The SaaS / Software Procurement Playbook: Nobody Asked What a User Was. It Cost Them £219,150

Most buyers leave vendor meetings holding a proposal and no information.

They got the pitch, the slides and a price. They learned nothing about the person opposite, their pressures, their actual flexibility, or the parts of the contract that will cost money in eighteen months.

That’s rarely because nobody asked questions. It’s because the questions were the wrong ones, asked in a way that triggered the pitch rather than the truth.

The most expensive question nobody asks

Here’s how it goes.

You’re negotiating a per-user contract. Three weeks on the price per user. You get it from £500 down to £440. Twelve percent. Good work, everyone’s pleased.

Nobody in that room asked what a user is.

Eighteen months later an audit arrives. Under your agreement a user isn’t a person, it’s an account. Which means your forty service accounts count. Your integrations that authenticate via API count. Twenty-five leavers whose accounts were deactivated but never deleted count. Contractors sharing a login count.

A hundred and twenty additional users you didn’t know you had.

Charged at list price and backdated eighteen months, that’s a £90,000 invoice you have to explain, plus a hundred and twenty seats sitting permanently in your baseline, carrying the annual uplift, compounding into every future renewal. Total exposure across the remaining term, £219,150.

You saved £60 per user. The definition cost you more than three times what the negotiation won.

Why suppliers stop telling you the truth

There’s a mechanism behind this and it’s worth understanding.

The moment a supplier feels negotiated against, they stop giving real answers and switch to pitch mode. Everything after that point is marketing.

So you buy permission first. At the start of the meeting, before anything else:

“I want this to feel like a conversation rather than a presentation. So push back on us, add context, be candid. I’ll be direct with my questions and I’ll expect the same back. The best partnerships come from both sides being honest about constraints early, because that’s what stops the fights at renewal. Can I assume a deal that works for both of us is what you want too?”

Almost nobody says no to that last line. And having agreed to it out loud, every direct question you ask afterwards is something they signed up for. Refusing to answer now contradicts a position they just took publicly.

That’s the whole mechanism. People stay consistent with what they’ve agreed to.

Asking the question properly

Then you ask concretely, with the edge cases named, rather than generally.

Not “how do you define a user,” which gets you a definition from a brochure. Instead:

“What exactly counts as a licensed user under this contract? Is a service account a user? Is an integration authenticating via your API a user? If a contractor uses a shared login, is that one or two? And if we deactivate someone but haven’t deleted the account, are we still paying for them?”

Then stop talking.

That’s the second technique and it’s harder than it sounds. Most value in negotiations leaks because the buyer fills the silence. Ask the question and let it sit. They will answer, and they will usually tell you more than they intended.

Then the third move, which converts information into money.

Whatever they tell you verbally goes into the contract.

“That’s helpful. So service accounts and integrations aren’t counted. I’d like that written into the agreement as an express exclusion list, so neither of us is arguing about it in an audit.”

They’ve just said it out loud. Refusing to write it down is very difficult, and if they do refuse, they have told you the exposure is real.

Four more questions worth asking

“Where would we rank among your accounts by importance, honestly, not by size?” Their answer tells you whether you have room. Cross-check it against your own spend as a percentage of their revenue, because buyers systematically overestimate their importance.

“If you don’t win us, what’s the next-best account you’d put this capacity against?” If they can’t name a replacement, you are harder to replace than they’ve been implying, and your ask can go materially higher.

“How are your own people compensated on this, on signing or on what we actually use?” If they’re paid on bookings rather than consumption, expect to be sold more seats than you need, and put reduction rights at the top of your list before the commercial conversation opens.

“Which clause in here are you hoping we won’t read too closely?” Ask it at the end, with a smile, after rapport is built. The pause before they answer tells you more than the answer does, and it tells you which clause to have your lawyer read twice.

The discipline

Ask one question at a time. Stack three and they’ll answer the easy one and bury the rest.

Write down what they say as they say it, because anything a supplier commits to verbally becomes your contract language later. This is the single highest-return habit in the list and almost nobody does it.

And don’t negotiate while you’re still discovering. Gather first, decide later, strike when you’re prepared.