We call it a free trial, but we know the truth. Trying out a new project management tool is never truly free, because it requires time and energy from you to figure out if it’s right for your team. And your time and energy costs money.

In a way, it’s a lot like dating. Most people don’t meet someone and know instantly if they’re going to be together forever. You spend time together, learn to appreciate each other’s assets and discover each other’s flaws. And ultimately come to a conclusion about whether you want to commit. It’s the same with project management software, because the tools teams use to run their projects is absolutely core to the way they function day in and day out.

It’s even possible to map the stages of a relationship to the stages of the selection process:

We appreciate how much work it is for you to come to a decision, and we try to help you along in the process as much as possible (with free trainings, demos, and personal support). But it’s really up to you to get into the system, take it for a test drive, and ask the hard questions.

So what are the questions you should ask yourself before making a final commitment about your project software? (Hint: they’re pretty much the same as the ones you ask yourself before popping the question.)

At LiquidPlanner, we place a high value on the ability to keep plans up to date. We value realistic views of when you’re going to be able to get projects done (statistically likely best case/worst case scenarios). We value communication and transparency between team members. But most of all, we value systems that get out of your way and let you actually get your work done. That’s what we work towards every day. If you share these values, we’re off to a good start.

2) Can you live together in harmony?

If you’re going to spend time every day with a tool, interactions with it should be quick and painless. Can you easily make updates and changes? Can you immediately find out what you need to work on and get to it? Does the interface flow and make sense to you? They seem like small details, but they add up to a big part of the big picture. And this question is key to overall adoption. It may be unrealistic to expect everyone on your team to fall in love with your favorite tool, but if enough people get hooked to give you critical mass, momentum will likely take you the rest of the way.

3) Do you communicate well?

Centralizing team communication in your project management tool has undeniable benefits – creating a single information repository, improving efficiency by minimizing switching costs between platforms, and developing a community around project work. But it has to be seamless. We put comments (or Workspace Chatter, as we call it) front and center on your dashboard. In the same way that your Facebook news feed keeps you up to date with what your friends are doing, this comment stream gives you situational awareness into your teammates’ activities. And email notifications bring those comments to you in real time (and you can even reply directly from email.)

4) Do you challenge each other to be better?

One of our more lofty goals is to transform project management by scrapping the old paradigm and starting from scratch, giving you a way to schedule projects that is truly different (and better) than any other system out there. Part of that difference is a fundamental shift away from single-point estimates and overloaded schedules, toward a priority-based model that discourages multi-tasking and keeps you in touch with reality.

This is occasionally a tough pill to swallow for teams used to Microsoft Project’s scheduling method, which allows you to give each person as many tasks as you like on a single day. It allows you to build schedules so complex and cryptic that they’re useless to any outsider trying to decipher them. We want teams to be better at delivering, and that requires schedules that are more realistic and easier to maintain.

We’ve had some bumps along the way, and we continue to improve, thanks in large part to our dedicated customers that give us detailed feedback on a daily basis. We are a much better platform, thanks to them.

5) Do they want you to sign a pre-nup?

Last but not least, we know that the experience of using LiquidPlanner is as much about the service as it is about the software. We don’t ask you to sign anything or hand over your credit card before you get to fully experience what it’s like to be a customer.  If you have to enter into a contract before getting access to the tool, or pay a single dollar before seeing all the features, your vendor may be hiding something.

To everyone out there looking for the perfect fit: best of luck in your search. We hope we’re compatible with your team. If you’d like to talk to us to find out more, just call.