What do I do with longtime employees who can't keep up with the new direction?

Have the honest conversation, then take care of them the right way if they need to step aside. Kris Kluver, in The Dysfunctional Family Office, has Robert Mitchell raise this with his daughter Gail before the handoff. His longtime CFO Brett and longtime attorney Frank have been with him for decades. He loves them. They have also become conflict-avoidant and less growth-minded over the years. They feel like they're on a glide path to retirement. Gail will need her own team of people who are energized about building something amazing with her, willing to look at things differently. The conversation isn't easy. The right move is to be direct, generous, and respectful. Generous severance. A path that lets them step away with dignity. Real acknowledgment of what they built. Robert eventually does this with Brett over coffee at the Corner Bakery. Both men know what the meeting is for. The conversation is short and respectful.