How to Choose Project Management Software
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Choosing the right project management software can make or break your team's success. It saves time, boosts accuracy, and ensures compliance, all while maximizing your ROI. But pick the wrong project management solution, and you're stuck with inefficiencies, missed deadlines, and frustrated team members.
This guide is for project managers, team leads, and anyone responsible for steering projects to success. Whether you're looking to improve collaboration or streamline processes, I'll help you find the right project management tool for your unique needs.
8 Things to Look for When Choosing Project Management Software
Evaluate project management software by considering factors that impact your team's efficiency and project success. Here are the essential elements to examine:
1. Plan Flexibility
Plan flexibility allows your organization to adapt to changing needs without being locked into a specific plan. When evaluating project management software, check if you can easily upgrade or downgrade plans as your project, team, or business scales.
Ask about any hidden fees associated with changing plans, or if there are opt-in add-ons you might benefit from when you’re in an in-between phase. Knowing about a provider’s scalability ahead of time helps you plan for the future—even if you’re just starting out with a free project management tool.
2. Data Access and Reporting
Access to data and reporting tools help you make informed decisions about your projects, resource management, and more. Look for software that offers customizable dashboards and reports, so you can track projects and identify dependencies.
Ask vendors about the types of reports available and if you can tailor them to your needs. A tool that provides clear insights into your team’s performance and lets you track project progress helps you stay agile and adapt as needed.
3. Integration with Your Tech Stack
Integration with your various different tools is key to maintaining workflow efficiency. Check if the software supports integrations with tools you already use, like Slack, Google Workspace, or CRM systems.
During a demo or free trial period, test these integrations to ensure smooth data flow. A well-integrated project management app reduces manual work and errors.
4. Onboarding and Support
Good onboarding and support make a big difference in how quickly your team can start using the software effectively. Look for vendors that offer comprehensive training and responsive customer support.
During your evaluation, ask about onboarding processes and support response times. Strong support helps your team get the most out of a PM tool, and use it to its maximum capabilities from day one.
5. Role-Based Permissions
Role-based permissions ensure that team members have the appropriate access to project information and project management features. Look for software that lets you easily assign tasks, define roles, and set permissions. Ask vendors how permissions are managed and if they can be customized.
6. Customization Options
Speaking of customization, the ability to customize your project management platform allows you to tailor it to your team’s specific needs. Look for tools that offer customizable workflows, fields, and templates.
During a demo, explore how easy it is to adjust these elements, and whether they can be tailored to different team requirements. A customizable tool supports your project planning workflows, not the other way around.
7. Automation Features
Automation features help streamline repetitive tasks and reduce manual errors. Look for software that offers automation for task assignments, notifications, and updates. Automating routine tasks frees up your team to focus on more important work.
8. Mobile or Multi-Location Support
Mobile or multi-location support ensures that your team can access the software from anywhere. Look for tools with strong mobile apps, real-time sync, and cloud-based access.
Test the mobile app to see if it offers the same functionality as the desktop version. A tool that supports remote work keeps your different team members connected and productive, even when working in remote or hybrid settings.
How to Choose Project Management Software: A 5-Step Framework
The project management software market is projected to become a USD 20.50 billion industry by 2030—so it’s safe to say that you have a lot of options.
Selecting the right tool can streamline your projects and improve team collaboration, but you have to focus on your team's needs and align the tool's features with your workflow.
Need expert help selecting the right tool?
With one-on-one help, we guide you to your top software options. Narrow down your software search & make a confident choice.
Here’s a step-by-step guide to help you choose the best project management software for your team:
Step 1: Identify Needs
Start by defining your team's needs to ensure the project management software aligns with your goals and challenges:
Gather Stakeholder Input
Talk to key stakeholders like team leads, IT, and employees to understand their needs and challenges. Organize workshops or surveys to collect their input. This helps you identify what different departments require from the software.
For example:
- Team leads want the ability to apply different methodologies (Kanban boards, Gantt charts, sprints, etc.)
- HR needs robust reporting to facilitate effective resource allocation and track team performance
- IT is focused on integrations, and getting everyone to stop using Excel spreadsheets
List and Prioritize Pain Points
Gather feedback to identify the pain points in your current system. Then, make a list and rank them by impact. Look for recurring issues like communication gaps, complex project needs, or task management inefficiencies. Prioritizing these helps you focus on solutions that address your biggest challenges.
Align with Internal Policies
Ensure that the software meets your internal policies and security protocols, and check for compliance with any regulatory goals relevant to your industry. Work with your IT and legal teams to create a checklist of project management software requirements to make sure you don’t miss anything.
Must-Have vs. Nice-to-Have
Differentiate between features you must have and those that are nice to have. Must-haves are things that are essential for your team’s workflow, like task assignment, timeline view, and time tracking.
Meanwhile, nice-to-haves might include collaboration tools like file sharing or messaging features. This distinction helps you focus on what truly adds value, instead of chasing shiny objects that won’t make a real impact.
Ask These Questions:
- What complaints, blockers, or bottlenecks come up most often?
- What needs aren’t being met today?
- What key features would solve your top 3 pain points?
- What ROI are you expecting from this investment?
- How does the software align with our security protocols?
Step 2: Research Vendors
Dive into researching and comparing project management software vendors to find the best fit for your team:
High-Level Vendor Scans
Start by conducting high-level scans using review sites, rankings, and case studies. Look for feedback on the software’s performance, learning curve, and user satisfaction ratings.
Pay attention to industry-specific reviews if applicable—some PM tools are well-suited for startups and small businesses, but won’t work as well for a large software development team. This will give you a broad view of the options available and highlight leaders in the field.
