Change Management

Coaching and Mentoring Questions

A few weeks ago, I tried to explain the difference between Coaching and Mentoring. Consequently, as there are subtle differences, there may also be differences in the questions we ask of our coachees and mentees.

In both cases it is important to use open questions.  See our video on questioning techniques available in our Resources Page. Effective questionining helps both Change and Training Managers position themselves more successfully to coach and mentor others.

Here are some examples of the questions and hints and tips that can be used.

Mentoring Questions

One of the most important characteristics is to ask insightful questions.

What does success look like to you?

The benefit of this question is that it will provide information on where the mentee sees himself/herself both now and in the future.  Adding a timeframe may also provide information on the timescale involved and therefore can give information on planning – What does success look like to you in 5 years time?  It can also determine what the first and subsequent steps may be.

What are your expectations and the goals you want to achieve?

Similar to the previous question, this question is effective for situations where there is more than one equally viable solution or course of action.  When you start with the specific outcome you want, the best action to take becomes clearer. For example, if you’re having a conflict with a team member, the best solution will be different if you want to try to repair the relationship versus if you think it’s hopeless and just want to get away from that person.

What do you want to be different in three to five years?

Since the business world changes at such a fast pace today, focusing on a shorter window—perhaps 3-5 years—still allows enough time for creative, aspirational thinking without the distraction of how different the workplace might be at that time. The answers may reveal how the mentee wants to grow, or fundamental changes they need to make in order to achieve their goals.

What are the challenges or concerns you’re facing?

Mentors can be invaluable in providing insight to overcome challenges. Answers to this question may highlight strengths and weaknesses in addressing them.

What can you do to manage the challenges?

It is important that the mentee takes responsibility. You might not be able to change an unfair corporate policy immediately, but you may be able to find short-term answers to help them deal with it while they work on longer-term solutions.

What are the available options?

When faced with obstacles or challenges, both mentor and mentee may have ideas of how they can be addressed.   This allows an open discussion on what can be done, pros and cons and gives consideration to the right and agreed approach.

Are there any other influences we need to be aware of?

This question draws out more detail about what led them to form their opinions or helped them reach a conclusion. That can help reveal biases or blind spots that are affecting their . With the benefit of some objectivity and another degree of separation from the situation, the mentor can help them expand their thinking and possibly find new ways of looking at a situation.

What are your hobbies?

It is important to also ask about interests – this after all is a relationship.  Getting to know each other to work more effectively together is vital.  This often gives more considerations on approaches to attaining goals based on personal characteristics and preferences.

Now let’s look at possible questions for coaching.

Coaching Questions

Which areas of your job would you like to improve?

This questions pinpoints where the coachee feels he/she has a weakness or perhaps a lack of confidence which is dependent on where he/she wants to be.

What will be the impact if things stayed the same?

This is important because one choice is to stay as is.  Coaching is about change, about introducing improvements and the coachee needs to be equipped with the right skills to deal with these changes.  Improvements often affect others, so it is important to see what the status quo means to him/her and other affected parties.

What do you mean when you say ‘success’ in this area of change?

It is important that the coach understands what success is for the coachee.  Everyone’s vision of success is different which means there is a different level of skill required and a different level of skill needed to be developed.

What practical actions do you want to take over the next 7 days?

Coachees may have some opinions on what tasks can be put in place in the short-term to start the process of development. Facilitating next steps of what is important to them provides ownership of these steps.

What else?

Getting coachees to delve deeper can bring about some surprising results.  Allow coachees to speak, giving them time to reflect.

How important is this to you?

It is essential to establish how committed the coachee is to put things in place.  This will show motivation levels which may also need to be addressed as part of coaching.

What if you could wave a magic wand – what would you do?

This question draws out some more improvements and perhaps where challenges lie.

Where will this lead?

Constantly determining and readdressing goals is important.  Not only does it verify the approach required but also justifies the goals.

What would your best friend tell you to do?

Coachees will discuss the goals with partners and close friends. Getting coachees to divulge on what their friends think about what they should do, may reaffirm feelings, considerations and actions.

What have you done before that has helped with this issue?

This is another question which will provide insight into the actions which have already taken place, how successful these were and the challenges presented.

Coaching is all about asking the right questions, so explore and experiment with them and make them your own whilst developing your relationship.

Coaching and Mentoring are important skills that Change and Training Managers often need to get the best result in changes and education.

Our Change Management and Train the Trainer courses are packed with useful skills including Coaching and Mentoring skills.  If you need any further information on any of our courses, feel free to contact us.


3rd February 2020


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