The One Mile — Buyer's Toolkit
The 10 questions that make a great vendor shine
After a decade on the vendor side of the table, these are the ten questions I'd want every buyer to ask me. They help you decide faster — and they give a genuinely good startup the stage to prove it.
Dennis Luks · theonemile.com
01 — Product Reality
Let the product speak, not the demo
Can we run this workflow on our own data during the pilot?
Why it works: The fastest way to a confident yes. Great products welcome real data — and you skip months of hypothetical debate.
Which parts of what we just saw are generally available today, and which are on the roadmap?
Why it works: A clear GA-vs-roadmap answer lets you plan honestly. Vendors with strong products draw this line proudly.
What happens when it fails — a bad input, an outage, a wrong answer?
Why it works: Mature products have thoughtful failure behavior. Asking early saves both sides a surprise in month two of the pilot.
02 — Trust & Compliance
Clear the security gate early
Where does our data live and is it ever used to train or improve your models?
Why it works: For EU buyers this is the first gate anyway — asking in call one means the answer is on the table before anyone is emotionally committed.
Which certifications do you hold today, and can we see the report under NDA?
Why it works: Vendors with real SOC 2 / ISO 27001 coverage share reports routinely. Settling this early keeps Procurement from stalling the deal in month three.
03 — Commercials
Know the real price, together
What will this cost in year two and three if our usage grows as you project?
Why it works: Multi-year clarity protects the relationship. Renewal surprises are how good partnerships go sour.
Which line items are not in this quote — implementation, support tiers, SSO, API limits?
Why it works: A complete picture now means no budget re-approval later. Transparent vendors itemize without flinching.
04 — Partnership Fit
Are you betting on the right company?
How is the company funded, and what happens to our contract if you are acquired?
Why it works: A fair question every startup selling to enterprises expects. Confident answers here are a strong positive signal.
What is the median time from signature to first measurable value for customers our size?
Why it works: Vendors who measure this have done it before. It also gives you the honest baseline for your own pilot plan.
Can we speak to a customer who has been through a renewal?
Why it works: Renewed customers are the best endorsement a vendor can offer — and great vendors are glad to make the introduction.
Evaluating an AI or data vendor right now?
I've already asked these questions of the startups I work with — that's the point of a scout. Thirty minutes, zero cost to you, and you'll know if there's a fit.