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5 Questions To Ask During an HR Software Evaluation

Oct 20, 2022| Reading time: 12min

BY Brett Ungashick

Founder of OutSail

As a software buyer, you want to ensure that the HR tools you’re evaluating will be a good fit for your organization. Coming prepared to your vendor meetings with smart, challenging questions is a great way to ensure you properly vet the various HR tools on your shortlist. 

Have you ever felt pressure when tasked with purchasing a new HR software platform?

If so, you’re not alone. That’s because many leaders want to find the right technology solutions but don’t have enough time to thoroughly prepare for the software-buying process.

And without proper preparation, it can be easy to go into software evaluations passively, allowing oneself to be “sold to” rather than being the one driving the software evaluations.

You therefore need to ask the right questions when it comes to buying software to complete your HR tech stack. Below are five challenging and insightful questions that you can ask any vendor during an HR software evaluation process to help reveal the differences between the various platforms in consideration. Keep in mind that these questions are complementary to the functional questions you should also have about any system’s capabilities.

Make sure you have the right technology in place to support your organization and your people. Read The Ultimate HR Tech Buyer’s Guide to make informed decisions when it comes to choosing the right software.

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1. What are the three reasons that customers pick your platform over your competitors?

Why Ask This Question

Another result of the fast-paced software development world we live in is that it has never been easier for companies to build new features.

The good news is that many companies have similar features and functionalities (if not live now, then in the works). The bad news is that…many companies have similar features and functionalities. The similarities therefore make it challenging to distinguish one HR software platform from another. 

Instead, what you really want to know is what problems the HR tools solve for customers and what unique value they bring to the market.

By asking these questions, you’ll understand the different key outcomes that each vendor aims to achieve for their customers. You might find that there is a perfectly great platform with many of the features you need, but the technology is focused on solving a different problem than the one you want to solve.

On the same note, the answer to this question may help you understand the company’s roadmap. While you shouldn’t choose software based on future features, knowing what’s to come can help you decide if their platform is aligned with your needs.

When to Ask This Question

During your initial call with a vendor when they are asking you discovery questions and starting to introduce the company as a whole.

2. How has your product evolved and added new functionality – internal development, acquisitions, white-labeling, or some combination of the three?

Why Ask This Question

One aspect that is nearly impossible to understand about HR software platforms during a sixty minute demo is how the back-end of the system works.

During your software evaluations, any vendor can offer you a polished presentation that makes everything look seamless, automated, and borderline magical.

But an experienced HR software buyer knows that once you start implementation, there are oftentimes bugs, limitations, and disruptions that weren’t obvious before.

One of the biggest differentiators between great software platforms and mediocre software platforms is a truly elegant product architecture. This is a fancy way of saying that you want to find an HR software platform where all of the various capabilities work in harmony, rather than in silos.

Luckily, you don’t need to know how to code or need your IT team to look at the system’s databases (which would never be allowed) to understand a system’s product architecture.

Instead, just ask the above question. If you hear that some growth was via acquisition and white labeling, then start digging into how those third parties were brought into the core system. If they were integrated thoughtfully, you shouldn’t have a problem.

When to Ask This Question

During the initial demonstration is a great time to ask this question. If you find that parts of the system weren’t natively built together, then you can ask the salesperson to show those separate parts of the system interacting together.

3. If we wanted to integrate your platform with [Vendor X], what integration methodology would be used, who would be responsible for the buildout, and what costs would be associated?

Why Ask This Question

The word integration has become a huge buzzword in the HR software space.

All buyers want their new platform to be “integrated,” but very few software buyers know what to ask to better understand integrations.

On software vendor websites and in sales pitches, you’ll often hear “we integrate with [Vendor X]”, but this can often be a gross oversimplification.

Most buyers take this to mean that: 

  • This integration will be no-cost.
  • This integration will not require any set-up work since it already exists. 
  • This integration will be bi-directional. 
  • This integration will automatically pull/send the exact data fields you want.

Unfortunately, having everything listed above isn’t a realistic expectation. It’s therefore critical to understand what’s involved when it comes to integrating with your HR tech stack so you can plan accordingly. 

By digging into the actual set-up process – as well as the time, resources, and costs involved in getting an integration live – you will be able to differentiate vendors selling the idea of an integration with those who actually have done the work to bring different systems together.

When to Ask This Question

During the initial demonstration or a follow up call with your IT team on the phone.

4. Can we speak to references about your support services and product experience?

Why Ask This Question

Most companies are leaving their current providers, in part, due to bad customer service. It’s therefore crucial to not only learn the ins and outs of the product you’re evaluating, but also understand the company’s customer success model. 

However, no salesperson is going to tell you their customer support is lacking. So how do you get a real sense of what to expect from a customer support standpoint?

You should ask about their implementation methodology, read the company’s service agreements, and search for online software reviews. But the best way to understand what to expect is to talk to real users of the platform.

Keep in mind that most vendors don’t make references available until the latest stages of the evaluation process to protect their customers from a constant barrage of reference requests.

But once you are honing in on the right platform, it is always a great idea to speak to a customer or two about their experience.

When to Ask This Question

After you’ve selected a vendor-of-choice but before you’ve signed a contract.

5. Can you provide security and compliance documentation, specifically around SOC II, HITRUST, and GDPR?

Why Ask This Question

Every company should focus on cybersecurity as they evaluate different HR software platforms. 

Just last year, a massive data breach at one HR software company led to the withholding of paychecks for thousands of employees. This scenario is obviously something you will want to avoid, and hopefully something you can by asking the right security questions.

Thankfully, there are some industry standard security and compliance regulations, including SOC II, HITRUST, and GDPR.

A software company that is truly committed to protecting their customers will be certified by some of these organizations and will be happy to share that documentation with you.

When to Ask This Question

After you’ve selected a vendor-of-choice but before you’ve signed a contract.


About the Author: Brett Ungashick is the founder of Outsail, a Denver-based company that provides free services to help HR teams research, evaluate and select new technologies. Brett started his career by selling software to HR teams at LinkedIn, before recognizing a growing need from software buyers for support throughout their buying processes. OutSail was founded in 2018 and has helped over 600 companies with new HR software purchases including companies like SalesLoft, DoorDash and the Boys & Girls Club of America.

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