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How to Choose Project Management Software in 2023

Maggie Tully
March 8, 2023

There’s a lot riding on the project management software tool you choose. Project managers already have enough on their plates and the tools they use should make their lives easier, not harder. 

This begs the question: How should you go about finding the right project management software? The search process can be tedious, long, and oftentimes, feels like a project in and of itself, especially without the right guidance. 

In this blog, we’ll cover what to consider when looking for a project management tool, the steps to follow to choose the right one, and how to make the adoption process easier for your team. 

What is a project management tool and why use one? 

Project management software tools can be used to guide projects through their entire lifecycle, including the planning, execution, and monitoring phases. These software tools typically offer a range of features – such as time tracking, task management, and budgeting – to keep projects organized. 

The idea is that by having a single centralized place to manage project activities and store documentation, projects are more likely to be delivered on time and under budget

And the data shows that project management tools are key in delivering top-notch projects. 44% of survey respondents said that using project management software improved the quality of their final product, while 38% said that their use of a tool improved customer satisfaction as well. 

With better quality deliverables and happier customers, why wouldn’t you want to use a project management tool? In case you’re still not convinced, here are a few other benefits: 

  • Keep tabs on your budget spending in real-time: Many project management software tools allow you to view your budgeted vs. actual spending metrics in real time, allowing you to quickly identify which activities are eating up too much of your funding. 
  • Better team communication: Software tools can help streamline communication by keeping everyone on the same page regarding what’s being worked on and when – particularly when your management tool has collaboration features. In fact, 52% of survey respondents said their team communication improved with software use. 
  • Automatically generated reports: Reporting is a valuable part of project management, although creating reports manually can be a huge hassle. Project management software tools have the power to turn your team’s usage of the platform into valuable insights. 
  • Improved capacity planning: Task planning is a key feature in most project management software, which allows you to better assign tasks and manage each team member’s workload. This way, you can prevent burnout and cut down on employee turnover. 

What should I consider when evaluating project management software? 

With so many project management software tools on the market, where do you even begin? You need a software solution that’s easy to understand and that also delivers the features your projects require. 

This is no easy task, which is why we’ve curated this list of the main criteria to consider when looking for new project management software. 

#1 Ease of use

Online reviews of popular project management software solutions tend to cite steep learning curves and complex interfaces as the main reason they switched tools, which is why it’s crucial to pick a tool that’s easy to use right from the get-go. If not, you’ll probably find yourself looking to switch to a new tool soon. 

Consider each tool’s interface when evaluating its ease of use. Is it cluttered with too many features? Does it feel intuitive? Will it take weeks to onboard a new employee, or does it seem simple enough to get the hang of in just a few hours?

Rodeo Drive's planner

These are all questions you’ll want to ask yourself during the evaluation process. And of course, taking advantage of the free trials or plans offered by most project management software tools on the market is a great way to try it for yourself. 

#2 Feature set

Knowing which features each tool offers is a critical factor to consider in your decision-making process. Certain feature offerings might be new for your team, whereas others are critical to your existing workflows. 

Certain project management tools have a strong focus on a single feature – Trello primarily focuses on task management, for example. Unless you’re looking for a very specific solution, you’ll probably want a tool that can do it all. 

#3 Whether you’ll need integrations

Some project management software solutions are all-in-one – like Rodeo Drive – while others rely on integrations to support your projects at every stage. 

After you evaluate a tool’s feature set, identify any gaps in its offerings and determine whether integrations are available to fill those holes. If a project management tool is lacking all of the features you need and doesn’t provide an integration option, it’s likely not the tool for you. 

Keep in mind that third-party integrations can be costly, so you’ll need to factor this expense into the overall cost of the tool when evaluating your options. 

#4 Pricing structure

The cost of project management tools can add up, particularly for bigger teams. You’ll want to find a solution that provides all the necessary features without breaking the bank. 

Selecting a tool with a Free plan option is a great way to try it out before committing. For example, Rodeo Drive’s pricing model includes a Free plan with a limited feature set as well as a flat fee $14.99 per user/month paid plan with unlimited access to all features. 

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Three stacks of coins sitting next to a calculator

#5 Customer support 

Picture this: you’re just days away from an important client deadline, and suddenly, your project management tool stops working. In this moment, you’ll be happy you went with a project management solution that has a live support team to help fix the issue in minutes. 

Some project management tools charge extra for priority support, leaving users with basic licenses to seek help via email exchanges with long turnaround times – or simply leaving them with no support at all. 

