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Project management software: how to choose the best one for your team!
Pick the right tools to stay in control of your projects and make your team productive
Jasper Polak
November 15th, 2022
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"But Jasper, which tool is best?"
If I had a dollar for every time I get this question, I'd be rich.
Project management software is a booming business. There are more than 1,400 tools to choose from, and the market is expected to continue growing by 11% per year.
Choosing the right project management software is overwhelming, but it shouldn't be. Today, we're breaking down how you can choose the software that works best for you and your company.
Start with why
Let's get the big question out of the way: why are you looking for PM software? Don't answer this off the cuff and move on, really dig in. Knowing the true reason helps you select the right tool, but will also make it much easier to get your team to use it.
Common reasons include:
Switch to async and/or remote work
No single source of truth for project status
Team members are working on the wrong things
No good way to collaborate with external team members
Multiple places to share documents & information causes chaos
PM software is not a silver bullet
Project management software can solve most of the issues listed above, but only if it comes with the right people & matching processes.
You set up your processes, you train your teams, and you support them with tools. Don't go out and buy the tool that looks best or has the nicest salesperson - it has to fit your business.
Get your team involved
The person closest to the issue usually knows how to solve it. That's why you should get your team involved and brainstorm around key processes & recent issues. How would a solution look & feel in their ideal world?
A well-run brainstorm not only gives you endless inputs and ideas, it also gives your team ownership over the solution - a crucial step in user adoption!
Here are my top 3 resources for running a brainstorm:
Strategic: Better brainstorming by Harvard Business Review
How-to & techniques: Brainstorming from the Zapier blog
Tactical: Brainstorming tools from Miro
Requirement checklist
Your users and stakeholders will focus on what's important to them, and where they see most issues. To ensure all aspects of the requirements are covered, I've made a checklist of the 22 areas for you that I include when choosing PM software with clients. For each of these areas, note how you currently use it so you can check software features and test in the demo.
Project dashboards
Smaller projects with tasks that go from one member to the other usually prefer Kanban boards, while projects with a longer timeline & critical path risk use a Gantt chart. If you're unsure, keep it simple and stick to a board.
Views
Does your setup require individual views, or will an overview shared on a screen suffice? Individual views help people stay on track but add layers of complexity.
Task management
Consider how tasks get created, assigned, completed, reviewed, and archived in a typical project. Note who does this, when, and where, so you can test it.
Scheduling and planning
The bigger the project scope and timeline, the higher the need for calendar-based planning, resource management modules, and critical path calculations become.
Communication & file sharing
Do you want the PM software to take care of communication (messaging) or file sharing, or do you use other applications for this which need integrating? In smaller organizations, integrating with what you have and linking to existing files usually works just as well and reduces implementation complexity.
Document management & version control
Should your PM software take care of version control in either code or documents? If so, you're instantly looking at enterprise solutions. I recommend keeping this out of PM software.
Integrations & compatibility
What other software in your company stack should be integrated? Consider that Zapier might cover most of your needs at a fraction of the complexity.
Security, access & compliance
Check for authentication & security risks in combination with your existing stack, and consider legal issues around hosting location & data storage.
Automated workflows
Do you want any automation inside the application? A good example is "if task X is done - mark for review by Y". Think of this as Zapier, but within the application.
Project requests & approvals
Some tools have built-in workflows for new requests and approvals, both from team members and external stakeholders. Consider if this would add anything to your current process.
External parties
Consider whether external stakeholders like vendors, clients & freelancers will be using the application. This impacts both your licensing model and access management.
Customization
If the tool will be used by different teams, business units, or entities, you could consider adding branding to the environment for added team feeling. Saying yes to this instantly puts you in the enterprise tier (discussed later).
Customer service & SLA
Your user profile & dependency on the tool for business-critical processes determine what kind of support you need: office hours vs 24/7 or even dedicated support. Also, the Service Level Agreement (SLA) should reflect your dependency on the tool.
Configuration, onboarding & learning
The more complex the tool you choose in combination with your setup, the more help you'll need with onboarding and education of users. Simple tools require little setup and work out of the box, with an intuitive interface.
Templates
If your company does repeatable projects, templates save you a lot of time and ensure consistent execution or processes. Not every software package allows you to do this.
Reporting
Will you require the PM application to provide reporting? Do you just need data, or do you expect the software to provide a (customized) report in a specific format? When in doubt, stick to either out-of-the-box reports or extract data into a proper business intelligence tool. Custom reports are a maintenance nightmare!
