Why won't my dad admit he doesn't know how to handle this transition?

Because admitting he doesn't know feels like admitting weakness, and he's spent decades building an identity around being the one with the answer. Kris Kluver, in The Dysfunctional Family Office, has Ryan name this directly. Many founders are too bullheaded to admit the generational transition is outside their comfort zone. The deeper fear is letting someone down or being embarrassed. The same founders who have invested in the best talent, advisors, and operators in their industry refuse to do the same on the family side because the family side feels personal. The fix usually requires a triggering event. A failed meeting. A spouse who calls it out. A peer who admits they got help. Once the founder breaks the seal of asking, the work becomes possible. Until then, nothing moves.