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5 Questions to Ask a Leave Management Software Vendor

Author: Eugenija Steponkute
Published: 07/07/2025

This article presents a list of questions to ask a vendor when considering leave management software. Since most will try dazzling you into committing to their solution, it’s important to ask the right questions to determine if they’re the right fit.

It’s no secret that the SaaS market is oversaturated and, no matter how unique and specific your needs are, there is a tool that’s a perfect fit. However, the problem is that vendors are keen to sell, and sometimes, closing the deal is prioritised over your best interest. But it’s easy to get the answers you need if you ask the right questions. 

To avoid falling victim to salespeople glossing over, you, first of all, need to know the areas of interest. Secondly, you need to define the extent of specific features you need to reach your goals. From there, you just need to ask the questions we’ve outlined in this article and compare the answers to what you have written down as your requirements. 

5 Features of a Leave Management Software to Influence Your Decision

There are five features you need to understand the functionality of when choosing a leave management software. How they perform and to what extent should be aligned with your goals and existing processes. These are areas to inquire about:

  1. Onboarding and support

  2. Usability 

  3. Compliance

  4. Reporting

  5. Integrations

Below, we will share and discuss the right questions to asks to learn more about each of these areas.

1. What Does Onboarding and Ongoing Support Look Like?

A good start can determine your success moving forward. Not to mention, it’s always best to know what to expect. The onboarding process should be clearly defined, as it could be a major decision-making criterion. For example, if your team isn’t tech-savvy and the vendor only offers a hands-off onboarding, it might not be the best fit for you.

Understanding the level of ongoing support is equally important, especially because things go wrong sometimes. Similarly to onboarding, your team’s overall technical knowledge plays a major role in determining how much support will be needed. Keep in mind that some vendors charge extra for support, while others are accessible 24/7. Similarly to choosing the features, you need to go support-level shopping when making a decision. 

2. How Does the Software Support Employee Self-Service and Manager Dashboards?

The next question on the list when choosing a leave management software is its usability. Specifically, how it looks to different parties that will be using it. The very purpose of getting the solution is to make the process of booking, approving, and tracking the leave centralised and simplified; hence, you need to understand how it will look in practice. 

On the employee side, the interface should be simple and easy to navigate, requiring only a few clicks to send their request. As for the approvers, some vendors go an extra mile where the ruling could be made from the email inbox, without logging into the system. What both parties should have in common, however, is a centralised calendar showing the entire team’s availability. Both requests and approvals should be made in accordance with it. 

3. How Does Your System Handle Local and Global Leave Compliance?

If you’re working with staff from all over the globe, be they from different branches or contractors, ensuring the system can cater to compliance on all fronts is vital. And some tools are not equipped for that, hence warranting the question. 

A versatile system will be able to accommodate individual holiday needs based on the location through its customisation capabilities. For example, a customisable leave management software will let you block out certain days as public holidays. And, as an extra layer, you will get to choose if this is applicable for the whole company or selected users only. 

4. What Analytics and Reporting Capabilities Are Included?

In SaaS technology, reporting is often among the key selling points. However, because it's being marketed as such, it’s often forgotten that it’s a feature that’s non-debatably part of every solution. The true question lies within its capabilities. Namely, the extent of customisation, how granular the data is, the presentation, and many more. While every leave management software will come with a reporting module, not all of them are useful.

Ideally, you want to focus on presentation, customisation, and automation. A combination of these three will help you create custom reports that are easily read and analysed. What’s more, instead of having to generate them manually, they will be created and set to you automatically at the chosen time. If having a demo, ask the vendor to show how the reports are generated and how they can be adjusted to your business. 

5. Can the Platform Integrate with Our Existing HR or Payroll Systems?

If you’re looking for leave management software, you certainly have other solutions your company is already using. Since SaaS technology is stackable, it is in your best interest to adopt a solution that fits right into your existing setup. 

For a holiday management system specifically, look for the integrations with your HR or payroll tools. Most companies have their integration partners listed, but sometimes they will only focus on the biggest vendors, leaving more niche ones behind. Alternatively, some companies are willing to work with you and create custom ATPs.  

Summary

Although the myriad options available guarantee that there’s a perfect leave management software for everyone, finding it isn’t as easy as some may think. Given the priority of most vendors is closing the deal, they will often gloss over things, and you may find yourself with a piece of software that isn’t 100% fit for your needs. 

There are five key areas you need to inquire about to make sure the solution is perfect for you: onboarding and support, usability, compliance, reporting and integrations. Asking the right questions will leave the vendor no choice but to answer them thoroughly, ideally demonstrating the functionality too, which should conclude your decision. 

Are you ready to talk to a vendor that’s 100% transparent? Book a demo with us - we are happy to answer all your questions.

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