Time tracking
Will your teams use the PM software for time tracking? If yes, does it need to be linked to tasks, budgets, or clients? Or worse, to existing time management software?
Resource planning
Will you use your PM software for planning resources & capacity, or is that done elsewhere? I've seen everything from complex Enterprise Resource Planning (ERP) models to Excel sheets from hell. Consider how you do this on a team level, and whether you need to aggregate this across multiple projects.
Budget management
Some PM tools come with integrated budget reporting, billing, and invoicing modules. If you already do this in-house, check for integration & compatibility.
Search
Think through your process to determine how you access data, and specifically, how you search: within categories, tags, projects, programs, or otherwise. Check search for your business needs in a demo. This seems trivial, but is a major differentiator between PM packages!
Program management
Does your company run multiple projects, and are you looking to manage a program or portfolio within the PM software? If you're unsure, don't - the added complexity rarely outweighs the benefits.
Risk management
Do you want to manage risk within the software, or do you have another program/method for that? This applies to your risk identification, risk log, assumptions, and ongoing evaluation & mitigation.
Take your team's input and combine it with input from other key stakeholders within the organization. Armed with this long list, it's time to prioritize must-haves and put nice-to-haves on a separate list ranked for ROI.
When in doubt, keep it simple.
Now it's time to get honest and make some tradeoffs. Don't shop for features, support your business with the right tools, and with adequate room to grow.
To do so, it helps to look at the market in 3 different tiers:
Task management, project management & program management
A startup does not have the same software needs as Google. Fortunately, project management software comes in many shapes and sizes. I find the following distinction from G2 useful:
Task management:
Task management software helps teams manage daily work across functions, projects & tasks. They're light applications that work off-the-shelf, with limited customization. Best suitable for early-stage startups, or those that don't need to interact between teams.
Project management:
Project management software adds a layer on top of task management. It helps you plan full projects including scope, resources, and timelines. They offer different ways to view, report, and extract data, and add customization, templates, and integration.
The applications in this group usually also include communication, file sharing, and other related business tools. Consider if you need this built-in, want to integrate it, or prefer to keep things separate. They're best suited for startups that are scaling but don't need a full program management setup yet.
Program management software/enterprise solution:
If your company runs multiple projects and needs to aggregate progress reporting, status, timelines, and other information. They allow larger organizations to have a cockpit view of the total portfolio of projects and offer a level of customization, integration, and reporting tools.
Tools like these often come at a much higher price, of up to 5x the price range of task management software. For large organizations that run more than 10 projects at the same time, this is a no-brainer though. Imagine the peace of mind if you had all the management information, for all projects, in one place!
Which tier do you fit in?
Take your prioritized list of requirements, and see which tier best matches your needs. This narrows your search and gives you clear directions on where to look. You're not making a choice for life, and you're better off using a lighter tool to full capacity than a heavy tool at 10%.
Time to make a shortlist
Ok, I hear you. Time to cut the crap, which one do I actually recommend? I have had a great experience with Asana, ClickUp (aff), Monday, Trello, and Jira. Also, good old MS project has its place alongside Primavera for enterprise solutions. You can't go wrong with either of these outside of the enterprise space, and the differences are minor.
It boils down to preference, look and feel. Use these three resources and narrow it to a shortlist of 3 options:
G2's grid shows the leaders in the space
Capterra's project management software shortlist
Softwareadvice.com lists all 1,570 (!!) available PM applications
Demo & decide
For each of these 3 on your shortlist, get a demo account set up with some actual project data from your company. This takes time, but it's a few hours very well spent. Spend a few hours in each, and involve your team.
In the end, the user experience should be leading. If you've narrowed your homework down using the above resources, all vendors on your shortlist will help you do your job. The question is, which one makes you feel most at home? The time for rational decision-making was earlier, now it's time to go with your gut, and that of your team!
In summary
Managing a project without project management software is like driving blindfolded. Just... don't do it. Selecting the right tool can feel overwhelming, but it's surprisingly straightforward:
Start with why
Involve your teams
Define your requirements
Figure out what tier you fit in
Make a shortlist, demo & decide
The real challenge comes next: implementing it and getting people to use it. That's part of change management; we'll leave that for another day.
If you're looking to select new software and are looking for someone to guide you through the process and save you weeks of time, please hit reply. I have limited capacity, but unlimited ways to help you out.
Thanks for reading!
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That's it for this week - until next Tuesday!
Cheers,Jasper