How To Choose Project Management Software

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Once your team has decided to make the shift from spreadsheets and Post-It notes to a formal project management software system, it can be a game changer for your organization. But first, you need to find the right fit. Read on to learn about the 10 criteria you should consider when choosing project management software. 


Read more: What is Project Management?




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10 Key Considerations When Choosing Project Management Software

Factors to Consider:What You Should Be Considering: 
1. Ease of Use
How easy is it to navigate and use this software?
•How intuitive is this software’s interface? 

•How easy is this tool to learn and onboard?

•What do user support options look like and how easily accessible are they? 
2. Task Assignments & Scheduling
How easily can tasks be scheduled, assigned, and rearranged?
•How easily can I assign and schedule tasks?

•How can deadlines be easily moved, if needed?

•Can I assign multiple users to a task?
3. Collaboration
How easy is it for the team to share information?
•Can team members message each other?

•What types of files can be shared within a workspace? 

•How will team members be notified about project updates and can those processes be automated?
4. Customization Features
How can individual teams customize this software to fit their unique needs?
•Are there specific template offerings or settings that can benefit specific users? (Ex: sales teams, technical teams, etc.)

•Do API and other advanced customization options come built into this solution?

•What project management methodologies does this solution support compared to the methodologies we use most often? (Agile, Waterfall, Scrum, etc.)
5. Dashboards
What type of data insights can be extracted across one or more project(s)?
•What are the most significant data points we would like to ideally extract from a dashboard view?

•How far can data insights be broken down? By team? By individual user/team member?

•How can data trends help us identify and predict potential issues?
6. Project Views
In what ways can you view projects and deadlines?
•What views are most important for our teams’ uses?

•How easy is it to populate new views?

•When certain views are limited by plan type, does our subscription include the views we need most?
7. Integrations
What other applications can be integrated with this solution?
•Which integrations are most crucial for our teams’ needs?

•Are new integrations introduced over time? If so, how often?

•Are the integrations connected directly or facilitated through a 3rd party, such as Zapier?
8. Automation
How can work actions be automated?
•Are automation actions limited to a set number per month or user?

•Does this software offer automation shortcuts or templates?

•How much time can we expect to spend setting up automations and maintaining them over time?
9. Security
What security features does this software offer?
•How can we limit and manage individual user settings and access?

•How is security prioritized across desktop and mobile app usage? 

•How does this software provider manage or use our data?
10. Unique Features
What added selling points does this software offer that might be useful for specific team use cases?
•How do the needs of our team align with unique features within this solution? (Ex: time tracking for teams that work with freelancers, budgeting features for external clients, etc.)

•How often are new features introduced and released?

•Who is this specific solution best for?

What Features Can I Expect in Project Management Software?

While individual features may vary from product to product, in general, project management software typically includes a few basic essentials:

Task tracking and project planning

Assign tasks, track schedules, deadlines, task dependencies, and review project status as it relates to overall project progress – promoting clearer team-wide expectations and accountability.

Screenshot of a project management tool showcasing project planning and task tracking functionality.
Example of project planning and task tracking functionality from GanttPro. Source: GanttPro, accessed August 2023.

Collaboration features

Collaborate and communicate with team members across the organization at large, through commenting, tagging, messaging, and more – promoting transparency and helping organizations problem-solve faster. 

Screenshot demonstrating the chat-based collaboration feature within the Basecamp application.
Example of chat-based collaboration feature within Basecamp. Source: Basecamp, accessed August 2023.

Resource management

Resource management features enable teams to track team workloads, project budgets, freelance hours, client billables, invoices, and more – helping prevent budget overrun and promote proper resource allocation internally and externally.

Visual representation of a budget breakdown displayed within ClickUp’s dashboard overview feature.
Example of a budget breakdown within ClickUp’s dashboard overview feature. Source: ClickUp, accessed August 2023.

Project dashboards and analytics

Monitor key statistics across multiple projects, while analytics power data-driven patterns and insights to help teams uncover trends and adjust accordingly. 

Screenshot illustrating a project overview on the dashboard of monday.com.
Example of a dashboard project overview in monday.com. Source: monday.com, accessed August 2023.

Multiple project views

Project views give teams flexibility in how they choose to visualize project schedules and assignments. 

Image depicting a Kanban board view in Jira.
Example of a dashboard project overview in monday.com. Source: monday.com, accessed August 2023.

Read More: Key Features of Project Management Software


Common Project Management Software Roadblock Tips

While getting ahead of the curve by researching and thoroughly vetting project management solutions can help maximize your chances of success when it comes to implementing a solution in your organization, there are still a few common pitfalls you should be aware of:

Problem:Solution:
Learning curve

Naturally, certain project management solutions rank higher in terms of ease of use, but there’s an inherent learning curve associated with learning new software.
Give your team adequate time to adjust to the change and take advantage of solution-sponsored education and training opportunities whenever possible to help ease the growing pains of learning new software. 
Poorly matched software solution

Despite your best efforts to carefully select the best-fitting solution for your team, it, unfortunately, doesn’t guarantee that that software will be a good fit in practice. In some instances, once an organization has selected a solution, they find that it’s a poor fit or unable to scale alongside them in the long run. 
Prioritize research and careful consideration throughout your selection process – and be sure to take advantage of free trials, demos, and even free plans to get an accurate feel of how a solution will react in practice. 
Lack of support

When it comes to customer support options, not all software solutions were built equally. One of the most significant complaints users have about project management software solutions is a lack of user support or long wait times for support.
When it comes to avoiding a support service disaster, research is your best friend. Read up on each solution’s support resources as well as what customers have said about those resources. 
Difficulty integrating with the team & organization

Unfortunately, when it comes time to integrate your new software solution with your team, even the best-laid plans can go awry. 
If possible, designating a team member(s) as a well-trained go-to source for other colleagues during training and onboarding can help ease support woes. 


Read more: Remote Teams and App Development: Overcoming the Project Management Challenges


How to Get the Most Out of Your Project Management Software Solution

Investing in a new project management solution for your organization means a significant investment in time and financial resources. Here are a few of the top tips to get the most out of your new project management software solution: 

  • Prioritize finding the right fit for your organization: While it may sound redundant, the work you do before selecting a project management solution is crucial to your success in implementing it in practice. 
  • Consider a specialized solution. Certain project management solutions are designed to fit the needs of specific industries, either with industry-specific templates or features. For example, Jira Software is designed to fit the needs of technical teams, such as software developers. If your organization operates within a niche industry, consider a more specialized solution with features an templates to fit your unique needs over a more general one.
  • Be clear about your plans to integrate the new solution into your team: Before you begin rolling out your new solution within your organization, you need to ensure that everyone is aware of the changes that will be taking place. Consider trialling the solution with a smaller group to test out your assumptions before announcing the implementation of a new system. Especially if your team has worked in one project management system for an extended period of time,  your team will need time and hands-on experience with the new solution before your organization moves all production-level work over to the new system will help ease the transition while creating extra time to answer questions and create support systems as implementation begins. 
  • Use integrations whenever possible: Your shiny new project management software solution is likely chocked full of exciting features – but you can unlock more capabilities through integrations with other applications. Be sure to integrate your existing tech stack with your new software solution as much as possible and explore other integration options to expand the functionality of your solution. Pay special attention to how complex the integrations are to implement, and be aware of how those integrations may impact your existing workflows.
  • Take advantage of free training and seminars: In order to make the most out of your software solution, you first need to understand how to use it to its full potential. Make sure you’re aware of the training and education resources available from your software vendor and take advantage of as many resources as possible to ensure you’re making the most out of the solutions functionality. Most paid plans provide extensive onboarding resources including videos, webinars, live and email support, and even customer success agents to help your team working at pace quickly and efficiently.
  • Prioritize solutions that scale: Growth is inevitable. In order to prevent your organization from outgrowing your software solution, make sure to consider how each vendor can grow alongside your business over time, for example, by adding additional users, increasing file storage, the number of projects able to be hosted, and more. 

When to Invest in Project Management Software

If you find that your team is relying on spreadsheets, scattered Post-It notes, and whiteboard scribbles to plan and execute projects, it might be time to consider investing in project management software. According to a survey published in PMI’s Pulse of the Profession report, organizations that invest in proven project management practices – such as project management software and project management roles – waste 28 times less money than organizations with poor project performance, according to the annual global survey of project management professionals, senior executives, and project management office directors.

With hundreds of vendors on the market today, offering plans that fit a wide variety of team needs and budgets (including free plans), there’s never been a better time to make the transition into a formal project management solution. Regardless of industry or use case, all organizations can consolidate files and project essentials in one place while streamlining work processes using project management software. 


Read more: Best Project Management Software for Small Teams


What to Expect When You Begin Using a New Project Management Solution

There will be a short setup process involved for everyone who will be using the new system for the first time. Before you dive in, it can be helpful to understand what to expect. Typically, after users complete an initial set of questions about their intended use of the software and the number of collaborators, they are redirected to the home screen which typically includes links to specific projects, notifications, a personalized list of tasks, and more. 

