Ask questions, pose challenges

To follow up with your coachee, consider asking him or her what has been going well and what could be improved upon after each coaching session. Augment these questions with challenges designed to encourage your coachee to demonstrate his or her new skills or knowledge.

For example, suppose you're helping Alex, an employee, strengthen his presentation skills. You might follow up an initial coaching session with Alex by saying something like, "Last week we reviewed a software program that makes presentations more compelling. Have you made any progress learning how to use the software?"
If Alex says yes, you could challenge him by asking him to create a sample presentation using market data on one of your company's products. Provide him with the raw data and ask him to develop a set of pie and bar charts using the presentation software. Pose the challenge in the following manner: "Let's work together using the presentation software to see what you can do with this market data. Prepare some pie and bar charts—just as you would if you were preparing a presentation for our marketing group."
If the resulting presentation contains problems, you could practice some on-the-spot feedback to help Alex fix any errors and continue learning.

Sessions like these give you opportunities to check your coachee's progress, praise him or her for achievements, and spot signals that continued coaching and feedback are needed.

Following up also helps you identify ways in which the coaching action plan might need to be changed.

For example, you might realize that you need to review your employee's progress more frequently than you originally anticipated. Or maybe you decide that your coachee might have more success if you broke a daunting challenge into smaller, more manageable pieces.