How to Choose Your Project Management Software: Beginner’s Guide

When deciding how to choose project management software, there are many things to keep in mind.

That’s why we’ve created a checklist of the most important things to keep in mind when choosing your software, from key features to other crucial factors to consider.

We also have compiled a brief project management buyers guide you can check out.

Key Takeaways:

The process of selecting project management software can be separated into three phases: before research, during research, and after research.

Before you start to research software seriously, it’s good to establish why exactly you need project management software.

While generic reasons such as efficient workflows or better process control are fine to some extent, getting into more detail will help you get better results from your implementation.

Before getting into serious research, consider your:

By clarifying these needs upfront, you can select software that directly addresses your challenges, leading to better chances for a higher return on investment (ROI).

Project management tools come with a range of features designed to address different needs. However, there are some basic capabilities that all kind of project management solutions should offer to simplify project planning.

These project management features include:

Customization options are essential for ensuring the software adapts to your team’s working style. This is especially important for creative or design teams that require a user-friendly interface to enhance productivity and creativity.

The ability to personalize project dashboards, project layouts, and various platform settings (such as notifications) can significantly improve user experience and adoption.

Simple tools can very easily achieve user-friendly design, but this is often due to their more limited feature set.

Complex tools with more comprehensive and powerful features, such as budgeting, resourcing, billing, and more, are naturally more complex.

However, even tools with advanced features can stand out from other software with their approach to design. Jumbled navigation, unclear terminology, and a lack of color can all contribute to user fatigue, which then impacts adoption.

Look for collaboration features that enable seamless communication and task management within the team.

Most collaboration tools will offer communication over task assignments, and even indirect forms of communication such as assignments, task dependencies, setting deadlines and updating task statuses.

You can also look for integrations with apps like Slack, which can let you create project management tasks from messages, or send automated notifications when a task is updated.

Documentation and file sharing are also useful to consider, as it helps keep your business know-how and details on various project stages in one place.

Whether you’re working within a remote team or your entire team is in-office, collaboration features help break down work silos and improve team cohesion.

With a client portal, project managers can also communicate with clients from the platform.

Workflow automation features can save time by streamlining repetitive tasks.

Basic automations might include notifications, recurring tasks, and retainer budget creation.

Tools with more advanced features allow you to set up custom automation sequences, such as triggering invoice creation when a budget status is changed.

All of these features can help you improve your accuracy. It also frees up an employee’s time and energy for more decision-intensive tasks, rather than manually managing repetitive tasks.

Reporting features can vary significantly from tool to tool:

There are also solutions that function as databases, and can aggregate data from various platforms. However, these types of reporting tools are usually not meant to be used as tools for project management, but as specialized business intelligence software.

For most firms, the third type of software solution will be just right.

While choosing your key features carefully is important, there are several other project management software evaluation criteria you should include. Some of them are more directly connected to software, while others are linked to the vendor. These are:

Software-related:

Vendor-related:

Let’s explore them in more detail:

Nowadays, most modern project management tools are cloud-based.

This means that data is hosted remotely on secure servers, which means that the software can be accessed online. This makes it more flexible, and easier to maintain and use.

On the flip side, enterprise solutions store data locally on-premises, which provides greater control over sensitive information and ensures compliance with specific regulatory requirements.

However, on-premise software can’t be accessed from anywhere but where it’s installed, and it’s more expensive to both implement and maintain.

Licenses for on-premise software are usually also large up-front investments, so you need to be sure you’re ready to invest in it.

Scalability refers to the software’s current and future feature set, and the speed at which new functionalities are developed.

Software that offers a couple of pricing tiers with features of different complexity can be useful, as it will be easier to switch to a different pricing tier within the same software, than an entirely different tool.

However, the frequency at which the software is being updated with new features and improvements is also important.

Having the latest software features helps businesses stay competitive with their peers. Especially relevant here are automation and AI features, which can support workflows in unexpected ways.

You can check scalability through a company’s roadmaps, or feature release pages (if available).

