How do I let go of longtime executives who can't make the leap to the new generation?

With dignity, a generous severance, and the truth said plainly in a private conversation. Letting go of senior executives who built the company with you is one of the hardest parts of the transition. The instinct is to delay, hope they adapt, or quietly minimize their influence. Kris Kluver, in The Dysfunctional Family Office, watches Ben Christoff fire two senior executives he loved because keeping them would have sunk the entire transition. Ben gave them space to step away with honor. The conversation broke his heart. He still describes it as the right call. Robert Mitchell does the same near the end of the book with Brett, his CFO of twenty years. Both men know what the meeting is for. The conversation is short and respectful. Some partnerships end with fireworks. The best ones end with mutual respect.