The AI transition is a change problem before it is a technology problem. The tools are new. The human response to a floor disappearing under you is not.
I’ve crossed a change this size once before. I watched the internet rewrite how companies sell and serve, and I helped rebuild businesses on the other side of it. The pattern of a radical change rhymes, and that pattern is the thing worth hiring for.
What a guide who has done it gives you is not a prediction about the technology. It is the ability to read where you are on the curve and keep you off the two cliffs: freezing, or torching what still works.
Everyone is suddenly an AI advisor. Most of them met the disruption the same month you did. They can tell you what the models do. Far fewer can tell you what a company does when the ground underneath its go-to-market motion moves, because they have never stood on it while it moved.
That second thing is the job. The AI transition is not, at its core, a tools problem. It is a change problem wearing a tools costume. And change of this magnitude is something a small number of operators have actually lived through and come out the other side of. I’m one of them.
I watched the last one rewrite everything.
Before the internet, business was sold and served in person. Relationships and territory. You knew your accounts because you drove to them. The seller held the information, and the information was the advantage. That was the whole model, and it had worked for decades.
Then the web took the floor out. The buyer got informed faster than the seller could adapt. Channels that had been load-bearing collapsed inside a few years. Whole categories of role and motion stopped making sense. Companies that had been good at the old game discovered that being good at the old game was now a liability, because it made them slow to admit the game had changed.
I was in the rooms where that played out. I helped scale NetSuite from roughly $30M to over $1B through the exact stretch when software stopped being something you installed and became something you logged into. That was not a feature change. It was a change in what the customer expected, how they bought, and what the company had to become to keep selling to them.
The lesson from that decade is the one I carry into every AI conversation now. The technology is the trigger. The failure is always human.
Radical change rhymes.
Put the internet transition and the AI transition next to each other and the surface looks different. The underlying shape is nearly identical.
- The floor moves under the go-to-market motion. The way you found, won, and kept customers stops working at the same rate, and nobody can tell you exactly when the old way crosses from slowing to dead.
- The buyer gets informed before the seller adapts. Last time it was search and the open web. This time it is models that summarize your category in a paragraph. Either way, your buyer shows up knowing more than your motion was built for.
- The advantage shifts from holding information to doing something with it. When everyone can access the answer, the scarce skill becomes judgment, framing, and trust. That is a different muscle than the one most companies trained.
- The failure modes are denial, then panic, then over-rotation. First the team insists nothing has really changed. Then they realize it has and lurch. Then they tear out things that were still working because tearing out feels like progress.
That last sequence is the one that costs companies the most, and it is the one a guide who has been through it can see coming a mile off. When you have already watched a leadership team talk itself from denial into panic into a fire sale of its own strengths, you recognize the early signs in week one. You can name it before it runs.
What a guide who has done it actually does.
The value is not a forecast about where AI lands. Nobody has that, and anyone selling it is selling certainty they don’t have. The value is in managing the human response to the change, inside your team and inside yourself, so the company moves at the right speed instead of too slow or too fast.
In practice that looks like a small number of things, done relentlessly.
- Separating fact from fear. Most of what feels urgent in a transition is interpretation, not evidence. A guide who has been here pulls the two apart so you stop making permanent decisions out of temporary panic.
- Naming the pattern you’re inside but can’t see. You are too close to your own company to know whether you’re in denial or already over-rotating. Someone who has crossed this before can place you on the curve.
- Protecting what still works. Radical change tempts you to throw out everything. Some of what you built is exactly what you need on the other side. Knowing the difference is the whole skill.
- Holding you to a decision, not a feeling. The transition ends, for you, the moment you commit to a move and the reasoning holds. A good mentor gets you there and won’t let you mistake activity for a decision.
You don’t hire the person who knows the most about the technology. You hire the person who has already kept a company calm and moving while the ground moved under it. Chris, on who to put in your corner for a transition
What the research says about carrying it alone.
This isn’t only an operating argument. It’s a documented one. Research reported in Harvard Business Review found that roughly half of CEOs experience feelings of loneliness in the role, and most of those believe it is hurting their performance. The seat itself isolates, and the isolation carries a cost you can measure.
The mechanism underneath it is uncertainty. A 2016 study in Nature Communications (de Berker and colleagues) found that not knowing whether something bad will happen is more stressful than knowing for certain that it will. The brain treats an unresolved threat as a live one. A transition is uncertainty at scale, which is exactly why it grinds people down faster than a known crisis does.
