September 11, 2017

The 5 W’s of Buying Project Management Software

Written by
Steve Pogue

The idea of using project management software can be daunting to those of us who don’t think of ourselves as project managers.

Yet while you may not have an official degree or have gone to a certain class to be certified as a PM, if you’re delivering products, completing tasks, motivating your team, or tasked with creating things, then you’re managing projects. And project management software could be really beneficial for you.

But what’s the right solution for you and your team?

To get to the bottom of that, we can go back to our school days and use the five W’s to investigate and evaluate the options.

1. Why?

This is where you begin to define if you truly need project management software, and just how robust of a solution will meet your needs.

Truth is, more than 75 percent of participants in large IT projects feel like their project will not succeed. Those odds aren’t good. A solid project management solution won’t solve all of your problems, but it can definitely help (when used the right way). Here are just a few of tell-tale signs that a PM solution might benefit you:

  • You’re always nagging your team about deadlines and deliverables.
  • Your team is using too many tools to track different aspects of your projects.
  • Your team is spending too much time on emails and meetings and not enough time on creating deliverables.
  • You’re not getting adequate updates or enough visibility on projects.
  • Issues are not properly tracked and risks are not flagged in time.
  • Your current software is too complex, so much so that it’s creating inefficiencies (e.g. it takes a long time for new hires to get up to speed) rather than increasing productivity.

2. Who?

Who will be using your project management software? It isn’t as obvious as it seems. Are you buying it for just yourself or for your whole team? If it’s just for you, you probably can get away with a few quick to-do lists in a task management app and avoid the extra costs of a dedicated project program.

If it’s your immediate team, how many people is that? And who do you regularly work with? Does upper management need to be on there too? Finding a tool that can support multiple users, multiple teams, and even different permissions is a good idea.

3. What?

With this question, you have to tackle what you’re trying to achieve and what you need to get there. The typical questions are: What are the deliverables? What resources are needed?

Consider the resources, workloads, and materials needed to get the project done. This is important when purchasing software because some programs offer a better suite of features for your particular needs than others.

The best project management solutions have calendars, Gantt charts, and workload reports so you know who is available and when. But not all project management software has those features. It’s important to decide upfront what you can and can’t live without.

Does your team do the same tasks repeatedly in a set process? Then having repeatable project templates would be the way go. Are you billing external clients? Then you need something that accurately tracks human capital resources.

4. When?

This isn’t only about when project deadlines and deliverables are due, but when you should implement new software. There are a few things to consider:

What’s the status of your current tech stack? If you’re trying to combine a few tools into one, it may be better to wait until a few of those contracts expire. It’s hard to integrate your work into a new tool if the old solution is fully available. There will not be as much urgency.

What’s your business cycle look like? Plan on implementing new software when your business “slows” down (ha, right?). That sounds impossible, but think about the initiatives you have on deck and when you may be able to roll out a new solution with the least interruption. You want your team to have the bandwidth to learn and adopt something new, and not be stressed about finishing a huge deliverable. The PM solution is meant to make their lives easier, not add more to an already tense situation.

When is your business growing? It’s important to let your business grow into your tool, rather than trying to stuff too much into a tool that can’t handle what you really need. This doesn’t mean buying the fanciest or most expensive solution. But you can reasonably predict hires and future work for the next six months or so. That will impact your team communication and the tools you select. You want a tool that can grow with you, not one that you’ll have to discard after only a few months.

5. Where?

Yep, where. This question isn’t as obvious, but it has important ramifications. Where is someone doing the work? Remotely? In a different office across the country? At a manufacturing plant with limited insight from your team? In the field?

And where will the majority of your projects deploy — are they events, printed materials, digital deliverables? The locations of team members, collaborators, partners, and vendors, workers are key points that affect how your projects look.

They also affect the type of project management software that you buy  — what level of in-app collaboration and communication is needed, which app integrations, which languages it should be available in, and how you want approvals to be made.

Bonus Question: How?

This one is a bonus, but don’t let that take away from its importance. How your team works will absolutely make or break your success with project management software. If your team prefers list-based tasks, but you offer them a tool with Kanban boards meant for agile development, they’ll end up hopelessly confused and frustrated. The PM solution will go unused.

Look for a tool that works how your team works, but also one with world-class customer support and product specialists to help when the inevitable bumps rise in the road. Good customer support will help your team adopt the software and continue to use it well.

Buying project management software doesn’t have to be hard, but it does take a little forethought, research, and patience. If you don’t think it through and the tool you choose doesn’t work for your team, they’ll be wary the next time you roll out something new. Take these steps into consideration and you’ll start and stay on the right foot.


Steve Pogue is the marketing operations manager for Workzone, a cloud-based project management solution. Previously, he worked at First Round Capital, a seed stage venture capital firm. Connect with Steve on LinkedIn.