Spyware for the team trust

When my agency was small enough to fit in one room, I had the best monitoring system in the world: my legs.

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I'd walk up to a designer's desk, lean over, look at the screen. "What are you working on? Show me." Then I'd wander over to a developer, ask the same thing. Sometimes I'd sit down next to them and start giving advice — how to do it better, what I'd change, what I'd seen on a similar project. Then I'd drift to the next desk. I told myself this was leadership. Being involved. Caring about quality. Understanding what my team was doing. And when we were eight or ten people, it felt natural. Like a small workshop where the master walks around checking everyone's craft.

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Then we hit thirty. Moved into a bigger office. Multiple rooms. I couldn't see everyone from where I sat anymore. But I kept walking. Desk to desk, room to room, hour after hour. I didn't count how much time it took. I didn't think about how many people I was interrupting — pulling them out of focused work because the founder wanted to peek at their screen. Then we opened offices in other cities. And I couldn't walk anywhere.

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The itch that almost broke me

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That's when the anxiety started. Not a little worry — a physical, grinding itch. I'd sit at my desk thinking: what are they doing right now? Are they working? Are they on their phones? Are we paying someone to sit there and do nothing?

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When someone didn't respond to a message within twenty minutes, my mind would spiral. Maybe they're not working. Maybe they never were. Maybe we've been paying for an empty chair this whole time. I started calling people individually. Writing messages. Asking for updates at random times. Each interruption cost them focus and cost me time, but I couldn't stop. I needed to know. I needed to see.

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Then we hired remote workers — people who didn't go to any office at all. No manager could walk by and check if they were even at their computer. And I started looking at monitoring software. The kind that takes screenshots of your employees' screens every few minutes, like the tools on Upwork and Elance back then (where I actually took that idea) that prove contractors are actually working.

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I was this close to installing it. And then I remembered something that stopped me cold.

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The founder I never wanted to become

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I started my career as a freelance designer. Years before any screenshot tools existed. Nobody watched my screen. Nobody tracked my minutes. I had deadlines and obligations, and sometimes that meant working at two in the morning to finish something — but I delivered. Because that was the deal.

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And the reason I started my own agency in the first place was to get away from a toxic boss. Someone who micromanaged, who treated people like interchangeable parts, who made the office feel like a surveillance state. I left because I hated it. And I promised myself: I'll build a place where people actually want to work. Where they're trusted. Where nobody breathes down their neck. Now here I was, about to become that exact boss. Different tools, same energy.

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So I sat with the conflict. On one side: the itch. The genuine, painful need to know what everyone was doing at every moment. On the other side: the kind of company I actually wanted to build — and the kind of company talented people would choose to stay at. I couldn't have both. Screenshot monitoring and a culture of trust don't live in the same house.

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What I chose instead

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I made a rule. Said it out loud to the team, made it official. The words were simple: "I don't care when you do the work. I don't care how you do the work. What matters is that it's done on time, the client is informed, and everything is coordinated with your project manager." If someone wanted to take a day off — fine, as long as the PM knew, the client was covered, and nothing slipped. We built flexible schedules: each person agreed upfront whether they worked from the office, hybrid, or fully remote — and during which hours they'd be available. Within those boundaries, freedom.

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Then we introduced Friday status updates. Every project manager sent a written email — copied to me and relevant leads — covering project statuses, any risks, client communications, schedule changes, decisions they'd made. Not a call. An email. I could read it when I had time, comment where needed, and move on.

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The key part: I gave PMs the authority to make those day-to-day decisions without asking me. That first rule — "I don't care when, as long as the client is covered" — was really a delegation of power. The PM could approve a day off. The PM could adjust a timeline. The PM could handle client communication. I didn't need to be in the middle of every small decision anymore.

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And the itch? It went away. Not immediately — it took weeks. But once I had those Friday emails landing in my inbox, something shifted. I didn't need to know what every developer was doing at 2:15 on a Wednesday. I needed to know that projects were on track, clients were informed, and problems were being handled. The status updates gave me that. Everything else was noise. What surprised me most was the culture that grew from it. When people knew they had real freedom — and that freedom wasn't being tracked or monitored — something unexpected happened. Some of them, when they finished their work early, would come to me or their PM and say: "I have free time. What else can I help with?" Not because anyone pressured them. Because the culture made them want to contribute.

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And when difficult conversations did come — because they always do — I had something better than screenshots. I had clear agreements and documented outcomes. "You committed to this deadline and this result. Here's what actually happened. Let's talk about why." That's a real conversation. Not "I saw you weren't at your desk at 3pm."

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Something to try this week:

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If you're feeling that itch right now — the "what are they even doing" anxiety — ask yourself: is the problem that you don't know what they're doing minute by minute? Or that you don't have a weekly rhythm that shows you whether things are on track?

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Try one thing: ask each person who reports to you to send a short written update on Friday. What they worked on. What's on track. What's not. One email. Takes them ten minutes. Read it over the weekend. See if it changes how Monday morning feels.

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So here's my question: are you still walking desk to desk — physically or digitally — checking what everyone is doing? And what would it take for you to stop?

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P.S. I never installed that monitoring software. Best decision I almost didn't make. The developers and designers who stayed with us for years told me later that one of the main reasons they didn't leave for bigger companies with higher salaries was the freedom. Turns out, not watching people is a competitive advantage. Who knew.