12 Questions To Ask HR Software Vendors: What Large Businesses Need To Know 

Large organisations operate with tight budgets, rising complexity and growing expectations from CEOs who continue to prioritise growth, technology and workforce strategy. Gartner’s 2025 CHRO Budget Benchmarks show that HR receives one of the lowest investment levels compared to other corporate functions, representing a median of 0.80 percent of revenue, yet HR leaders are still expected to support productivity, talent needs and technology‑driven transformation at scale. 

Asking the right questions when evaluating HR software helps teams make informed investment choices at a time when budgets are tightening and every spend must clearly link to strategic impact. 

Many CHROs lack the foundational data needed to guide optimisation decisions, so a structured questioning approach ensures that vendors can demonstrate how their technology supports scalability, efficiency and enterprise level outcomes. It also helps HR functions align technology investments with business priorities such as automation, workforce productivity and global consistency. 

Good preparation makes vendor conversations more productive. It also helps surface the most useful questions to ask before you begin shortlisting suppliers. 

Recent Gartner data shows that many HR functions lack the baseline staffing and investment insights needed to guide technology decisions.

This makes internal clarity even more important because it ensures any new system directly supports priority areas such as productivity, efficiency and technology enablement. 

What internal questions should you answer before contacting software vendors? 

Clarify HR and business objectives 

Start by identifying what you need the new system to improve. This could include reporting, employee experience, line manager self‑service, compliance or global standardisation. Define measurable outcomes so the team knows what success looks like, for example shorter time‑to‑hire, lower admin load or stronger engagement scores. 

Understand your current HR technology landscape 

List the systems already in use, such as HR, payroll, finance, ATS and LMS. Map where data lives today and note common pain points. Repeated data entry, inconsistent records, limited analytics and reliance on manual approvals are typical issues that shape the questions you will need to ask. 

Define scope, timeline and constraints 

Be clear which regions, legal entities and business units fall into the first phase. Capture any regulatory requirements that must be met, for example data residency needs or sector rules that influence configuration. 

Identify key stakeholders and decision makers 

Because HR functions typically deploy one HR FTE per 58 employees, according to Gartner, teams need to be deliberate about how they allocate time and resources to selection projects. Bringing the right groups in early avoids rework and ensures that the eventual vendor questions cover security, integration, performance, compliance and financial considerations. 

How should you document your requirements and use them to shape vendor questions? 

Build a prioritised requirements list 

Start by separating must‑haves from nice‑to‑haves. Record both functional needs, such as onboarding workflows or flexible benefits, and non‑functional needs like security, performance and availability. This gives you a clear baseline for judging vendor responses. Philippa Barnes, Director at ReThink HR covers this in our webinar, ‘Make your HR Tech Investment Count: Master Implementation Success’: 

“You’re not wanting to recreate your existing processes in the new system. You need to ask why each step exists and whether it’s still relevant.” 

Convert requirements into questions to ask a software vendor 

Each requirement should guide the questions you take into conversations. For example, a high‑level need like multi‑country HR becomes a set of specific prompts about supported countries, local workflows, compliance rules and language options. Scenario questions help here. Ask vendors how their system would handle a particular process in your environment, so you see how the product behaves in real conditions. 

Use our Vendor Evaluation Checklist to structure your preparation and capture the questions your teams will need to ask.

Feed these questions into any RFI or RFP documents used by your organisation. A consistent structure helps teams compare vendors side by side and ensures that early conversations match the formal assessment criteria later in the process. 

Use our Vendor Evaluation Checklist to structure your preparation and capture the questions your teams will need to ask.

It’s important to consider the business fit and scalability of your organisation and the vendor. If the vendor is stable, respected, and well-reviewed, they’ll likely be capable of handling your large organisation and support your further growth. 

How well does the HR software support your people strategy and business goals? 

Look for signs that the vendor understands the realities of operating a large organisation. This includes familiarity with complex structures, governance requirements and global operations. The discussion should focus on measurable outcomes the software can support, not just features. 

Is the HR software scalable for large and global workforces? 

Ensure the system can handle increases in headcount, entities and regions without performance issues. Pay attention to how the platform manages complex organisational models, multi country operations and multi-language needs. 

How stable and future‑proof is the vendor? 

Assess the vendor’s long term product direction, release cycle and financial position. Understanding ownership stability, customer involvement in roadmap decisions and their approach to innovation helps you judge whether the software will continue to evolve in line with enterprise needs. 

For organisations considering how to scale their HR technology over time, our Moving Up the HR Tech Stack Guide provides a useful overview of what the next stage of maturity looks like. 

IT and HR teams need confidence that the software can integrate smoothly with existing systems and meets enterprise standards for architecture, security and compliance. 

What integration and architecture questions should you ask a software vendor? 

