Leadership & team

Someone on the client’s executive team kept overruling the team every week. The project was about to end... badly.

This was on a long-running retainer. A senior executive on the client side suddenly started showing up to the weekly meeting, looking at decisions the two teams had already worked through together, and overturning them. No context, no discussion. Just “let’s try a different way.”

The agency team was frustrated. So was the client’s own product team, who felt like they couldn’t stand behind anything they’d agreed to. The relationship was heading toward an ending nobody really wanted.

They thought about just firing the client, but I wanted to cut past the frustration and ask some valuable questions.

Do they like the work they’re doing? Yes. Do they like the team they work with? Yes. Does the executive seem like a bad guy? No. Suddenly, this all seemed salvageable.

So instead, the founder ran a full retro with everyone in the room: the executive, the client’s product team, and the agency’s design team. Not a true retro, actually — the project was still under way. Call it a reset.

The most important thing was the order. They let every side speak first and put all the cards on the table. Only after everyone else had said their piece did the founder share their own view.

It changed the temperature of the room. People on the client side who’d been quietly frustrated for weeks—and going behind their own executive’s back—finally said so. And it turned out the executive didn’t have a problem with the work. They just didn’t understand how the decisions were being made, because they weren’t around for any of it.

As soon as that executive got a walk through the process, they were apologetic and even impressed.

The fix was almost boring. The executive joined the team’s channels and came to a couple of working sessions a month. They stopped arriving cold, and the feedback was instantly more constructive.

The project got extended instead of ending.

When projects are mid-flight, it can seem like nothing can change the course. But sometimes, you need to slam your foot on the brakes and wrestle a stray project back on track.

A client cancels this week’s work. What does your team do on Monday?

A client of mine hit a slow stretch recently. Part of it was intentional, because they’d turned down work that wasn’t a fit. Part of it was just summer. Either way, people had nothing on their plate, and the founder wasn’t sure what to do with them. He was worried, because downtime is too easily interpreted by the team as a distressed company.

This is one of those problems that’s much easier to solve before it happens.

What I suggested: ask everyone to bring their own downtime project to the table ahead of time. Not something you assign. Something they choose.

The question is basically this. If you had a free day every week, what would you work on? Ideally it’s something connected to the company, like case studies, an internal tool, or a talk they’d love to give. But it can also be pure skills development.

At a brand studio I worked at years ago, one designer was fantastic at type design. Whenever they had downtime, they worked on a custom typeface we could sell. Nobody had to think about it. The project was just there, waiting.

That way, when a client suddenly pauses, the message isn’t “sorry, nothing for you this week.” It’s “good news, go work on your thing.”

One caution. If downtime is a gap between projects, it doesn’t really matter how much there is, as long as work is coming. But if more than about 20% of your team’s billable time is going to side projects, that’s not a gap anymore. That’s a pipeline problem.

Plan for downtime before it hits.

Ten wins. One slide each. Applause after every single one.

A client asked me how to get the whole team excited at their quarterly all-hands. They had an offsite planned, and they wanted people to leave feeling bought into where the company was going.

The way I’ve always done it is pretty simple. Lead with wins, and really lean into them.

I don’t mean one slide titled “Highlights.” I mean ten big wins: an exciting new client, a great piece of work, someone who went above and beyond, a key new hire. Give each one its own slide. Pause. Let people clap.

It sounds a little corny. It works.

The tricky part is the goals that didn’t go well. If you only talk about the ones on track, people notice what you skipped. But if you put the misses up there with someone’s name next to them, that person spends the rest of the meeting feeling awful in front of their peers.

So I frame misses as opportunities, and I make them the whole team’s problem. Something like: “We didn’t get as many leads this quarter as we wanted. Later today we’re doing a short workshop on it, and I want everyone’s ideas.”

That doesn’t mean nobody’s accountable. It just means accountability happens one on one, not on a stage.

It’s simple psychology, really. Encourage the behaviour you want to see, and find creative ways to correct the rest.

Celebrate in public. Hold people accountable in private.

“Are we working to hit a high standard, or are we working to get his approval?”

Someone on a client’s team asked me that, and I haven’t stopped thinking about it.

I’ve seen this pattern at a lot of agencies. The founder drops into a project, asks for changes, and the result is... almost the same thing. Just done their way.

Nobody means harm by it. Founders usually got where they are by caring a lot about the work. But from the team’s side, it looks like this: you make a call, it gets changed. You make the next call, it gets changed. Eventually, you stop being opinionated and start guessing what the boss wants... instead of what the client wants.

One person put it perfectly: “I’m paid to be creative, but in practice I’m doubting myself the whole time.”

The question I give founders now is simple. Before you step in, ask: is this the company’s standard, or is it just my way?

If it’s the company’s way, great. Write it down. Make it a standard everyone can see, so the next person doesn’t need you to tell them.

If it’s just your way, let it go. You pay a lot of people to make these decisions so you don’t have to. Plus, the outcome probably isn’t worse. It’s just different from how you’d do it personally.

And here’s the bigger fix: if you’re a founder working at the right level, it should be almost impossible for you to micromanage. You should be far enough from the work that you don’t even get the chance.