35 questions, written to be read out loud in the meeting. Each one asks for the thing rather than the claim, because every vendor says yes to "do you support that" and almost none of them can show you.
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Human Resources Assistants, Except Payroll and Timekeeping, 19 rated tasks in the exposure report. 13 of them need software built first, and that is what a tool in this category has to earn its price on. The 2 in the first band are already reachable with a chat window you have.
Two thirds of this job needs software built first, and it is the most concentrated single opportunity in the People profession. Ask whether the tool actually moves the documentation, or whether it is a checklist that reminds a person to move it.
A salesperson cannot show you real candidates, cannot post to your job boards, and cannot open another customer's account. Asking anyway wastes the meeting and tells them you have not bought one of these before. So every question below says where it belongs.
Their sandbox and their invented people. Everything here is something a salesperson can do live in forty minutes without touching a real record.
9 questionsAsk for a sandbox and a fortnight. Use made-up employees and CVs with the names taken off, so nothing real is involved. Whether they hand one over without a sales process is worth knowing on its own.
4 questionsAsk for two customers your size, and ask each for a screen share rather than a phone call. Real volume, real reporting and real mess only exist here, and almost nobody asks.
6 questionsNot a conversation and not a slide. Ask for the document, and get anything you are relying on into the contract rather than into the product.
16 questionsTheir sandbox and their invented people. Everything here is something a salesperson can do live in forty minutes without touching a real record.
Two thirds of the work in this job needs software built first, and most of it is moving documents. Start with the person it is being done to, using their demo starter.
Show me everything a new starter sees between signing and day one, on a phone.
The gap between offer accepted and first day is when people change their minds. Count the separate logins, and look for anything that explains what happens next.
Worry ifA portal that opens on day one and nothing before it.
Send a contract for signature to one of your demo users, and countersign it.
E-signature is either built in, an add-on, or a separate product you are about to discover you need. Find out which today.
Day one. IT needs an account, payroll needs a bank record and the manager needs a plan. Show me all three triggered from one place.
Onboarding is the largest single opportunity in the People backlog by number of people affected, and it fails at the handoffs rather than inside any one system.
Your demo starter has not returned three documents a week before they start. What happens without anybody noticing?
Chasing paperwork is the job. A system that only shows a red status has moved the chasing rather than removed it.
How much of this is you moving the document, and how much is you reminding a person to move it?
A checklist that chases a human has not done the work worth paying for. Ask which steps complete without anybody touching them.
Worry ifA workflow that is entirely notifications.
Show me the full audit trail for that starter, as you would hand it to an inspection.
The trail is the product in this category. Look at what is timestamped, what is missing, and whether anything can be edited after the fact.
A start date moves back three weeks. Show me what happens to everything already scheduled.
Start dates move constantly and the reschedule is where these systems either save the day or generate forty wrong notifications.
Ask these at the end, when the demo is over and the room has relaxed. They are worth more than the previous hour.
Which of the things you showed me today are live for every customer, and which are on the roadmap?
The most common complaint from buyers in this market is feeling misled afterwards, with promised features never arriving. Ask in the room, write the answer down, and put anything you are depending on into the contract with a date against it.
Worry ifAnything demonstrated in an environment no customer is on yet.
What are the three things your customers complain about most?
A good salesperson answers honestly, because they know you will find out in month two. "Nothing really" means either they do not talk to their customers or they will not tell you.
Worry ifA strength dressed up as a weakness.
Ask for a sandbox and a fortnight. Use made-up employees and CVs with the names taken off, so nothing real is involved. Whether they hand one over without a sales process is worth knowing on its own.
Build the onboarding for one of our real roles, ourselves, and run a made-up person through it as the starter.
Doing it as the new starter, on your own phone, is the only way to see what you are actually sending people. Most buyers never look at it from that side until somebody complains.
Add a task that goes to a team outside HR, and see what they receive.
The handoffs to IT, facilities and payroll are where onboarding fails. What lands in their inbox, and whether they need a login, decides whether the process holds.
Worry ifA task that requires the other team to have a paid seat.
Can we have a sandbox for two weeks with our own test data, without a sales process attached?
Everything you learn in a demo is about their product being used the way they use it. A fortnight with your own made-up data tells you whether your team can use it. A vendor confident in the product hands one over.
Worry ifA trial only available after a commercial conversation, or a guided tour rather than an account.
Set up one thing we would need on day one, ourselves, while you watch.
Pick something ordinary: a workflow step, an approval, a template. If it needs the vendor, then every change for the next three years needs the vendor, and nobody put that in the quote.
Worry ifConfiguration that turns out to be a professional services ticket.
Ask for two customers your size, and ask each for a screen share rather than a phone call. Real volume, real reporting and real mess only exist here, and almost nobody asks.
How often does a start date slip because of this process, and where does it usually stick?
Screening delays and missing documents are the usual answers, and only somebody running it at volume knows which.
Did it become your employee record, or a second copy that drifted from your HRIS?
A second copy of everybody, diverging from the main record, is a problem you are still fixing two years later. A customer a year in already knows which happened.
What did you have to keep doing outside the system?
There is always something, and it is usually the thing the demo covered fastest.
