Over the past few months I’ve found myself in a surprising mix of meetings — founders preparing for investor conversations, teams working on enterprise sales, others on product strategy or commercial validation.

On paper, these conversations have almost nothing in common.

Yet I keep leaving with the same notebook, filled with almost the same questions.

For years I thought that was a coincidence. I assumed fundraising, product strategy and enterprise sales belonged to different worlds. Different meetings. Different people. Different vocabulary.

I’m no longer sure.

One meeting has stayed with me. I was reviewing an investor deck with a founder ahead of a raise. It was a good deck — attractive market, credible product, a vision that was ambitious without tipping into fantasy. Not much to criticise in the slides themselves.

But twenty minutes in, I’d stopped looking at them. My notebook was filling up with questions instead:

• Who is likely to become your first paying customer?
• What have you actually learned from the conversations you’ve already had?
• Why would customers buy now instead of waiting six months?
• Which pricing assumptions are backed by evidence, and which are educated guesses?

It wasn’t that the founder was trying to avoid the questions.

None of us were.

It’s remarkably easy to slide from evidence into intuition without noticing you’ve crossed the line.

Every time we reached a difficult question, the conversation drifted, almost politely, from what we’ve learned to what we believe is probably true.

Nobody steered it there on purpose.

A few days later, a different company, a different problem. This one wasn’t raising capital — it was struggling commercially. We’d spent weeks making the analytics better. More telemetry. Better models. More signals.

Nobody had asked whether we were helping the customer make a decision.

At one point, someone in the room asked a deceptively simple question.

”Given everything you’ve just shown me, what should I actually do?”

The room went quiet.

It wasn’t that we didn’t have an answer. It was that we’d never really agreed on the decision the product was supposed to support.

If you’d walked into those rooms, you would never have guessed they were wrestling with the same problem.

The more I thought about it, the stranger the similarity became.

One group was trying to convince investors. The other was trying to help customers make operational decisions. Both conversations stalled in exactly the same place.

That also made me question how we talk about investor readiness. We tend to treat it as a communication problem. Better decks. Better messaging. Better storytelling. Those things matter — a confusing story creates unnecessary friction. But looking back, I don’t think either of those meetings was really about communication.

They were about helping another human being make an important decision with less uncertainty than they had when they walked into the room.

I’m beginning to suspect that’s what evidence is really for.