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The Ultimate Guide To Choosing The Best Project Management Software For Your Team

The Ultimate Guide To Choosing The Best Project Management Software For Your Team

By Josh Spilker

Have you noticed this trend?

The number of project management software solutions available has exploded in recent years.

These apps feature user-friendly interfaces designed to improve collaboration among team members and provide a variety of reporting capabilities to keep everyone in the loop.

That’s great and all, but it leaves with a very important question: “Which software is right for my company?”

Your choice will impact how you manage your work, how your team collaborates and how your work is stored and approved.

Quite simply: Project management software and collaboration software is a big deal.

How can you find the one that’s right for you?

In this guide, you’ll…

  • Learn about the various features of project management software
  • Determine how your team works
  • How to define requirements
  • Figure out how to transition your team to a new project management solution.

Let’s start…

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So…Why Do You Need New Project Management Software?

A well-designed project management software will keep everyone on the same page, ensure that projects are progressing as planned, allow you to get visibility into all your projects, and make high-level reporting as quick as a push of a button.

Many of you might have been tracking projects (or even making Gantt Charts) using Excel, Google Sheets or other spreadsheet programs.

They work fine up to a point for simple projects that involve just a few resources and don’t take very long.

However…they fall way short compared to what a dedicated project management solution can do.

Excel can’t handle…

  • Complex projects with large scopes
  • Multiple stakeholders
  • Different teams simultaneously working together

On the other hand…

You may have been using a personal task list app or basic project management app that no longer accommodates your needs. It may look good on paper, but it can’t handle the needs of your organization.

Should you consider a new project management tool?

Here are some tell-tale signs:

  • Your team is using too many tools to track different aspects of your projects.
  • Your team is spending too much time on emails and meetings and not enough time on creating deliverables.
  • You want to move your project management system to the cloud so everyone can access information from anywhere with an Internet connection.
  • You’re consistently breathing down your team members’ necks to remind them on deadlines and deliverables.
  • Your business and organizational needs have outgrown the capacity of your current software.
  • You’re not getting adequate updates or enough visibility through your current software.
  • Issues are not properly tracked and risks are not flagged in time.
  • Your software is too complex, so much so that it’s creating inefficiencies (e.g. it takes a long time for new hires to get up to speed) rather than increasing productivity.
  • Collaboration among team members is not efficient or effective.
  • You’re spending too much time analyzing data and generating reports.

10 Signs You Desperately Need a New Project Management Tool

Is this you?

Want to track projects, manage resources and just overall get things done better than the other departments?

This is the right place then and guess what? You probably fit one of these categories…

You’re part of a non-technical team that needs something that’s easy to use. You may be a marketing manager, product manager, IT manager, or even an agency creative lead – wearing many hats and one of which includes making sure that teams are organized and projects get done.

You are a professional project manager, trying to streamline your company’s project management process so your team can be more efficient and effective in their work.

Maybe you are a small business owner who has realized the need to implement guidelines and procedures around how projects get finished.

Or perhaps you’re on a team that’s part of a larger organization and you need software that interacts with your company-wide system, but is used primarily with smaller teams.

Whatever the case, the information in this guide will help you wrap your head around the seemingly complicated world of project management tools, and help you navigate the decision-making process.

So, this is what you need to think about when choosing project management software…

What’s your work style? Figure it out.

The first factor to think about is your team’s work style. You have to figure this out before going forward.

You want project management software to complement how you work. You don’t want to fight against the software.  

That doesn’t mean that the project management software you ultimately choose won’t force you to do new things or develop new habits. It will.

How do you and your team prefer to work together? Understanding this can help you identify a tool that complements your team’s collaboration style instead of having the software dictate how team members interact with each other.

Teams are set up in different ways, and different types of project management software mirrors those ways. You can find a solution that is set up for the way your team functions, or how you want it to function.

However, we can group work styles into two large buckets:

Proactive Work

Teams following a proactive methodology, such as the waterfall method, emphasize record keeping and a well-defined workflow within a sequential process. This methodology focuses on prioritization and setting dependencies.

In the case of website development, it could look like: conception, initiation, analysis, design, construction, testing, implementation, and maintenance.

This methodology makes it easy to manage expectations and ensure work gets done. Each team member works on a different part of the project and there’s a clear delineation of roles and tasks.

Reactive Work

Teams following methodologies like (Agile, Scrum or Lean) are more flexible when managing their workflow, but often have little insight into what’s next. Typically a team would divvy up a “pile” of work, which will be completed in bits and chunks as different team members pitch in to develop a feature in an iterative process. Often, team members don’t know how much is left to be finished.

