Counsel vet trial lawyers, experts, and appraisers with care, and then sometimes select the mediator from whoever has an open date. For a high-value estate or trust dispute, that is backwards. The mediator will spend more consequential hours with your client than almost anyone else in the case. The selection deserves the same diligence.

Part of the problem is how the pool gets assembled. Most courts keep a roster of approved mediators, and most legal communities keep a shorter list still: the same familiar names, traded by habit, hired because they were hired last time. Both lists have their place, and I sit on one myself. But a roster tells you who is available, not who is right for your dispute, and courts routinely approve a neutral the parties choose together, on the list or off it. When the matter is a family’s estate or a trustee’s conduct, the search should run on fit: subject matter, temperament, preparation, stamina. Start with the list. Do not let it end the search.

Here are the questions I would ask any mediator being considered for a matter of consequence, myself included. A good neutral will welcome every one of them.

Subject matter is not a garnish in estate and trust work. Construction questions, fiduciary accountings, capacity, undue influence: a mediator who has lived with these issues can test positions credibly. One who has not can only carry numbers between rooms. Ask what role the candidate has actually played in disputes like yours.

Listen carefully to this answer. You want to hear that the neutral reads the instruments, the accountings, and the key filings, and speaks with every lawyer before the day, and you want to know whether that preparation is included in the fee or billed around it. A mediator who arrives cold spends your client’s most expensive hours getting oriented.

Pre-mediation calls change outcomes: they shape who sits in which room, which issues lead, and where the last negotiation died. A conference with counsel for each side should be a matter of course, and if the candidate does not do them, ask why.

The better question is what comes after it. A second conference that includes the client, where counsel agree it would help, does something the lawyer's call cannot. The client hears the process described by the person who will run it, and the neutral hears how the client actually talks about the dispute. Trust in the process is built before anyone is in the room, not on the morning itself. Not every matter needs it, and it is counsel's call to make, but a mediator who has never considered it is telling you something about how the day will go.

You are listening for two things. First, a considered view on joint sessions versus caucus in family disputes, because these rooms are not interchangeable. Second, stamina: these matters settle in the evening, and a mediator with a five o’clock train is a mediator for a different kind of case.

Some neutrals see their role as pure facilitation and will not evaluate. That is a legitimate school, but in my experience it is the wrong one for estate litigation, where parties are often held apart less by numbers than by unexamined confidence in their own case. Ask whether the mediator will, in caucus, tell your client what they need to hear. Then ask yourself whether this particular neutral has the standing for that message to matter.

The number is worth knowing. The structure is worth more. An all-inclusive fee, agreed in advance, means preparation is not rationed and nobody’s meter shapes the length of the day. Whatever the candidate’s answer, you want the economics of the mediation pointing toward resolution, not duration.

The answer reveals how the neutral thinks about the process: whether the day ends with a signed term sheet or a handshake, whether they follow up in the weeks after, whether an adjournment is managed as structure or surrendered as failure.

None of these questions has a single right answer, and different disputes genuinely call for different neutrals. But every one of them has revealing answers, and a mediator who is impatient with the interview is telling you something useful too. And not one of them can be answered by a roster.

Your client will make the most important financial and family decisions of the dispute in a room this person runs.

Choose accordingly.