You’ve shown them how to do it a few times, but they still don’t get it. Even worse, you’re now behind on your own work from all the time spent trying to get them up to speed.
Sound familiar? If you’ve ever hired, managed, or mentored someone, you’ve been here!
One of the most important attributes of a leader is being able to develop the skills and abilities of others. And although some organizations do provide leadership training for their managers, very few organizations show them how to successfully teach others.
Being proficient at something doesn’t make you great at teaching it. In fact, your expertise can make you forget what it was like to not know.
So when someone you’re teaching isn’t “getting it,” what can you do to help them get up to speed?
- 1Stop “telling” them what to do: Instead of simply telling them what they’re doing wrong, one of the best ways to teach a skill is to switch your language to inquiry. Asking questions to understand their thought process is a powerful way to identify where they need to correct their approach, and it’s a more effective way to help them think through a problem.
- 2Let them fail (safely): Some of the worst teachers are the ones who never let their students fail. Accept that most people won’t get it right the first time, and the few that do may have gotten there by luck. Assign them to tasks where the cost of failure is low, let them get plenty of reps in, then guide them through inquiry so they can improve.
- 3Adapt to the person, not your playbook: Even though it’s the same skill, different people need different paths to learn it. Analytical people want the data and time to process it. Creative people learn best when you challenge them to find their own solution. Cautious people need clear, step-by-step structure before they’ll try something new.
- 4Reinforce what they’re doing well: Most of us only receive feedback when we’re doing something wrong, but it’s equally important to give feedback when something is done right! When you see productive behavior, acknowledge it on the spot while it’s fresh in their mind. Just be sure it’s earnest (no empty praise or compliment sandwiches).
Teaching is communication, and that’s what I help teams get better at. Have a question about communicating at work? Email me and ask! Whether it’s about sales calls, client 1:1s, or presenting to leadership, I’ll answer every question and feature the best ones in upcoming posts.

