The right person to lead your AI initiative is the living embodiment of AI, and you judge them on three things: culture, technology, and leadership. Not on energy, not on buzzwords, not on how well they present. You find this person with one question, and then you listen to how they answer it.
The question that exposes them in thirty seconds
Ask them what they have done in the last forty-eight to seventy-two hours with AI. What were the pain points, how much sleep did they lose, what did they struggle with, what questions were they asking, what did it uncover, what did they learn. Then stop talking. The right person will go for thirty minutes without pausing, and you should come away overwhelmed by everything they said. The wrong person gives you a sentence about ChatGPT and changes the subject. This is the same litmus test that separates a real AI speaker from a futurist on a vetting call: recency and depth, not polish.
Culture: they have already been changed by it
This person lives inside AI, and it has changed how they see everything. They have used it enough that it tore up their own assumptions, and they cannot see their work, or their life, the same way anymore. They keep pushing, and they have made themselves genuinely comfortable inside the discomfort. That is the cultural marker, and it matters more than any certificate.
Leadership: a visionary who holds the vision loosely
This person has a picture of where things are going, and intends to use AI to tear that picture apart, because whatever they imagine today, the real outcome will be something else. If they are experienced, they have done this before. If they are young and have not, they are willing to sacrifice everything, they listen exceptionally well, and they respect the value of data and of the people who came before them.
Technology: a tool, never the answer
They understand the hype around every model and can tell you which ones solve nothing. They see how the pieces fit and can architect a solution in their head. But they know the technology is just the rope that ties the trees together in the forest. It is a tool. This is the same trap that makes AI demos fail in front of a leadership audience: mistaking the tool for the solution.
The part most leaders get wrong
This person understands that the honest answers will expose where leadership was wrong, or lazy, or pointed the company in the wrong direction, and they will say it anyway. It is the emperor’s new clothes. Someone finally says the emperor is naked, and that means the whole organisation has been walking around exposed. Which is why the real job is yours, not theirs: you have to decide, before they start, that you will protect the person who tells you the truth on the day nobody wants to hear it. That decision is leadership, and it is the same uncomfortable honesty that determines whether your P&L ever actually moves.
That is who you hire. Not the most eloquent person about AI. The one already living it, who will tell you the truth you do not want, and who you have decided in advance to protect when they do. If you want this thinking brought to your own leadership team, that is the work I do from the stage and in advisory rooms.
Frequently asked questions
Who is the right person to lead an AI initiative? The living embodiment of AI, judged on three things: culture, technology and leadership. Not energy, buzzwords or presentation skill. It is someone already living inside the technology, who will tell you the truth you do not want to hear and who you have decided in advance to protect when they do.
What single question reveals whether someone genuinely uses AI? Ask what they have done with AI in the last forty-eight to seventy-two hours, the pain points, the lost sleep, the questions, what it uncovered, then stop talking. The right person will go for thirty minutes without pausing. The wrong one gives a sentence about ChatGPT and changes the subject. Recency and depth, not polish.
What is the cultural marker to look for? That the person has already been changed by AI. They have used it enough that it tore up their own assumptions and they cannot see their work or life the same way. They keep pushing and have made themselves comfortable inside the discomfort, which matters more than any certificate.
How should the right leader treat the technology itself? As a tool, never the answer. They understand the hype around every model and can tell you which ones solve nothing, and they can architect a solution in their head. But they know the technology is just the rope that ties the trees together in the forest. Mistaking the tool for the solution is what makes AI demos fail.
What is the part most leaders get wrong? That the real job is theirs, not the hire’s. The right person will expose where leadership was wrong or lazy, the emperor’s new clothes, and say it anyway. The leader has to decide before they start that they will protect the person who tells the truth on the day nobody wants to hear it. That decision is leadership.
Thomas Anglero is a Strategic AI Advisor, keynote speaker and author of Intro to Artificial Intelligence. He has delivered over 450 keynotes across 30 countries for organisations including IBM, the WHO, the World Government Summit and the European Commission. He founded the IBM Watson AI Lab for Cancer at the Oslo Cancer Cluster and closed over $500 million in enterprise transformation deals as CTO and Chief Innovation Officer at Cognizant.