Agency Management

Project Management Software and Tools: The Complete Buying Guide

by Hannah Ouzer, December 26, 2018

The project management software you choose will have a lasting impact on your productivity and effectiveness. This guide will help you pick a project management tool that works for your organization.

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Confused, disorganized, and overwhelmed.

Have you ever felt like this during a project?

If you answered 'yes', chances are that you're not using the right project management software.

It doesn't matter what kind of organization you run or projects you work on, a capable PM tool can transform your effectiveness.

You'll be more productive, communicate better, and won't feel that things are always slipping through your fingers all the time.

The trouble is, not every project management software is equally effective. And not every tool is meant for your particular use case.

So in this article, I'll tackle this key issue. I'll share a detailed buying guide to help you zero in on the right project management software. You’ll learn how to understand your requirements, shortlist tools, and create an implementation plan.

Ready? Let's start!


How to Buy Project Management Software

Let me preface this by saying that choosing a project management tool isn't easy.

You have to:

  1. Pick the right tool
  2. Get buy-in from team members and stakeholders
  3. Get everyone to commit to using the tool

In fact, I'd even say picking a PM tool is a complex project in itself.

What makes matters particularly hard is that not every tool is right for every team or organization.

Some teams might drown in the feature-bloat of a complex tool. Others might feel underwhelmed by the limited capabilities of a simpler software.

As with Goldilocks, there is a project management software that's "just right" for your needs.

Here's how to find it.




Understand Your Current Project Management Processes

One of the tougher tasks in choosing a project management software is finding something that:

  • Aligns with your current PM methodologies
  • Pushes you to move towards greater PM maturity

Organizations don’t switch PM tools easily. Once you pick a tool, you’re likely to stick with it for quite a while.

If the tool is too inaccessible, you’ll find adoption difficult. And if it is too limited, it won’t be able to support your growing maturity.

So before you start the search, introspect. Analyze where you currently stand and the trajectory of your PM formalization. I’ll show you how below.

Assess Your PM Maturity

An organization with a fully-developed PMO needs a very different project management software than one which has no formal PM documentation.

Your first step, therefore, should be to assess the maturity of your existing PM practices.

This can be divided into five levels:

  • Level 0: You have no awareness or adoption of any project management processes. You don't use any PM-focused software or have any PM-related roles.
  • Level 1: You have some awareness of project management practices. You've explored or even tried some PM tools, and have been thinking of adopting some PM frameworks.
  • Level 2: You have a defined PM framework and well-documented rules for project planning and execution. You've also adopted simple project management-focused software, or have a PM-related role.
  • Level 3: You're using a well-defined project methodology, have one or more trained project managers, and there is organization-wide alignment on PM practices.
  • Level 4: You have a fully-functional, mature project management office (PMO) that is aligned with your broader business strategy.


 Project management maturity assessment model

The more mature your PM practices, the more mature a PM tool you'll want.

While you're at this, also consider how fast you're increasing your PM maturity.

Ask yourself:

  • Is there a defined budget for investing in project management? If there is, what are the trends - is the budget increasing or decreasing?
  • Is there stakeholder buy-in for improving PM practices?
  • Are there plans to hire and train project managers?

You can get away with a basic project management software if you have no concrete plans to invest in this field.

But if there is organization-wide agreement that PM is important (and it is important), you'll want a software that can accommodate your growing ambition.


Document Your Current Processes

You want a PM software that can replace and streamline your existing solutions. But to do that, you have to first document how you currently work.

Map the path a project takes right from inception to final delivery and debriefing. Document each step that happens post-initiation and the processes, tools, and protocols you use for it.

As a frame of reference, these are the five phases in a well-documented project management process:



Some questions you can ask yourself are:

  • What documents do you create at project initiation? How do you create them?
  • Post-initiation, how do you document your project plan? What tools do you use to break down and map deliverables?
  • How do you keep track of progress? What tools or documents do you use to keep stakeholders updated about the project status?
  • Do you have any process to forecast the project's progress - both in terms of work completed and budget used/remaining?
  • How do you track activity? What tools do you use to share documents and manage conversations?
  • How do you create and share reports? Do you have any fixed process to analyze the project and track KPIs?

Make a note of every question for which you don't have a clear answer. This signifies a process that needs to be streamlined.

Use this list of "to-be-streamlined" processes as a checklist when you go shopping for project management software.

For example, during your documentation process, you might find that you don't have any tools to create project reports. You rely on Word/Excel templates which are difficult to use and share.

Thus, when you're looking for project management tools, pick something that has report creation capabilities built-in.


