How mismatched expectations disguise themselves

There's this moment that happens when you're managing your first team. Someone misses a deadline, and you think the problem is them. You give feedback, adjust their work style, maybe check in more often. Sometimes it helps. Usually it doesn't.

Took me about 15 hires to realize I was solving the wrong problem.

The issue wasn't that people needed managing. It was that nobody knew what anyone else expected. I'd assume someone understood the urgency of a project. They'd assume I wanted them to polish it before shipping. We'd both end up frustrated, blaming effort or communication style or work ethic.

But the actual gap? We never agreed on what done looked like. Or when it needed to happen. Or what trade-offs were acceptable.

When someone joins your team, they walk in with a set of default expectations. They're invisible until they clash with yours.

Some people think "end of week" means Friday at 5pm. Others think it means Monday morning is fine. Some people think a bug in production is drop-everything urgent. Others think you fix it in the next sprint. Neither is wrong, but if you don't align them, you get friction disguised as performance problems.

Started tracking this after a project went sideways. Had an engineer who kept missing deadlines I thought were clear. Turned out he thought "we need this soon" meant "when you're done with your current work." I meant "cancel your weekend plans."

We'd both been annoyed with each other for weeks. The gap wasn't in his work or my management. It was in two completely different mental models of what "soon" meant.

After watching this pattern repeat, I started being explicit about three things:

What does success look like? Not the platitude version. The actual version. If I'm expecting a prototype that proves the concept works and they're building something polished enough to show customers, we're going to have problems. I started describing the end state in concrete terms. "This should answer whether the API can handle 100 requests per second. I don't care if the UI is ugly." That kind of specific.

When does it need to be done? And why that timeline matters. People work differently when they know a deadline is because there's a customer demo versus because you arbitrarily picked a date. I started saying "We have a board meeting Thursday, and I need to show this working" instead of "Can you have this by Thursday?"

What are we willing to sacrifice? Every project has trade-offs. Some people default to sacrificing speed for quality. Others go the opposite direction. If you don't say which trade-offs are acceptable, everyone just uses their default. Started being clear: "Ship this incomplete if you have to, just make sure the core function works" or "Take the extra two days, this needs to be right."

The tricky part is that expectation gaps look like other problems.

Someone who seems slow might just think you wanted something more thorough than you did. Someone who seems careless might think you wanted speed over precision. Someone who seems like they're not taking initiative might be waiting for clearer direction because their last job punished people for moving without approval.

I had a designer who kept asking for feedback at every stage. Seemed insecure. Turned out her last role had a founder who'd blow up projects if you got too far without his input. She wasn't insecure, she was optimizing for a different set of expectations.

Once I told her "I trust you to make these calls, just show me when you're done," she moved three times faster.

Started doing this thing every Monday. Takes 10 minutes. I list out what I'm expecting from each person that week. Not tasks, expectations. What needs to be done, why it matters, what I'm okay with them punting to next week.

Then I ask: Does this match what you thought I needed?

About 30% of the time, the answer is no. Someone thought a project was exploratory when I needed it shipped. Someone thought they were blocked waiting for my input when I thought they were moving forward. Someone thought they had flexibility on timeline when I needed it done by Wednesday.

Catching those gaps on Monday instead of Friday changes everything.

Teams that have aligned expectations move faster. Not because people work harder, but because there's less friction. Nobody's rebuilding work because they misunderstood the bar. Nobody's waiting for clarity that they thought was implied. Nobody's frustrated that someone isn't meeting standards they didn't know existed.

I stopped having conversations about work ethic or communication skills. Started having way more conversations about "Here's what I'm expecting, does that match what you heard?"

The work got better. But more than that, people seemed less stressed. When you know exactly what good looks like, you can just build toward it. When you're guessing, every decision carries this low-level anxiety about whether you're doing it right.