The Complete Process of Choosing the Best Project Management Software

If you own a small project-based business, you know by now that’s almost impossible to manage projects with only pen & paper or spreadsheets (if you can do it though, feel free to share your methodology with us in the comments section). It might work for very simple projects, or in some isolated cases, but as soon as the project gets a bit complicated and several people are involved, you’ll definitely need a software or a combination of several apps (keep reading to see exactly why).

Before we move forward though, I have to debunk a myth: no matter how hard you try, you won’t find the “perfect” solution. You have to get used with the idea of making compromises, wait for missing features to be implemented or negotiate a better price for your subscription. You need to be wise and find the balance between what you need and what’s been offered to you.

One more thing: choosing the right PM software is not easy. That’s the reason why many companies or individuals end up using apps they don’t find useful and have to replace them after a few months or weeks. In this article though I’ll show how you can simplify this process… a lot!

Create a list with problems and needs

You’ll start by writing down your problems and needs. The better you understand them, the bigger the chances to make a better choice.

What projects are you dealing with? Are they short-term simple projects, or more complex long-term ones? How many people will take part? Where are the bottlenecks?

The complexity of your projects is an important factor, because most of the time it’s correlated with the complexity of the software you’re gonna use. And trust me, it’s very frustrating to have to use a complex software for simple projects, or vice versa.

After you put on the list everything that you can think of, sort the elements by how important they are (do not miss this step!).

“Translate” problems and needs into features

You now have the list of features. Depending on the problems they solve, you know which are mandatory, which are good to have and which are nice to have or bonuses (that might be useful at some point).

This is how a list could look like:

Create a list of 20 project management apps

The feature list is ready, so you have to look now for project management apps. The good news is that there are hundreds of apps out there. The bad news is that you have to sort them out and come up with a list of at most 20 apps that offer the mandatory features (and all or some of the “good to have” features).

Or, you can try a simpler alternative. You already know what you need, so why don’t send the list and ask for feedback. You don’t even need to personalize the email, you can send a bulk email (you’ll need the contact email addresses of all).

Here’s a template you can use:

Strip down the list even more and start testing

After you get responses from at least 20 companies, compare the results and pick 4–5 “winners”. In theory, these are the apps that could be the best fit.

And now, the fun part begins! The majority of these apps offer a free trial, so it’s time to get your hands dirty and see exactly what these apps are capable off.

While the trial period differs from app to app (from 10 to 30 days, or even more), my advice is to limit the testing to the shortest trial period offered. This is good for a couple of reasons: it helps you stay focused and get a result faster, without having to ask for trial extensions.

The best practice is to simultaneously test all the apps with the same project. It can’t be a real project because you don’t have the time to take it to completion, but you can emulate one and put it in fast-forward. Even if it’s not something easy to do, it has many benefits: you and those involved in the project will be able to compare the apps in parallel, test the speed with less or more data, check usability, the level of support you receive etc.

Create a spreadsheet, share it with everyone that’s going to use the app and encourage them to leave feedback. Picking the “winner” together with your team is much better than choosing it yourself.

How about pricing?

I believe pricing should be the last deciding factor (unless you have a strict budget which you can’t exceed, or if there’s a huge pricing difference between 2 apps that offer the same set of core features). Sometimes there are hidden costs, so you need to be aware of them.

Key takeaways

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