 Workamajig’s reporting capabilities reduce the need to buy additional reporting tools or templates




Analyze Your Requirements

Choosing a project management tool can't be a solitary endeavor. Your entire organization (or at least your team) has to use the software.

If you don't understand everybody's habits and needs, you'll find that adoption rates suffer.

Your next step in the project management software buying process, therefore, should be to analyze your requirements.

Here's what this involves.

Understand Your Collaboration and Communication Habits

It's a rare business that sticks to a single tool for collaboration and communication. Most have their own habits, jumping from tool to tool based on the situation.

You might use email for long-form communication, Skype for audio calls, for video conferences, and Slack for informal messages. Individual team members might go beyond these to use their personally favored tools - Whatsapp, iMessage, Dropbox, etc. - to share documents.

Every organization is different; it's a key responsibility to figure out how yours works.

Go across your organization to figure out how teams handle the following:

Document sharing (internal):

  • Where do you keep all shared documents, i.e. your central document repository?
  • What cloud storage tools do you use if any?
  • How do you manage document editing/sharing rights?
  • How do you share documents with team members (email, Google Drive, etc.)?
  • How do you share documents outside your team (but within the same organization)?
  • How do you manage document version control, edits, and comments?

Document sharing (external):

  • How do you gather feedback on documents from clients and other external stakeholders?
  • How do you manage access control for people outside your organization (freelancers, contractors, etc.)?
  • If you need to share passwords, how do you manage it?


  • What are your primary tools for the following (both internal and external:
    • Long-form communication
    • Video calls
    • Audio calls
    • Messaging and chat
    • Video/audio conferencing
  • For the above tools, what are the most desired features? What are the least desired? What gaps would you like to see filled?
  • How do your communication tools tie into document sharing and collaboration?


  • What tools do you use to work together on the following:
    • Text documents
    • Spreadsheets
    • Presentations
    • Mockups, wireframes, and design drafts (both internally and with clients)
  • How do you track and share your progress
  • How do you assign and manage to-dos and tasks?
  • How do you handle communication-related to tasks?


I know this sounds like a lot, but there’s an extraordinary amount of fragmentation in most organizations’ collaboration habits.

For example, if you use a Kanban system like Trello to manage tasks, you can share updates via Trello’s internal comments.



If Trello did not have these comments, you would have had to resort to email, Slack, Skype or other chat tools to share updates. This would end up creating heavily fragmented communication where no one really knows what’s going on.

Your goal is to centralize and streamline as much as possible. By documenting the above, you’ll move a little bit closer towards achieving that aim.


Interview Stakeholders

Choosing a project management software can't be an entirely objective decision. A tool that has all the features you need might still go unadopted if your team members don't like its design or UI.

Solve this problem by interviewing your stakeholders. Understand what are their frustrations, complaints, and recommendations with respect to your current project management process.

A few questions you might want to ask include:

  • What do you like about our current project management process?
  • Do you prefer web-based or desktop tools? Why?
  • What is your workflow for [their role]? How many tools do you use to create, share, and edit a deliverable?
  • What is your communication workflow for discussing things with colleagues, clients, and managers? What would you change about it?
  • Which software do you enjoy using? What do you like about it? (Could be any software; not just the ones you use)
  • Which software do you dislike using? Why?
  • If you're stuck with using [a tool you currently use], how do you go about finding help - customer support, Google, or colleagues?
  • Would you rather use multiple specialized tools for different work functions, or a single tool that combines everything in one dashboard? Why?
  • What are your chief concerns about using a new software?

Your goal is to figure out the “pulse” of your organization’s software use.

For instance, if most of your team members like using web-based tools, you can safely remove desktop project management tools from your options.

Similarly, if your people say that they’re concerned about the learning curve for a new software, you’ll want to pick something that offers extensive training and learning material.

For a project management deployment to be successful, you need buy-in from the entire organization. Understanding what they like, what they don’t is crucial for picking something they’ll actually want to use.

Once you’ve done the above, list your requirements based on their importance. The MoSCoW method is a good framework to adopt:

  • Must have: Features that you can’t do without. These are essential for your team to work.
  • Should have: Features that are nice to have, but not crucial for your day-to-day functioning.
  • Could have: Features that you don’t mind having, but which won’t swing the decision.




Calculate the Costs

Good project management software pays for itself. The productivity gains you make trump the price you pay for the tool.

The problem is that people tend to look at only the overt cost of the software.

Deploying any new system takes time and resources. You're not just paying, say, $15/month/user. You're also spending the time to learn how to use the software and adapt it into your workflows.

For agencies, this is particularly important. Any time you're spending learning a new system is the time you can't bill clients for.

Therefore, it's crucial to keep these hidden costs in mind when evaluating your options.

