4 Huge Mistakes Most People Make When Rolling Out New Systems

I bought and implemented countless digital tools over the years, spanning both back- and front-office functions. User acceptance was mixed, but over time, I learned a lot about what not to do and how to do it better. Still, I consistently run into experienced leaders who just don’t learn these lessons and repeat the same mistakes.

Modern software is too easy to trial.

This low entry barrier sets up a treadmill for someone prone to “shiny object syndrome.” Without constraints, many of these tools get implemented inconsistently throughout an organization. Over time, you’re left with a balkanized environment where everyone is on different tools, making integration nearly impossible.

The key is to approach system selection the same way you approach any other investment.

Below are the four biggest lessons I learned over the past few years.

No Clear Definition of “Done”

When buying anything, a clear definition of what you want to achieve is critical.

Too often, we accept the company’s sales-and-marketing definition of the problem, so their product becomes the clearly dominant solution. The problem with this approach is that your problem may have some overlap, but it’s not a direct analog.

Approaching a solution without a clear understanding of the problem usually leads to addressing each symptom of the root cause individually. When we don’t fully understand the problem, the solution to each symptom feels like progress. Therefore, the key to getting the best solution is to take the time to clearly define the problem.

Once we have a firm grasp of the challenge, we can design a solution that addresses as many root causes as possible. When designed well, this leads to downstream impacts that address the various symptoms holistically. We escape the endless loop of solving one problem only to see another, seemingly unrelated, issue arise.

In addition to clearly defining the problem, a clear definition of “done” empowers us with a metric from which to measure success.

A clear target helps reduce scope creep, which is an absolute killer.

Scope creep is the enemy of any project. I’ve seen hotel renovation projects more than double in cost and time to delivery because the goal was never locked in. The same principles apply when purchasing and implementing a new system.

Too Much at One Time

The solution exploration stage is one of great wonder. It opens a wondrous world in which opportunity abounds. All problems look solvable with simple fixes at this stage.

That’s where the risk lies.

When exploring solutions, we must adopt a more cynical attitude. We must understand that everything will always be harder, take more time, and cost more than expected.

Unfortunately, we often stretch ourselves too thin before we know we’re doing it. We decide to take on projects we don’t have the staffing or expertise to complete. This inevitably leads to failure and burnout.

In addition to putting on my cynic hat, I like to step back and look at things from a multi-year macro picture. The reality is that nothing is as urgent as it seems. In fact, slowing down in the planning stages allows us to accelerate during execution.

The key here is to think in terms of roadmaps.

While a complete solution, implemented all at once, often seems best, a staged approach allows for better user acceptance. Forcing ourselves to think through training and delivery opens the door to better understanding where the potential failure points are. I can assure you that the salesperson won’t do this for you. It must be a discipline to master.

No Perspective on Debt Accumulation

In business, we run into all kinds of debt. While tangible financial debt is easy to measure, the more insidious and destructive debt takes the form of shortcuts.

Every workaround, delayed decision, and undocumented process accumulates over time until the machine no longer functions as intended. This is a natural part of growth, which isn’t problematic so long as it’s well understood.

Most businesses wait too long to address management and technical debt.

They let the issues compound to the point where inaction is more painful than action.

At this point, deleveraging is incredibly painful and costly. Small fixes earlier in the cycle often yield tremendous returns later, which is why tight feedback loops are critical for avoiding excessive accumulation.

Tracking management and technical debt can be formal or informal. I like to approach it with a formal issues log. This method allows anyone to report “bugs” over time, which becomes your backlog in a regular sprint cadence.

Once we have a solid system for identifying and tracking issues, we can systematically address each item in turn.

Deciding Too Early

Finally, when the selected solution is in place, we must evaluate performance.

“Hire slow, fire fast” is a nice theory, but it doesn’t capture many practical realities.

Slow selection is often misconceived as a drawn-out process to evaluate all options. It’s more comprehensive than that. When we lay the proper foundation, our selected solution should operate without incident. However, laying an incomplete foundation almost guarantees failure.

Leaders who thought they did everything right on the front end often default to that old adage and judge success well before it has a chance to take root. Setting a clear expectation of time-to-results is a big part of defining success and laying the foundation.

For all these reasons, I like to establish contracts within my process to avoid as many of these mistakes as possible. The fluidity of many systems makes them feel unbounded.

Creativity dies without constraints.

Internal contracts ensure that we hold ourselves to a higher standard.