Responsive customer support can make a significant difference, even for simple software.

During the implementation phase, support from the vendor helps project managers and software champions find the best way to support their workflows.

Sometimes, customer support or success can help set up custom solutions that are more suitable to your processes. Other times, they can help you adjust your workflows to get even better results.

It can be hard to gauge the quality of support before you’ve committed to a provider, but Capterra and G2 can be useful for checking reviews. Users often comment on the quality of customer support.

While you should take these reviews with a grain of salt, an overwhelming amount of mostly negative or positive reviews usually indicates a real issue.

Pricing models vary widely, from pay-per-user to tiered pricing based on features.

It’s important to carefully compare each pricing plan to ensure you’re getting the best value. While some solutions may appear more expensive at first glance, they may offer features that ultimately provide a better return on investment.

Sometimes a tool will offer a single pricing tier, which can simplify the decision-making process, but might also be inadequate to support the needs of diverse teams.

Look for software that complies with industry security standards, such as SOC2 or ISO 27001, to ensure rigorous protection of your data.

Key security features to consider include two-factor authentication (2FA), which adds an extra layer of protection, and end-to-end encryption, which ensures data remains private during transfer.

Another important aspect is role-based access control (RBAC), allowing you to restrict access based on user roles, minimizing the risk of unauthorized data exposure

Implementing a new project management platform comes with its own set of challenges. Here are a three important factors to consider during the process:

Software with a free trial can be very useful, as it can help you get first hand impressions into the solution before going further into the implementation. By trying out the software firsthand during the free trial, you can also gather feedback from your team, ensuring that everyone is on board before making a final decision.

If you’re switching from an old system, consider how easily your existing data can be migrated to the new tool. Historical data is valuable for reporting and decision-making, so a smooth migration process is essential to avoid data loss and disruptions.

Make sure to reach out to the vendor and iron out the details of the migration process beforehand.

Integration with existing tools—such as accounting software, HR systems, or collaboration apps—can streamline your workflow and eliminate redundancies.

So, a tool that offers integration capabilities with other software in your toolstack can be a good pick.

Some basic integrations include Slack and Google Calendar. Other important integrations to consider include accounting software, such as QuickBooks or Xero.

Project management software is designed to help teams and organizations plan, execute, and track projects from start to finish.

It can be used in industries of various types, and businesses of all shapes and sizes. Project management platforms are especially popular for client work, as it ensures that project teams can deliver projects within budgets and timelines.

Features of popular project management software can vary significantly, though some features are usually in common.

Many businesses start with spreadsheets. While this can work for some time, you won’t be able to get the level of control needed to really optimize your processes.

Without a better understanding of your project’s profitability, and how it relates to your resource planning, timelines, and strategic planning, you’ll have difficulties in scaling your business.

It might also lead to unaddressed project inefficiencies and roadblocks, and missed opportunities overall.

These issues usually crop up when agencies are managing more complex workflows or multiple projects at the same time.

A system that can centralize processes into one platform, support collaboration, and provide visibility in project status, resource allocation, and budgeting can help businesses streamline their operations, reduce errors, and make data-driven decisions.

We’ve mentioned that there are many varieties of popular project management software, which are design to cater to different industries, larger teams or smaller teams, and specific needs. Here’s a simple categorization:

These tools focus primarily on task creation, assignment, and tracking. They are often known for their visual design and ease-of-use, and are best suited for smaller teams. The most popular example of this type of tool is Trello, which uses a Kanban-board interface.

Simple project management software is still focused mainly on simplicity, but offers some more extensive features for teamwork and collaboration. Some typical features include shared calendars, group chat, document collaboration, time tracking, and file-sharing. However, these tools still lack capabilities for more in-depth business management. An example of this type of tool is Asana.

Customizable project management software are focused on providing a range of features for supporting various types of workflows. This can include workload charts for simple resource planning, custom dashboard creation, and workflow automations. A popular example is Monday.com or ClickUp.

