The Three Conversations Every Growing Business Needs to Have Before It Is Ready

A founder I know spent eighteen months building toward a target that half his team did not even know existed.

Not because he was secretive. Because he assumed everyone understood where they were going. He had said it in all hands. It was on the website. It was obvious, to him, in the way that things are obvious when you have been thinking about them every day for three years.

His head of sales was optimising for volume. His operations lead was optimising for margin. His product team was building for a customer segment that the founder had quietly deprioritised six months earlier but never actually told anyone.

They were all working hard. They were all working in completely different directions.

That is not a strategy problem. That is a conversation that never happened.

The first conversation. Where is this actually going?

Not the offsite version with the nice catered lunch and the slide deck that took three weeks to build.

The real version. The honest, slightly uncomfortable one where everyone in the room says what they actually think the business is trying to become. Out loud. To each other.

Because in most growing businesses there are at least two or three completely different futures living in the heads of the people running it. The founder has one version. The senior team has another. And everyone is executing confidently toward their own ending while assuming, quite reasonably, that they are all in the same film.

They are almost never in the same film.

One question. Three years from now what does this business look like? Go around the table and actually answer it. You will learn more in those twenty minutes than in most strategy sessions you have ever sat through.

The second conversation. Who owns what.

I once watched a client relationship completely collapse because three people thought they were managing it and none of them actually were.

Each one assumed one of the others had handled the difficult conversation that needed to happen. Nobody had. The client left. The team spent two weeks trying to figure out whose fault it was. The honest answer was that it was nobody’s fault and everybody’s fault simultaneously, which is what happens when ownership is assumed rather than assigned.

Get in a room. List every critical function in the business. Put one name next to each one. Not two names. Not a committee. One name. The person who takes the credit when it goes well and the responsibility when it does not.

That conversation is about forty five minutes long. It is worth approximately six months of confusion, missed handoffs and very polite emails where everyone is waiting for someone else to go first.

The third conversation. What happens if this does not work?

Nobody wants to have this one. It feels a little like standing up at your own birthday party and asking everyone to discuss what happens when you die. Slightly awkward. Completely necessary.

A founder I deeply respect told me once that the best decision he ever made was sitting his leadership team down during a really good quarter, when everyone was feeling confident and the numbers were strong, and asking them what they would do if the business lost its biggest client tomorrow.

They had the conversation. Built a rough plan. Nobody thought they would ever need it.

Fourteen months later they needed it. And because they had already had the conversation in a calm room with clear heads, they moved faster and cleaner than anyone expected.

The businesses that navigate hard moments well are almost never the ones that got lucky. They are the ones that talked about it before it happened.

Hard conversations are considerably easier before they are urgent.

One last thing.

None of this is complicated. All of it keeps getting pushed to later.

Later has a way of arriving at the worst possible time. Have the three conversations now. Before you think you need to. That is exactly the right time to have them.

Regards,
Rupesh