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Let me tell you about a CRM that nobody wanted to use, and what it cost the company that bought it.
Early in my career I was brought into a business specifically to help turn things around, the kind of situation where the fundamentals are solid but something has gone sideways and the people at the top know they need outside eyes. One of the first things I noticed was the CRM. It was genuinely awful. Not awful in a subtle, hard-to-pin-down way, but clearly, obviously, demonstrably not fit for the job it had been purchased to do. The owner had felt the pressure to modernize, moved quickly, picked something that seemed reasonable from the outside, and rolled it out to the team without a whole lot of ceremony.
And here's the part that has stayed with me ever since: years went by, and nobody wanted to change it. Not even the people who complained about it every single day. The employees who used it constantly, who understood better than anyone how much time it was costing them and how many things it couldn't do, had settled into a kind of resigned coexistence with a tool they genuinely disliked. The idea of switching felt worse than the pain of staying, and the owner had long since moved on to other problems.
That CRM became a permanent fixture of the business. Not because it was good. Because the window to do it right had closed and nobody had the energy to reopen it.
That story is about a CRM from years ago, but I think about it constantly in the context of what I'm seeing businesses do with AI right now, and the parallels are uncomfortable enough that I feel like I need to write this post.
Why top-down mandates almost always fail
Here's what a top-down AI rollout typically looks like. The owner reads something, or attends a conference, or has a conversation with someone whose business seems to be running more efficiently than theirs, and comes away convinced that AI is the move. They research tools, maybe demo a few, make a decision, and announce to the team that the company is now using this new thing. There's a training session, maybe a YouTube video sent around, and then everyone is expected to integrate it into their workflow.
And then, quietly, they don't.
The tool gets used sporadically, or performatively when leadership is watching, or not at all, and six months later the business owner is wondering why they're paying for a subscription that doesn't seem to be doing anything. The team, meanwhile, has gone back to doing things the way they've always done them, and nobody is particularly eager to bring this up in a meeting.
The reason this happens is not resistance to change, even though that's usually how it gets characterized. The real reason is something more specific and more fixable: the people who were expected to change their daily work habits had no hand in the decision that changed them, and as a result they have no investment in making it work.
People support what they help build. It's not complicated. It's not controversial. And it's violated constantly by well-meaning business owners who are moving fast and assume that a good tool will sell itself.
It won't.
The question that changes everything
So here's what I want you to do before you spend another dollar on AI software, or on any software for that matter.
Ask your team this question: what parts of your job are repetitive, slow, or genuinely frustrating?
That's it. That's the whole thing. Not "what do you think about AI?" and not "would you be open to trying some new tools?" Just an honest, open question about where the friction is in their actual day-to-day work, asked in a context where they feel safe enough to tell you the truth.
What you'll get back, if you create the right conditions for the conversation, is a map of your business that you almost certainly don't have right now. The office manager who has been rebuilding the same spreadsheet every Monday morning for three years. The sales person who spends an hour a day on data entry that feels like it should take ten minutes. The project manager who is manually sending the same update emails over and over because there's no system that does it automatically. These are your AI opportunities, and the people who can identify them most accurately are the people already living inside the problem.
But here's what's equally important about that conversation, and it's the part that most business owners skip over entirely. When you ask people what's frustrating about their work, and then you come back with a tool that directly addresses what they told you, something shifts. They don't experience the software as a thing being done to them. They experience it as evidence that someone was listening. And that changes how they engage with it completely.
The fear underneath the resistance
I want to be honest about something that doesn't come up enough in these conversations.
When employees resist new AI tools, the stated reason is often that the tool is complicated, or that the timing is bad, or that they're not really sure it applies to their role. And sometimes those things are true. But underneath a lot of AI resistance right now is something that doesn't always get said out loud, which is a genuine fear that the tool is there to replace them, and that the business owner knows that and isn't being straight about it.
That fear is rational. It's coming from somewhere real. And if you don't address it directly, it will quietly undermine every AI initiative you try to run.
So say the thing out loud. Tell your team what you're trying to accomplish with AI, what you believe it will and won't change about their roles, and what you're actually hoping they'll be able to do with the time it frees up. If your honest answer is that you want your team to be able to do more meaningful, higher-value work because the repetitive stuff is handled, say that. If you're not planning to reduce headcount as a result of AI efficiency gains, say that too, and mean it, because people can tell the difference between a reassurance and a commitment.
The businesses I've seen handle AI adoption well have one thing in common, which is that the leadership was transparent about the why before the what. The tool came after the conversation, not before it, and by the time the software showed up there was already a shared understanding of what it was for and what it wasn't.
What this actually looks like in practice
I'm not suggesting that buying software requires a months-long committee process or that every employee needs veto power over every tool decision. That's not realistic, and it's not what I'm recommending.
What I'm recommending is something much simpler. Before you evaluate a single tool, have a genuine conversation with the people who will use it about where the real friction is in their work. Use what you hear to guide what you look for. When you find something worth trying, involve a couple of people from the team in the evaluation, not to rubber-stamp the decision, but to actually pressure-test it against the real conditions of your specific workplace. And when you roll it out, do it with enough context that people understand what they're being asked to do and why, rather than just receiving a new login credential in their inbox.
That process takes maybe a few extra weeks. What it buys you is a team that feels ownership over the tools they're using, which is the single biggest predictor of whether those tools actually get used, which is ultimately the only thing that determines whether your investment in AI produces a return.
The alternative is what happened with that CRM. Years of paying for something nobody wanted, nobody liked, and nobody had the momentum to change, sitting in the middle of the business like a piece of furniture everyone has learned to walk around.
The compounding advantage of getting this right
Here's the thing I find most interesting about businesses that involve their teams in AI adoption from the beginning: the benefits compound in ways that are hard to predict.
When employees feel like they helped choose a tool, they use it more consistently. When they use it more consistently, they get better at it. When they get better at it, they start finding applications for it that nobody anticipated when the tool was selected. The office manager who helped pick the scheduling software figures out that it can also handle a communication workflow nobody had thought to automate. The sales person who was brought into the CRM evaluation discovers a feature that changes how the whole team manages follow-ups. The people closest to the work are also, if you let them be, the people most likely to find the highest-value uses for the tools you're giving them.
That's the version of AI adoption that produces compounding returns over time, and it starts with a conversation that most business owners haven't had yet.
If you're trying to figure out where to start with AI in your business, the free Business Modernization Assessment takes about five minutes and gives you a clear picture of where the real opportunities are before you spend a dollar on anything. And if you'd rather just talk it through, book a call directly and we'll work through it together.