Compare Based on Business Needs
Compare tools based on your business size, integration needs, and whether you prefer outsourcing versus creating in-house models. Smaller businesses might prioritize cost-effective solutions with easy onboarding and simple to-do lists, while larger organizations may need robust integrations and API access.
Identify Key Differentiators
Identify key differentiators like implementation support, user experience, or flexibility for niche use cases. Look for vendors offering comprehensive support during and after implementation, and assess user experience through demos to ensure it's intuitive for your team.
Document Findings
Document your findings to keep track of the pros and cons of each vendor. Create a comparison chart that includes features, pricing, and any standout elements. This organized approach makes it easier to present your findings to decision-makers and narrow down your options.
Ask These Questions:
- What does each tool do best?
- Does it fit your team size, budget, and stack?
- What support and documentation are available?
- How does it compare in terms of user experience?
- What differentiators make it stand out?
Top Project Management Software to Consider
Here's my pick of the 10 best software from the 10 tools reviewed.
Step 3: Make a Shortlist and Reach Out
Next, it’s time to narrow down your vendor options and start engaging with potential partners:
Shortlist Vendors
Based on your research, create a shortlist of 2-4 vendors that best meet your needs. Focus on those that align with your team’s size, budget, and must-have work management capabilities. This targeted approach helps you concentrate efforts and save time.
Send RFI or RFP
Consider sending a Request for Information (RFI) or Request for Proposal (RFP) to gather detailed information. Use this to clarify vendor capabilities like resource allocation, invoicing, or automation options. RFPs are especially useful when evaluating different project requirements or pricing tiers.
Book Demos
Book demos with your shortlisted vendors and ask focused questions. Use this opportunity to see the software in action—evaluate task dependencies and subtasks, project timelines and roadmaps, and how the tool handles workload management.
Consistent Evaluation Criteria
Use consistent evaluation criteria across all vendors to ensure a fair comparison. Create a checklist that includes essential features such as real-time updates, sprints, or timesheets. This helps you objectively assess each tool and make a well-informed decision.
Ask These Questions:
- Can you walk me through a real customer story like ours?
- What support or onboarding resources do you offer?
- What features require an upgrade?
- How does your pricing model work for our team size?
- What integrations are available with our existing tools?
Need expert help selecting the right tool?
With one-on-one help, we guide you to your top software options. Narrow down your software search & make a confident choice.
Step 4: Build the Business Case
Translate your vendor research into a business case that your leadership team will support:
Demonstrate Value
Summarize the pain points and expected outcomes to demonstrate value. Highlight how the software will address current challenges like missed deadlines, unclear project lifecycle stages, or poor communication.
Show potential outcomes such as improved project delivery times, better ability to track progress, and enhanced transparency across initiatives. This helps your leadership team see the tangible benefits.
Present Cost Estimates
Find and present basic cost estimates and implementation timelines. Gather project management software pricing information and outline the expected timeline for deployment and training.
Then, put this information together for some clear forecasting of the costs associated with investing in a project management SaaS solution. Providing this data helps in budgeting and planning, and shows you’re on top of it.
The pricing across tools varies astronomically. It’s important to consider how many seats you need, how guests are managed, and what add-ons are required, because it can spiral quickly.
Articulate ROI and Risks
Articulate the ROI, efficiency gains, and financial or operational risks of doing nothing. Calculate potential savings from reduced project overruns or increased productivity. Discuss the risks of staying with the current system, like continued inefficiencies. This comparison highlights the value of investing in new software.
Ask These Questions:
- What business problem will this solve?
- What are the risks of doing nothing?
- What are the financial and operational upsides?
- How will this improve team productivity?
- What is the expected timeline for ROI?
The DPM's PM Software Buyer's Guide
Get a full breakdown of how to buy the right project management software with our complete buyer's guide:
Get the PM Software Buyer's Guide
Step 5: Implement and Onboard
You’ve made your pick of the best project management tools, and you’re ready to implement it! Here’s how to plan a smooth onboarding process:
Communicate Rollout Plan
Clearly communicate the rollout plan to all users. Share timelines, key milestones, and what each team member needs to do. Use meetings or internal newsletters to ensure everyone is informed, and provide forums where people can ask questions. Clear communication helps set expectations and fosters stronger teamwork from the outset.
Assign Internal Owners
Assign internal owners and points of contact for the implementation. Designate team members who will oversee the process and handle any issues, and ensure they have direct lines to vendor support.
This structure provides accountability and enables fast resolution, especially during the initial stages of scrum workflows or new types of projects. Adoption of new software solutions can take time, so set your team up for success by equipping project managers, team leads, and managers with tools to support them.
Ensure Consistent Training
Schedule training sessions and track participation. Encourage users to explore features like task management, progress reports, and initiatives dashboards. Comprehensive training is essential to flatten the learning curve and help small teams build confidence in the new tool.
Create Feedback Loops
Create feedback loops during rollout, including vendor resources. Regularly check in with users to gather feedback and address concerns. Use vendor support for troubleshooting and additional training materials. Feedback loops ensure continuous improvement and promote long-term adoption success.
Ask These Questions:
- What’s the change management plan?
- Who’s responsible for roll-out?
- How will you track early success?
- What resources will support training?
- How will feedback be collected and used?
What’s Next:
If you're in the process of researching how to choose project management software, connect with a SoftwareSelect advisor for free recommendations.
You fill out a form and have a quick chat where they get into the specifics of your needs. Then you'll get a shortlist of software to review. They'll even support you through the entire buying process, including price negotiations.
Before You Go…
Want a handy visual checklist to help you remember the steps? I've got you covered! Download our visual checklist here: