You bought the shiny new software system. The sales pitch promised efficiency, automation, and “transformational results.” You even sat through the three-hour kickoff meeting. So why, six months later, are people still using Excel and forwarding screenshots?

Because buying the software was the easy part. People are the hard part.

The Dream vs. The Mess

In theory, software makes life better. In practice, it threatens everything people are comfortable with.

Let’s take a stroll through a few rollout classics (yes, I’ve got a real story behind every single one of these):

The “We’ve Always Done It This Way” Wall

Sharon in Purchasing has a color-coded spreadsheet from 2006 that works for her. She doesn’t care that the new system calculates lead time automatically—she trusts her gut (and those neon highlights). And if you mess with her process, expect a passive-aggressive email chain by lunch.

Solution: Sell the why, not the features. People need a reason to care. Show them what gets better for them—not just the company. If it makes someone’s life easier, shout that from the rooftop.

The Training Nobody Showed Up For

You scheduled sessions. You made slides. You even had a fun ice breaker planned. But half the team “had a conflict,” and the other half sat silently with glazed eyes (or worse - muted, off camera). Fast-forward: three weeks in, everyone’s asking which shared drive has the “real” production schedule.

Solution: Train like it’s your job (because it is). One training session won’t cut it. You need follow-ups. Office hours. Cheatsheets. Make it easy to succeed. Make it hard to go back. People also fear change because they fear screwing up. Create space for learning. Praise early adopters—even if they mess up. Especially if they mess up.

The Manager Who Doesn’t Use It Themselves

Leadership signed the contract. But when it’s time to enter a BOM or approve a quote in the new system? Crickets. So the company maintains a dual process: one to keep the leadership’s outdated habits working and another to adopt the new system. Until one day, someone says “let’s just do it the boss’ way since that’s how they like it and scrap the new system.”

Solution: Use it in leadership. Publicly. If managers aren’t logging in, approving requests, and calling out wins, the rollout’s already dead. Set the tone from the top.

The Quiet Saboteur

Someone, somewhere, didn’t want this software in the first place. Maybe it exposes inefficiencies. Maybe it makes their job “less important.” Whatever the reason, they’re now the bottleneck. Misentered data. Late updates. “Technical difficulties.” It’s sabotage wrapped in plausible deniability.

Solution: Don’t tolerate opt-outs. If someone’s still using their old workaround after two months, it’s not “transition period”—it’s resistance. Address it. Fix it. Move on.

Tech Won’t Save You. Change Readiness Might.

Buying software is easy. A PO, a signature, and boom—new tools. But changing how people work? That’s the real game. It’s not about UX, AI, or APIs. It’s about trust, habits, and leadership follow-through.

Want your next software rollout to work? Spend less time picking the perfect system. Spend more time making sure your team actually uses it.

Because the tool doesn’t matter if no one picks it up.