Everyone nodded. Nobody got it.

A little over a year ago, I started teaching Jiu Jitsu classes.

In most academies, teaching is part of the transition from brown belt to black belt. It’s a shift from focusing exclusively on your own skills to helping others develop the craft and progress. Like most sports, and honestly, like most corporate or startup roles, teaching was a reminder that being good at something and being able to explain it are entirely different skills. It’s the difference between being a great individual contributor and being a manager who can actually develop their team.

I took teaching seriously from the start. Most martial arts follow a familiar structure: warm-up, technique demonstration and sparring. During the technique portion, I’d show the moves of the day, answer questions, and send everyone off to practice in groups.

I had the right intention but here’s what caught me off guard. I would demonstrate the technique, ask if everyone was ready, get a room full of nods and “yeses,” and then watch nearly everyone do the move incorrectly once we broke into groups. Week after week, the same pattern.

After some reflection and conversations with my professors, I realized the issue: I was communicating the steps clearly enough, but missing what actually mattered. I wasn’t showing the movement from different angles. I wasn’t pausing to read the room or invite more questions. I wasn’t explaining why the technique worked or when to use it.

I was telling people what to do without teaching them how to think about the situation they were in.

The same pattern, different context

This dynamic shows up for founders, or really any leader, in startups all the time.

Just because something has been said doesn’t mean it has been understood, and just because people nod in a meeting doesn’t mean they have the context they need to execute well. I’ve made this mistake leading teams and working cross-functionally more times than I’d like to admit. It’s easy to assume clarity happens in a single pass—share the strategy, outline the plan, and move forward.

In reality, people are busy, bombarded with too much information, and context switching non-stop. Most of us pick up fragments the first time we hear something (the parts that relate directly to us) but miss the deeper context.

That’s why teams struggle. They heard the message but didn’t absorb it:

• The reasoning behind it
• The tradeoffs involved
• The situations where judgment matters

Repetition is what turns fragments into shared understanding.

Repetition isn’t redundant

It’s why effective founders repeat the strategy at all-hands meetings, even when it feels obvious. It’s why they remind investors what the product does and who it’s built for, knowing that most investors are juggling multiple companies at once. And it’s why good managers take the time to explain not just what the team is working on, but why that work matters and how it connects to the broader goals of the company.

Sometimes that means saying the same thing again (and again, and again). It could also mean saying it differently. Or doing both!

Overcommunicating isn’t redundant. It’s a founder’s responsibility.

In Jiu Jitsu, if an entire room is practicing a technique incorrectly, the coach doesn’t blame the students. They slow down, adjust the explanation, and find a better way to communicate what matters.

Leading a team or a company works the same way.

A better question

There’s usually a signal when something isn’t showing up in execution. It’s not that people don’t care or aren’t capable, it’s that the important details haven’t landed yet.

One shift that’s worked for me: when I see misalignment or tension, instead of asking “why aren’t they getting this,” I ask “what am I assuming they already understand”. It has helped me figure out what context is missing and what needs to be repeated or reframed.

It’s a question I return to now, whether I’m teaching on the mats or working with founders: What am I assuming they already understand?

Give it a shot and let me know your experience!