Have I actually prepared for the human side of handing off the wealth, not just the legal side?

Most founders prepare the legal side and assume the human side will follow. It rarely does. The legal side is the part most founders are comfortable with. Trusts, governance, tax structure, board composition. These get attention because they feel solvable and there are advisors who specialize in each piece. The human side is harder. Have your kids read your intentions in writing. Do they know what you want the wealth to do and what you don't want it to do. Have you sat down with each adult child individually and asked what they actually want. Kris Kluver, in The Dysfunctional Family Office, calls the document that bridges these two sides a Founder's Mandate. Most founders haven't written one, even if their estate plan is fully signed.