How to Choose the Right Project Management Software for Your Organization

Posted by on May 17, 2019

project management software

While a simple to-do list might work for keeping track of chores at home, business projects require a much more in-depth process to break up big tasks into achievable chunks. This is where effective project management software comes into play.

What Is Project Management Software?

Project management software helps your business cultivate an efficient workflow so you can execute strategic projects, like migrating to a new database or launching a new service.

Effective software represents a valuable tool in your business arsenal that enhances employee productivity. It can help organize more than just notes and deliverables, but people and resources as well. It helps facilitate communication between team members and make sense of complicated schedules and budgets, so that project outputs come through on-time and on-budget.

Your team likely spends a good amount  of their time working on a computer. Instead of meandering through your office to update a colleague, project management software can make it easy to file share so information can be read, modified, and—if needed—acted upon instantaneously.

If your help desk is swamped with request for assistance, understanding what each team member is working on can be a challenge. Team leaders can use a project management software that includes Gantt charts to create dynamic timelines so progress can be seen in real-time.

Project management software that offers the ability to create team dashboards can be a useful way to present graphs, charts, and other visual metrics.

If you team is in charge of implementing a new office technology, creating KPI reports with project management software makes it easy to share key information with other team members. This fosters more informed decision-making since the actual results can be cross-checked against the projected implementation schedule.

RELATED: Project Management Service Overview

Common Challenges and Pitfalls When Selecting the Right Project Management Solution  

As companies dedicate more time and resources to discovering technology to gain a competitive edge, the scope and number of project management tools has increased.

It might be tempting to buy the first project management solution that looks appealing.

Some might do a quick Google search, skim the first few results, and then sign up after making a quick decision. However, making a snap choice on this kind of software does more harm than good because, as you’ve been able to see, project management software directly impacts strategic alignment and business outcomes.

There is no "one size fits all" when it comes to project planning and management software. Teams and tasks are very different across companies. What might work for one organization might not be the best for yours.

Trying to find the right project management software can be a tedious effort. Capabilities across solutions vary greatly, and you might not even fully understand what your organization actually needs until you put them into play.

However, the undertaking is well worth it because the right one can revolutionize your business. A quality project management software can streamline your business’s entire workflow, which helps you deliver high-quality project outcomes and ensure greater customer satisfaction.

7 Easy Steps to Follow When Choosing a Project Management Solution

It’s hard to know where to start when starting your project management software search.

If you have a lot of demanding projects on your plate, time is of the essence. How can you know what type of software is going to be most effective? And what happens if you choose a project management software that is too basic for your needs? You could be burning valuable time trying to keep your complex projects on track.

Let’s not forget cost. If your business is on a shoestring budget, an expensive piece of project management software can tank your finances, especially if it does not end up meeting your needs as expected.

All of these questions are very important and crucial when deciding on the right project management software.

But don’t worry—we’ve got you covered. Keep reading to learn more about our seven-step process to choose the right project management software. The guide will help you find a solution that meets your project demands, the needs of your team, and fits in perfectly with your budget.

1.  Get Down to the ‘Why’  

First and foremost, when beginning your search for the right project management software, you should be able to answer one simple question: Why? The decision-making process should start with an open and honest discussion about why you actually need a project management solution.

Is it because you’ve outgrown your current project management tool or approach? Maybe you don’t have an approach at all. Does your organization have any upcoming strategic initiatives that are going to warrant project management software? Once you’ve nailed down your "why," it’ll make selecting and communicating the value of project management software to your team that much easier.  

2. Assess Your True Requirements: Look Beyond the Obvious

Who  comes to mind first when thinking about project management software?

Most think of trendy solutions like Basecamp or Asana. While these options do have value, there are a lot of other useful and more robust choices available in the project management world. Making an uninformed decision is very poor decision for your business because tools are not all created equal. Different companies often offer very different bells and whistles that might not directly meet all of your professional and business requirements.

When it comes to project management software, you need to gain a thorough understanding of the capabilities and functionality your business needs and take a deep dive into what your options really are and.

Speak to others in your network to find out what project management solutions they are using. Ask your colleagues if they have suggestions. Conduct research on your own and see what experts are saying.

Most people tend to latch onto the first thing they see. This is especially true when it comes to buying a home or apartment. The first option may seem like the perfect fit…until you visit the next property.

