STEPHEN
STILWELL
u/p.
← Software Decision WorkspaceWORKFLOW / SOFTWARE SELECTION

Run a software trial that answers a buying question.

Leave with evidence, tradeoffs, and a next step.

1. Write the job before the shortlist

Define one real workflow and a usable outcome. Choose a decision owner, a date, and a first-year budget. Include staying with your current approach as an option.

2. Separate preferences from requirements

Give each requirement a weight from 1 to 5. Mark a must-have only when failure would stop the purchase. Add a repeatable verification task so each option faces the same test.

3. Compare the actual plans

Record the quoted plan, seats, billing period, usage assumptions, and migration costs. Verify that the features you test are included in that plan. Use the same currency and scope for every option.

4. Test the awkward cases

Use synthetic or non-sensitive sample data. Include an exception, an export, a permissions check, and a handoff. Record what happened, when, and which plan you used. Distinguish documentation from firsthand observations.

5. Resolve the gaps before committing

In the workspace, unknown scores remain a range. Failed must-haves block an option. Missing evidence creates a follow-up task. A fully evidenced high score supports a discussion; it does not replace judgment about cost, risk, or adoption.

6. Keep a decision record

Write why you chose an option, the tradeoffs you accept, and a review date. Download the decision brief for your team and a JSON backup if you want to reopen the editable project on another device.

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