuck With Me

 

One company I worked with saw a spike in customer complaints. Leadership quickly decided it must be an “expectations” issue-customers asking for things we just couldn’t deliver. The plan was to redo onboarding, spell things out more clearly, and hope for the best.

 

Before we jumped in, I asked to sit with a support rep for an hour.

 

Ten minutes in, the real problem jumped out. To answer a single customer question, this rep had to juggle five different systems. One for the account. Another for order history. A third for billing. A fourth to check shipping. And finally, a fifth just to respond. Every customer chat took as much tech gymnastics as a mini ‘IT project’.

 

The truth? People weren’t upset because their expectations were off. They were mad because it took forever to get a simple answer. And the rep, who was sharp and quick, kept getting tripped up by a process clearly designed by folks who never worked in support themselves.

 

We overhauled the workflow. Fewer tools, less switching, one simple interface.

 

What changed?

      Response times dropped fast

      Customer satisfaction shot up

      Support team burnout, even though no one had talked about it, started going down

 

We didn’t add staff. No one needed retraining. The people were never the problem. The system was.

 

How to Go on Your Own Ride-Alongs:

This is seriously one of the most valuable things you can do as a leader in just three hours. Here’s how:

 

Set up three ride-alongs, an hour each. 

Cover three angles:

1.    A frontline worker-the person actually doing the core job 

2.    A middle manager-the one turning strategy into action 

3.    A customer-facing role-the folks who hear it straight from the customer

 

Your only job: observe. Don’t coach. Don’t fix. Don’t overexplain why you’re there. Just watch. Pay attention to the slowdowns, the heavy sighs, or when someone quietly opens a spreadsheet labeled “workarounds.”

 

At the end of each session, ask one thing: “What’s the one thing making your job harder than it needs to be?” Then just listen.

 

What I’ve Learned

 

Reports are helpful, but they’re only a filter. They leave out the messy edges. The biggest disconnects between what’s supposed to be happening and what actually is? That’s where most of your operational problems are hiding. And the only way to truly see the gap is to look right at it.

 

I wasted so much time trying to solve problems I’d never really seen. I let myself get fooled by the summary, not the system.

 

Now, before I build, change, or cut anything, I watch it happen first.

 

That’s how you speed things up in the long run. The people closest to the work will always show you what the data can’t.

 

So, when was the last time you sat beside someone doing frontline work? If you can’t remember, maybe that’s your first move this week.

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