Encouraging people to step out of their comfort zone is one way to help them to develop and grow. However, you don’t want to set them up for failure. Follow these tips to challenge people the right way:
Offer them a valid reason. If what you are asking employees is essential for them to keep their jobs or you want to help them advance within the organization, tell them so. Then let them decide whether their career is worth the discomfort of learning a new skill.
Focus on employees’ strengths. Start with something they are already pretty good at, and set stretch assignments from there. If you want them to tackle something entirely new, do so. Just explain why you want them to take it on, and have some patience as they do.
Ask them to give it a shot. People may feel apprehensive. Acknowledge that, ask them to at least try, and tell them you trust they can do it. Say: “I know this seems like a challenge to you, but will you please do it? I believe that you can be successful.”
— Adapted from “How to Stretch People Without Breaking Them,” Dan Rockwell, Freak Blog, https://leadershipfreak.blog.