A fair wind

A Roman captain did not decide when to enter port. The wind decided.

That is where opportunity comes from: the Latin ob portu, toward the port. It was not a metaphor, it was a technical instruction: the moment when wind and tide lined up enough for a ship to come in without running aground. Getting that moment wrong was not a bad deal. It was going under.

The port never moved. It was always there, still, waiting. The only thing that changed was the reading: someone with a trained eye watching the sky, the water, the wind, and deciding that those loose signals, taken together, meant something.

Before instruments, a sailor read the color of the water to know its depth, the flight of certain birds to know how close the coast was, the shape of the clouds to anticipate a storm that did not yet exist on the horizon. None of those signals, on its own, said anything useful. Water always has a color. Birds always fly. What turned that into information was the judgment to know which of those signals mattered now, and which were only scenery.

The difficulty was never getting signals. There was always water, sky, wind, birds. The difficulty was, and still is, deciding which of all those available signals deserve to become a decision. A sailor with too much information and no judgment drowns just as fast as one with none at all.

No opportunity is visible while you are living it. That happens afterward. A call, a complaint email, a renewal meeting that ran twenty minutes long: none of that is, on its own, an opportunity. It is scattered information, the same kind as the color of the water or the flight of a bird. Someone has to look back, decide which of those signals matter, put them together, and only then name what was happening.

And naming it is not a minor detail. The moment a captain said toward the port, that phrase stopped being an observation and became an order: sails were raised, the crew was reorganized, a concrete risk was taken on the basis of that reading.

Naming something an opportunity does the same. The moment someone says “this is an expansion” or “this is a churn risk,” that phrase stops describing the relationship with a customer and starts directing it: it gets prioritized, assigned to someone, given urgency. The word does not describe what was already happening. Something else starts happening the moment you say it.

That is why getting the reading wrong cost a sailor so much, and why it still costs so much today: it is not just the lost opportunity, it is the credibility of the next reading. A captain who declared favorable conditions and ran aground twice stopped being listened to on the third. A team that labels as “opportunity” something that was nothing trains everyone who comes after, without meaning to, to distrust the next label.

No ship had a single lookout. There was one at the bow, another at the mast, another at the stern; each watching a different quadrant of sea and sky, because a storm building to port does not announce itself to starboard. A captain who based his reading only on the report of the lookout watching the calm side of the horizon, ignoring the other two, was not reading the sea. He was confirming what he already wanted to see.

That still happens, only the calm quadrant goes by another name today: the meeting. A forecast built solely from what was said on the video call, even with the tidiest summary of that video call, ignoring the email before, the WhatsApp after, the phone call that resolved the real doubt, is not a forecast. The sale does not happen only in the meeting. It happens spread across all those touchpoints, and the meeting is just one of them, almost never the most revealing.

But each lookout, besides watching his quadrant, kept his own watch notebook: he wrote down what was worth remembering to him, in his handwriting, his way, so he could do his own shift better next time. That notebook did not sail the ship. It served the lookout. What sailed the ship was the logbook: a record that answered not to what each crew member found convenient to note, but to what the whole ship needed to know in order not to run aground; regardless of who was on watch, or what had struck that particular person as relevant.

Today it is easy to confuse one for the other. Much of what is sold as “AI for sales” is, at bottom, the lookout’s notebook: a tool that works for the person using it. It summarizes her meeting, organizes her day, spares her the work of writing her own follow-up email. It is genuinely useful to that person. But its judgment about what is worth recording belongs to an individual optimizing her own shift, not to an organization trying to understand where each customer is heading. It can be excellent personal help and, at the same time, tell the ship nothing useful.

At diio, we launched a while back, in testing with some customers, a feature called, plainly, Opportunities: it groups the conversations with a customer —calls, emails, messaging, video calls, in-person meetings— under a label that says what that relationship is about right now. Retention. Expansion. New business. Whatever it is. It is not a lookout’s notebook optimized for his own shift. It is the ship’s logbook: the criterion is not “what helps whoever took this call,” it is “what the organization needs to know about this customer.”

Almost everything being said today about AI in sales insists on the same thing: assistants that anticipate, that prioritize, that act before anyone has to ask. Proactivity is not the problem. The problem is who that proactivity works for. An assistant that anticipates by optimizing one person’s day, without having read an email or a WhatsApp that person did not consider relevant to herself, anticipates just as fast as one that looks at everything with the business’s judgment; but it serves a different owner.

What makes diio able to say, with authority, “this is an opportunity” is not that it acts before you do. It is that it works with the criteria the organization defined, across the whole of the conversations that exist, answering to what the ship needs to know, not to what was convenient for whoever was on watch that afternoon.

The Romans had no weather forecast. They had a trained eye, clear judgment about which signals mattered, and a logbook that answered to the whole ship, not to each lookout’s convenience. Today there is more data than any Roman captain could have dreamed of, spread across more channels than a single lookout —or a single meeting— could cover. What is still missing, for that data to become something, is the same thing that was missing then: clear judgment, working for the ship and not only for whoever is on shift, and something willing to hold it while looking in every direction, so you can say, with certainty and not with luck, that now yes, toward that port.