George Bernard Shaw said it plainly: “The single biggest problem in communication is the illusion that it has taken place.”

He was right then. In a world of Slack threads, asynchronous updates, and all-hands decks, he is more right now.

The illusion works because sending feels like communicating. You write the email. You share the update. You present the strategy. There is a moment where you feel like you have done the work. You have not. You have transmitted information. Transmission and communication are not the same thing.

The gap nobody closes

There is an old maxim in marketing: a message needs to be heard seven times before it sticks. Leadership is no different. Research consistently shows that people need to encounter an idea repeatedly, across multiple contexts, before it genuinely lands. Once in an all-hands does not do it. Once in a team meeting does not do it.

But most organisations treat communication as a one-time event. Send the update. Run the meeting. Brief the team. Done.

It is not done. It has barely started.

What actually goes wrong

The dangerous part is not the misunderstanding itself. It is what happens next.

People leave the meeting with different versions of what was said. Decisions get made on those different versions. Work gets done, plans get built, and by the time the divergence surfaces, there is a lot of expensive output sitting on a foundation that was never solid. The post-mortem almost always includes the phrase “there was a miscommunication.” What it rarely includes is why no one thought to check.

The deeper problem is the assumption chain. Person A assumes they communicated clearly. Person B assumes they understood correctly. Person B then acts, and person C assumes B’s actions reflect A’s intent. Three steps in, you are operating on a game of telephone while everyone believes the signal is clean.

The sender’s responsibility

There is a tempting version of this where the problem belongs to the receiver. They should have asked a clarifying question. They should have flagged the ambiguity.

That framing makes things worse. If your communication did not land, that is a communication problem, not a comprehension problem. The person who wanted something understood is the person responsible for checking that it was.

Part of owning the communication is knowing your audience before you open your mouth. An executive needs the outcome first and the context second. Give them a wall of detail and they will either disengage or extract the wrong signal. A technical audience can handle depth, and often needs it to do the work properly, so cutting corners there creates its own problems downstream. A sales team needs something different again: they need to understand what the thing is not, just as much as what it is. Assumptions grow fastest where the edges are unclear, and salespeople are extraordinarily good at filling gaps in ways that serve the deal.

Acknowledging a message is not the same as understanding it. “Got it” and “sounds good” are reflexes, not confirmations. The only real check is asking someone to demonstrate understanding: what are you going to do differently as a result of this? What does this mean for your team this week?

Those questions are uncomfortable to ask. They surface misalignment. That is exactly the point.

Say it again

The antidote to the illusion is not more communication. Most teams are already drowning in it. The antidote is repetition with intention. Say the important thing in the team meeting. Reference it in one-to-ones. Connect it to the decisions people are making week to week. Let people encounter it through their work, not just in the briefing.

Seven times sounds like a lot. Once you accept that one time almost never works, seven starts to feel about right.

Shaw was describing a trap that has caught every organisation that ever assumed alignment without checking for it. The words went out. The meeting happened. The deck was shared. And somewhere in the gap between what was sent and what was understood, the wheels came off.

Say the thing. Then find out whether it landed. Then say it again.