Does your team still run its projects from a cluttered, clunky Excel spreadsheet? Do you even have any processes in place for handling projects? If not, it’s time for an upgrade. Project management software is the equivalent of Marie Kondo — it’ll sweep into the life of your projects and bring order to the chaos. But only if you pick the right solution. We put together a project management software evaluation guide to help you do just that.
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With the right project management tool, you can escape the clutter, hit your deadlines, always know what your resource availability is and improve accountability — all from an intuitive interface instead of the black hole of Excel cells and tabs.
The problem? There are a gazillion vendors to choose from, and making a choice can seem as daunting as keeping your projects on track.
This article will help you cut through the confusion and focus on what really matters: finding PM software your team can use and will love. Here’s what we’ll cover:
- Outline Your Needs and Goals
- Look for the Non-Negotiable Features
- Determine the Cost
- Test the Software
- Evaluate the Vendors, Too
Let’s begin your journey toward organized, effective project management!
Project Management Software Evaluation: 5 Keys to Success
1. Outline Your Needs and Goals
Deciding to invest in project management software isn’t like getting off work and thinking, “You know what? I want pizza for dinner.” There’s a lot more to it, and your evaluation will be worlds less complicated if you first know what you’re looking for.
To be successful, involve your team in this step as much as possible. Their perspectives are valuable, and since they’ll be using the software, it’s important to understand what they need in order to execute effectively.
Start by asking these questions:
What roadblocks are we currently facing?
You’re probably already familiar with the challenges plaguing your team. That’s what led you to look for project management software in the first place. Even so, it’s still good to write down your exact problems.
Be specific and concrete. Maybe you don’t have a way to see each team member’s workload, so they’re constantly overloaded with tasks. Or maybe you collaborate extensively with clients, but the communication process is messy, and you spend hours digging through emails.
Whatever your unique situation, get it on paper (or whiteboard, tablet, etc.). You may be surprised by what you find when you start going through item by item. Some issues are obvious. Others may take some digging to uncover, but the extra effort will pay off in the end.
No problem is too small to address, though it’s best if you rank them in order of importance. That will help you tell the difference between necessary and nice-to-have features later on.
Speaking of which …
What features do we need (not merely want)?
This one’s tricky because on the surface, it’s easy to assume everything is equally important. That’s a dangerous place to be in while you’re evaluating software.
Taking that mindset into your search will lead to either disappointment because your expectations were too high, or it’ll lead to a budget that’s blown out of the water — the higher your demands, the higher the cost.
Use the list of challenges and needs you came up with to guide you. It may be helpful to create a spreadsheet with a row-by-row breakdown in one column. Then include which specific features will address those issues in adjacent columns.
Dashboard views, like this example, provide an overview of project metrics.
For example, if one of your challenges is a lack of visibility into projects as a whole, dashboards and reports would be two critical features that will solve that problem.
What fits with our team?
Are you entirely remote? In-office only? A combination? Your team’s structure will help determine what features rise to the top of your requirements list. If you all work remote, user access and robust collaboration tools won’t be optional.
Your team’s size is another variable to consider. Some products have a required minimum number of users or different price points for different team sizes.
You also need to take your team’s background into account. Have they all worked with project management tools before? If so, you may want to look at products with more functionality.
If most or all of your team is new to the PM software realm, simplicity will be your friend. You need a solution that can solve your challenges. But getting software that’s overly complicated or too feature-rich will hinder your team from performing at their best. They’ll be too busy trying to navigate the complex system rather than using the tools to guide their work. Sometimes, less is more.
Finally, look for software that will cater to your team’s methodology. If you’re in the Agile camp, for instance, you’ll want to look at products that include Kanban or Scrum boards to visually track tasks and structure your sprints.
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What type of projects are we managing?
Not all project management software will serve your project types. Some are more generic, but others specialize in certain practices. Jira Software, for example, bills itself as the top PM solution for dev teams.
The type of system you look for should fall in line with the specific intricacies of your projects. The good news is, most PM tools can be broadly applied. And if you need a niche solution, there are options for that, too.
2. Look for Your Non-Negotiable Features
Every product is different, but most come with a healthy range of project management features. After visiting a few vendor websites, you might easily become overwhelmed at the smorgasbord of capabilities they tout. (What even are webhooks, anyway?)
As you evaluate your options, it’s important to keep your needs in mind. Sure, the software may have forecasting capabilities, but do you really need them?
Every company’s needs vary, but here are some common features you’ll probably want to look for:
Collaboration
Like building a house or winning the Super Bowl, executing projects takes teamwork. Collaboration tools make it possible for your team to do its best work without feeling like you’re always scrambling to recover a fumble.
A few main tools are:
- Messaging: Keep communication in one place, tag team members and sort messages with hashtags.
- User Groups: Align multiple teams on a project, control access levels, assign different roles and keep everyone moving toward the same goal.
- Guest Accounts: Have outside collaborators? Give them access to certain project details so they can keep track of what’s happening. It’ll save you a lot of time sending updates.
- Access Control: We’ve all experienced that embarrassing faux pas — clicking on a link days after saying you’re on it and discovering you don’t have access. Manage account access by teams, user roles or even objects to keep projects on track (without the added cognitive burden of sweating permission controls).
