Repeat Until It Hurts
Getting your team from "I didn't know that" to genuine buy-in
Last week, I was traveling from a startup conference in Stockholm back to Helsinki. I arrived at the airport well in advance, had lunch and coffee, and was patiently waiting next to gate E4.
I had my AirPods on and half-missed the announcement about the boarding order.
I realized my mistake when I found myself going against the flow, trying to reach the back of the plane while everyone else was moving forward. It felt awkward dragging my luggage and laptop bag while dodging people coming in the opposite direction. When I finally settled into my window seat in the second-to-last row, I thought, “There is always someone. This time it was me.”
My name is Roman, I am the CTO at a startup. I write High-Impact Engineering — a weekly newsletter for engineering managers, directors, and CTOs.
This issue is about getting your message across, ensuring a shared mental model, and securing buy-in from your team.
The biggest mistake in getting a message to your team
For every message we broadcast to a team, there will always be someone who misses it, misinterprets it, or hears it too late.
You introduce a new field in the ticketing workflow and explain how to use it. Then half of the team asks how to use it.
You explain a new architectural approach. Implementation starts. Then developers who are supposed to work on it begin asking questions, and it becomes clear that they built a completely different mental model from the one you intended.
You can probably think of several similar situations immediately.
The biggest mistake in getting a message across is assuming that because something was said once, it was understood by everyone.
That assumption is almost always wrong. Understanding is neither perfect nor uniform across the team. Some people missed the message. Some heard it but misunderstood it. Some understood the words but not the implications. Some agreed in the meeting but forgot the next day
From unawareness to buy-in
Depending on what we want the team to do, the message needs to move through different stages: unawareness → understanding → familiarity → adoption.
First, the person does not know about the thing you are saying. Then they hear the message and try to understand it. When the message is repeated several times, it becomes familiar. When the message stays top of mind long enough, it starts to become part of how the person thinks and acts.
Different goals require different levels of communication. If we only want to inform people about something, understanding might be enough. For example, we expect everyone to be at the office next Tuesday at 10:00 for a workshop. We do not need to drill this message in. We only need to make sure everyone knows what it is, when it happens, and has the invitation in their calendar.
Familiarity is different. It requires more than hearing the message once. It requires building a mental model. This might be a software architecture, cross-team dependencies, project phases, or a new operating model. These topics are more complex. They have details that are easy to miss and assumptions that are easy to get wrong.
Adoption requires even more work because adoption means behavior change. For example, maybe you want your team to become responsible for creating end-to-end tests. The team needs to understand why this matters, how to do it, and what good looks like. Some training might be needed. Some people might resist the change at first. Others might agree in theory but not change how they work in practice.
The further we move from awareness to adoption, the more repetition is needed.
The good news is that repetition has a compounding effect. People who move further to the right help others move with them. In the end-to-end testing example, once part of the team starts writing good tests, others can learn from them. The behavior becomes visible. The norm starts to shift. The hard part is getting the ball rolling.
The Golden Rule
This leads to the golden rule: repeat until it hurts.
The bigger the change you need to make, the more repetition is required. A simple message, such as a change in the ticketing workflow, might require three or four repetitions. Something like a vision for the organization might need to be repeated dozens of times before it truly sinks in.
Something obvious to you may still be unclear to others. Or they may understand the idea intellectually but not yet be bought in. Continuous repetition over time improves both the quality and the coverage of understanding. More people hear the message. More people hear it in the right context. More people get enough exposure for it to become familiar.
Using multiple channels
Another important addition to repetition is using multiple channels for different levels of detail. In the end-to-end testing example, the idea and the reasoning behind it can be introduced in a team meeting. After the meeting, a short memo can be shared in Slack. That Slack message can link to documentation with technical details and best practices. The topic is the same, but the medium and level of detail are different. The meeting creates initial alignment. The Slack memo gives people something to refer back to. The documentation helps later, when the team starts applying the idea in practice.
I’ve got it across. Have I?
Repetition and multiple channels help us push the message out. But broadcasting alone has a blind spot: we do not know what actually landed. The most effective tool I have found is simply asking people to tell you what they understood. Not in a “pop quiz” kind of way, but naturally. In a one-on-one, you can ask: “How are you thinking about the end-to-end testing approach?” or “What’s your take on how this will work?”
The answer will often surprise you. Sometimes the person understood the message perfectly, but has a concern they have not voiced. Sometimes they missed a key detail. Sometimes they built a completely different mental model from the one you intended. This works much better than asking, “Is everything clear?” because the answer to that question is almost always “yes,” regardless of whether everything is actually clear. People do not want to be the one who did not get it. Asking them to explain their thinking gives them a safer way to surface misunderstandings without having to say, “I am confused.”
There is also a bonus: these conversations improve your own message. When you hear how people interpret what you said, you notice which parts are confusing. You see which examples work and which do not. You learn where people need more context. Then the next repetition becomes sharper.
Mandating vs buy-in
When we talk about adoption, it is also important to distinguish compliance from buy-in. Suppose we want to rapidly increase the number of end-to-end tests. We mandate that every ticket touching the UI must include at least one end-to-end test. You can probably see where this is going. Very soon, we may have a large number of useless tests that do not meaningfully improve quality, slow down our pipelines, and keep breaking.
A better approach is to help developers understand how proper end-to-end tests reduce firefighting in the long run and make their work more enjoyable. Nobody likes being told what to do without understanding why.
Mandating sounds efficient, but it often backfires. Buy-in takes longer, but it scales.
Help them board that plane
So before sending an important message, it helps to ask: Do people only need to be aware of this, or do they need to adopt a new behavior? How many repetitions will this require? Which channels should carry which level of detail? How will I check what people actually understood?
Getting a message across in an organization is not about getting a bigger loudspeaker. It is not only about the authority of the messenger. It is about the unglamorous work of repetition, different formats, multiple channels, and feedback loops.
Most people want to do a great job. Most people do not want to be the one who misses the announcement and ends up dragging heavy luggage against the stream. Our work as managers is to help people move in a coordinated and effective way toward common goals. And getting our messages across effectively is a big part of that.
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That's very helpful advice. Often I wonder why everyone keeps forgetting things, but you're right, not everyone actually understands it the first time, or people just aren't bought into the idea yet. Will definitely apply that "repeat until it hurts" strategy from now on!
The compliance vs. buy-in gap is where most leaders quietly fail, because buy-in is slower and you can't put it in a status update.
When you mandate without explaining, people don't adopt, they perform. They do just enough to look aligned.
"How are you thinking about this?" has caught more misalignment in my 1:1s than any formal rollout ever did. It feels inefficient. It's actually the fastest path to real change.