Why Software Implementations Fail

After 25 years in restaurant tech, here’s what I’ve learned

After 25 years in restaurant technology—from managing Aloha POS implementations to selling back-office platforms like MenuLink—I’ve seen one pattern play out over and over:

The excitement is real on Day One.

Everyone is ready to go. The new software promises better control, more visibility, and a streamlined process. But then something happens. That same excitement turns into silence. Calls stop getting returned. Tasks don’t get done. Momentum fades.

Yet at the same time, another client—same industry, same software, same onboarding process—is thriving.
So what’s the difference?

After decades of watching this unfold, I’ve narrowed it down to three things that make or break a software implementation:

  1. The Who – Who is chosen to lead the implementation
  2. The What – What are the company’s actual goals
  3. The How – How the implementation is managed and executed

Let’s break this down.

The Who: It Starts with the Right Person

Here’s what I’ve learned the hard way:

There are two types of people when it comes to software:
People who know how to use software, and people who know how to implement it.

They are not the same.

So many times, I’ve seen operators say, “Our manager used [insert software] at their last job—they can handle the setup.” What they don’t realize is that person walked into a fully implemented system. They never had to make the decisions behind the scenes.

Implementation requires a completely different mindset. It’s not about clicking buttons—it’s about:

  • Seeing the big picture
  • Making cross-department decisions
  • Thinking through the edge cases
  • Creating structure and consistency
  • Keeping the team engaged and on task

When you assign software setup to someone who’s only ever been a user, without the business acumen or follow-through to lead a project, you’re setting the whole initiative up to fail.

So how do you choose the right person?

You need someone who:

  • Understands your business
  • Has authority to make decisions
  • Has the time to lead (and protect that time)
  • Can follow through and manage a timeline

It doesn’t have to be your most tech-savvy person—it just has to be your most accountable one.

The What: Know What You’re Trying to Accomplish

Once the right person is in place, the next step is to get crystal clear on the goals.

This sounds obvious, but it’s where many teams derail. Why? Because modern software has hundreds of features. Without focus, it’s easy to try to implement everything at once—and fail at all of it.

Software implementation is a journey, not a destination.

If your mindset is, “Let’s get this implemented and move on,” you’re already off track.

You need to ask:

  • What business challenge are we solving first?
  • What does success look like in the next 30, 60, 90 days?
  • What can wait until Phase 2 or 3?

You have to resist the temptation to chase the next shiny object until your first set of goals is fully achieved. That’s the difference between completing a rollout and getting stuck halfway.

What master are you serving right now?
Focus on that—and only that—until it’s done.

The How: Creating a Process for Change

Even with the right person and clear goals, implementations still fail. Why?

Because there’s no process for change.

Here’s the truth: change doesn’t happen by itself. It has to be managed. It requires timelines, accountability, communication, and repetition.

Even the best tools can’t fix a company that doesn’t know how to implement change.

Let me give you an example.

A restaurant owner once bought our software to manage everything from ordering and invoicing to inventory counting and recipe costing. He made his chef the point person.

Three months later—no progress. The chef wasn’t showing up to meetings, wasn’t engaging with the process, and hadn’t moved the project forward. The owner finally gave him an ultimatum: “If it’s not implemented in one month, we’re canceling.”

But instead of supporting that directive with a structure, the owner just let it play out. And when nothing changed, he canceled.

What message did that send?

  • That ignoring change is acceptable
  • That follow-through isn’t required
  • That failure has no consequence

You can’t build anything new under those conditions.

Culture change is a long game.

Look at Chick-fil-A. It took them two years to get every employee to say “my pleasure.” That wasn’t a one-time memo. It was daily reinforcement—meetings, coaching, feedback—until it became part of their culture.

If you’re serious about implementation, it’s the same process.
You need to build change into your business, not hope it happens.

Final Thoughts: Why Most Implementations Fail

To summarize, here’s why most software rollouts fall apart:

The Who – You picked someone who can use software, not implement it.

The What – You tried to do too much without clear, focused goals.

The How – You had no structure or culture to manage change effectively.

These same patterns apply whether you’re rolling out inventory software, a gift card program, or just trying to keep the kitchen cleaner.

If you can master the Who, the What, and the How, you won’t just implement software—you’ll create lasting change in your business.

And that’s what separates companies that grow from those that stay stuck.