Image illustrating the setup wizard walkthrough that new users encounter in Smartsheet.
Example of the setup wizard walkthrough new users experience within Smartsheet.

While specific layouts may vary, most project management solutions include a toolbar with quick access to project essentials, as well as a button or link for creating new projects. Within each project are a variety of view options, with some of the most common including board views, calendar views, and table views. In most software solutions, tasks can easily be dragged and dropped in any project view to easily alter deadlines. Dashboard views are also included, and typically highly customizable so that users can easily access project data and overviews across one or more projects. 

It’s important to note that usability and user experience overall will vary across multiple solutions – making it crucial for you to examine an application’s usability and level of intuitiveness when vetting potential solutions. 

Image showcasing ClickUp’s kanban board style task setup in project management software.
Example of ClickUp’s kanban board style task setup in project management software. Source: ClickUp, accessed August 2023.
Image displaying Asana’s dashboard reporting view, featuring project data and statistics.
Example of Asana’s dashboard reporting view, complete with project data and statistics. Source: Asana, accessed August 2023.
Visual representation of a board task view with customizable columns and fields.
Example of a board task view, with customizable columns and fields. Source: monday.com, accessed August 2023.

Read more: Top Kanban Project Management Software Solutions


Where Do I Begin When Selecting Project Management Software?

Before you get to enjoy the perks of a new project management solution, you need to go through the process of selecting it. Here are the top considerations to keep in mind as you begin the process of choosing a project management software:

  1. Understand your team’s unique pain points

If you’re in the market for a new project management solution, it’s likely that your team has unique pain points when it comes to project management. Has your team struggled to keep projects on budget? Consider a solution with budgeting functionality built in. Worried about hitting key project milestones? Software with project progress tracking can help. The ideal project management solution should solve more problems than it creates for your organization. 

  1. Define your budget and estimated number of users

Before you can properly identify your organization’s best-fitting project management solutions, you need to determine your budget and projected number of users. While most software vendors price subscriptions per user per month, pricing models can vary from free to $20+ per user/month. Establishing a clear estimate of total users and budget can easily narrow down your top vendor options. 

  1. Consider the features that are most important to you

When choosing a project management application, you need to consider your team’s unique needs, use cases, and background. Is your team new to the world of project management software? Consider a more intuitive solution with excellent usability. Dealing with a highly technical software development team? Consider a solution with advanced functionality to support their needs. Every project management solution has its’ own flair and area of expertise, so considering how those features can align with your organizational needs is key. 

Aaron Upright, co-founder of ZenHub, encourages teams to consider integrations when evaluating potential solutions. “Integrations should be a key consideration – the more integrated project management tools are with where the team already works, the higher the likelihood of successful adoption. For example, gravitating towards solutions that have a strong integration with familiar tools like Slack, Notion, or GitHub,” he said, “Having to learn a brand new  interface can be daunting, especially for those teams that are onboarding into project management tools for the first time.”

  1. Research options

Once you have a foundational understanding of your team’s needs, it’s time to dive in. Take your time exploring the websites of multiple vendors, taking in the key features, pricing, and user reviews, in particular. Need help narrowing down your choices? 

Check out our top 10 project management picks for 2023

  1. Demo a few top choices

Finally narrow down your selections to a few top software vendors. Now, it’s time to get testing. Most project management software solutions offer an industry-standard 14-day free trial – which gives you a great opportunity to test-drive numerous options before making a significant investment in time or resources. 


How Can I Successfully Introduce Project Management Software Into My Organization?

Once you’ve settled on a software solution, it’s finally time to introduce it to your team – and that can be an intimidating topic.

Consider the three “T’s” for a smooth transition:

Testing

Before taking the plunge to ultimately settle on one solution, consider taking advantage of software demos and free trials with a few select team members, rather than one individual, to simulate how that solution specifically can integrate with your organization. Prioritizing hands-on experience early means you have a clearer picture of how your team will react to the new software. 

Rae Foote, Project Manager at Visor, says “You always want to find that perfect balance between functionality and adaptability, understanding that out of the box, you’re looking to set things up as simply as possible to get from point A to B –  with the ability to add-on and explore more complex features as time goes on.”

Training

Adequate training can ease learning-curve-related concerns and anxiety about adapting a new system. Beyond taking advantage of solution-sponsored training and resources, consider investing in an in or out-of-house training specialist who can work through potential hiccups and questions with your organization directly. Set realistic expectations when it comes to onboarding new software, designating anywhere from a few weeks to a few months to properly train staff. 

Talking

The “talking” phase of implementing a new project management software solution involves direct communication with your team while prioritizing feedback, from the very beginning. 