Projects are initiated, divided into sprints and at the end of each sprint, the project priorities are evaluated and the tasks are re-assigned.

With no firm due dates, team and scope could grow over time as the project develops in response to client feedback or new discoveries. This methodology is most commonly followed by software development and technical teams.

Finding Your Groove

Understanding how your team works can help you find a project management software that fits your current habits and team dynamics.

Remember, you want your new project management tool to make your team more productive, not to create inefficiencies.

Selecting a software that complements your team’s current work style will help minimize the learning curve, and will make for a smooth transition and implementation of the new process.

By staying in line with the current work style, you will have a much easier time getting your entire team on board.

Needs & Challenges, We Have a Few

See that? What’s over there? Oooh, oooh another shiny thing.

Before you get sucked into the rabbit hole of the flashy features of project management, you need to be clear on your project management needs so you can find the best solution for your team.

For any project to be successful, you need to gather and define project objectives, needs, specs and requirements. Otherwise, you’d have no idea what constitutes a good solution to your challenges.

And you’ll feel empty when that bright shiny thing doesn’t pan out the way you want it to.

What Does Your Team Need?

Teams are made up of different skill sets and work habits, and as a result, need project management tools with varied features sets.

Team size, nature of the business, and the complexity of your projects will affect the type of project management software that you need.

Some teams only need a simple tool to help keep track of specific tasks or to-do lists. Others (e.g. small business, HR, administrative projects) could benefit from additional features such as task assignment, progress tracking, and reporting. Companies that require professional and business-critical PM activities (e.g. system integration services or consulting) will need broader functionalities including task assignment, resource allocation, budget planning, and invoicing.

Understand Your Challenges

Sometimes it’s hard for team members to articulate what they need exactly from a project management tool. They’re not going to tell you, “hey we need better task management and reporting tool over here in marketing!”

Instead, you may have to sit down with your team to map out how work is currently being done to figure out where the inefficiencies are.

Is there a process? Or are the challenges caused by the lack of a cohesive process that everyone understands and follows? Do team members know where to look for information or who to go to for questions and support? Is there sufficient accountability built into the process?

After you understand the current challenges, you can define the specific project management software features that can best help you streamline your process and increase productivity.

The Perfect Project Management Scenario

Think about typical workday and note down the various project management tasks you normally encounter.

What do these tasks involve? What do you have to do to get them done? Is the current process ideal, or do you wish there could be tools to help you get them done more efficiently?

How can you make the current procedures repeatable?

What is the projected growth of your company? What kind of project management needs do you anticipate in the next few years?

That’s how to determine your ideal project management scenario.

Go through the same exercise with your key team members from various departments, e.g. strategy, UX, design, copywriting, development, and QA, to understand what tools and features can help them do their job more efficiently.

You want to be intentional while defining your needs based on your current processes. Ask whether you’re following all the steps because they are all necessary, or if you’re following them simply because “that’s how it’s been done” and nobody cares to question their validity over time.

Integration with Existing Apps and Software

Some project management apps offer comprehensive functionalities including invoicing, communication, time tracking and expense tracking.

If you choose one of these apps, you can take care of all of these tasks inside one software and no longer have to switch from tool to tool for different tasks.

However, bigger isn’t necessarily better. You may not need everything such complex software has to offer.

In fact, their often-complicated interface could be so overwhelming that they actually increase transition time and slow down your team rather than help them become more productive. These apps also tend to cost more, and you probably don’t want to be paying for features you don’t need.

Alternatively, you can select a simpler project management tool and add on apps such as Slack for communication, Dropbox for file sharing or ResourceGuru for scheduling for specific needs. You can then make these tools link up with each other and with the project management software using apps such as IFTTT or Zapier.

If you’re already using these cloud-based apps and your team likes the way they work, you may want to integrate them with your new project management tool so you can keep using them. Project management software can serve as a central hub for all of the apps that you need. When they’re separate and piecemeal, details, task dependencies and files can get lost in the shuffle causing more harm than good.

In that case, make sure that the project management software you select offers integration with your existing apps to help your team become more productive.

Matching Your Needs To Features

All the bells and whistles in a software may look good on a demo video, but are they relevant to your team’s project management needs? Are you paying for features that are helping you increase ROI?

By first defining your team’s needs and challenges, you can select a project management software most relevant to your team and your company.

Need a break? Get a free PDF copy of this guide and read it later.

What are the right features & functionalities?

With the growth of project management apps, going through a feature list could feel like reading gibberish if you have no idea how they work.