What blunts that is having someone to think with. The stress-buffering hypothesis, one of the most replicated findings in health psychology (Cohen and Wills, 1985), holds that social support softens the impact of stress on the body and the mind. And studies of executive coaching specifically (Grant and colleagues) show measurable gains in resilience and wellbeing alongside measurable drops in anxiety and depression. A mentor is not a luxury you add when things are calm. It is one of the few documented buffers against the exact load a transition puts on you.
This is also where the Three Cs come in: Creativity, Confirmation, Communication. In a transition, all three are under attack at once. You need Creativity to invent the new motion, Confirmation to act on what is true instead of what you fear, and Communication to keep the team aligned while the ground moves. Those are precisely the capacities that erode when you carry the load alone, the science above says so. The mentoring exists to protect them.
Five years on the front of this change.
This is not theory I dusted off from the dot-com era. I’ve spent recent years coaching companies through exactly this kind of disruption, leaders trying to change momentum, reset a culture that the old technology shaped, and stand up a new go-to-market motion before the market gives them a vote.
The combination is the point. I’ve lived a transition this size as an operator, and I’ve spent the years since helping other leaders cross the current one. The history tells me what to expect. The current work keeps it sharp. You get both in the room.
How I run the work. HELP.
The mentoring is not a venting session with a smart person. It runs on a method, the same H.E.L.P. Operating System I install in leadership teams, applied one-on-one to whatever you walked in carrying.
- Hear. Get the whole situation on the table before touching it, including the part you haven’t said out loud to anyone.
- Evidence. Separate what is actually true from what the fear is telling you is true. This is where the expensive mistakes get caught.
- Learn. Find the pattern. Most of what feels unprecedented to you, I’ve seen a version of before. We name what is really happening.
- Proceed. End on a decision and a move you can defend, not a framework to think about later.
You don’t need another briefing on what the models can do. You need someone who has crossed a change this size and can keep you moving through this one. That’s the work I do one-on-one.
The honest version of the pitch.
I can’t tell you where AI lands. Neither can anyone else. What I can tell you is that the way companies fail in a transition like this is well-worn, human, and avoidable, and that having someone in your corner who has watched it up close changes the odds.
That is what one-on-one executive mentoring is for. Complete access to a 25-year operator while you make the calls that decide the next chapter. Visible to your team if you want the change to have a face, or private to you alone if visibility would cost you. Roughly 15 to 20 hours a month, shaped around your week.
If you’re a leader staring at a transition you can feel but can’t fully name yet, that’s exactly the conversation worth having.
A mentor for the transition. The actual mechanics.
Why hire a mentor who lived through the internet transition to help with AI?
Because the AI transition is a change problem before it is a technology problem, and the human pattern of a radical change repeats. A leader who already rebuilt a business when the internet disrupted how companies sell and serve has crossed a change this size once. They read where you are on the curve and keep you off the two cliffs: freezing, or torching what still works.
What does an executive mentor actually do during a major transition?
They separate fact from fear, name the pattern you’re inside but can’t see, and hold you to a decision rather than a feeling. The work is not predicting the technology. It is managing the human response to it, inside your team and inside yourself, so the company moves at the right speed.
Is the AI transition really comparable to the internet?
The mechanics rhyme. Both took the floor out from under the existing go-to-market motion, informed the buyer faster than the seller adapted, and rewarded the companies that rebuilt early. The trigger is different. The failure modes are nearly identical: denial, then panic, then over-rotation.
Is there evidence that a mentor helps during stressful change?
Yes, and it’s worth knowing. Research reported in Harvard Business Review found about half of CEOs feel lonely in the role and most believe it hurts their performance. A 2016 study in Nature Communications found uncertainty is more stressful than a known bad outcome. The stress-buffering hypothesis (Cohen and Wills, 1985) shows social support softens the impact of stress, and studies of executive coaching (Grant and colleagues) show gains in resilience and wellbeing and drops in anxiety. A mentor is one of the few documented buffers against the load a transition creates.
How do I get an executive mentor through OnDemand Leaders?
Book a 30-minute call. I offer one-on-one executive mentoring, Extreme Mentoring 101, at roughly 15 to 20 hours a month, as a visible figure to your team or privately to you alone. The call is a fit check, not a sales call.
Last updated · June 2026