I know two people named Gary.
My dad is 78. About 20 years ago he bought his first sailboat with nothing behind him aside from years of recreational boating on lakes. It was not a small sailboat. That kind of decision tells you a lot about a person. He has since built a YouTube channel covering Pacific Northwest coastal history, gold panning, how-to sailing guides and ASMR soundscapes of life on the water. AI became his engine diagnostic tool, his content strategist, and his research assistant. Not because anyone pointed him toward it. Because that is who he is.
My close friend Gary is a Product Designer for a successful tech company. In the last two years he built a large infrared sauna, drones and a specialist app for childcare services (amongst other things). Mostly using AI. These projects have nothing to do with his career, and that is entirely the point. He decided he wanted to do them, found the tools, and saw each one through. No obvious connection between his profession and the projects. Just a person who goes all the way in when he is interested in something.
When you think about the hires that have really mattered in your organisation, the ones that changed its trajectory, how much of what you saw was actually them, and how much was the team, the timing, the tailwind?
It is a question most hiring processes never get around to asking.
The two Garys were not trying to make a point. They were just being themselves. And that quality, the one that made them back themselves when there was no roadmap, is what most hiring conversations never get around to looking for.
The roles where this matters most
These are not always the roles at the top of the org chart. Think about the heads of, the directors, the senior managers sitting just beneath it. Not the vision at the top, but the engine underneath it. Get them right and everything accelerates. Get them wrong and the damage is quiet, cumulative and expensive by the time it surfaces.
Most hiring for these roles still optimises for the best version of the job as it exists today. Relevant experience. A referral. A credible track record from a recognisable place. These things are not meaningless but they are lagging indicators. They tell you who someone was in an environment that may no longer exist. They tell you almost nothing about what that person will do when the environment shifts. And the environment is shifting.
Is this person's track record a reflection of their capability, or their circumstances?
Naming the Adaptation Gap
I have started thinking about this as the Adaptation Gap. The distance between who someone is today and who the role needs them to be in 18 months, and whether they have the disposition to close it. It is not a skills gap. Skills can be taught. This is something underneath that. It is about whether someone backs themselves when the path is not clear and the job description has not caught up with reality yet.
AI has made this visible in a way almost nothing else has. Not because AI proficiency is the point. But because how someone has responded to AI is the clearest real-time signal of adaptability most of us have ever had access to. Two candidates, identical CVs. One has been quietly experimenting, learning, integrating. The other is waiting to be told what to do. The Adaptation Gap was always there. Now you can actually see it.
What I have learned to pay attention to
There are a few things I have started paying close attention to. Less as a formal process, more as a pattern I have learned to notice.
The first is how someone enters a new context. In a conversation, do they ask questions about the business, or only about the role? The ones who want to understand the system they are walking into, before they have established where they sit in it, are the ones who tend to navigate it well. It sounds like a small thing. It is not.
The second is what they have figured out on their own recently, outside their job description. Not a work achievement. Something they chose to learn because they were curious about it. If the answer is vague, or years old, or simply does not exist, that tells you something worth knowing.
The third is how they handle the edge of their knowledge in conversation. When they do not know something, do they bluff, go quiet, or say "I don't know, I would want to look at that" without any embarrassment? That third response is rarer than it should be. It is also the one most people have been quietly trained to suppress.
A better question to ask
The Adaptation Gap does not show up on a CV. But it shows up in how someone talks, what they have done when no one was watching, and whether they back themselves when the path forward is not obvious. The leaders who learn to see it will hire differently. Not because they have a better process, but because they are asking a better question. Not who is the best person for this job. Who is the person that will close the gap when the job changes.