Below, I'll share a few tips to understand your costs and fix a budget.


Research the Product Landscape

Project management software varies a lot in terms of cost and infrastructure requirements.

There are enterprise solutions that you need to host on your own servers and which will set you back by thousands of dollars.

Then there are online-only tools like Workamajig that charge you by the seat.

It's essential that you get a lay of the land before you come up with a budget.

Look out for:

  • On-premises vs cloud-based: The former requires more maintenance and underlying infrastructure, but afford more customization options. The latter is easier to deploy and switch.
  • Pricing structure: Project management software is sold either on a flat fee (usual for on-premises tools) or as a monthly subscription service. Analyze what you're comfortable with (upfront costs vs recurring costs) and what you can afford.
  • Training and support: Time spent in training and seeking support is time you can't bill for. Further, many software companies charge for extra training and phone support. Factor these costs into your decision.
  • Growth potential: Some tools might bump you to a higher priced plan once you hit a certain team size. In other cases, you might end up buying a 10-person license upfront even when you don't have as many people. So factor in your own growth goals as well as the way the software provider treats additional users.

You also need to know how much time it will take for a SaaS solution to cost as much as a software paid-for upfront.

For instance, a 10-person perpetual license might cost $3,000 upfront. A $10/user/month SaaS solution would take 2.5 years to cost the same. Beyond that, you’re effectively in the red compared to the upfront priced tool.


 Cloud-based SaaS tools incur lower upfront costs and give you the flexibility to upgrade/downgrade as necessary

Ask yourself: do you intend to use the software long enough to hit the break-even point? What if something about your situation changes?


Create a Budget

How much you can spend on a project management software depends on:

  • The combined cost of all the tools it’s going to replace
  • The amount of time it takes to deploy, adopt, and be productive with the software

For the first part, go back to the previous step where you documented all your existing tools. Identify which of these tools you can replace with your new project management software.

The combined cost of all these tools is the minimum you can spend on your new PM software and still come out ahead.

For example, Workamajig has the following capabilities:

  • Sales tool (replaces CRM)
  • Creative management (replaces scheduling and to-do tools)
  • Accounting and finance (replaces accounting tool)
  • Communication tool (replaces team chat tool)
  • Document management (replaces cloud storage)

And of course, project management capabilities

Therefore, how much you can spend on Workamajig would equal the cost of all the above tools it replaces. This includes the $10+/user/month you would spend on a basic CRM, the $15+/month for a basic accounting tool, and the $5+/month for any cloud storage software.


 Workamajig’s sales features can easily replace basic CRMs for small sales teams

Calculating the cost of your current system is easy enough, but it’s much harder to fix a price tag to the productivity lost in deploying a new software.

Start by asking your sales rep how long it takes on average for a team to be productive with their software.

Also, factor in:

  • How much free training and support is provided?
  • If you can buy additional paid training, how much does it cost?
  • How much does extra phone or in-person support costs?

Add this to the total cost of the software.

For instance, if it takes 50 hours and 3 months to be productive with a $10/user/month software, and you need to buy $2,000 worth of extra training, your actual initial costs for 10 users are:

[50 * $100 (average billing rate)] + ($2000) + ($10 * 10 users * 3 months) = $7,300

While you’re at this, also consider how much time your new system will save you.

If you save 20 hours/month across all your teams, at a billing rate of $100, it will take 4 months to recoup the $7,300 initial cost in the above scenario.

Anything after that is your profit.

This will give you a fair idea of how much you can spend on your new project management software.




Create a Trial Plan

You’ve mapped your requirements, gathered feedback, and studied the product landscape.

Your next step is to try out the options on the market.

As with cars, you don’t want to buy a project management software without taking it out for a spin. At the very least, you should be able to walk through a detailed demo, if not a free trial.

Here’s a two-step process to create a trial plan.

Make a List of Products to Try

Start by creating a spreadsheet with a list of every product you intend to try. Next to each product, list its must have, should have, and could have features.

For each product, mark its feature availability in the spreadsheet. Like this:



Also note whether the product offers a free trial, free demo, or no trial/demo. And of course, mention the price.

Based on this list, you should be able to disqualify a number of options. Some might not have the features you need, some might be too overpriced, and some others might fall short on support and integrations.

Once you have your final list, start taking out every product for a spin. Involve the most important stakeholders and do a trial run with a mock project.

You want to know how the software behaves in a real-world setting, not just how it looks or what features it has.

 See Workamajig In Action – Request a Personalized Demo Now!

Gather and Analyze Feedback

When taking a project management software out for a trial or demo, your goal should be simple: test the water and see if it complements your workflow.