Evaluating each tool’s customer support policy prior to committing can save you major pain later on. This can also make onboarding significantly easier, as tools like Rodeo Drive provide your team with a dedicated customer success manager to help your team through the process of transitioning to a new project management software tool. 

Illustration of a woman providing customer support on the phone

#6 Implementation process

If you’re looking to migrate from one project management software to another, the implementation process is something to look into. You don’t want to lose your valuable past project data during the switch, so selecting an option that allows for a smooth transition is key.

Some project management software solutions provide your team with a dedicated customer support manager to help oversee your onboarding process, making the switch much easier for you and your team. 

How to choose the right project management tool for your team 

For many teams, your project management software tool is the backbone of your project. It’s where you store notes, assign tasks, and track your progress. And if you’re going to be using a tool every single day, you want to make the most informed decision possible. 

If it’s your first time searching for a project management tool – or maybe your first time in a while – don’t worry. We’ve compiled this list of 9 steps to guide you through every step of the process. 

1. Assess what you like (and dislike) about your current processes 

If you’re in the market for a new project management tool, chances are you’re not satisfied with your current processes. Determine what it is you’re looking to improve on and which features can help get you there. 

On the other hand, if there’s something that you love about your current project workflows, jot that down too. There are numerous project management tools on the market – many with similar features – so finding a new one doesn’t mean you need to give up the things you love about your current system.

Person evaluating different feature sets on a white board

2. Choose team members to lead the search

Switching project management tools (or implementing one for the first time) is a time-consuming task – one that not all project managers have time for. 

Putting a few team members in charge of the search process is a great way to delegate. For smaller organizations, your “selection committee” might just consist of one person with the bandwidth to research new tools. 

While it’s helpful to include team members with more decision-making power on the selection committee, it isn’t necessary. This group will primarily focus on researching new tools before pitching their recommendation to higher management for approval at the end of this process.

Team members in a circle stacking their hands together

3. Decide on your team’s must-have features

At this point, your team has already discussed what is and isn’t working about your current processes. It’s time to turn that discussion into a list of features you want in a new project management tool. 

For instance, if the team complained that your existing timesheet system is confusing and error-prone, you’ll want to add time tracking to your must-have feature list. 

This step is incredibly important, as it will determine which tools warrant further investigation versus which don’t come close to providing what you’re looking for.

Rodeo Drive's time page

4. Schedule product demos for an in-depth look at each tool 

A project management tool’s website can tell you a lot about its capabilities, but sometimes you need to see the software in action to fully understand how it works. 

Most software tools offer product demos led by their sales team, which provide a personalized look into how specific features can enhance your workflows and boost productivity. Demos are also a valuable opportunity to ask questions and get answers right on the spot. 

5. Evaluate the administrative features and cost 

Once you’ve evaluated the capabilities of a tool, it’s important to take a look at its administrative features. This might include things like privacy permissions, the different access levels, admin controls, and the tool’s overall security. 

For instance, if you work with a large team of freelancers, you’ll probably want the ability to control what information they’re able to see or which features they can access. 

All organizations deal with some level of employee turnover, so having the ability to easily add or remove employees – as well as guest users – is important too. 

Man and woman sitting together discussing a new tool

6. Conduct a trial run

After you’ve narrowed your search down to a few project management software options, you should test out the tool on your own as proof of concept. You’ll want to have a diverse array of perspectives and opinions on how it works, so be sure to have your pilot group include more than just one person. If your selection committee is large enough, assign a few members to each tool to test it out. 

Ideally, you’ll use this trial to work on real project tasks to get a better sense of how it performs. If quality customer service is one of your top concerns, you might want to test out the customer support experience as well. 

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7. Make a final decision

After you’ve collected feedback on the various trial runs, it’s time to come to a final decision on the right project management tool for your team. We recommend referring back to the list of must-have features that you created earlier in this process and making sure the tool you select fits those criteria.

8. Pitch the tool to executives for approval 

Larger organizations that have been relying on a selection committee to guide them through this process will ultimately need to present their final software recommendation to executives for approval. 

Be sure to clarify why you chose this tool over other options and how it will upgrade your processes over what you’re currently using. Executives might be price sensitive, so your pitch should certainly include a breakdown of the cost per user and how that squares up against alternatives. 

Committee pitching a new tool to executives

9. Begin implementation 

Now that a decision on a new project management software tool has been signed off on, it’s time to begin implementing the tool and transferring your data over. 

Obviously, many of your projects will still be ongoing during this process, so your implementation may have to occur in phases in consultation with the project managers. Your new project management software’s support team will hopefully help you figure out the nuts and bolts of data migration. 