According to Foote, communication is key when onboarding a new solution with your team. “When your team is already a bit intimidated by the idea of learning a new solution, dialogue is key – not just someone at the top making a decision, or else you can add tension to the situation before they ever touch the software,” she says. “Explain the rationale behind the solution, they need to buy into your vision and workflow. The human aspect of choosing software is often lost. Collaboration is key because it’s a team effort – the less friction the more seamless the transition.”

Once you’ve begun working hands-on with the solution, continue to prioritize communication with your team. What struggles are they having when using the new software? What do they like? Are there any features they feel are missing? Any potential use cases to explore? Providing a space for open discussion can help team members feel more supported and comfortable as they learn and familiarize themselves with the solution. 


Download Our FREE Guide of Top Considerations When Choosing Project Management Software


FAQs

Project management software enables teams and organizations to organize projects, assign tasks, manage workflows, store documents, and collaborate with teammates – all while extracting valuable data insights about those processes. While individual features may vary from product to product, project management software serves as a virtual workspace for project management, organization, and collaboration.

Some of the most notable perks of transitioning into a project management solution include:

•Better organization of project details and essentials (such as documents and files)
•Increased visibility of team objectives and individual responsibilities
•Increased visibility of project progress and workloads per team for administrators and managers
•Enhanced collaboration among team members, particularly for cross-departmental work
•More predictable project timelines, scope, and budgeting

Research from PMI highlights that 11.4% of all resources are wasted due to inferior project management processes, with surveys suggesting that organizations that fail to properly integrate project management into their strategies will see their outright project failure rate increase by a factor of 2/3.

Simply put, the impact of not utilizing project management software within your organization can be devastating. Conversely, organizations that utilize and properly integrate project management solutions benefit from a heightened ability to allocate project resources, track KPIs, collaborate effectively, and ultimately, deliver positive project outcomes.

Conventionally, project management software vendors offer users a variety of paid subscription plans, paid either monthly or annually. Most vendors offer a free 14-day trial (on average), and a majority of vendors offer a free version of the software, with limited features.

According to data from Cloudwards, on average, project management software costs $8.90 per user, per month.

Pros:Cons:
Streamlined workflows: Automation features built into project management software combined with heightened organization options mean more efficient, streamlined workflows – and more productivity. 

Better transparency about workloads: Because project management software provides details about individual workloads and assignments, it’s easy to monitor organization-wide workloads and redirect resources as needed. 

Enhanced data insights: Features such as dashboard views make it easy for users to extract data insights and analytics trends – enabling teams to make better informed, data-driven decisions while identifying key trends throughout the project lifecycle. 

Consolidated document and file storage: An added bonus of project management software is the ability to house and store documents and files in one place. 

More organized approach to projects overall: Project management software consolidates all of the key project essentials within one application – helping organize projects overall. 

Stronger collaboration: Teams that utilize project management software are better equipped to share updates and keep key stakeholders informed throughout the project lifecycle. 
Streamlined workflows: Automation features built into project management software combined with heightened organization options mean more efficient, streamlined workflows – and more productivity. 

Better transparency about workloads: Because project management software provides details about individual workloads and assignments, it’s easy to monitor organization-wide workloads and redirect resources as needed. 

Enhanced data insights: Features such as dashboard views make it easy for users to extract data insights and analytics trends – enabling teams to make better informed, data-driven decisions while identifying key trends throughout the project lifecycle. 

Consolidated document and file storage: An added bonus of project management software is the ability to house and store documents and files in one place. 

A more organized approach to projects overall: Project management software consolidates all of the key project essentials within one application – helping organize projects overall. 

Stronger collaboration: Teams that utilize project management software are better equipped to share updates and keep key stakeholders informed throughout the project lifecycle. 

Read Our Project Management Software Buyers’ Guides

Let’s be honest, selecting the right project management solution for your organization can be a daunting task – but don’t worry, we’re here to help.

Check out our selection of project management software buyers’ guides below: 

10 Best Project Management Tools For Remote Teams 2023

Marketing Project Management Software Buyers’ Guide

8 Best Project Management Software for Architects

Best Project Management Software for Small Teams

Top 5 Agile Project Management Software Tools 2023

Best Construction Project Management Software 2023

10 Best Open Source Project Management Software for 2023

About Our Sources

Aaron Upright is co-founder & head of strategic accounts at Zenhub. Learn more about Zenhub here and connect with Aaron on Linkedin

Rae Foote is an expert on all things Jira Software and a Project Manager at Visor. Learn more about Visor and connect with Rae on Linkedin

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