The vendor diligence kit

A typical evaluation spends most of its energy on functionality, which is the question least likely to differentiate, because by shortlist stage most candidates can do the thing.

What determines whether a decision looks good in five years is rarely on the scorecard. Whether your data can leave. Whether a workflow depends on a component you could not replace. What happens to the roadmap when the vendor is acquired. What the renewal looks like once switching has become expensive.

Forty questions across five sections, each grouped by the risk it protects you from, with a note on why it matters and what a weak answer sounds like. It is deliberately vendor-neutral: nothing here is written so that only we can answer it well.