Years ago I had an employee who had been with me for over a year and hadn't taken any vacation. I encouraged him to plan a vacation sometime in the coming month

Years ago I had an employee who had been with me for over a year and hadn't taken any vacation. I encouraged him to plan a vacation sometime in the coming months, in part, because wend don't really know what things he did at work that weren't fully documented and cross-trained on. Got other people cross trained, things documented, and his vacation went smoothly. A few months later, he got offered a dream job offer, and the transition went smoothly.