Most people hear the executor question as a compliment and answer it like one. Someone you care about is telling you she trusts you, above everyone else in her life, with the thing she spent decades building. Declining feels like declining the friendship itself.
That framing is what gets people into trouble. A listener said yes for exactly that reason and is now having second thoughts, and I think her instincts are good. Her friend is worth roughly $15 million, with three properties, an operating business, and two adult children who do not speak to each other. She wants to know what she actually signed up for, and whether there is a graceful way out.
A Messy Fifteen Million, Not a Simple One
Fifteen million dollars sitting in an investment account, maybe with a house or two attached, is a manageable estate. You value it, you follow the will, you divide it, you close it out. That is not this.
Three properties and a business mean illiquid assets, and illiquid assets mean somebody has to decide what they are worth. That somebody is the executor. You will be hiring appraisers, weighing their conclusions, and then dividing assets that have no obvious price tag between two siblings who will not sit in the same room. Every valuation judgment you make will look, to at least one of them, like you picked a side. Realistically, this is a one to two year commitment, and the hardest part will not be paperwork. It will be standing between two grieving people who already do not trust each other.
Fiduciary Is a Legal Word, Not a Courtesy Title
The part that gets glossed over most often is that executor is a fiduciary role. This is not signing some documents as a favor. You take on legal liability for how the estate is handled. If the business valuation is later challenged, if an asset is distributed in a way an heir believes was improper, you are the person answering for it.
Stack that against the profile of this estate: complex, illiquid, contested, and running for a year or two. Second-guessing is the correct response. I would be more worried about someone who did not.
Backing Out Later Is Much Worse Than Backing Out Now
Here is the timing piece, and it matters more than people expect. Having an awkward conversation with your friend today is far easier than the alternative. Once she has passed and you are the named, serving executor, stepping down generally requires court approval. You would be resigning mid process, in front of a family already under stress, and the children who are watching you leave will draw their own conclusions about why. That is a genuine disaster compared to a slightly uncomfortable coffee this month.
The Co-Executor Middle Ground
Fortunately this is not a yes or no question. Naming a co-executor is common in exactly these situations, and I would point her toward a trust company or a bank as the partner. They carry the same fiduciary duty you do, they have handled complex estates before, and they can absorb the technical work: valuations, tax filings, the mechanics of dividing a business.
That leaves you handling the relationship side. Some people would tell you that is the harder half, and they may be right. But there is real value in being able to say to two adult children that the person answering their technical questions has done this many times before. You become the calm presence in the room rather than the sole decision maker who is also improvising. If your friend already works with an advisory team, this is a good moment to loop us in as well, since we can usually help identify which corporate trustees are a reasonable fit before anyone signs anything.
What to Actually Say to Your Friend
Lead with the friendship, because that is the true part. Tell her the trust means a great deal and you want to help. Then be honest that you do not think sole executor is where you help best.
It is worth understanding why she asked you in the first place. She almost certainly does not want an anonymous institution making decisions about her assets and her children’s futures. She wants someone who knows her family. Offering to serve as co-executor gives her that and solves your problem at the same time. You stay personally involved, and the technical liability gets shared with someone equipped to carry it.
Framed that way, this is not a rejection. You are telling her you took the request seriously enough to think through where you are strong and where you are not, and that you will commit under conditions that let you do the job well. In my experience she will say yes, and she will feel better about her plan than she did before you raised it.
This post is adapted from a recent episode of the Scholar Wealth Podcast. For more perspective on what the executor role really involves, listen to the full podcast episode here.