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4 (Human) Reasons Software Implementations Go Wrong

Lindsay McGuire
April 7, 2022
Min Read

Software implementation.
Tech launch.
Process overhaul. 

If you’ve experienced any of the above and had it go wrong, you may have some particular feelings bubble up when you read those words. 

Technology is incredibly powerful, but if it’s not implemented well, it can make your workday complicated, stressful, and unproductive. Even the most successful organizations have fallen victim to a software implementation failures

So what can you do to ensure your organization's next software launch is a success? Drew Weiss, VP of Global Business Technology at VICE Media, is here to help. He’s spent the last decade leading IT teams, improving operations, and implementing new technologies, so he’s seen how software implementation can be smooth sailing or a complete disaster.

Below, we highlight four common human errors Drew has seen negatively impact software implementations and what you can do from the beginning to ensure these mistakes don’t derail your next tech project. 

Listen Now: Drew shares even more tips on how to best use technology, manage projects, and gather buy-in on our Ripple Effect podcast. Listen to his Future of Work: Navigating Digital Transformation episode now! 

1. Expectations are not set.

A lot goes into planning, testing, launching, and maintaining new software. To make each step of the software implementation process go smoothly, you need to set expectations early on, across all teams involved. 

Drew thinks this may be the most common mistake organizations make when implementing new software. He points out that there are actually two very distinct groups you need to set expectations with: those who requested the tech, and those who must adapt to using it. 

“When you implement a new system, there are two sets of expectations you have to set. One is the people who want to see the change,” he said. “You need to set expectations on when you may actually be able to roll this out; how you're going to roll it out; who you're going to introduce it to first; and how you're going to make sure that when it's in place, it is, in fact, a step in the right direction.”

Most organizations do a good job of setting expectations with this first group. Where many fail is setting expectations, early and often, with end users who are not part of the requester group. 

“The second piece is setting expectations with people who are day-to-day users of the system,” Drew said. “If I've been doing something for years, then I'm very comfortable with it. And now you're telling me that I have to reinvent the way that I do things?” 

Drew’s advice is to involve these end users who may be more resistant to change in the project planning as early as possible. “When people feel like they're part of discovery, when they're part of the initial roadmapping of a project, they feel like it's a collaboration and not something that's been put on them.” 

2. Zero time is spent building trust.

Change can be difficult. That’s why building trust early on in any tech project is crucial. 

This is an especially important tip for organizations that are making changes after relying on systems, processes, or technology for years. In these situations, many employees may feel very comfortable, confident, and secure with the systems and technology in place. If leaders make a sudden, large change with little prep or explanation, it could cause much more harm than good. 

Drew points out that people are what can make or break a software implementation. Trust must be built from the beginning through open conversations and clear communication. “It's so important that when you talk to somebody at the outset, you say, ‘We want to understand what your current workflow is. We want your help implementing.’ Gaining that buy-in is important up front.”

If there’s no time spent building trust in the beginning, people may feel like they were not considered in the decision-making process. This can cause resentment, frustration, and resistance to change. And once you build that trust, it must be maintained to the end to achieve success. 

Drew stated, “The worst thing I think you could do is go to somebody up front, bring them into the process, and try to build that trust only to break it later. I think we sometimes have a propensity to gain buy-in and then go run and build something. Keeping people up to date and meeting deadlines is important so that you continue to foster that trust that you built up.”

Related: 5 Change Management Tips Everyone Should Follow

3. Decisions are only made from the top down.

Drew believes there’s one stumbling block that causes many organizations to struggle with tech projects: The belief that decisions can only be made from the top down. 

Leaders should be creating strong foundations for their teams and leading major process overhauls, long-term projects, and system improvements. But that’s not to say that front-level employees don’t have the power to do the same. 

During his Ripple Effect episode, Drew shared how he’s seen some of the best tech implementations come directly from individual contributors or specific teams: 

Empowering employees to suggest new technology and spearhead implementations can lead to incredible innovation. When leaders and individual contributors work together to identify problems and propose solutions, projects can progress faster, easier, and with more buy-in across teams and departments. 

“Over the last couple of years, one of the things that's really come to the forefront is how do we promote collaboration amongst our teams?” Drew said. 

Read Next: How Digital Agility Empowers Employees and Boosts Productivity

4. Important stakeholders are not involved.

If you walk away from this article with only one takeaway, it should be this: Err on the side of involving too many stakeholders. 

Drew has seen lots of software projects fail because not enough people were involved in the initial planning phases. From departments performing duplicate work to teams feeling out of the loop, not involving enough stakeholders can cause many issues along any digital transformation journey. 

But stakeholder involvement doesn’t just happen at the beginning; they need to be included across all steps of the implementation process. “Gaining that buy-in, bringing somebody in up front is important, but you must then maintain a relationship with your key stakeholders throughout the process,” Drew shared. 

He does point out that having too many people involved can backfire, so find the balance that works for your organization and project. That may be identifying the teams that must be involved and inviting them to the initial discovery, or bringing in representatives across all teams to be in on the process. ​​”If you have 75 people helping you on the outset with discovery, you're never going to get anywhere. But I always say I'd rather have too many people in the room than not enough.” 

Ready to launch your next piece of software? 

Drew’s best advice for organizations on how to implement software is to involve people up front, clearly communicate across the entire process, and set expectations early and often. If you follow these guiding principles, you’ll find that the entire process—from gathering buy-in to optimizing—goes smoother. 

Want to hear more excellent advice on implementing software and navigating digital transformation initiatives? Listen to Drew’s Ripple Effect podcast episode Future of Work: Navigating Digital Transformation now! 


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Lindsay McGuire
Lindsay is the Content Marketing Manager at Formstack, splitting her time between creating blog content, writing reports, and hosting Formstack's Practically Genius podcast. She's a proud graduate of the University of Missouri School of Journalism (MIZ!) and loves connecting with others on LinkedIn.
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