Software decision checklist for small teams

How to use this checklist

Copy the list into a doc, or print it. Go through it with the people who will actually use the tool — not just the person paying.

Answer every item. If you cannot, that is the answer — do not commit yet.

The four evaluation gates

Gate 1: Problem and fit

• We have written the problem in one sentence, without naming any tool.
• We have agreed on three outcomes we expect in two weeks.
• This tool is explicitly built for a team at our size.
• The people who will use it every day were part of the evaluation.

Gate 2: Workflow reality

• We ran a pilot on one real, current project — not a demo dataset.
• Common actions take a reasonable number of clicks.
• Mobile experience works well enough for the 20% of work that happens on a phone.
• It integrates with the two tools we will not replace.

Gate 3: Cost and exit

• We calculated cost for 12 months at the next likely team size.
• We are on a plan appropriate for our current usage, not the biggest plan “just in case”.
• Data export is available and we have tested it.
• We know what it costs to leave — data, integrations, training.

Gate 4: Risk

• No single person has exclusive access to the account or billing.
• The vendor has been around long enough to trust for our current horizon.
• We are not storing anything that would be catastrophic to lose.
• Security and privacy match our actual needs (not a generic checkbox list).

Commit

• One person owns the rollout.
• A review date is scheduled for 60 days from now.
• We know exactly what will make us cancel at that review.

Scoring the result

Related tools

• Estimate ongoing cost with the small-team SaaS budget calculator.
• For specific categories, see best project management software or the best CRM for freelancers and solo founders.