Team Management
The bigger your team, the more important it is to be able to track where everyone’s at. Resource management tools make that process much easier. Managers can easily view each team member’s workload so no one suffers burnout. It’ll also help your project avoid bottlenecks due to teammates having more work than they can handle.
Project managers can monitor and change team member workloads, as shown in this example. Source
Time tracking is another useful aspect of team management. Project management tools display workload not only in terms of tasks, but also based on how many hours each person has been assigned each week.
Projects are often fluid and evolve based on changing demands. The ability to see resource availability, and shuffle responsibilities as necessary, will ensure your team is always focusing on the right tasks.
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Task Management
Project management software provides a variety of visual tools for managing your tasks. This includes Gantt charts, Kanban or Scrum boards with cards that represent each task, calendars and timelines. Drag-and-drop features make it easy to switch tasks, progress tasks to the next phase and rearrange deadlines.
These tools let you get as specific as you want. For example, with Trello, you can view an activity log, add checklist items, add tags and set due dates for each card.
Example of a Gantt chart showing project tasks, timelines and dependencies. Source
You can also zoom out for the wide-angle perspective. Gantt charts are helpful in that regard, presenting your individual tasks and phases in one comprehensive view. That helps you determine where everything stands, as well as spot potential bottlenecks and tasks behind schedule.
Budgeting
Completing projects within budget is a continual bane of project management. In fact, PMI’s Pulse of the Profession found that the global total of projects that came in under budget was less than six in 10.
Budgeting features help deliver insight on project expenses so that your projects are less likely to end up costing more than anticipated. Capabilities include:
- Generating invoices
- Recording each project expense
- Cataloging billable hours
- Forecasting
- Tracking bids
- Viewing reports
Integrations
Integrations are becoming more and more popular. They let you extend the software’s functionality, and most project management software offers integrations with a large number of applications.
Your requirements will determine which integrations matter most, but here are some key ones:
- File Storage: Most systems integrate with OneDrive, Box, Dropbox and Google Drive. That makes it easy to attach, share and manage files.
- Email Clients: Connecting your email and project management tool streamlines communication.
- Identity Management Systems: Plugging one of these apps into your software lets users take advantage of single sign-on (SSO).
Paying close attention to features is important, and not just because they’ll improve your execution. You might hit a point in your search where a decision requires you to make some sacrifices. If so, you need to know which features are most important and why.
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Here’s an example:
Let’s say you absolutely need to manage complex task dependencies and have a Kanban layout. You’ve also determined that building custom reports and creating guest accounts would greatly enhance your project management. You’ve narrowed your list to three products.
Product X and Y both have Kanban views, along with custom reports and guest accounts. But their task dependency capabilities are pretty basic. Product Z has killer task dependency functionality, and the custom reports and guest accounts are adequate. But it doesn’t offer a Kanban view.
See the dilemma? That scenario, while overly simplistic, makes the point. If you run into a similar situation, you need to be crystal clear on which features you’re willing to sacrifice or accept as adequate, versus which you need to be top-notch.
Using a spreadsheet list, you can enter information for specific products, putting the features next to the requirements. Make it easy to analyze by color-coding each cell based on how high a feature rates (excellent, good, adequate, poor, not offered).
Our project management comparison report lets you view all the top vendors and get a quick but comprehensive look at the market. Check it out if you want an easy way to find out which products have the capabilities you need.
3. Determine Cost
This is one of the biggest aspects of your evaluation. And the total cost involves a number of factors.
First is whether you want to deploy the software in the cloud or on-premise. Typically, vendors only offer cloud deployment. Some enterprise-grade products, however, such as Microsoft Project and Jira, have a self-hosted option as well.
In most cases, cloud pricing is based on the number of users per month using a subscription model. If you choose on-premise deployment, you’ll usually pay a flat fee based on the number of users, and the pricing is license-based.
Vendors usually offer monthly and annual plans, with the latter being cheaper. Some may also require a minimum commitment. Keep these factors in mind when weighing the cost of the solutions you’re considering.
On-premise solutions require ongoing maintenance after installation, which is another factor to weigh. Maintaining a system isn’t free, and you also have to consider the time cost involved for IT to keep everything running. With cloud solutions, vendors handle the maintenance, making them the preferred option for most situations.
If all you need is a bare-bones system for a small team, some popular vendors such as Asana, Airtable, Teamwork and Zoho Projects have a free option. Just remember that “free” is code for limited features and functionality.
Ideally, you shouldn’t pay for features you won’t use. However, that can be hard to achieve in the real world. If a more expensive pricing tier has five non-essential features included but it’s the only way to get a feature that’s a top requirement for your team, then dishing out the extra money may be worth it.
I’m not saying you should always go more expensive. Again, it comes down to your individual situation and which features are most important to you. It can be a hard balance to strike.
If you push for a pricier option that gets you the right features, be sure to justify the cost. Project management metrics may be difficult to tie to hard numbers, like in marketing or sales, where it’s easy to see the ROI. But you can focus on the productivity gains and time saved from using software rather than manual processes.
