5 Best Practices For Implementing Project Management Software

Tips for Smooth Implementation


Implementing a project management software can be an exciting time. One centralized system to manage teams, tasks and projects increases team engagement, bolsters cross-functional collaboration and improves overall communication.

However, getting an entire team or company to adopt and actually use a new tool effectively is a major undertaking. One that can lead to undue stress and aggravation, and in many cases, failure.

At Project Insight, we’ve helped manage hundreds of successful software implementations, and though no one implementation is the same, there are a few common obstacles amongst teams that we’ve identified and helped rectify. The following are five best practices to consider as you work toward a successful project management software implementation with your team.

  1. Leadership buy-in is paramount. If you are trying to implement project management software (or any software for that matter), the directive for change must come from the top down. Without leadership backing, just a few negative people on the team could derail the entire project. Senior leadership needs to mandate that this is the entire team’s (or company’s) objective. Once leadership affirms this directive, negative feedback is no longer seen as negativity toward the new software, but instead as negativity toward leadership -- which greatly decreases the risk of pushback.

  2. Embrace your naysayers. Even with leadership on board, chances are you will have your fair share of sticks in the mud--and that’s okay. Instead of trying to stifle them, give them the floor to air their grievances, fears and points of contention. This will not only make them feel heard, but it will also serve as your risk register for the implementation project. What are all of the things that could possibly go wrong and what will you do about them? Address them, record them, and as you hit new milestones in the project, cross off the ones that become irrelevant.

  3. Maintain reasonable expectations. Decision makers are often wooed by the seemingly boundless capability that enterprise project management software offers. With everyone updating projects in one place, the prospect of rolling all of that data up into enterprise-wide portfolio reports is tantalizing (and for good reason). Enterprise project management software can track a lot of data which makes valuable insights easily accessible. But a common pitfall we’ve seen in many cases is when management expects too much too soon.

    Negotiate what you expect to get out of the system with what’s reasonable to put into the system and keep updated, especially within the first 30-60 days of implementation. Management may have a lot of demands, and eventually you will be able to deliver on them, but during the first days of implementation you will overwhelm your team. Allow teams to be more high level with their inputs so they can keep projects up to date more regularly, and ease into more sophisticated uses once everyone is acclimated to the new system.

  4. Micromanagement is the enemy of project management. Project managers can’t plan every detail that will be involved in every piece of work. Micromanagement is hard to manage, plan and forecast. If your work breakdown structure is too exhaustive, it makes managing changes far more difficult than it needs to be. Allow a project’s history to tell the details, it’s much less complicated. All future work should be kept high level.

    For example, if your development team is working on an app and you need to know what your programmers are doing on a daily basis, plan for larger tasks like “Complete prototype of new widget,” but don’t itemize all of the different components needed to get there. You can collect detailed updates using avenues like comments on the task or daily time entries.

  5. Adaptability is key. Your project management software of choice will not be a perfect fit for everyone, but good software will offer adaptability. For instance, if your projects follow differing methodologies, many software platforms can support that. However, perhaps your projects require different methodologies within the same project. For example, a new software development project may start off using kanban, then graduate to agile, then shift to waterfall as it is rolled out to customers. Project Insight supports blended methodologies like this, but if you’re using a system that does not, you may find yourself needing additional tools to get the job done.

    This is where integrations become key. If your team needs to work in other environments throughout a project, whether to support an additional methodology or otherwise, integration offers another level of adaptability that will help you seamlessly collect the data you need without disrupting productivity. Set yourself up for implementation success by knowing what your software is and isn’t capable of, and what integrations can help fill those gaps.


Project management software implementation can be daunting, but following these steps to mitigate common roadblocks will hopefully make the transition smoother for you and your team. If you found this article helpful or you’d like to share your own implementation tips with us, please do share to your favorite social media channels like Twitter and LinkedIn. Don’t forget to tag @ProjectInsight!