10 Questions to Ask Yourself When Looking for Project Management Software

August 22nd, 2019

If anyone were to look at my desk, they would see a maze of sticky notes with near-illegible chicken scratch I use to manage my short-term project goals. While my sticky-note methodology is near and dear to my heart, it also falls tragically short when it comes to team-based projects or long-term planning and coordination. If you’ve come across this article, you’ve likely felt this shortcoming yourself, and have some experience with the reality that digital project management is a necessary part of making the most out of employees’ limited time and resources.

In any case, it can often pay dividends to invest in a project management software to address inefficiencies or costs, or to supplement an existing management style. Thankfully, there are myriad options that have emerged in the market to service these needs. Project management (PM) software offers a centralized platform and set of tools for developing, executing, completing, and evaluating definite projects. These tools can add value across industries and within any level of business or organization, but the variety of available options can be overwhelming. 

If you are starting to explore what project management software would be best for your situation, it is crucial to understand exactly what you need from the product in the first place. We have developed 39 key questions that can help buyers build a personalized set of requirements for their future project management software as part of our new Project Management Software Buyer’s Toolkit. If you’re unsure how to search for or choose between software, these questions will help clarify what to look for in a product and whether a given product is able to deliver on those requirements or not. As a sneak peek, these 10 questions can provide a strong starting point for exploring the marketplace. 

1. What types of projects need to be managed?

This is the most broad question, but also the most foundational for understanding what to look for in a product. For instance, some software is designed specifically for certain industries, such as construction. If there isn’t a product tailored for your industry, consider the department you want to deploy the software in, or what level of the organization you’re working at.

Will your projects be financial or IT-based? Client-facing or internal? Understanding what types of projects your team will use the project management software for will set a solid baseline for your software search. 

2. What’s the scope?

How “big” are the projects you’ll manage? Is this software for personal use, or should it support an entire team, multiple teams, or multiple companies? Explore software options with an eye towards the scope of the product, based on both vendor claims and user feedback. 

For instance, the scope of a PM software to replace my sticky-note process is far smaller than a software that can manage the project workflow of an entire Engineering team. If you scope your needs too high, you could end up paying for more functionality and capacity than needed. Also, keep in mind how scalable your project management software should be, with an eye toward future growth or development.

3. Who will the end-users be?

Broadly speaking, you should consider how many people will be using the software and what their role is. Knowing this can help ballpark the budget that should be allocated. 

It can also be advantageous to consider the demographics of your user base. Will users be managers, team members, contractors, or some combination thereof? For example, if your company or team is organized in a rigid, top-down hierarchy, having administrative data and project controls could be critical. If not, administrative controls in your project management software may not be necessary. 

Finally, consider the software that you already use. For example, if your user base uses Gmail, find a PM software that plays well with Gmail! Take stock of all the tools your team uses, like Slack, Jive, Confluence, and more. If some products are already ubiquitous, it’s efficient to find a PM software that can integrate with those collaboration tools. 

4. What project management methodology will be used?

The project management methodology you plan to use will heavily influence how effective products will be. For instance, do you usually use “waterfall” or “agile” workflows, or some other framework? Whatever you have in place, the tool you choose should work effectively with your processes. A good way to evaluate this is to examine peer-to-peer reviews for others employing the same methodologies as your team. Understanding their experiences can give you a real picture of how well a software will work for your team!  

Another way of approaching this question is determining how best to visualize projects. Are project contributors already using calendars, Kanban boards, flowcharts, tasklists, Gantt charts, or some combination thereof? How effective are these methods? Explore products that offer your preferred functionality. However, if you are looking for a change, onboarding a new PM software may present a natural opportunity to modernize your existing workflow practices. 

5. Do projects need to be collaboration-ready with internal and external stakeholders?

This question is highly dependent on the kind of projects that will be managed. Will project managers need to pass data from the PM platform to higher management or external stakeholders? What user access permissions does the software offer? Can external stakeholders be given temporary access? Some PM software are optimized to allow different types of collaboration with external stakeholders, such as customers, vendors, or partners. Determining what sort of user-access permissions and controls you’ll need can help  narrow down the list of potentially viable products.