All-in-one project management software offer all or most of the features from simpler tools, but add functionalities that help businesses manage their core processes. This includes CRM, budgeting, billing, strategic resource planning, forecasting, and reporting. An example of this type of tool is Productive.

We’ve explored some general project management practices, but how do you get the most out of your software? Here are some tips to get you started:

According to Capterra’s project management software research, the main benefits include:

Let’s explore them in more detail:

According to McKinsey, the average interaction worker spends an estimated 28% of the workweek managing e-mails and nearly 20% looking for internal information.

By centralizing all project details, from tasks and timelines to documents and communications, project management software provides structure and organization. Instead of having all information scattered across various tools, teams can stay focused and efficient within a single platform.

With clear task assignments and progress tracking, project management software makes it easy to hold team members accountable for their responsibilities. Everyone knows what’s expected of them and when, which reduces the chances of missed deadlines.

Project management tools provide a shared platform for asynchronous communication. This means that less time is spent on exchanging meetings and emails, which can lead to more efficient collaboration and teamwork.

By tracking time, associating it to tasks, and creating automatic timesheets, project managers can make better decisions for both current and future projects. With features such as estimated vs actual time spent reports, reminders for time tracking, and timesheet locking, teams can manage time more reliably and get better insights.

With resource planning features, project managers can take their management to the next level. These tools allow businesses to create plans for longer periods of time, such as quarterly, in order to manage hiring needs and understand their financial health better.

With built-in reporting and analytics features, project management software helps teams track key metrics like project progress, costs, and performance. This data provides insights that can guide better decision-making and improve future project planning.

If you’re interested in real results, check out a case study of how a software development agency was able to make more informed business decisions and improve efficiency:

Clear Launch initially struggled with optimizing utilization rates, managing project profitability, and predicting future work. They relied on a mix of tools for project management, but these systems were disconnected.

This led to challenges with client communication, such as not being able to provide accurate, real-time updates on budgets and project progress, which sometimes resulted in cost overruns and unhappy clients.

After implementing Productive, Clear Launch gained a comprehensive, integrated system that connected project management with time tracking and invoicing.

Productive’s Resource Planning also allowed Clear Launch to optimize their planning by balancing resources across projects and forecasting future requirements.

Overall, the biggest benefit that Clear Launch experienced after implementing Productive is more predictability—being able to manage different teams across multiple projects, and having consistent and reliable data.

If you’re looking for a more insights into some popular project management software, their key features, pros, and cons, here’s a quick overview of four tools for supporting different project types:

Productive is an all-in-one project management software designed for professional services of all shapes and sizes.

It integrates collaboration features with operations management features, which helps businesses reduce the tools in their stack and consolidate workflows into one platform.

Key features of Productive include:

While Productive isn’t the simplest solution out there, it’s best for growing businesses that want improved financial oversight and customizable reporting.

Trello is a user-friendly software centered around managing boards, lists, and cards with visual overviews. It’s best for organizing workflows in smaller teams or businesses, as it offers a variety of official or community-created templates for different needs.

For more advanced features, Trello has integration capabilities with third-party tools and powerups.

Pros:

Cons:

Learn more about Trello and how it compares to other tools.

Asana offers more features than Trello, but is still a fairly simple solution to use. It provides multiple project views, including List, Board, Calendar, and Timeline. There’s also a workload chart for project resourcing, which lets project managers visualize workloads and allocate time.

Another feature that sets it apart from Trello is integrated time tracking.

Pros:

Cons:

Learn all about Asana and its best alternatives.

Monday.com is a versatile work management system that lets teams plan, track, and collaborate on projects. It offers customizable dashboards with a variety of views such as Kanban, Gantt, and calendar.

Monday.com also includes a workload view for managing resources and budget planning templates.

Pros:

Cons:

Check out our comprehensive review of Monday for a comprehensive project management software evaluation.

