Best Practices for a Successful Project Management Software Implementation (Pt. 1): Tool Selection

By: on January 16, 2017

Buyer’s remorse: The nagging, worrying voice in the back of your mind that accompanies a sinking feeling in the pit of your stomach just as your transaction goes through.

“That was impulsive … Do you really need this? You should have shopped around more. Weren’t you supposed to be saving?!?”

As consumers, we’ve all experienced buyer’s remorse at one time or another. Maybe you return the item, and maybe you pay a restocking fee, but there’s no real harm done.

However, when you’re a small or midsize business (SMB), it’s not as simple as paying a restocking fee to get out from under a bad project management (PM) software investment.

In fact, impulse buying or getting upsold on unnecessary features often herald a failed PM software implementation—an investment of time and money that most small businesses can’t afford to waste.

That’s why we’ve created this two-part series: Drawing on Gartner research, we’re sharing several tips for selecting and rolling out a new PM system at your SMB so you have the best chance for implementation success.

Here in part one, we’re detailing tool selection, while part two focuses on facilitating user adoption.

See “Next Steps” at the end for a checklist summarizing our tool selection best practices.

Three Tips for Selecting Project Management Software

In a report titled “Best Practices for PPM Tool Selection” (this content is available to Gartner clients), principal research analyst Teresa Jones estimates that the average project and portfolio management (PPM) tool life span is less than five years.

“Uncertainty in the market and changing user needs make it impossible to expect that the same tool (or vendor) will support the business beyond two to three years.”

With so little time to turn a bad investment around, it is imperative that SMBs invest in the right tools from the start. The following software selection tips outline steps that businesses should take prior to investing to ensure the tool they choose delivers the greatest value.

#1: Follow an Outcome-Driven Approach

When considering a new PM tool, keep in mind that tool selection is relative and depends entirely on use case. A solution that worked for a team at your last company, or even a different department at your current company, may not fit with your team’s workflows or match your PPM maturity.

As such, it’s important to conduct the following team-specific evaluation each time you consider adopting a new tool:

  • Define the near-term outcome you want to achieve and/or problem you want to solve
  • Perform stakeholder analysis
  • Identify key capabilities

Define desired outcome: Defining the specific problem you are trying to solve helps decision makers home in on what the tool is being asked to deliver.

When you know what the expected results should be, you are in a better position to choose a tool that is capable of delivering those results.

This is why it’s important to be as clear as possible when defining outcomes. For example, “increase efficiency” is vague and as such would not only be hard to measure, but equally hard to translate into system capabilities.

However, the objective “reduce inactive time between lead and cycle time,” is easy to measure and translates to a specific system capability. In this example, the outcome could be achieved by tracking lead and cycle time with a report commonly used by Kanban teams called a lead and cycle time diagram.

Perform stakeholder analysis: Identify your key stakeholders, i.e., the people who will actually be using the tool. Then, focus on their requirements with the goal of creating a list of “must-have” versus “nice-to-have” capabilities that you’ll share with vendors.

Prioritizing stakeholder’s needs helps ensure that you are fitting the new tool to existing workflows, rather than retroactively trying to fit your processes around a tool’s constraints.

Identify key capabilities: Once you know your stakeholder requirements, you can narrow down your list of must-have capabilities. Focus on the capabilities that will drive the most value and help you accomplish the near-term objectives you’re working toward.

Julie Wyman, senior consultant and agile coach at Excella Consulting, advises that teams start as small and as simply as possible:

“You don’t want to end up tracking a bunch of info you don’t need simply because the field exists in the tool. Make sure that whatever tool you select is easy to use and highlights the information that people will actually use to make decisions and take action.”

Julie Wyman, senior consultant and agile coach at Excella Consulting

The following use cases demonstrate how the objectives and requirements of different teams can influence tool selection.

Examples of an Outcome-Driven Approach to PM Software Selection

Team Desired outcome Stakeholders Key capabilities
Advertising/PR Improve on-time delivery and adherence to budget Creative director, media director, project manager, web designer, copywriter Reporting, resource management and time and expense tracking
Engineering Need better project tracking, especially change orders and file version control Project engineering (PE) team, PE manager, CAD manager, customer Portfolio management, demand management and user management
Information technology (IT) Increase visibility into backlog and in-progress items IT project manager, software developer, help desk support Collaboration, agile PM tools, integration with help desk tools


#2: Vet Potential Products

Once you’ve defined your outcomes and the capabilities required to achieve your objectives, you can start to evaluate different solutions.

To effectively vet products, follow these steps:

  • Focus on a shortlist of products
  • Read user reviews
  • Demo each product

Focus on a shortlist of products: Narrowing down the hundreds of PM solutions on the market to a shortlist of those that meet your stakeholder requirements and key capabilities can be a daunting task.

At Software Advice, we offer several free services designed to assist you with this endeavor, including:

  • An online software evaluation: Answer a short questionnaire about your business and industry needs, and we’ll send you a list of five products that meet your requirements.
  • One-on-one consultation with PM software experts: Contact our advisors at (844) 686-5616 for a personalized review of your pain points and feature requirements. After the call, we’ll send you a list of products customized to your needs.
  • An interactive market guide: If you prefer to do some of the leg work yourself, use our interactive guide to review the more than 220 PM systems listed on our site. You can filter products based on price point or deployment model and see a list of leading systems based on each criteria chosen.

Read reviews: Once you have your shortlist, it’s important to read customer reviews and see how your peers have rated each system for qualities such as ease-of-use and customer support.

Real-user reviews of Smartsheet on Software Advice

Demo each product: Take advantage of product demos and free trials. Gartner analyst Jones encourages teams to use demos as a practice run, asking the vendor to run through a “day-in-the-life” scenario for each stakeholder rather than simply allowing the vendor to show off the product’s feature list.

In addition to key capabilities, it’s important to review the following with the vendor during a demo:

  • Timeline for implementation
  • Integration requirements
  • Configuration requirements
  • Data transfer services

#3: Invest in a Tool That Supports Current Processes

Finally, although it can be tempting to purchase a feature-rich system that you expect to “grow into,” you’ll get more value from a tool if it supports your current processes* and drives progress toward a near-term goal.

Excella’s Wyman says, “Teams do not always grow or evolve as anticipated, so you do not want to buy a system that overloads teams with many features that do not aid them or support their current needs.”

Then, Wyman says, if additional needs arise over the life span of the tool, teams can supplement the existing system using plug-ins or add-ons.

That way, you’re only paying for what you’re using, rather than purchasing an overly-robust system upfront and finding you don’t use half of what you paid for.

*Keep in mind: Gartner analyst Jones estimates that teams can only reasonably expect to use a tool for two to three years before changing user needs requires them to re-evaluate tool selection. As such, “current processes” should include immediate needs and any expected or known process updates within two to three years.

Next Steps: Download Checklist

For the best chance at avoiding buyer’s remorse and selecting the right PM software for your team, download our checklist summarizing the tips we discussed above:

Download Checklist

If you’d like more information about the PM tools available for SMBs, email me at I’m happy to answer any questions you might have or get you set up for a software consultation, price quote or demo.

You may also like:

Best Practices For A Successful Project Management Software Implementation (Pt. 2): User Adoption

What Executives and Managers Want in Project Management Software

Top Capabilities SMBs Should Look for in a New PM System

Compare Project Management Software