If user access management is an important factor for your situation, there are some products that stand out. TrustRadius reviewers have praised Workfront, Smartsheet, Microsoft Project, Trello, and Basecamp for their user management and collaboration capabilities. Consider what level of collaboration and external accessibility is needed for you and your team to find the feature set that best fits you.

6. Will you need project-based time tracking capabilities?

Time spent on a project can be an important factor, if employees are on an hourly compensation model (contractors, billable hours, etc.), or if efficiency and time management is a concern. Time tracking capacities are fairly common across the larger PM software offerings, but it is not a universal feature. 

If time management is of particular importance, some PM software may fulfill that capacity more effectively than others. For instance, OpenAir PSA designs time tracking as a core part of the software. Some market leaders, such as Workfront and Zoho Projects, are also noted by TrustRadius reviewers for their robust time tracking capabilities.

7. What project info needs to be reported?

Project evaluation is a crucial part of the management cycle and has even become significant mid-project cycle with the growth of Agile workflows. In fact, your project management software can also be your right-hand man in project reporting. Buyers should consider what costs are associated with the project, or what other efficiency statistics will be used to evaluate a given project. 

Many PM software products have reporting capacity, but the specific metrics that are measured and analyzed can vary dramatically, as can the robustness of the reports that are generated within the platform from the data. When determining what reporting features matter to you, think about what metrics you want to track, such as the average time spent on a project or who is assigned to a project or task. If your goal is to shift project reporting onto the PM platform, the strength of each software’s reporting tool can be a significant differentiator. 

8. Do you want an online application, a desktop/on-premises app, or both?

When considering what form of software to deploy, buyers should factor in the broader system that your company already uses. Is data stored on local servers or the cloud, or a hybrid system? Is it important that people be able to work and access the PM software remotely, or is everyone centralized to one workspace?

This consideration is a limiting factor mostly if a buyer is actively looking for a desktop application. Most products on the market are natively cloud-based, but some of the larger players in the space offer on-premises options as well. If you’re not sure how to address this, you may need to bring in your IT team into the evaluation process.

9. What will onboarding look like?

Change almost always entails a transition period, and PM software is no exception. PM software users have described the implementation process as heavily influencing the long-term effectiveness of the software in their teams. Learning curves get steeper the more complex and customizable the software is. Buyers should develop an idea of how intensive an onboarding process they want, particularly if they plan on doing the onboarding personally. Would you like implementation and training support as part of your project management software launch, or will a person on your team be in charge of leading others? Will there be training sessions or instructional videos, or will users be expected to self-teach? 

This ties back into knowing your end users. If they are tech-savvy and have used PM software before, formal training sessions may not be necessary. However, if your users have not used PM tools before, it may be worth exploring which products have training services or tools available either for someone internally to take charge of implementation or to utilize developer tools towards that end. 

10. What will it cost?

Are you surprised that this is the last question on the list? Its placement is quite intentional. While cost is undoubtedly important, knowing the answers to the questions above  is a prerequisite to knowing the comparative or absolute cost of PM software. After all, the most expensive software purchase happens when you find that the tool you’ve already bought doesn’t meet your needs!

When exploring cost, the most common factors that affect price are scope and functionality. The changes in price can be quite dramatic, even between different tiers of the same product. It may be worth evaluating different pricing tiers of a product as distinct products themselves for comparison purposes. Once your requirements for PM software are established, you will be much better equipped to make the right decision, while minimizing unnecessary bundling and costs. 

Asking the right questions leads to Project Management success

Making the right project management software purchase is important! Making the wrong choice can lead you back to the same frustrating position from which you started six months down the road. Fortunately, answering these questions can provide a solid starting point for knowing what requirements are most important to look for in PM software. But there’s more where that came from!

If you want more of the best questions to help you  differentiate between software, the Project Management Buyer’s Toolkit provides even more questions you need to see. Plus, it includes a whole suite of interactive tools to help you evaluate, compare, and decide upon the best PM software for you.