I am a big fan of mentoring when done right. Many companies have mentoring programs where they connect people over a reasonably short period for mentoring purposes. My experience with most of these is that they don’t work very well. They provide some limited value. But that value is more like taking a class. Good information but not life or job-changing. That is because there is no real relationship built and because the mentor does not know how to ask questions that will help them to fully understand the mentee.

The Article

The article “The Best Mentors Ask These 8 Questions” by Gwen Moran, does a nice good job. The questions provide a good mix of who the person is and what they want to grow into, together with what the challenges are that they are facing and how are they working through them.

Below are a few specific comments on the 8 questions.

What does success look like to you?

This one is good both in terms of their current situation as well as their bigger picture.

What is the outcome you want?

This is pretty generic and can be used for short-term situations as well as their vision for the future. I think that it would be better to keep this short term. There are other questions to help understand how they see themselves in the future.

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

This is a fairly standard question. I think that it is both good and bad. People have heard this kind of question many times, especially during the hiring process. As a result, they frequently have a standard answer. If you are going to use it, be sure to probe deeper.

Two similar questions that you might consider using:

Tell me about your ideal career journey.

What would the perfect job be for you in three to five years?

What are the obstacles you’re facing?

This one is great as it relates to a specific situation. Especially followed by the next two.

What can you control?

I really like to ask what is in your control. It is often surprising how much is under your control.

There can be a bit of a downside. If the answer is none, they might feel worse after your conversation. And if they underestimate the control that they can have, you might not realize it and therefore can’t address the core issue.

What are the options you’ve come up with?

This is another great question. Just by asking – you often get them to think about the options more thoroughly!

Tell me more

Pretty generic, but fine to ask. I would more likely tie this to the other questions to make sure they tell you everything that you need to know to help.

What are you reading?

This is good to know. It tells you something about the person and gives you an opportunity to suggest a few books, websites, or podcasts based on the rest of your conversation.

What’s Missing

There are at least three things that I think are missing – all related to really understanding the mentee better.

A set of questions about leadership style

I really like to understand the leadership style of anyone that I am mentoring. It tells a lot about how they think, how they act in different situations, when they will be successful, and where they will be challenged.

The kinds of questions that I ask in this are typically related to specific situations and how they handled them.  I recommend asking about at least three different situations – the more diverse the better. Drill into each answer to make sure that you fully understand how they interacted with the team, how decisions were made, meeting cadence, and so on.

I prefer not to pass judgment when understanding the mentee’s leadership style. I instead prefer to take their style mostly as a given and help them to understand how to successfully work within it. Any recommendations to change their style tend to be limited and incremental in nature.

Some questions about work-life balance

My opinion is that understanding your mentee’s work-life balance is critical to helping them over the long haul. Spending time on this upfront and throughout can lead to a very positive and long-lasting relationship – which is where I believe the most mentoring value is derived.

These are easy questions. People, in general, like to talk about themselves, or at least about their families. Take advantage of their openness. But don’t stop only on the family. Make sure that you understand where the right work-life balance is and help them to achieve both their career and work-life aspirations!

And questions related to their ability to navigate the organization in getting things done

This area is difficult to fully uncover, but it is worth the effort. As you are talking with our mentee, probe into the organizational aspects of everything that you discuss. Understand how strong their network is, how well they understand the company culture, and how many different ways they approach organizational-related challenges.

What you will want to do is help raise awareness and where possible make suggestions for new, different, and better ways to get things done.

Closing Thoughts

I am a huge fan of mentoring. There are benefits for both the mentee as well as the mentor. So jump in.

But if you want the most out of a mentor relationship, and you are compatible during your interactions, then consider continuing for the long haul. Ask the right questions that will build the kind of relationship that will last. You will really enjoy the result!

See Also

Become Way More Productive

Finding Work Life Balance

What Does It Mean to Give as a Leader

Categories: People


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