Every technology vendor demos beautifully. The product gleams, the salesperson is delightful, the pricing “works for businesses just like yours.” Then you sign, and the relationship you actually bought reveals itself: the support queue, the renewal pricing, the data you can’t easily get back out. Evaluating a vendor well means evaluating the parts the demo doesn’t show — and it comes down to a handful of questions that predict the relationship better than any feature list.

First: does it solve your problem?

Before any vendor conversation, write the requirement in your own words — the workflow it must handle, the systems it must connect to, the people who’ll use it daily. Then evaluate against your sheet, not their tour. Demos are choreographed around strengths; your one-page requirement is choreographed around your Tuesday. Two requirements almost everyone forgets to write down: integration (does it work with your Microsoft/Google identity for sign-in? talk to your accounting or line-of-business system? single sign-on isn’t a luxury — it’s how access stays governable) and the ordinary-user test — have the actual daily users try it, because the tool the team quietly hates becomes shelfware with a subscription.

Second: will the company still be good to you in year three?

The product is what you’re shown; the company is what you live with.

  • Support, specifically. Not “do you offer support” — how: channels, hours, real response times, and whether it costs extra. Send a pre-sales support question and time the answer; the treatment you get as a prospect is the ceiling, not the floor.
  • Viability. For a tool your operations will depend on: how long in business, how many customers like you, and what happens to your data if they’re acquired or fold. Small vendors can be wonderful — but dependency on a fragile one is a risk you should be choosing knowingly.
  • Security posture — mandatory if they’ll hold your data. Where’s the data stored, is it encrypted, do they support MFA, have they had breaches, and can they produce a security overview or SOC 2 report without acting wounded? A vendor holding your Restricted data is inside your risk perimeter whether or not anyone says so — that’s the entire logic of vendor risk management, and hesitation to answer is an answer.
  • References you choose. Ask for customers your size, in your industry, two-plus years in — then ask those references one question that cuts through: what do you know now that you wish you’d known at signing?

Third: read the contract like it’s year three

The terms that actually bite, in descending order of scars we’ve seen:

  1. Renewal pricing. Intro pricing that resets, auto-renewal with 90-day cancellation windows, annual increases uncapped. Ask directly: what will this cost in year three? Get caps or at least notice periods in writing, and put the renewal date on your calendar the day you sign.
  2. Your data’s exit. Can you export everything, in a usable format, yourself, at any time? What happens to your data after termination — and how fast is it deleted? A vendor that makes leaving hard is telling you how they plan to negotiate renewals. This one question predicts more about the relationship than any other.
  3. The fine print trio: liability caps (usually trivial — know that going in), where your data may be stored, and whether the vendor can change terms unilaterally mid-contract.

None of this requires a lawyer for routine tools; it requires reading the order form and asking the awkward questions while you still have leverage — which is only ever before signing.

Right-size the diligence

Not every tool deserves the full treatment. A cheap utility touching no sensitive data: check the basics and move on. The system your operations or Restricted data will live in: everything above, references included. The vendor who’ll have remote access to your environment: all of it, plus the access rules. Matching diligence to stakes is the whole discipline — the goal is judgment, not paperwork.

The bottom line

A vendor demo shows you the honeymoon; evaluation is about predicting the marriage. Your written requirement, the daily users’ verdict, the support test, the security answers, year-three pricing, and a clean exit path — those six things are knowable before signing, and they’re what the relationship will actually be made of. Vendors who answer them readily tend to be the ones who never make you regret asking.