Choose Software or a Vendor Without a Six-Month Evaluation

    You are a procurement lead who runs fast evaluations. Help me choose without spending three months on it.

What I'm buying: {{category}}
The problem it solves: {{actual_problem}}
Who will use it: {{users_and_how_many}}
Budget: {{budget}}
Candidates so far: {{shortlist_if_any}}
Deadline: {{when_I_need_this_running}}

Step 1 — Requirements, split into three lists, and hold me to the split.
- Must-have: if it cannot do this, it is out. Cap this list at five. Every requirement here must be traceable to the actual problem, not to a feature I saw in a demo.
- Nice-to-have: influences the choice, does not decide it.
- Don't-care: write these down explicitly. Naming what you are not buying is the fastest way to shorten a shortlist and the best defence against a good salesperson.

Challenge any must-have that is really a preference, and any that describes a solution rather than a need.

Step 2 — Shortlist to three. More than three is procrastination; the fourth option almost never wins.

Step 3 — The trial. Do not take the guided demo as evidence — a demo is a rehearsed path through the product's best day. Instead:
- Define two or three real scenarios from my actual work, with my actual data
- Have the person who will use it daily run them, not me
- Time how long the most frequent task takes in each candidate; a five-second difference repeated forty times a day is the whole decision
- Test the thing you are most worried about first

Step 4 — Ask the questions that surface year-two problems:
- What does the price look like at double our usage, and what has your list price done over the last three years?
- What is the notice period and what happens to our data on exit, in what format?
- Show me your status page history for the last twelve months.
- Who does implementation, and is it included?
- What are the three things customers most often ask for that you do not do?
- Give me a reference at a customer my size who left the product I'm replacing.

Step 5 — Decide with a weighted scorecard, but write the decision down: what we chose, what we rejected, and why. In eighteen months someone will ask, and the reasoning is the only thing that ages well.