Take a few minutes to familiarize yourself with what the various functionalities are and what they do, so you won’t feel overwhelmed when you start reading through various feature lists.

What Should You Look For?

Many project management solutions have similar features, but may approach them in different ways. Think about how these points and features will impact your team dynamic.

1. Ease of Use

A project management software is not going to be useful unless your team uses it.

Some project management tools are very complex and could take a few days of training just to get an entire team fully transitioned. Then it’d also take every new team member the same amount of time to get up and running.

Even though some businesses require such complex functionalities, others can operate just as efficiently with simpler features and interfaces.

Select a tool that offers the right mix of features delivered via an intuitive interface that complements the way your team works.

2. Task Management

This feature not only allows you to list out all the tasks but also assign team members to each. You can then focus on the highest priorities and set deadlines so everyone knows what needs to get done and by whom.

Some project management tools let you sort tasks in different ways, e.g. by resource, department, completion day etc., so you can locate and organize information quickly.

Most apps notify the responsible team member when a deadline approaches to make sure assignments are finished in a timely manner.

3. Scheduling and Planning

You may be able to manage a small project (e.g. creating a set of banners) with just a list of tasks on a spreadsheet. However, things can get hairy really fast in a large project (e.g. launching a new website) if you don’t have the ability to visualize your timeline and understand how the various timelines and dependencies can impact each other.

A Gantt chart is an important feature that allows you to visualize your task list and project schedule.

4. File Sharing

Most software gives you the capability to share files internally with team members so they can have quick access to information that they need to get the work done.

If you often work with people outside your company, such as vendors, contractors or clients, you may also want to have the ability to share files with these external parties as well

5. Communication

Good communication is key to facilitating collaboration and making sure tasks get done efficiently. The need for streamlined communication is becoming increasingly critical as more people work remotely or are distributed across offices in different locations.

A built-in messaging app helps team members quickly communicate with each other in real time without having to sift through a pile of emails.

In addition, other team members can glance through a thread to quickly get up to speed (instead of having someone dig through folders of old emails and forwarding five dozen of them) – which helps facilitate collaboration and transition.

6. Real-Time Reporting

Reporting tools collect your previously inserted project data and create reports on project budgets, expenses, resource allocation, team member performance and more.

Most project management tools have a pre-defined set of reports you can generate, and some also support customized reporting.

7. Dashboards

Getting a high-level view of project statuses with a team dashboard shelps keep everyone updated on projects status with graphs, charts, visual metrics and key performance indicators (KPIs).

These graphic reports communicate the project status to stakeholders and sponsors who may not need to see the details presented in a written report.

8. User Interface

Although visual design may not seem to be a top priority, you probably don’t want to be staring at an eyesore every day!

A poor, cluttered interface could make it difficult for users to find what they need, thereby hindering your team’s productivity.

A clean, simple and professional interface makes the user experience more pleasant and may even help your team members get excited about using the software.

A well-designed interface is even more important if the project management tool has a client-facing component that you use for client communications. A modern and professional design will enhance the image of your company’s brand.

9. Customization

Customization allows you to create a “work environment” that reflects your preferences – from logo to color scheme to custom exports and how you prefer data to be organized.

Customization of reports and data columns lets you selectively display information in your charts and reports so you can easily show relevant data and metrics to different stakeholders quickly.

10. Time, Budget & Resource Management

These three aspects often overlap, and when they’re centralized in one project management software they can often inform each other and help you allocate your team and resources more efficiently.

  • Time Management

A team calendar that synchronizes with popular calendar apps can help you schedule and organize meetings efficiently.

A planner allows you to outline all your project tasks, so you can have an overview of each team member’s responsibilities. This helps you allocate your resources efficiently and make sure workload is evenly distributed so you can increase the overall productivity of your team.

  • Resource Management

Resource management covers more than managing team members’ time and availability. You can also allocate resources such as meeting venues or materials used in a project.

A project management tool can outline all the scheduled and planned resources to help you calculate the cost of their usage and make sure everyone has what he needs to complete a task.

  • Budget Management

There are many features that can help you stay on budget and save time on hours tracking and billing tasks.

Look for a project management app with integrated budget reporting, time tracking, time billing and automated invoicing so your budget report will reflect the real-time status and resource usage of your projects.

Advanced Features To Consider

Based on the nature of your company’s business and the complexity of your projects, you may find the following features useful:

1. Visualization Tools

If you often deal with complex data and reporting, you might have to go beyond the basic Gantt chart and utilize additional visualization tools to simplify the communication of various data and metrics involved in your projects.

