Patrick Rooney

Your AI transformation won't be won or lost on the technology. It'll be won or lost on the people.

Let's be clear about something up front: the AI technology is really and truly incredible. Clearly, I'm not one of the skeptics. The tools are powerful, the pace of development is staggering, and the potential upside for GTM teams is tangible.

But here's what the organizations who are successfully making AI work for them have learned: the technology is not the variable. The technology is the easy part.

The hard part – the part that determines whether AI transforms how a business operates or just becomes a very expensive line item – is people. And most organizations are dramatically underestimating what that means.

What you're really asking people to do

When we talk about AI adoption, we tend to frame it as a tool rollout. Deploy the platform. Train the users. Measure the adoption rate.

But that framing misses the actual ask.

You are asking people to change how they do their jobs. Not tweak. Not optimize. Change – fundamentally, in some cases – the workflows, habits, and instincts they've built over years or decades. The way a rep qualifies a lead. The way a marketer writes a campaign brief. The way a CS manager prepares for a renewal conversation. These aren't just processes. For a lot of people, they're professional identity.

And you're asking them to change all of it, at a pace the organization has never moved at before, in a direction that isn't fully mapped yet, using tools that are still evolving.

That's a big ask. A really big ask. And most change management programs aren't built for it.

The spectrum is real — and it's wide

If you've started rolling out AI in your organization (which is probably the case here since you’re reading this), you've already seen this: people are not all in the same place.

Some people are all in. They've already figured out their own workflows, built their own prompts, and are quietly running laps around their peers. They don't need convincing –they need structure and guardrails, so their enthusiasm doesn't get ahead of the program.

Some people are curious but cautious. They can see the potential. They're watching carefully. They want to understand the "why" before they move. Give them clarity and a safe place to experiment, and they'll get there.

And some people are scared. Scared that the tools will replace them. Scared that they'll look incompetent while learning something new. Scared that the skills they've spent years building are about to be devalued. That fear is legitimate, and it deserves to be met with honesty and empathy, and certainly not corporate talking points about "augmentation" and "empowerment."

All three of these people are on your team right now. Your change management approach has to work for all three of them.

What most organizations get wrong

The typical AI rollout treats adoption as a logistics challenge: Here are the tools. Here is the training. Here is the timeline. Hit the targets.

That's a reasonable approach if you're rolling out a new CRM module. It is inadequate for the kind of change AI requires.

Real change — the kind that fundamentally shifts how people work — requires something most organizations aren't comfortable offering: space. Space to be uncertain. Space to ask questions that feel basic. Space to experiment without being judged on the first attempt. Space to give honest feedback when something isn't working.

It also requires something even harder to manufacture: trust. And trust doesn't come from a launch email and a 90-minute training session. It comes from leaders who are honest about what they know and don't know, who model the behaviors they're asking for, and who show up consistently over time, not just at the announcement.

The need for clarity and leadership, from leadership

If you're leading an organization through an AI transformation, here's a what I'd ask of you:

Be clear about where you're going, and honest about what you're asking. Vague mandates — "we're leaning into AI" — create anxiety, not alignment. People need to understand what's changing, why it matters, and what's specifically being asked of them. The clearer you are, the less room there is for fear and uncertainty to fill the gaps.

Model it yourself. Nothing signals to your team that AI adoption is optional faster than leaders who don't use the tools. If you want your team to change how they work, show them how you're changing how you work. This doesn't require you to be the most advanced user in the room, but it does require you to be visibly in it with them.

Have the honest conversations. Some of the conversations that need to happen in an AI transformation are uncomfortable. What happens to roles as processes get automated? What does the organization look like in two years? Most leaders avoid these conversations because they don't have clean answers yet. But the absence of a conversation is not neutral — it gets filled with rumor, assumption, and fear. A direct "here's what we know, here's what we don't, and here's how we'll navigate it together" is worth more than a polished all-hands deck.

Meet people where they are. Your most enthusiastic adopters need different support than your most hesitant ones. A one-size rollout will accelerate the enthusiasts and lose everyone else. Invest in understanding where your people actually are — not where you wish they were.

The things that move people

Applying the term “change management” doesn’t quite do justice to what is required to move people from AI resistance to adoption. AI is unique because it is so far reaching and so utterly disruptive, and while many traditional change management methods are applicable, there are several more that should be considered.

Early wins that belong to them. When someone experiences a genuine "this just saved me two hours" moment – and that win is theirs, not the company's – something shifts. Design the rollout to manufacture those moments early, and make them visible.

Permission to be a beginner. Organizations that create explicit psychological safety around learning AI — where it's acceptable to not know something, to ask basic questions, to try something that doesn't work — see dramatically faster adoption than organizations where people feel they're being evaluated on their proficiency from day one.

Real reduction in friction, not just addition of capability. For every AI behavior you're asking people to add, identify something you're removing. If AI is genuinely making people's work better, it should make their day lighter in some way. If it's just more — more tools, more inputs, more things to manage — you're adding load, not creating value.

Consistent encouragement over time. Transformation doesn't happen in 30 days. The organizations that sustain it are the ones where leaders keep showing up — checking in, sharing wins, acknowledging the difficulty, and reinforcing the direction — month after month. Not just at the launch.

The frame we come back to

There is no doubt the tools will keep getting better. That part is not in question. The question is whether your organization builds the human foundation that allows it to capture the tangible value by providing the clarity, the culture, and change management capability that turns a powerful technology into a transformed business.

Get the people part right, and the technology part is straightforward.

Get it wrong, and you'll spend a lot of money finding out that the most advanced AI stack in the world can't overcome a workforce that was never brought along for the ride.


Related Articles

Turn AI activity into GTM performance.

Privacy Policy

Terms of Service

Legal

© 2026 Shore GTM LLC. All rights reserved.

Turn AI activity into GTM performance.

Privacy Policy

Terms of Service

Legal

© 2026 Shore GTM LLC. All rights reserved.

Turn AI activity into GTM performance.

Privacy Policy

Terms of Service

Legal

© 2026 Shore GTM LLC. All rights reserved.