The same can said of project management software. Go beyond the surface-level and make sure your choice accurately matches your needs.

3. Are There Any Implementation Barriers? Identify Them!  

Once you have a good software candidate, the next step is figuring out any implementation barriers. This step is arguably the hardest part.

Many providers offer demonstrations of their product that can give you a good feel for how it might work for your business. Invite team members and customers to test out the software. Capture feedback from them in a structured manner. Run your own beta with one of your  smaller projects as the test subject so you can see how the system works with your existing processes, software, and technology.

You might find that one of your implementation barriers is something simple, like general resistance from your team to the software. Maybe it’s more serious, like problems with data migration that could significantly slow down progress and cost your company money. Or it could be that the software is simply incompatible with other key systems, removing it as a candidate completely.

Once you have identified any barriers, make sure everyone is on the same page before moving forward. This could mean calling a meeting with senior managers to let them demo the solution so they can better explain transitioning to the software and its capabilities to their own team members. Or you might have to reach out to the software provider to get a quote about how much it would cost to migrate data and set up the system.

4. Solve the Cost vs. Functionality Puzzle  

It is only natural that project management software varies considerably. There are simple project management solutions that cost around a hundred dollars. More robust software might total in the thousands.

Don’t lose focus on what is truly important. Some software sellers will try to entice you with fancy bells and whistles that sound exciting, but have no tangible benefit.

And keep in mind, a non-negotiable is making sure the features in your next project management software will enhance communication and collaboration. It is probably not worth it otherwise.

When it comes down to cost, it is prudent to consider what is ahead for your company. Do you have any upcoming initiatives? Are they short-term or long-term? Choosing to spend a bit more money now for features that will be used down the road can be a smart choice. Just be sure these features genuinely future-proof your organization and are not just an unnecessary add-on.

5. Make the Most of Your Free Trial  

Everyone loves a free trial. It’s cost-free and gives you a low-risk chance to see if a product is right for your business.

The vast majority of quality project management software will come with the option of a free trial to test-drive the service—and you should absolutely take advantage. And even if a company does not offer one on their website, most will be happy to accommodate. Don’t be afraid to take advantage of a free trial!

Make the most of your trial by getting every employee involved and having them experiment with legitimate project scenarios. You want to test out a project management solution to the limit with real-life use cases before you make a final purchasing decision.

It is smart to keep the lines of communication open and set up a way so that feedback and other important usability and compatibility information can be collected and analyzed. You do not want to waste company money on software that nobody ends up using. This kind of feedback can be tracked via meetings or documentation, but the end goal is to simply help you figure out and decide if this particular project management software is a good match.

6. Strike a Balance Between Control and Collaboration

Project management software has rapidly evolved  the business environment over the last ten years. It is now seen as a collaborative tool that fosters communication rather than a monolithic system or a delivery mechanism.

Good project management software lets employees log on and off with ease and allows them to stay in constant communication with other team members. It fosters knowledge-sharing and helps keep all stakeholders informed.

A sense of collaboration and camaraderie between your team and the rest of your organization can really drive progress and better project outcomes. This in turn helps your team run more smoothly and can also dramatically increase the operating efficiency of entire company.

7. Analyze Onboarding Timelines and Go-Lives

Once you have found the best project planning software for your company and are ready to make a purchase, one final step remains.

It’s critical that you build out your software deployment plan to make sure the implementation process can go smoothly. If there’s no implementation plan in place, you may experience unexpected delays and be facing a lot more problems than you initially set out to solve.

You should carefully consider the logistics of deploying your new software. Are you looking to implement it with just a few of teams, or are you interested in introducing it across your company in one sweeping rollout?

How will your proposed solution mesh with other software systems your company already has in place? How will training sessions (if needed) fit into employee schedules?  All of these are important factors to consider as you introduce and transition to a new project management software.


The right project management software can hands down transform how your organization’s work flows. It can help you better align to strategic initiatives, create efficiencies across teams, and improve customer satisfaction.

Cherwell’s Project and Portfolio Management solution offers comprehensive task breakdowns so you can stay abreast of important deliverables, foster communication and knowledge-sharing across your team, integrate with other point solutions like MS Project, and more.

If you are ready to learn more about Cherwell’s comprehensive project management solution so you can meet organization objectives, check out our on-demand webinar to get an in-depth overview and demonstration of Cherwell’s Project & Portfolio Management solution.

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