The hardest part of buying software is no longer finding options. A single search returns dozens of credible products, each with a polished site and a confident pricing page. The hard part is deciding which three deserve a serious look -- and doing it before the team loses momentum.
Start with the problem, not the product
Before opening a single vendor page, write one paragraph that describes the problem in your own words. Who has it, how often, and what it costs you today. If you cannot describe the problem without naming a product, you are not ready to shortlist yet.
A shortlist built before the problem is written down is just a list of whoever markets best.
Define your non-negotiables
Separate requirements into two buckets. Non-negotiables are the handful of things that, if missing, end the conversation immediately. Everything else is a preference. Most teams invert this and treat every wish as a requirement, which makes every product look disqualified.
- Non-negotiables: deployment model, core workflow, data residency, a hard budget ceiling.
- Preferences: reporting depth, integrations, the polish of the interface, onboarding support.
Filter in three passes
- Catalog pass. Use category and feature filters to drop anything that fails a non-negotiable. Expect to cut half the field here.
- Evidence pass. Read recent reviews from companies that resemble yours in size and industry. Ignore star averages; read the one-star and three-star reviews for the real story.
- Fit pass. For the survivors, spend fifteen minutes each imagining your messiest real workflow inside the tool. Friction you can picture now is friction you will feel later.
Stop at three
Three is enough to see meaningful contrast and few enough to evaluate properly. Two invites a false binary; five guarantees the evaluation never finishes. If a fourth tool keeps pulling at you, that is a signal your non-negotiables are not sharp enough -- go back and tighten them.
The bottom line
A good shortlist is a decision you have already half-made. By the time three names are on the page, you should know what you are testing for and how you will tell a winner from a runner-up. The demos that follow become confirmation, not exploration -- and that is exactly the position you want to be in.