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The Best Mentors Ask These 8 Questions

An essential part of being a good mentor is asking the right questions. Here’s a cheat sheet to get you started.

The Best Mentors Ask These 8 Questions
[Photo: littlehenrabi/iStock]

It’s hard to deny that good mentors are important. The best workplaces have formal programs to develop mentoring relationships. LinkedIn has even launched a feature to help you find one. And how to be a good mentor is a topic of perennial interest.

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One of the most important characteristics the good ones have in common is their ability to ask insightful questions, says Lisa Z. Fain, CEO of The Center for Mentoring Excellence, a mentoring consultancy and coaching organization.

“For mentors, the most important thing, really, is to ask questions, to be this guide on the side, rather than the sage on the stage,” she says. And to do that, you need to be inquisitive. Here are eight questions good mentors ask.

What Does Success Look Like To You?

The beauty of this question, which is another version of asking about the protégé’s goals, is that it can be adapted for big-picture scenarios or specific situations, says transformation management consultant Christie Lindor, author of The MECE Muse: 100+ Selected Practices, Unwritten Rules, and Habits of Great Consultants.

Asking what success looks like can refer to long-term goals and planning. However, when applied to a specific situation, it can help determine what the immediate priorities are for a project or situation, she says.

What Is The Outcome You Want?

Similar to the previous question about what success looks like, this question is effective for situations where there is more than one equally viable solution or course of action, says Jennifer Labin, principal at mentoring consulting firm Terp Associates, and author of Mentoring Programs That Work. 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.

“If [the protégé] is facing a really complicated situation, that is often the best question you can ask to help them lift their head up and start to look at the situation from an entirely new angle,” she says.

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What Do You Want To Be Different In Three To Five Years?

Fain likes this question because it focuses the protégé on a long-term outcome while focusing in on areas that may require growth or change. Since the business world changes at such a fast pace today, focusing on a shorter window—perhaps three 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 protégé wants to grow, or fundamental changes they need to make in order to achieve their goals, she says.

What Are The Obstacles You’re Facing?

Mentors can be invaluable in providing insight to overcome obstacles, Fain says. However, protégés may be reluctant to share the challenges they are facing, or may not have really thought them through. Asking about them outright allows the mentor to explore the challenges with which the protégé is struggling, and also discuss the individual’s strengths and weaknesses in addressing them.

“Most of us know where we are weaker, and yet we haven’t been able to address it. Identifying what the obstacles are is a really great place to start,” she says.

What Can You Control?

Labin likes this question because it shifts the focus from ruminating about factors that are beyond the protégé’s control and onto what they can actually do about the situation. You might not be able to change an unfair corporate policy immediately, but you may be able to find short-term answers to help you deal with it while you work on longer-term solutions.

What Are The Options You’ve Come Up With?

When faced with obstacles or challenges, Lindor expects her protégés to also have some idea of how they’ll address them. Even if the protégé is struggling with what the right answers are, having at least a few ideas ensures that the individual has given the matter some thought and isn’t just relying on her for answers.

“I facilitate a conversation where I allow them to discover the answer in a safe space, and they can walk away and own the solutions,” she says. “I can fill in gaps or, depending on the person, I may trigger another thought [or] chain of thought.”

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Tell Me More

“We’ve all heard that saying, ‘There are typically three versions of every story—your story, their story, and the truth,'” she says. While not technically a question, this statement prompts the protégé for 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 judgment. 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, she says.

What Are You Reading?

Lindor asks about interests, hobbies, reading habits, and other similar questions to get to know her protégés on a more personal level. Doing so helps give her a more holistic understanding of who they are as people, she says. That can be important in helping to guide them to the right answers and insight, she says.

About the author

Gwen Moran writes about business, money and assorted other topics for leading publications and web sites. She was named a Small Business Influencer Awards Top 100 Champion in 2015, 2014, and 2012 and is the co-author of The Complete Idiot's Guide to Business Plans (Alpha, 2010), and several other books.

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