Determine how well the platform connects with core systems such as payroll, finance and identity providers. Clarify API availability, data flow design, hosting approach and any architectural considerations your technical teams need to review in detail. As Oli Quayle, AI Evangelist at Access, explains, many organisations underestimate the hidden cost of poorly integrated HR systems: 

“I’m spending too much time on the tech, not enough time with my people. Frankenstack was a great intention - it was the right thing to do to get the depth - but you’re not leveraging that depth if you’re spending all your time servicing the integration between those two points. The promise didn’t quite live up. You think, ‘I’ll take product A and product B and integrate them and of course this will flow from here to here.’ But what’s happening now is customers are saying, ‘I’m spending too much time on the tech, not enough time with my people.” 

Mastering the Employee Lifecycle, part of our Do the Best Work of Your Life series.

How does the vendor handle security, data protection and compliance? 

Check that the vendor follows recognised security standards, completes regular audits and provides clear controls for privacy and access management. You should also understand their incident response process and how they support compliance with regulations such as UK GDPR. 

What are the key performance, availability and resilience questions to ask? 

Review the vendor’s service levels, performance at scale and approach to monitoring. Strong business continuity and disaster recovery plans are essential for large organisations that rely on high availability. Our ‘Make your HR Tech Investment Count: Master Implementation Success’ webinar reinforces how important vendor experience is. As Philippa explained: 

“Different vendors have different approaches to implementation. You need to understand how much time you will get with consultants and what support is included.” 

These areas strongly influence whether the project succeeds.

Understanding the vendor's experience and expectations helps you prepare your teams effectively.

How experienced is the vendor in large‑scale HR implementations? 

Look for evidence of successful delivery for organisations with similar complexity. This includes understanding their partner model, project team structure and implementation methodology. 

experience and expectations helps you prepare your teams effectively. 

What is the realistic timeline, effort and resource requirement? 

Clarify the expected delivery stages, where the most effort is required and what support you need to provide internally. This includes data migration, testing and the roles required from HR, IT and change teams. Philippa Barnes as Director of ReThink HR has significant experiences with implementation timelines and her advice is as follows: 

“Realistically you are looking at six months, even without payroll. With payroll, you need time for parallel runs to ensure accuracy.” 

Make your HR Tech Investment Count: Master Implementation Success 

How will the vendor support change management and user adoption? 

Review the training, enablement materials and communication support available. Preparation can be as important as the support you provide during the go-live: 

“People don’t magically know how to log in or use the system. You need to telegraph change early, build training resources, and plan communications before go‑live.” 

Philippa Barnes, ‘Make your HR Tech Investment Count: Master Implementation Success’ 

Monitoring user adoption and providing post go live reinforcement should form part of the vendor’s approach. 

Clear commercial terms help large organisations plan long term costs and ensure they receive appropriate protections. 

How is the pricing structured for large organisations? 

Understand how the pricing model works for enterprise scale customers and whether costs change as your organisation grows. Review what is included in the subscription and which services generate additional charges. 

What contractual protections and service commitments should you look for? 

Pay attention to data protection clauses, liability limits and terms related to service levels. Flexibility for organisational changes such as mergers or acquisitions is also important. As Philippa says: “The client and vendor both need clarity on responsibilities. Neither can deliver the project in isolation.” 

How can you ensure ongoing value and partnership? 

Look at the vendor’s account management model, the governance they provide and how they support continuous improvement. Consider what renewal planning and exit support look like to ensure long term value. 

A simple scoring framework helps. Group your questions into themes such as strategic fit, technical fit, implementation quality, commercial terms and support. Weight each theme according to your priorities so the areas that matter most carry the most influence. When reviewing answers, separate information from softer impressions. Certifications, SLAs and architectural details can be scored objectively. Cultural fit, responsiveness and rapport should be noted separately so they do not dominate the assessment. Involving different teams ensures each part of the organisation evaluates the areas they know best, which creates a more balanced view of each vendor. 

Verification is essential. Speaking to customers of a similar size helps confirm whether the vendor’s claims hold up in real delivery. These conversations often highlight what worked well and what required more effort during implementation. A small pilot or proof of concept can also help test critical processes in your own environment, especially where integrations or data handling are involved. Finally, make sure that key promises made during discussions appear in the contract or service documentation. This reduces risk by ensuring there is no gap between what was said and what is formally committed. 

Large organisations make better software decisions when they start with clear objectives and a structured set of questions. The most successful HR technology projects are usually the ones where teams prepare thoroughly and explore strategy, technical fit, implementation plans and commercial terms with equal attention. 

The questions in this guide give you a framework for understanding how each vendor works and how well they can support your organisation. Adapt the list to suit your context and use it throughout the buying process, including RFIs, RFPs, demos and reference calls. The goal is not to catch vendors out. It is to find a partner who can support your organisation for the long term and help you deliver the HR outcomes you need. 

To continue your evaluation, you can: 

1. Download our HR software vendor question checklist 
2. Check out our guide to choosing HR software