1. What does it read, exactly? Email metadata only, or message bodies? Calendar? CRM? Public work history? A vendor who answers vaguely is telling you something.
2. How much of our network does it cover? Ask for the percentage of your employees' external contacts it can resolve to a real person at a real company. This is where products differ most and where demos hide the gap.
3. How is strength scored, and can I see why? A number with no explanation cannot be argued with, and a rep who does not believe the score will not act on it. Insist on the evidence behind each path.
4. Does it find relationships from before our company existed? The strongest paths are usually old - two jobs ago, a shared employer. A tool that only sees interactions inside your tenant will miss all of them.
5. What does the output look like on a Tuesday morning? Not the dashboard. The actual thing a rep opens: is it a ranked list naming a person to ask, or a graph they have to interpret?
6. Does it tell us when a champion moves? Job changes are the highest-intent signal in B2B, and most relationship tools treat them as an afterthought. Some products - UserGems is the clearest example - do only this.
7. Where does the data live, and who can see it? Whether the graph is private to your company or pooled across the vendor's customers is a material difference, commercially and legally. Both models exist. Ask which one you are buying.
8. What happens to the data when we leave? Ask now, in writing.
Give the vendor 50 target accounts from your real list - not their sample - and ask for the paths. Then score the output yourself:
The third number is the one vendors dislike. A tool that mostly surfaces relationships your reps could have listed from memory is not earning its price.
Beware the pilot that only maps the sales team. The valuable relationships are usually held by engineering, customer success and the executive team. A pilot scoped to sales will under-report coverage and you will conclude the category does not work.
Beware a score with no decay. A relationship from 2015 that has had no contact since is not a warm path, and a tool that ranks it as one will burn your reps' trust on the first three introductions they ask for.