Am I guessing what my family wants or have I actually asked them?

Most families operate on assumptions rather than explicit conversations. The founder assumes the kids want the business. The kids assume the founder wants them in it. The spouse assumes both sides will figure it out. None of these assumptions get tested. Kris Kluver, in The Dysfunctional Family Office, calls this the crappy psychic problem. The fix is structural. Sit down with each adult family member, individually, and ask what they actually want from the wealth, the business, and the family relationships. Write down the answers. Compare them. Most families discover the assumptions were wrong on multiple fronts, often in ways that change the entire transition plan. The conversations are uncomfortable. The discoveries are usually worth it.