ClickUp is a similar solution to Monday, as it offers flexiblemanagement designed to help teams of all sizes plan, track, and collaborate on tasks. It offers various views like List, Kanban, Calendar, and Gantt, along with customizable workflows and templates.

ClickUp also includes time tracking, goals management, and documentation.

Pros:

Cons:

Explore our in-depth ClickUp review for a detailed evaluation of its project management capabilities.

Here are some crucial steps to improving your overall project management, regardless of whether you’re using task management tools, spreadsheets, or anything else to manage workflows.

Begin by defining project goals. Set milestones for overarching goals, define tasks within milestones, and break up tasks into smaller to-dos. Make sure to set up dependencies between tasks, so that you can understand their critical paths—the chain of linked tasks that directly affects the project finish date.

Make sure that task lists are clear among team members—who is accountable, who can provide information, and who needs to be informed of progress. The SMART methodology and RACI matrix are valuable frameworks for managing team collaboration and task dependencies.

Ensure that all project members regularly update their tasks, share feedback, and communicate progress. Here, project management capabilities can be especially useful for ensuring that key information isn’t scattered across different tools, or lost during meetings. This is important for larger teams with dynamic project plans.

Periodically review project progress and adjust timelines, to-do lists, budgets, and resources as necessary. Software with forecasting features can be useful to enable you to predict your future requirements, and see how your current scheduling impacts performance.

A crucial part of reviewing progress is managing key metrics. Variance analysis is very useful for goal tracking, as it compares planned vs real budgets, timelines, and costs.

While the amount of contact you’ll have with the client can vary according to their preference, being proactive is always a good thing. Try to set up and maintain a regular schedule for sharing project progress and reports, to avoid misunderstandings or situations where work needs to be redone due to lack of communication.

A client portal can be a great way to collaborate with clients directly within your workspace, with specific permissions for controlling who can see and do what.

After finalizing a project, hold a restrospective meeting to analyze what went wrong, and what went right. This is a great opportunity to get feedback from all project team members and improve processes for future projects. The most important part of postmortem meetings is to ensure that everyone feels comfortable to share their thoughts and opinions, and to avoid casting blame for potential mistakes.

Choosing project management software is a critical decision that impacts your team’s productivity, collaboration, and overall business success towards achieving your larger goals.

By following a structured approach—evaluating your needs, identifying essential features, and considering factors like scalability, integration, and pricing—you can select a tool tailored to your organization.

To get the most out of your implementation, assign a central point of contact, establish best practices, and provide adequate training and resources to your employees.

Ultimately, project management software streamlines processes, improves communication (especially for remote teams), and offers data-driven insights to help businesses deliver projects within timelines and budgets.

If you’re looking for an all-in-one solution for professional services management, book a demo with Productive today.

What is the most commonly used project management tool?

Some popular project management software solutions include Productive for end-to-end management, Trello for visual organization and task management, Asana for essential project management, and Monday.com for customizable work management.

What are the best project management software solutions for small teams?

Some of the best project management tools for small teams include Trello and Basecamp. These tools offer very simple task management features and user-friendly design.

What are the best free project management software solutions?

The best free project management solutions are Trello, Asana, and Monday.com. Asana and Trello are free for up to 10 collaborations, while Monday.com is free for up to two seats and boards.

How to choose project management methodology?

For projects needing flexibility and frequent updates, consider Agile or Scrum, which are iterative and promote collaboration. Waterfall is used for clearly defined projects with sequential tasks. Other methodologies include PRINCE2 and the Critical Path Method. Ultiamtely, your best methodology depends on your project goals, team structure, and industry requirements.


What is the most commonly used project management methodology?

Agile is one of the most commonly used project management methodologies, particularly in software development and industries requiring flexibility. Other popular methodologies include Scrum and Kanban (a subset of Agile) and Waterfall for highly structured projects.

Is Gantt chart a project management tool?

A Gantt chart is not a standalone project management tool but a visual representation of projects used within project management tools such as Productive. It displays tasks, their durations, dependencies, and timelines, making it a vital feature for planning and tracking projects.