I looked around recently and realized something that made me uncomfortable. The people on my team—people I hired for their expertise, their opinions, their ideas—were waiting for me to tell them what to do.
Not all of them. But enough of them. And the ones who were waiting? They used to push back. They used to have opinions. Somewhere along the way, they stopped.
I didn’t yell at anyone. I didn’t shut anyone down. I never once said “that’s not how we do it.” But I failed them anyway.
Here’s what I think happened.
When someone joins a team, you give them tools. Software, dashboards, processes, playbooks. They learn the tools. They get good at the tools. And slowly, without anyone noticing, the tools become the ceiling.
When something breaks, they don’t ask “what do I need?” They ask “what can I do with what I have?” And when what they have isn’t enough, they just work harder. More hours. More calls. More of the same thing that isn’t working.
I watched a team send thousands of messages with almost no response—and their solution was to send more messages. They weren’t lacking intelligence. They just couldn’t see past the edges of what we’d given them. The tools defined the boundaries of their thinking. And I never broke them out.
That’s on me.
I’ve started thinking about teams in three categories: dreamers, makers, and doers.
Dreamers live in the theoretical. They ideate, they see around corners, they make everyone uncomfortable in the best way. But they’ll also commit you to things that don’t exist yet if you don’t put guardrails around them. Dreamers need a filter or they’ll overextend the whole company before anyone realizes what happened.
Makers see a problem and fix it. They don’t wait for permission. Engineers are makers. Some founders are makers. The danger is they’ll fill every vacuum—they’ll become everyone else’s doer because waiting is painful when you can just build the thing yourself.
Doers execute. They run the playbook, make the calls, keep the machine running. They’re essential. And they’re the ones I failed.
Because a doer without ideas isn’t a hiring problem. It’s an environment problem. I created an environment where the path of least resistance was to stay inside the lines. Nothing asked them to think bigger. Nothing gave them room to experiment. So they fell into patterns—not because they lacked capability, but because nothing demanded more.
What I actually needed was doers with ideas.
People with domain expertise who could say “I want to run a test where we change this one variable and measure that outcome.” Not dreamers who live in theory. Not makers who’ll just do it themselves. Doers who understand their function well enough to know what questions to ask.
The difference between a doer and a doer with ideas is this: one says “we tried everything, nothing works.” The other says “what if we tried this for three days and measured what happens?”
I had people who could’ve been the second type. I just never gave them anywhere to go with it.
So now what?
I don’t have a clean answer. But I know what I’m looking at differently.
When someone seems stuck, I’m asking what we’ve actually given them to work with. Not just tools—room. Can they experiment? Do they have any levers that aren’t the same five they’ve been pulling for years? If not, I built the cage.
When I hire doers, I’m hiring for curiosity. The ones who ask “why do we do it this way?” before they ask “how do I do this?” are the ones who won’t disappear into the constraints.
And I’m watching the makers—myself included—to make sure we’re not filling every gap just because it’s faster. That’s not leadership. That’s just doing everyone else’s job and wondering why they stopped trying.
I don’t know if I can undo what’s already happened with some people. But I see it now. And that’s the first step to not doing it again.