The Top Questions You Should Ask When Looking for a Project Management Software

Points Your Team Should Consider

As a PMP with over 20 years of experience, I have created and managed numerous portfolio, program and project management organizations. I’ve helped teams of various sizes and functions choose and implement project management solutions that work best for them. Along the way, I’ve noticed some common factors all project teams should evaluate while searching for a project management solution. If you are considering purchasing a new project management software, here are some of the top questions your team should consider:

How mature is our PMO? The first thing you and your team should think about is how mature your project management office (PMO) is. Ask yourselves:
  • What defines a project for us? Depending on what your function is, a project could mean anything from product development, to closing a sales deal, providing patient care, managing legal briefs, etc. Before you even start your search, you should be very clear about what and how many types of projects you need to manage in your new software.
  • What are our processes? One of the most important things to remember is that the project management software you choose should fit the processes you already have in place. If you instead try to fit your processes to the software’s constraints, the odds of a successful implementation will be against you.

How much sophistication do we need? Once you’ve evaluated how you define a project and how mature your processes are, think about the level of sophistication you’ll need from a project management software. If your PMO is sophisticated, you’ll want the bells and whistles of Gantt charts, resource management, workflows and more. But often times project teams realize that all they really need is a basic task list and calendar tool.

Alternatively, you may find that today you need the basics, but your goal is to advance your project management maturity--keep that in mind as you embark on your search. Do you really want to implement a basic tool now, then go through the approvals and change management steps that come with realizing you need a more advanced tool later? Consider looking at project management solutions that you can easily grow into.

How many methodologies do we use? Most project management solutions will support a standard waterfall methodology. If that’s all you need, you’ll have a plethora of solutions to choose from. However, if you plan to support various teams that use different methodologies, or if certain projects rely on multiple methodologies throughout their lifecycle, this is a good way to narrow down your search.

What customizations will we need? Depending on how you’ve defined what projects will live in this system and how many teams will be using it, you may find that out-of-the-box solutions that are meant to foster easy setup are too inflexible for your needs. Think about the custom fields you might need. Do you need to report on those fields? What other types of reports do you want to access? Do you need company branding for the tool’s interface?

How will we make it easy for team members to access and use? The easier you make using your new tool on your team, the easier it will be for your project managers to get the information and updates they need. Consider the following:
  • Do we want single sign on (SSO)? Most people have more usernames and passwords than they know what to do with. Adding a new set of login credentials to remember as well as another authentication step in order to send a project update isn’t an ideal user experience. SSO allows users to login to a network of multiple systems using just one username and password. Finding a project management software that supports SSO is a great way to provide the convenience your team will want when asked to use a new solution.
  • What integrations do we need? As useful as project management software is to project managers, the reality is that the rest of the team would probably rather stick to the tools that work best for their own job and working style. Ask yourself what information you’ll need to input into your new project management solution. Do you need updates from the sales team? The engineering team? Customer support or accounting? You see what I’m getting at here. By integrating with other systems such as Salesforce, Visual Studio, Zendesk, Quickbooks and others, teams can do the work in the solutions they prefer, while project managers still get the data and updates they need to track projects.
  • What do our executives need? You’ll want to show your exec team the value your new project management software is bringing to the company. But let’s face it, the probability of your execs logging in to your shiny new project management system and digging around for updates is pretty small. What expectations do your execs have? Do they want access to the system at all? If so, they’ll likely want a dashboard view to get the most pertinent information right away. If not, they may want portfolio reports sent straight to their inbox for easy access. Keep this in mind as you explore the functions and features of your prospective project management solutions.

Will Our Data Be Secure and Easily Transferable? Data security is of utmost importance no matter what your business function. You want to be sure the project management software you choose prioritizes the protection of your data, and will make it easy and safe to migrate that data should you ever need to do so. Here are a few things to consider when evaluating a project management software provider’s data security:
  • Where will our data be stored?
  • Who will have access to our data?
  • How are third party penetration & application vulnerability scans performed and how often?
  • Will our data be backed up and where?
  • What is the process for migrating our data should we need to?

What kind of reliability are we looking for? The level of support and reliability you receive from a provider is what makes a good software solution a great one. Define your expectations ahead of time so that you can determine whether your prospective vendors fit the bill, rather than letting the provider set the expectations for support. Here are a few things to think about:
  • What type of support do we expect? Are you okay with online-only forums and FAQs or do you want to be able to talk directly to a support representative?
  • Will we need implementation services? Are you comfortable implementing the software on your own, or would you prefer a specialist come onsite to facilitate a smooth transition?
  • What influence will we have on the product? Many smaller providers can be a true asset to your team because they are more willing and able to add features directly requested by customers. It’s harder for larger companies to be this nimble, so if you’re hoping to gain more of a partner who will actively work within your needs, keep this in mind.
  • If we choose a SaaS system, what is the minimum uptime we require? Nothing is worse than trying to access a system at a critical time and finding out they are experiencing downtime. Uptime is a crucial factor to consider. Uptime is usually measured in ‘nines’ and can vary greatly. For instance, five-nines or 99.999% availability means 5 minutes, 15 seconds or less of downtime in a year, while four nines or 99.99% availability jumps to 52 minutes, 36 seconds downtime per year. Drop that number down to three nines and you’re looking at 8 hours, 46 minutes of downtime per year. Make sure you know how much downtime your team is willing to tolerate.

  • I hope these recommended considerations come in handy for your project management software search. At Project Insight, we take a consultative approach with teams looking for a new solution. If you’d like to talk to a specialist about what your needs are and where you should begin looking, we welcome the opportunity to chat with you. Contact us to learn more.
Online 7/24/2018
Melvin Randle
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