2. API Integration

If you want to keep the cloud-based apps and tools your team is already using (e.g. for file sharing messaging, scheduling etc.,) look for project management software with a robust API so you can seamlessly connect to the apps that your team loves.

3. Risk Analysis

If you work with complex projects with many moving parts, a built-in risk analysis capability can help you identify, analyze and respond quickly to risk factors throughout the life of a project.

4. Issue Tracking

Often times a task involves a lot of back and forth, especially with product development. Or something might break.

For instances like that, you can use an issue-tracking feature to make sure nothing falls through the crack.

Issue tracking is also helpful during the QA phase for recording bugs and making sure everything has been fixed before deployment.

  1. Expense Reporting and Invoicing

Some advanced project management tools offer customer relationship management (CRM) and invoice automation functionalities so customer interactions and information can be synced up automatically.

The invoicing feature synchs with time tracking and expense reporting so all information can be consolidated before an invoice is generated to avoid error.

The Features You Need

After you have an understanding of the various features offered by project management tools on the market, next is to get clear on your requirements.

You need to consider different factors based on your unique circumstances to make sure the project management software you select meets the needs of your team, the nature of your projects, and the structure of your company – taking into account current requirements and future growth needs.

Share the included Feature Checklist with your team to help you determine priorities and to stay on track during your software selection process.

After they complete it, take the opportunity to address questions and resolve conflicts, so you can get your team’s buy-in before you proceed – this will make the subsequent implementation and transition much smoother.

You’re not going anywhere without your team.

If you have been involving your team in the software selection process, the implementation and transition shouldn’t come as a surprise.

However, some work may still need to be done so everyone in your team understands the reason for transitioning to a new software, so they are fully on board with adopting this new process.

Communicate Benefits To Your Team & Get Them On Board

Share with your team how a new project management tool can help them become more efficient and productive:

  1. Teams can spend less time in meetings and more time creating deliverables.
  2. Real-time project status tracking means managers no longer have to pop into cubicles and breathe down people’s necks asking about work
  3. A cloud-based application means team members can enjoy the flexibility of working from anywhere with an Internet connection and at different hours.
  4. A centralized place for document archive, commenting and approval means better collaboration and less confusion.
  5. The use of better planning and resource assignment tools means clear accountability that helps avoid finger pointing down the road.

Communicate Benefits To Your Superiors

Your boss (and boss’s boss) is probably not as “in the weeds” as you are. To get your superiors’ buy-in and support on purchasing a new tool and implementing a new process, you need to communicate high-level benefits and ROIs:

  1. A centralized dashboard means visibility to all projects in real-time to improve decision-making at the executive level.
  2. High-level, custom reporting means decision makers can view data and metrics that are relevant to them, instead of having to parse through details they may not need.
  3. Built-in risk analysis tool can help mitigate or avoid costly mistakes.
  4. A more efficient process means more time saved… and time is money.

Show, Don’t Just Tell

Take the time to work with your team so they can see the new process in action and experience the benefits first hand.

Many project management tools offer free trials, so you can let your team members take the software for a spin before committing to your final decision.

You may also want to record how the software helps improve your team’s efficiency during the trial period, and present the data to your superiors to get the support you need for successful implementation.

Will You Be Helped?

The best project management solution is backed by a dedicated customer support team that can walk you and your team through the software step-by-step so you can get onboarded quickly and jump right in.

Look for software providers that offer unlimited training and support for the duration of your contract. Inquire if there’s a dedicated resource to help your team get more productive with the software, and help individual team member fit into the process.

Is there a live chat on the site? Can you call the provider and speak to a human being? Can you contact the support team via social media? What’s the typical response time after a support ticket is submitted? Is the support team available during off hours and weekends? Is there a searchable knowledge base on their website?

Takeaway: Communicate and get buy-in from your team for your project management solution.


A project management solution selected with your team’s needs and process in mind is essential in helping everyone work more efficiently and become more productive.

When choosing your new project management software, make sure to match the various features to your business’ requirements and team’s process so you can find a tool that best serve your objectives.

Don’t forget to involve your team members during the evaluation and “test drive” period so you can incorporate their input into your selection process. This will not only help ensure that the software meets the needs of different departments but also get your team’s buy-in to make transition and implementation a much smoother process.

Last but not least, plan ahead.

Don’t wait till a large complex project to land on your desk before you scramble for a software that can handle the project management needs.

Anticipate future needs by working with leadership to make sure the solution you select has the features and capability to support the company’s projected growth.

Takeaway: Project management software should improve (not hurt) your team’s productivity.