4. Test the Software
Any product can sound good on paper. But until you log in and start navigating through the interface, you won’t know how good of a fit it actually is.
Bruce Mason, Delivery Director at TestFort, believes there’s a right way and a wrong way to evaluate software (and with 26 years of experience, he’d know).
The wrong way is to skim through promotional materials or aimlessly click around during a trial. This approach can make any tool seem suitable.
The right way is to set up a small, real project with your critical processes. Use the trial period to run this project. Focus on how the software integrates with your existing tools, how intuitive it is for your team, and how well it supports your key processes. It helps to make sure you’re not throwing money at a tool that looks shiny but falls apart in real use.
Easing into the swing of things is another way to take project management software for a spin around the proverbial block. Cache Merill, CTO of custom software development company Zibtek, advocates for experimenting with basic sprints before complex projects.
When we test a project management tool, we will run a few sprints for one project inside it. Typically, we start with a project that is a bit simpler. For example, we have a ClickUp board for just our marketing site at Zibtek, which is a simpler place to kick the tires. If we like it, then we can expand to other more complicated projects.
That’s why taking the software for a spin is a critical part of the evaluation process. Many vendors offer a free trial so you can test the platform out and see if it does everything you need it to.
The free trial length varies depending on the vendor, so make sure you know how much time you’ll have. Using the software for a few days may give you an overall feel for whether it will work long-term. But if you have it for a couple weeks or a month, it will let you get familiar with how all the elements work and perform a variety of tasks that may uncover shortcomings.
Since so many vendors offer free trials, it’s a good idea to sign up for some earlier on in your process.
Obviously, there’s no point testing software that you’ve already eliminated as an option. But if a handful of vendors are all possibilities, why not try them all out? Some real-world experience with the different systems may cause some products to emerge as front-runners.
5. Evaluate the Vendors, Too
Buying software is kind of like getting married — you’re not just getting the product (your spouse), you’re getting the vendor too (the in-laws). A strong relationship with the vendor will make for a positive, engaging experience. A poor relationship? You can probably feel the tension brewing already.
Just like there’s no universally perfect software, not every vendor will be a good match. If you need support or training, for example, look for vendors that don’t skimp in those areas.
They say teamwork makes the dream work, but sometimes that’s just not enough. John Conafay, CEO and Co-Founder of Integrate, believes in the importance of aligning your workflows with what the vendors offer.
The next time you see a collaboration tool that promises to make your life easier, take a closer look. Is it really designed for the way you work, or is it just another shiny object that will end up in the graveyard of failed software? Always ask vendors about features and functionality in the context of a proper project workflow, to make sure the capacity to collaborate actually works the way you do.
The more research you do, the better, so investigate as much information about vendors as you can. This list is a good starting point:
- If you choose cloud hosting, make sure the vendor has strong data security protocols in place, disaster recovery plans and consistently high uptime (anything under 99% can lead to more than 15 minutes of downtime per day).
- What’s the company’s track record? You don’t want to fall in love with a product only to see the vendor kick the can in a few years. Look for stable vendors who aren’t just learning how to stand.
- Find out how they’ll handle your data if you switch to another vendor. Otherwise, you may run into some unexpected consequences (paying extra, needing the data format converted, etc.).
- Asking for references is important, but take it another step. Check out forums, online reviews and other sources to get the most objective picture possible.
- Look at their clients. If they haven’t worked with anyone that’s similar to your company, that could cause friction.
- How often do they roll out updates? Fixing bugs, adding features, etc. is part of the software game. You don’t want to end up with a solution that grows old and stale while others continue to innovate and improve.
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Conclusion — Where Do You Go From Here?
Where do you go from here? Evaluating project management software is a challenging undertaking. However, by focusing on your goals, knowing which features to look for, considering the price, taking the product for a test run and vetting the vendors, you’ll position your company to find the right solution.
No matter which stage of your selection journey you’re at, we’ve put together resources that will help you succeed. Grab our free comparison report to start feeling out which solutions may be a fit and build your requirements with our free template with our free template. You can also download our pricing guide for a cost breakdown of the top systems.
What stage are you at in your project management software evaluation? Are you facing any struggles with finding the right product? Let us know in the comments!
SME Contributors
Bruce Mason is the Delivery Director at TestFort, a software testing company. An expert in business analysis, project management and service delivery for over 26 years, he currently balances out all QArea & TestFort’s delivery operations, from contract negotiations to client satisfaction records.
Cache Merrill is the Founder and CTO of Zibtek, a custom software development company. With a background in strategic innovation and technology leadership, Cache specializes in delivering robust software solutions across various industries including real estate, healthcare, AI and IoT. Under his guidance, Zibtek has become recognized for its ability to provide businesses with top-tier development teams and drive substantial business value.
John Conafay is a US Air Force Veteran and the CEO and Co-Founder of Integrate, building program management software with a systems engineering approach for the world’s most ambitious machines. Previously, he was an early employee at three space unicorns – Head of BD at ABL Space Systems, was one of the first ten employees at Astranis and interned at Spire Global. He also worked at the Office of the CFO NASA Headquarters while at BryceTech.