Ask the vendor for two customers your size, then ask each for a screen share. These four are for that call, with the vendor not on the line.
How long did implementation actually take, against what you were told?
The most useful number in the whole process, and the vendor will quote you their fastest. A customer will tell you what it cost in their own team's time, which never appears in any quote.
What did you assume it did that it turned out not to do?
Everybody has one. It is usually a reporting gap or an integration that needed building, and it is the thing you would otherwise find in month three.
What happened the last time you raised something serious with support?
Support quality tends to drop once a contract is signed, and a reference customer is a year past that point. Ask for a specific incident rather than an opinion.
Not a conversation and not a slide. Ask for the document, and get anything you are relying on into the contract rather than into the product.
The UK regime changes on 1 October 2026 and the digital verification rules change with it, so this is live rather than a box to tick. Ask for the answers in writing.
Are you a certified digital verification service provider under the UK trust framework, or do you pass that to somebody who is?
Certification is what gives you a statutory excuse on a digital check. If they subcontract, get the name and their certification.
Worry ifIdentity verification called certified without naming the framework.
Morgan Lewis, expansion of UK right to work rules, digital verification and onboarding, August 2026
A new code of practice applies to employment starting on or after 1 October 2026. What are you changing, and when is it live?
The change also affects how employers use digital verification services and confirm identity matching. A vendor here who has not heard of it has not been watching the only regulation that governs their product.
Morgan Lewis, expansion of UK right to work rules, digital verification and onboarding, August 2026
Which background screening providers do you integrate with, and who chases a check that has stalled?
Screening delays are the most common reason a start date slips. Find out whether the tool shows you a stalled check or just an amber dot.
How long do you keep identity documents after a check is complete, and can we set that?
Passport scans sitting in a system indefinitely are a liability with no upside. You want a retention period you control and evidence of deletion.
Is this priced per new starter, per employee or per user? Model a year with double the hiring.
Per starter pricing tracks your busiest quarter, which is the quarter the budget was set before.
Which of e-signature, screening, IT provisioning and the employee app are extra?
This category is assembled from parts more than most, and the demo usually has all of them switched on.
Implementation, migration, integrations and support tiers are where the quoted price stops being the price. Ask for the total before the demo ends.
What does year one cost in total, in writing, including implementation, migration and integration fees?
The licence figure is rarely the bill. Implementation, data migration, API charges, premium support and mid-term true-ups are all common and all appear after signature. A vendor who will put the year-one total in an email can be held to it.
Worry ifA licence price now and implementation "scoped later".
Is implementation a fixed fee or time and materials?
Fixed fee puts the risk of a slow implementation on the people running it. Time and materials puts it on you, and HR data is always messier than anyone expects.
Worry ifDay rates with no cap.
What is the renewal price, and is the increase capped in the contract?
Year-one discounts often disappear at renewal, which turns a good deal into an expensive one two years in. A cap written into the contract is a normal thing to ask for.
Worry ifUplift "in line with the market".
What notice do we give to leave, and does it renew automatically?
Thirty to sixty days is reasonable. Ninety or more with auto-renewal means one missed diary entry costs another full year. Ask for the clause and read it in the room.
Worry ifNinety days or more, auto-renewing, multi-year.
On the day we leave, what do we get, in what format, and at what cost? Is that in the contract?
You want every record you put in, plus anything the system generated about your people, in CSV or JSON, at no charge. A feature can change in a release note. A clause cannot, and this one costs nothing to ask for at the point of buying.
Worry ifA PDF export, a fee, or access cut off before the export arrives.
For each thing this system does, are you controller or processor, and is the data processing agreement attached to the contract?
The roles have to be settled activity by activity rather than once for the whole product, and the ICO expects a contract that says so. If they are a processor you have to give explicit written instructions, so ask what those will say.
Worry ifHesitation, or "we are the processor" as a blanket answer.
ICO, six questions to ask when procuring AI recruitment tools, November 2024
Where is the data hosted, which sub-processors touch it, and how do we hear when that list changes?
Employee data includes salaries, health information and grievances. You need to know who holds it and to have a route to object when a new sub-processor appears.
Do you train any model on our data? Is it off by default, and is that in the contract?
Ask plainly and get it in writing. "We do not sell your data" is a different sentence and is often the one that comes back.
Worry ifAn answer about anonymisation that never says no.
Send us your most recent penetration test summary and your ISO 27001 certificate or SOC 2 report.
A certificate number is easy to claim and easy to check. The pen test summary tells you whether anything serious was found and how fast it closed.
Worry if"Available under NDA once we have progressed further."
When an employee makes a subject access request touching your system, what do we get from you and how quickly?
You have a statutory deadline and the vendor does not. Ask for their internal service level in days and check it leaves you time to review before you answer.
Anything above that states a legal duty or a date carries its source. Everything else is our judgement about what is worth asking, and you should treat it as that. None of it is legal advice, and the law here is moving quickly enough that you should check a date before you rely on it.
Band figures generated from the exposure report. Ratings from Eloundou, Manning, Mishkin and Rock, GPTs are GPTs, Science 384, 1306–1308, 2024, applied to O*NET 30.3 task statements. O*NET® is a trademark of USDOL/ETA, used under CC BY 4.0 and modified here.