How do I keep family conversations from going in circles every time?

Start every conversation by defining what success looks like. Kris Kluver, in The Dysfunctional Family Office, gives this framework directly. First, define the destination. What would success look like for this conversation. Then dig. The problem people bring to the table is usually a symptom. Use the Five Whys, ask why five times in a row, to find the root cause. Once you've found it, have the conversation. Be bold. Be curious. Call out doom loops when you see them. Then close with action items that have dates and clear accountability. Someone owns each item. The work moves. The framework is usable in family meetings, business meetings, sibling conversations, and investment decisions. The discipline is what keeps every conversation from circling. Most families never define success at the start, never get to the root cause, and never assign clear ownership.