Coaching questions takes practice to become accustomed to how to use certain questions and under what circumstances. At first, coaches can work on memorizing coaching questions, referencing the Coaching questions: A coach's guide to powerful asking skills book, as needed. One of the main challenges is working on having an authentic coaching conversation that naturally leads to the coachee discovering their own answers.

Asking the wrong type of questions is the main challenge. Some examples of mistakes/challenges that can occur with this coaching model are outlined below.

Tony Stoltzfus's top 10 asking mistakes are:

1. Closed questions

2. Solution-oriented questions (SOQs)

3. Seeking the "one true question"

4. Rambling questions

5. Interpretive questions

6. Rhetorical questions

7. Leading questions

8. Neglecting to interrupt

9. Interrupting

10. "Why" questions