Key takeaway
The question that predicts adoption isn't on most buyers' checklists: will someone actually open this unprompted next week?
Buying a project management tool for the first time tends to produce one of two mistakes: asking no questions at all and picking whatever a colleague mentioned, or asking every question an enterprise procurement checklist would ask, most of which will not matter for a year or more. A small team doing real due diligence needs a shorter, more targeted list.
Questions worth asking now
Can I run one real project on it, not a demo, before committing the whole team? What actually happens to my data, can I export it, if I stop paying? Is the pricing per seat or per project, and which of those actually fits how my team is structured? Does adding my team mean inviting people one at a time, or can I bring in a roster I already have? And, honestly, the most predictive one: after a week of using it for one real project, is anyone opening it unprompted, or has it already started to feel like an extra chore layered on top of what people were doing before?
Questions that can wait
Single sign-on, custom approval workflows, a portfolio-level rollup across dozens of projects, and deep integration with tools you do not currently use, all matter eventually, at a size and complexity most small teams have not reached yet. Spending the first buying decision's attention on those instead of on whether the tool will actually get used day to day is a common way to end up with something technically impressive and practically ignored.