The Call Always Comes Too Late

Welcome to the first installment of Notes from a Cleaner’s Desk—a multi-part series sharing the gritty details of what really happens when you’re the one called in to fix the mess. In every job I’ve had, in every company big or small, I somehow end up in the role of “the cleaner”—the person who walks into chaos, tries to make sense of it, and sets things right enough that everyone can breathe again. The reference comes from my love of (mostly) 90s action films. Think Winston Wolfe in Pulp Fiction or Léon from La Femme Nikita: they’re called in when things have gotten…messy.

My line of work doesn’t quite require those particular skills, but I am called in when the wheels are long gone, the team’s stuck between promises and reality, and they need muscle to set things back on track.

This series is about those moments. The patterns that repeat. The failures nobody admits out loud. And the quiet lessons that emerge when you’re the one sweeping up the broken pieces and trying to rebuild a working system.

Which brings us to the first universal truth:

The call always comes too late.

Ambition Meets Reality (and Reality Loses)

Years ago, I worked in an embedded advertising team for a giant technology company. We built interactive ad experiences for the then brand-new “modern desktop.” It was a time when everyone was trying to reinvent the way people navigated their devices—tiles, gestures, apps, motion, all of it. That ambition extended into advertising opportunities too, because when you introduce a shiny new platform, your ads need to have those new capabilities too.

Our organization had three main groups working together: a sales team who brought in major global advertisers, a creative team who acted like an internal ad agency, and a tiny engineering team—four engineers, one tester, and two program managers—responsible for bringing everything to life.

Sales overperformed. They landed dream clients—big global brands with deep pockets and high expectations. Creative responded exactly as you’d expect an ad agency to respond when handed huge logos and a new medium: they pitched moonshots. Big, cinematic, futuristic ideas.

One concept in particular became almost metaphorical in its absurdity. They pitched something straight out of Minority Report—Tom Cruise waving his hands in the air while an entire interface bends to his will. The creative team told one of our advertisers that users would be able to sweep through the ad experience with that same fluid, sci-fi responsiveness.

It was imaginative. It was bold.

And it was absolutely impossible.

The platform didn’t support anything close to that. The hardware didn’t exist. The engineering team would’ve needed years—not weeks—to build even a fraction of that functionality.

But Creative didn’t pitch what was possible. They pitched what looked cool. And Sales didn’t sell constraints; they sold excitement.

Engineering—who had not been included in those conversations—was now being asked to perform a miracle.

And that is when someone finally said, “Who’s gonna clean up this mess?”

Walking Into the Fire With No Map

A cleaner doesn’t get to ease into the problem. You’re thrown into the deep end and expected to diagnose while you’re still underwater.

The first question I always ask is, What exactly have we promised?
And not a single person could answer it.

Not because they were hiding anything—but because no one had a complete picture.

There were contract documents scattered across folders and inboxes, creative assets living in four different versions of the truth, engineering notes scribbled in private files, and a growing sense that there were too many projects stacked on top of each other for anyone to see cleanly.

That tiny engineering team was already heads-down building foundational components the platform would need. They were juggling work that served multiple clients at once, trying to create the technical underpinnings for these gorgeous, impossible concepts. Meanwhile, Creative kept sending new assets, new requirements, new “wouldn’t it be cool if…” requests. And Sales kept feeding in new timelines the engineering team had never agreed to.

There was no single narrative.
No consolidated understanding.
No shared sense of what “done” even meant.

So the first thing I had to do was just… see it. All of it. I sat down and untangled every project, every deadline, every promise, every dependency. And once the full picture came together, the truth was harsh and simple:

A team of four engineers was on the hook to deliver twenty to thirty complex, custom, interactive ad experiences—on a brand-new platform—within thirty days.

No human team could do that.

And yet, we were on the hook for exactly that.

Changing the wheels on the bus as it drives down the road

Once you understand the scope of the mess, the next job is to reclaim the story. In an overcommitted, misaligned system, every group creates its own version of reality.

Sales tells the client one story.
Creative tells Engineering a completely different one.
Engineering keeps its head down because speaking up feels pointless.

So I stepped into the center and became the single point of integration—the clearinghouse for every requirement, every change request, every risk, and every question. Not because I enjoy centralizing control, but because the system had become unmanageable without it.

Then came the cold reality of expectation-resetting.

I had to go back to Creative and talk plainly about what the platform could actually do. They had envisioned beautiful cinematic moments, but we needed to reroute those ideas into something technically feasible.

Creative needed to recalibrate what they told Sales.
Sales needed to recalibrate what they told the client.
And I needed to protect Engineering so they could stay alive long enough to deliver anything at all.

These conversations were not fun. They were not quick. They were not one-and-done. They required pulling people back to reality without crushing their creativity or undermining their credibility. And at every step, we had to reinforce that this wasn’t about who was right—it was about what was possible.

We eventually got to a shared view of the work, but only because someone finally forced all the threads into one story.

Stitching the Team Back Together—Just Enough to Survive

Here’s the part people don’t like to talk about: very often, when a cleaner is brought in, the technical mess is just a symptom. The real wound is cultural.

This team struggled with the basics of working together. There was very little trust. People weren’t aligned around shared rituals, shared goals, or even shared definitions of success. Relationships were strained or nonexistent. We didn’t even have meetings together. And leadership, frankly, wasn’t prepared to tackle the deeper misalignment.

But we got the work done. We delivered every project. Some were late. Some were barely held together with duct tape and grit. But every client got something they wanted. Maybe not all they were promised, but enough.

That’s what cleaners do. Just enough to set things right. 

But stabilizing isn’t the same thing as healing.

What this team truly needed was leadership alignment, cultural repair, shared vision, and a real operating model—none of which were in place, and none of which the organization was willing to slow down and build. They wanted relief, not transformation.

So yes, we survived the immediate crisis. But the system didn’t evolve. And eventually, predictably, it unraveled.

The Real Lesson: Bring the Right Voices In Before You Need a Cleaner

If there’s a lesson here, it’s not “Creative should stop dreaming” or “Engineering should work faster” or “Sales should be more careful.”

The lesson is much simpler:

If you’re making commitments on behalf of another team, they need a seat at the table.

If you’re thinking about cool things, collaborate with technical teams to understand what’s feasible. If you’re designing an experience, invite Creative to shape the feel and flow. If you’re negotiating with a client, bring all dependent groups into the room so they hear the stakes and the constraints firsthand.

This isn’t about hierarchy. It’s about collaboration and respect.

Know your lane.
Know your partners’ lanes.
And remember that all of this—every pitch, every line of code, every creative flourish—is ultimately in service of someone outside your team.

If you work that way, you won’t need a cleaner to force accountability. The team becomes accountable to itself.