You want to be proactive and train up replacements for vacations and those “what if” scenarios. You know that employees like to learn new things and feel important. Watch out for backlash from the person going on vacation or in the position that you feel needs more depth. Don’t forget to reassure them that cross-training should be a non-threatening team building event, and that if they participate in training and show skill in cross-training others in tier skills that they will be more important to the company, and have more flexibility in the future. How much easier is it to promote someone who has properly assisted in the cross-training of reliable back-ups? An employee who will learn and can teach is worth praising. An employee who is secure and not threatened by others learn their job is invaluable. Remember to lay the ground work and establish the security first, then train away!