Don't focus on extensive customization or what a software "could be" with enough training or practice.

Rather, focus on what it feels like.

For every tool that you take to trial, gather your team's feedback. Ask them:

  • How difficult is the software to use? Could you find what you were looking for by yourself?
  • How often did you feel the need to get outside help?
  • Are the features compartmentalized? Or do you have to navigate conflicting features to get to what you want?
  • Is the UI user-friendly? Is it "delightful" to use?
  • How did you have to modify your workflow to use this software? How many additional steps did it require?

Finally, close your feedback by doing a quick NPS survey of your trial team members. Ask them:

On a scale of 1-10, how likely are you to recommend this software to a team member?

The difference between the percentage of “promoters” (i.e. people who scored you above 8), and detractors (i.e. people who scored you below 7) is your “Net Promoter Score”.



Add this score next to each software in your spreadsheet.

I know this might sound like a lot, but it’s crucial that you gather feedback accurately. You want to know what your team members really think about the software.

You’ll find far more success with a limited tool that your team likes to use, than a feature-rich offering that your stakeholders can’t stand.




Create an Implementation Plan

If you’ve done your homework above, you should have zeroed-down on your final choice.

The next step post-purchase is to create an implementation plan.

Implementation is crucial for successful deployment. The software might be well-liked and check all your feature requirements, but if it is thrust onto the organization without planning, your adoption rates will suffer.

Here’s what you can do to make the deployment go smoother:

Remove Complexities

Have you ever used a software you didn’t have prior expertise in and found yourself completely overwhelmed by the choices?

I’m sure you have.


 Software can be intimidating, such as this screenshot from Ableton, a digital audio workstation, shows (Image credit)

You don’t want your team members to feel the same way when they sign into your new project management system. They should only have to deal with features that directly impact their work - at least on initial roll-out.

For instance, if a creative needs to log into the PM software just to track time, that’s the only feature she should have access to. Everything else should be off limits.

PM tools that have strong compartmentalization of features are particularly handy in such situations. In Workamajig, for instance, a creative who logs in sees a list of “Tasks I need to work on” as the first thing in his/her dashboard.



This gives a team member the ability to log in, record their work, and log out without getting overwhelmed.

In your implementation plan, make sure that you include detailed instructions for each team member based on his/her responsibilities. Focus only on the features they need to use.

If you need to introduce them to additional features, do it gradually.


Map Out Your Plan

Your biggest challenge isn’t choosing the right tool.

It’s actually getting your people to actually use it.

Your team already has its own workflow and way of doing things. Getting them to switch to a new software means erasing their existing habits.

And old habits, as you know, are hard to break.

There are two approaches to go with this:

  • Forced implementation, where everyone switches to the new system en-masse. You will see a drop in productivity initially, but like ripping off a band-aid, it can sometimes be better to do things in one go.
  • Phased implementation, where a group of "pioneers" switches to the new system. These are typically tech savvy early adopters who are eager to try new software. They can help evangelize the new software for others while also testing it for flaws and limitations.

There is no “right” approach. If your people are tech-savvy and aren’t particularly habituated to their current system, a forced implementation plan might work better for you. Else you might choose a few pioneers to ease adoption.

More importantly, you must have a fully mapped out plan for each role. In particular, pay attention to the following:

  • Data imported from the old system
  • Integrations with other tools that you use
  • Protocols for data storage and communication
  • Documentation and where to find help/support

It might be worthwhile to create a new user onboarding plan. This can help not only your existing team members but also any new hires that join your company.

Finally, remember to use the software. Far too many deployments fail simply because people simply go back to their old tools. Insist that at least some of the work happens in the new system if you’re going for a phased implementation.


Over to You

There are a few things that will have a bigger impact on your day-to-day work than switching to a new project management software. A comprehensive PM system will impact everything from the way you manage projects to the way you communicate.

This makes buying project management tools especially difficult. You’re not introducing just another software to your team; you’re changing the way they work. Pick the wrong system and you’ll end up with lost productivity, resentful team members, and a hefty software bill.

Use this guide to help you buy a project management software that fits your requirements.

For a comprehensive project management tool that offers a vast range of features, check out Workamajig. With a single dashboard for every aspect of project management - reporting, communication, document sharing, time tracking, and traffic management - it will revolutionize the way you work.

Hit the link below to take Workamajig out for a spin today.

See Workamajig In Action – Request a Personalized Demo Now!

About The Author

Hannah Ouzer

Hannah O recently joined the Workamajig Marketing Team. She enjoys a healthy lifestyle, loves all things furry and is always looking to learn something new. Send her your best recipe, a picture of your dog or your secret tip for marketing success at

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