Basic But Brilliant Coaching Questions

Whether you are coaching someone or coaching yourself, ask three basic but brilliant coaching questions.

What is Coaching?

Coaching is the process of helping someone master a skill or the correct application of knowledge. Teaching focuses on learning something new; coaching focuses on mastering that something. Teaching ends when someone able to demonstrate that he or she can correctly perform the skill or apply the knowledge.

Coaching begins after someone has learned the new skill or knowledge. The coaching process should continue until after the individual has fully mastered the skill or knowledge application, capable of replicating the learning transfer with other people.

Coaching is best done at a brief interval after the individual has learned the new skill or knowledge application. Depending on the nature of what has been learned and its impact on the job, the interval can be hours or days following the point in time where you taught the skill or knowledge application. It is best done after you have observed the skill being applied, though observation is not a necessity.

Effective Coaching is Question-Driven Self-Discovery, Not Advice

The ideal coach is a thinking partner to the person being coached. The coach asks questions to lead the person being coached through the process of self-assessment, not offering any advice, observations, or opinions until after the person being coached has self-assessed. The objective of coaching is to ensure the person being coached can consistently replicate success, and that is based on what he or she knows or understands.

Advice, observations, and opinions come from what the coach knows, not what the person being coached knows. Coaching should start with what the person being coached knows and doesn’t know, which is why it is so important to lead the process with questions.

Basic But Brilliant Coaching Questions

Suppose a few days ago your employer launched a new initiative (we’ll call this Initiative X). You staff met and received training on the initiative. You’ve just observed Mike, a staff member, who put Initiative X to use. Here are three brilliant coaching questions you could use:

1. What is working well for you?

a. How to ask it: “Mike, it’s been a few days since we launched Initiative X and I noticed you have had an opportunity or two to put it to use. I’m curious…what has worked well for you the last time you had an opportunity to put Initiative X to work?”

b. Why the question is brilliant: The question tells Mike the initiative is important and you are aware of the opportunities he’s had to apply it. You are asking his opinion, which shows respect for him and genuine interest in how things are going for him. It allows him to identify what he thinks he is doing well rather than what you think he is doing well. It opens up the opportunity to ask follow-on questions and for him to demonstrate his expertise.

c. How to follow it up: Thank him for doing these things and encourage him to be consistent in doing what he’s done well. Use this as an opportunity to help him understand how the company/department/customers benefit from his correct application. If he missed anything he did well that you observed, then let him know what it was and that you appreciate it.

2. What didn’t go as well as you’d have liked?

a. How to ask it: “So…has there been anything that hasn’t gone as well as you’d have liked?

b. Why the question is brilliant: The question is broad and non-judgmental. It says that in anything new, there will likely be areas that won’t be perfect at the start. It allows Mike to identify any issues he is aware of. He’ll likely tell you what he should have done instead. This is a critical aspect of coaching – helping the person being coached to self-diagnose, learn, and improve. Because Mike is identifying the areas he didn’t think went well, it isn’t criticism.

c. How to follow it up: Probe for what he thinks caused it to not go well. Can he diagnose problem areas and so that in the future he can make the adjustments along the way? If he didn’t identify a significant shortcoming that you observed, you may need to use questions to help him see it. For example, saying something like, “When we had our training I thought one area that could be problematic was XXXXX. How did that go for you?” If he doesn’t see the problem you did, perhaps he was not taught thoroughly enough in the first place, which provides an opportunity for you to re-teach the area.

3. What things will you do differently next time?

a. How to ask it: “Mike, as a result of your experiences with Initiative X plus our discussion today, is there anything you will do differently next time?

b. Why the question is brilliant: It calls for him to move from learning toward mastery by stating the specific actions he’ll take in the future, which can be viewed as his commitment to improvement.

c. How to follow it up: Encourage him to take the step(s). Use questions to help him think it through more if needed. Ask when he thinks he’ll have his next opportunity to try out the new approach. And let him know that you’d like to learn how his new approach has worked – which you can ask about the next time you see him (unless he seeks you out to let you know).

Bottom Line

Three basic but brilliant questions, all designed for you to hold up the mirror of self-discovery, and be a more effective thinking partner for your staff and others who seek your opinion. As a result of consistently using this approach, your staff will begin to self-assess as part of their normal approach to assignments and work. Leading with questions in this way will not only make you a more effective developer of talent, but increase the respect the people around you have for you.

This article is based on principles presented in Boyer Management Group’s Leading Through People Staff Development & Performance Management Workshop.

Boyer Management Group works with employers, organizations, and job seekers alike to help them become more successful. For employers, we offer world-class talent development, leadership and management training, acquisition and onboarding tools and programs to help employees and volunteers achieve consistent, optimal performance. For job seekers and universities, we offer tools, assessments, books, and curricula to help connect people with careers. To find out more, please visit us at, or call us at 215-942-0982.


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