The secret tactics to getting enterprise software implemented

Let me paint a picture for you. If you work in a big enough company you will see this situation. Someone bought software signed a multi-year agreement. They did not come up with a plan of how to implement it. They did not hire a team to work on it. They did not bother with procuring any training. They hope it will be adopted and championed.

It won’t.

Now it is your job to drive the adoption. You are presented with a long list of tasks to optimize the software and stand it up. We’re multiple years in yet no one is using it. How can that be? Someone is working for years adding new features, servers, and requirements, and yet, the software languishes and the bills continue to come in. You might be asking yourself, “How did it get this way?”

“Things are the way they are because they got that way.” - Gerald Weinberg

Courage. Courage is rare. Courage means looking deep inside yourself and realizing you failed. Do you know what is easy? Looking at a task list and seeing many things checked off. What does effort, hard work, and perseverance matter if it is for nothing?

How to fix the situation

Assuming that you do not have a vaporware situation on your hands there is a strategy to get software implemented. You need to start with quick wins. Once you establish a quick win model, document, share it out.

The first implementation is the hardest. Once you have a win it gets easier. You will be tempted to take on more than one project at once and don’t bother. Come up with a list of projects that could implement the unused software. From the list determine the five which would be the easiest to implement while delivering value to the teams. Reach out to the product owners and find out who has flexible timelines. You want a team that is flexible and not stressed out. Set up a meeting and conduct an accusation audit in the invite as well as during the meeting. Your goal is to overcome objections before implementation.

Before or during the meeting with the team call out any concerns. Here are a few challenges you can point out immediately.

You are thinking:

  • We will abandon you
  • This implementation will fail
  • It will take too long

Consider implementing the software on your own time with a copy of their application. Nothing removes implementation fear faster than seeing a working version of their software. They still need to do the work. When you meet with this team make sure to relate the shared values of your organization and explain what is in it for them. Leadership is counting on you. It may sound silly but even an email to the whole department saying, “X team is the first to implement foo software” means something. Now you might think your job is done here and it is only beginning.

Further advancing tactics

This is the stage where you can screw it up. You need to continue following up and advancing adoption each week. You might hope that others will do it for you. Or the teams will start banging down your door demanding to use the software. This thinking is fanciful. You need to keep following up.

As you follow up, observe what is causing friction for onboarding teams and remove those obstacles before you are asked. The key to usage is designing for “the pit of success”. You want to make it so that everyone finds success by default with little to no effort. For this project that needs help, I asked, “Well, what do I need to do to get started”? I was given a list of four tasks to complete with the first two out of my control.

  1. Make a request and wait
  2. Make another request and wait
  3. Do some work
  4. Do some work

You might be asking yourself, “Alan, what’s the problem here? This is the process we have in place they just need to do their jobs.”. It’s natural to want to optimize our work and not others. Let’s give people a chance to be successful. It is your job to remove or ease the barriers blocking the adoption.


Look this is a common problem. You are not alone. There are a lot of reasons this happens and at the end of the day if you are reading this article it is your job to figure it out and solve it. You need to handle objections and remove the friction for people to adopt. People want to do what other successful people are doing. They want praise for following the orders of leadership. It is simple work on things people are asking for. If no one is asking for it you don’t do it. Keep track of your wins and share that out and persevere.

  • Establish a quick win
  • Market and share the list of progress and continue following up each week
  • Observe what is causing friction with onboarding and mitigate those points and remove objections

What do you think? Does this sound familiar to you? Have you overcome a situation like this?