Getting the team to adopt the project management tool 

Change isn’t easy, especially when you’re juggling multiple projects at once. Here are a few suggestions to help ease your team’s transition to a new tool.

1. Include team members in the selection process 

We’ve already covered what goes into an efficient selection committee, but it’s worth reiterating the importance of including people from all levels of the organization in the evaluation activities. 

This is because your role largely dictates how you engage with a project management tool on a daily basis. A project manager, for instance, might spend most of their time in the tool allocating resources, assigning tasks, and checking in on progress, whereas a copywriter may be primarily tracking time. 

Failure to include a range of perspectives can leave your team frustrated if you didn’t consider their needs when picking which software to switch to.  

2. Get team members involved early on via free trials 

Even after a tool has been chosen, the tool’s free trial offerings provide an easy way for your team members to play around with the new features and get acclimated to a new interface. 

Your organization’s account will be outfitted to your team’s needs with real project data, so signing up for a separate free trial is a very low-risk way for your team to get to know the project management tool. 

3. Make use of educational resources 

Many project management tools offer a Support Center, which serves as a place to get your questions answered without having to contact support directly. Support centers typically offer guidance on how to use various features, fixes to common issues, and how-to videos. 

This is an incredibly valuable resource when onboarding your team to a new software solution, as it can help drastically reduce learning curves that stand in the way of your productivity. Plus, support center information can be accessed instantly at any time of day, meaning you won’t have to contact the support team and wait for a response for every minor question you may have. 

4. Employ expert help 

If your project management software comes with personalized onboarding help, you should absolutely take advantage! Experts can help with data migration, answering employee questions, and providing basic training. 

Some tools don’t come with this level of onboarding assistance, in which case you can always hire a third-party expert for assistance. Turning to an outside expert for assistance is likely only worth it for larger teams who have already invested a significant amount of money into this new tool and need to ensure employees understand how to use it to make the most of their investment. 

5. Check in with the team 

Your team members will likely all have varying levels of technical expertise, so relying on each other for guidance is helpful during the adoption process. Conducting regular check-in meetings when rolling out the new project management software will help identify common roadblocks that are holding up progress and rectify them quickly. 

And let’s face it – sometimes we make mistakes. If the new software your organization chose to implement is giving you more problems than solving them, it might be time to go back to the drawing board. Having team meetings where participants can give you feedback and express their feelings on new changes can be very productive.

How Rodeo Drive can help you run your projects smoothly 

Rodeo Drive is an all-in-one project management software tool that helps creatives deliver high-quality projects successfully – without the need for third-party integrations. 

With detailed project analytics, budget tracking, and the ability to send invoices and estimates straight from the platform, we help handle the annoying administrative projects, leaving you with more time to spend on actual project work. 

Rodeo Drive will help your team eliminate scattered workflows by providing all of the features you need in just one app. Here’s an overview of our most favored features: 

  • Phase-based budgeting: Budgeting doesn’t have to be difficult. Estimate the time activities and expense activities necessary for each phase of your project and we’ll handle the calculations. Once you’re finished, you can send the budget estimate to the client for approval directly from the platform.  
  • Time tracking: To record time in Rodeo Drive, either start your live timer or add a timecard after your work is completed. All time activities must be attached to a budget item to ensure your budget numbers are kept updated. 
  • Invoicing: Rodeo Drive allows you to bill clients for your work right from the platform (UK) and via QuickBooks integration (US). Not to mention, invoices and estimates sent from Rodeo Drive are fully customizable, so you can add your own branding and terms and conditions prior to sending. 
  • Reporting: Since all of Rodeo Drive’s features are interconnected, we’re able to bring you in-depth project insights with our reporting feature. This includes data on your time registration, team productivity, and project margins. Or, if you prefer to compile your own reports, you can download your data as an Excel or CSV file. 
  • Contact management: Rodeo Drive offers a mini CRM feature, which allows you to store client and vendor contact information in one place. This helps ensure your entire team has access to the correct information, such as rate cards, payment terms, and other contact details. 
  • Free customer support and personalized onboarding: Our team of Rodeo Drive experts is always available to help via live chat support while you’re using the platform. Plus, when you switch to Rodeo Drive, you’ll receive a dedicated customer success manager to help oversee your onboarding process and answer any questions you may have. 

Why not try it out? Or – if you’re still on the fence – schedule a demo to learn more. 

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Originally published on May 20, 2021, updated on March 8, 2023.