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Sparking engagement in the mentoring relationship –  Questions to Ask

If you’re just starting out with mentoring up and coming Leaders, you might not know what to say to your mentee when you meet with them. After all, no one wants to end up telling long-winded, irrelevant stories to your mentee, or be too directive and giving advice, or too standoffish and struggle to connect with their mentee.

One of the qualities of a good mentor is listening. It’s helpful for the mentee if they do most of the speaking. Therefore, the best way to get the conversation rolling is to ask good questions.

The best types of questions that a mentor can ask their mentee are deep, probing questions that spark dialogue with your mentee. It’s best to avoid “yes or no” types of questions as they tend to limit discussion.

Additionally, questions can help prompt your mentee to reflect on their experiences to gain new insights.

At Anchor Excellence our AnchorMentor program uses our signature framework to balance working in and working on as well as explore key questions relevant to career and life.

Consider asking the following questions to your mentee at your next meeting.

What does success look like to you?

One of the first steps in a career mentoring relationship is to establish goals for the relationship.

If you’re in a formal mentoring program like AnchorMentor, then you can also take the conversation much deeper.

What obstacles do you see that might prevent you from achieving success?

Mentees may be reluctant to share the obstacles they are currently facing in their career.

Especially when the mentor and mentee first meet, they may be eager to impress their mentor and want to play up their strengths. Similarly, mentees may feel a little vulnerable early in the relationship.

However, for a professional mentorship to be successful, it’s necessary to identify what might be holding the mentee back from achieving their version of success.

What things have you tried to overcome these obstacles? What’s working well, and what’s not working as well?

By asking your mentee to think back to what they have tried in the past (or what they’re trying currently), you prompt them to reflect on their own experiences. This discussion can help the mentee come up with new ideas and solutions on their own or jointly with you.

Remember, the role of the mentor isn’t to be directive or tell the mentee what to do. Telling the mentee what they should do prevents them from reaping the benefits of mentoring. You can best help your mentee by working with them to think through problems.

In which areas do you feel confident that you can handle on your own, and in which areas do you feel you would benefit from outside support?
It’s not always helpful to ask your mentee, “What can I do to help you?” because your mentee is unlikely to know the answer. Your mentee isn’t likely to know your specific talents and how you can support them.

Additionally, in general the role of the mentor is more than just delivering what the mentor has to offer. The mentor should help connect the mentee to other resources and people that can support the mentee in achieving their goals.

By defining what the mentor has under control and what they need help on, the mentor and mentee can jointly come up with a plan to get the help that the mentee needs.

What other things do you know about?

Mentoring is no longer a one-way street. To get the most out of your relationship, consider “reverse mentoring” and find out what you can learn from your mentee.

Perhaps they have recently graduated  or completed a certification program, and their technical skills are more up-to-date than yours. They may work more closely with your organisation’s clients or customers, and could have important insights. Or, they may be more technologically savvy.

By engaging in reverse mentoring, you can gain new knowledge, skills and insights, and give your mentee the opportunity to take on a mentoring and coaching role themself.

From your perspective, how is this mentoring relationship going?

A good mentoring software program will help you answer this question by reminding you to check in with your mentee from time to time. It’s critical that both the mentor and mentee are able to speak openly about the professional mentorship itself.

Maybe there are specific needs that the mentee has that aren’t being addressed, or a more convenient time or place for the mentee to meet. But, you likely won’t find out until you ask.

The role of the mentor isn’t to give advice, but instead to ask questions and listen. Try a few questions out with your mentee next time you have a meeting. If you’re using mentoring software, you can even send these questions to your mentee ahead of time so that they have time to think about the answers before your first meeting.

Professional mentors can use these questions to build rapport with their mentee, prompt their mentee to think through issues on their own, and ultimately promote a more productive and successful professional mentorship.

For more information about the AnchorMentor program please visit or reach out to

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