Two hours were booked on his calendar, no more, squeezed between two board calls. I sat across from the CEO of a Danish design company that makes wooden objects meant to sit in people's homes for decades. Two coffees arrived. His sat untouched and went cold. He was ready for the usual pitch, a screen, a list of tricks, a term he had seen once on LinkedIn and half remembered. He had budget approved already and a quiet worry that this would go the way most software pitches go for him, exciting in the room, forgotten within a month. I left my laptop closed and asked him six questions instead. Where does your time go. What is hardest to find when you need it in a hurry. Where do things fall through the cracks. Which reports do you open every week without fail. Which meetings leave you with more work than they solved. If one AI tool could do three things for you tomorrow, name them. He paused longest on the third question. A task from a supplier meeting three weeks back came up, one that never got done because nobody had written it down anywhere that counted, not in an email, not on a whiteboard, not in his own head. I stopped thinking about which systems to connect first and started thinking about which part of the next two hours he needed to feel with his own hands, not hear about secondhand.
Most consultants sell a finished system. I sell the CEO on being the one who found it first, because he is the only person in the building who can make forty employees stop arguing about whether to bother. I have opened sessions this way with a hotel owner in the Algarve, a dental practice in Porto, and a transport company outside Lisbon. The industries change every time. The five places his fifteen minutes of questions turned up, email, meetings, sales numbers, product information, tasks nobody owns, almost never do. The two hours are less about installation and more about ordering three moments so each one lands before the next begins. Show him everything at once and none of it sticks. One small win, followed by a bigger one, taught him more than any explanation I could have given him. 1 / Give him a safe win firstGoogle Drive, Gmail, and his calendar, wired into one assistant with a single instruction behind it: use the company's own files as the source of truth, keep suggestions separate from facts, never invent a detail about the business. Nothing new for his team to log into or learn. I tested it in front of him. What do you know about our product line. Find last week's sales presentation. What is on my calendar tomorrow. Correct answers, pulled from his own files, in seconds. Low risk, fast, and his own information handed straight back to him. That is what got him to sit forward in his chair. 2 / Save the big moment for the middleI could have opened with his sales dashboard. I did not. I waited until Asana and his meeting notes were both connected, then asked one question with him watching: based on our sales performance and the projects sitting open right now, what should I pay attention to this week. He went quiet for a second. Then he named two people on his team, out loud, who needed to see this before the week was out. That naming was the real shift, not excitement on its own, a plan taking shape in his head. 3 / Hand him a story, not a manualHe never needed to understand how any of it worked underneath. He needed three things simple enough to repeat to his own team without notes: a real answer to a plain question, a Monday briefing built from sales, tasks, and last week's meetings, and this morning's meeting turned into logged tasks without a notebook. People who build these systems usually hand the owner a login and walk away, then wonder why he never brings it up again. A login sent by email gets forgotten by Friday. Something he watched happen with his own hands gets brought up in the next meeting he sits in, unprompted.
The real finish lineBy the end of the two hours, he had stopped asking whether to continue and started asking what else it could do. Could it check supplier emails. Could it flag which products were bleeding money before the monthly report caught up. Could it warn him before a delivery ran late instead of after. A man who walked in skeptical does not ask questions like that unless something already convinced him. A CEO turns into a champion in ways that have nothing to do with technical skill. He brings the system up in a meeting nobody asked him to bring it up in. He defends the budget the next time someone in finance questions it, describing exactly what he watched happen with his own eyes. He tells a manager who is dragging his feet to try it for a week and see for himself. That change, from answering questions to asking his own, is the real finish line for a session like this.
If you want your own two hours, the kind that puts you in that chair instead of him, book a call. We will find the thing worth showing you first. Talk soon,
The AI Solopreneur • AI Strategy for European SMBs |
