THE VENDOR PITCH CHECKLIST
Six questions for the vendor meeting

BEFORE THE MEETING
Write your problem in two sentences, in your own words,
using no vendor terminology:
____________________________________________

DURING — ask each question; note how specific the answer is.

1. PROBLEM FRAMING
"Can you describe the problem we're solving in plain language,
without using any of your product's terminology?"
Look for: a description that matches your own two sentences.
Red flag: pitch language; a problem that isn't quite yours.

2. WORKFLOW VOLUME
"What workflow volume does this engagement assume — per period,
per instance, total annual time cost?"
Look for: numbers they know or explicitly asked you for.
Red flag: ROI math that needs volumes bigger than your reality.

3. THE CUT
"Which specific steps in this system require AI, and which are
deterministic automation?"
Look for: a clear step-level split, with AI only where
judgment lives.
Red flag: "the whole system is AI-powered."

4. CAPABILITY EVIDENCE
"Will you run this system on twenty of my actual inputs for
two weeks before I commit?"
Look for: yes, with reasonable terms.
Red flag: demo data, case studies, or a money-back guarantee
offered instead. (The guarantee returns your dollars, not
your months.)

5. HUMAN PLACEMENT
"Where exactly do humans fit? For each point — what do they do,
and how do they know when their attention is needed?"
Look for: named roles, defined triggers, real authority.
Red flag: "humans review the AI outputs."

6. STAGED COMMITMENT
"Can this be structured in phases, with the first phase as a
pilot whose results determine whether the rest proceeds?"
Look for: yes, with a defined pilot scope and criteria.
Red flag: full upfront commitment "to be able to deliver."

AFTER
Clean answers: ___ / 6     Red flags: ___ / 6
5–6 clean: engage seriously.
3–4: probe further before committing.
0–2: decline politely — the offering depends on you not asking.

Decision deferred until: ______________

From "Before You Build" - topfiveaitech.com/worksheets