Who in my organization is loyal to the past instead of the future and what conversation am I delaying?

Kris Kluver, in The Dysfunctional Family Office, asks rising generation leaders to name the specific person and the specific conversation they've been delaying. Most leaders, asked plainly, can answer in seconds. The longtime CFO who manages backward. The legacy attorney who frames every new idea as risk. The senior salesperson who clings to old client relationships. Each of them was right for the founder's era. Each of them is wrong for the next chapter. The conversation gets delayed because it feels disloyal to the founder, the company, and the relationship. The delay is what costs the most. Every month the conversation doesn't happen, the wrong person continues to anchor the team to the past, the right path forward stays partial, and the new CEO's authority quietly erodes. The fix is to schedule the conversation. Be direct. Be respectful. Be generous. Make the change. Most rising generation CEOs wait too long.