There are several indicators that make it easier to give trust:
1. Pay attention to your gut feeling. If it is not positive, you have not yet found your building partner.
2. Focus on how interested your conversation partner is in finding out what you want. You can tell this because they ask questions outside of "their agenda" of "working through a list of questions." Is this a person who first just accepts answers, or do they use them right away to make a proposal or a counterargument? Trust only people who also have an interest in your matter. It is obvious that they have a self-interest anyway.
3. How much joy and enthusiasm does your counterpart seem to have for their job and topic? (For good reason, "lack of enthusiasm of the seller" is, according to a well-done study and survey, the most common trigger for CEOs to reject an offer.) Whoever enjoys their job usually does it fairly and well.
4. Give your contact person a "non-standard" homework task right at the beginning. Nothing elaborate. Observe how well and reliably they complete it.