8 Steps to Successful Software Adoption in the Enterprise

Here’s something that almost everyone can agree on: adopting new software in a large corporation is hard. In fact, depending on which study you read, a shocking number of attempts downright fail. After spending time at three enterprises and three more SMBs, I could not agree more. Thankfully, contrary to the sad state of statistics on the matter, my personal experience has been anything but. Is there a formula to successful adoption? Absolutely. After launching and operating several global marketing operations platforms at two different enterprises, here’s my secret sauce to successful software adoption in the enterprise.

Introduce Change in Bite-Size Chunks

Ripping bandages off slowly can be grueling and ill-advised in most instances, but when it comes to software adoption, taking it one team at a time is a point that should be stressed. We’ve all been there: asked to join a massive WebEx training session for a new tool or process. At the end, the floor opens to Q&A and everyone is so eager to get on with their day that nothing gets asked. Don’t fall into this trap. Most employees aren’t interested in doing more work and company wide training sessions turn into free time to check email, social media or play online poker.

Instead, recognize that each team has their own challenges and pain-points with the status quo, potentially deriving value from your new software in different ways. Breaking teams up into smaller groups will result in a discussion on how to improve everyone’s time at work, and who wouldn’t love that?

Take Training Seriously

It’s tempting to jump the gun and unleash a torrent of calendar invites across the company to show just how much value you’re delivering with your big idea. However doing so ill-prepared will often lead to a “flash-in-the-pan” moment, rather than lasting change.

Consider creating some training materials for several reasons:
1. It will help you think about the nuances of approaching each team with your software proposition.

3. It provides a great take-away from the training session and eliminates a many excuses that would-be adopters can make to avoid using the software.

4. Inevitably, some colleagues will miss your training sessions.

Unless you have dedicated resources with a relentless drive for following up, a visual step-by-step guide can be the next best thing to hearing you say it.

Lastly, you can and should keep record of who attended your training sessions. Post it in a public place. Whether it’s a list on an office wall or a wiki, use this proven method for tracking adoption and thwarting excuses.

Focus on User Experience

When selecting, customizing, or integrating a new product, remember to put yourself into the shoes of the end-user. Our smartphones are getting increasingly good at minimizing friction in typical usage. Expectations are high, so if you’re attempting to introduce outdated software with a clunky UI, get ready for failure. Remember that the ultimate purpose of your product is to deliver value for the company, and in many cases, this means your users should be receiving (or at least perceiving) value in their own right. An unneeded email notification here, an extra click there, or a confusing layout add dreaded friction. Friction is the enemy of software adoption, so trim it wherever possible and your colleagues will thank you.

Get Permission

Executive buy-in is an obvious first step in enterprise adoption, but as with anything, there’s a right and wrong way of doing it. Remember that like your end-users, executives are motivated by value. Perhaps the product you’re hoping to adopt promises new metrics opportunities. Perhaps it can save time or money. Whatever the case, it’s very likely that your vendor of choice has already dealt with selling to top brass. Ask for their help in constructing a compelling argument for ROI, MRR, or whatever acronym is important to management in your company. Once the head honchos are on your side, you’ll have a much easier time scheduling training sessions with end-users.


Sad as it may seem, in many large organizations, perception is just as (if not more) important as reality. Once a pilot team is on board and deriving real value from your software, nominate some early advocates as evangelists. If the application that you’re hoping to adopt truly delivers value in a frictionless way, you may be on the brink of something truly magical — product addiction. For the same reason that some people visit Facebook many times a day, your software may spread across the company like a social epidemic. This type of product fit is incredibly difficult to achieve, but luckily, it’s not a requirement for success. As long as many people see a bit of value or a bit of people see a lot of value in the product, you’ll find at least a few evangelists. These folks will be happy to advertise how their work lives have improved because of your initiative.

Make a Pact with Your Colleagues

If the software that you’re pushing is intended to help reign in unreasonable stakeholder expectations, establish a service level agreement (SLA). No one likes getting asked to do a lot of work in a little amount of time, so your stakeholders will understand the need to provide you with enough lead time to do the job. Just remember to get the seal of approval from all impacted parties and upper management.

Zealously Enforce Compliance

Getting everyone on board and trained does not guarantee success. In fact, in my experience, it’s here that most adoption efforts fail. Always remember to relentlessly enforce the usage of your software or process. Compliance starts with you and your team and extends to all stakeholders and executives. No one wants to be the bad guy, so find some acceptable ways of delivering the message. In a pinch, remember to focus on value to the end-user first and company second.


No software package, process or agreement is perfect, but how can you enforce and compromise at the same time? As with any aspect of business, remember that change is inevitable, so arm yourself accordingly. Measure all aspects of your process and engage in constant dialog with end-users at all levels of the organization. Remember that software adoption involves humans, so at the end of the day, it’s your relationship with your coworkers that matters most. Help them whenever and wherever you can.