8 Mentoring Questions

To nail the delicate chemistry required for a successful mentoring match, eight questions have proven to be particularly telling, says Narcisse — four that mentors should ask, and four that mentees should ask:

For mentors

1. Can I clearly be helpful to this potential mentee? Have they reached out with clear reasons or intentions for why they’d like my help? Are there specific needs they have that I can address?
2. Can this person be completely open and honest? Are they willing to provide deep context about their problems and vulnerabilities? Will they be able to share data, metrics, goals, slide decks, etc. that will help in the process?
3. Is this person prepared? Do they tend to be proactive about setting up time and providing enough context or an agenda upfront? Do they direct conversations and ask specific questions? (Be wary of people who want more general help or to touch base without a topic in mind.)
4. Does this person give me energy? Do I usually learn things from this person myself? Does talking to them allow me to reflect differently on my own business or path? Has talking to them in the past felt like a good use of time? Do they inspire me to think more deeply, even though they have less experience?

For mentees

1. Does this potential mentor remember key details about me? Have you had to continuously repeat yourself or remind them about who you are or the context of your job every time you see them? This doesn’t bode well.
2. Will it be hard to explain the concepts or context of my job? You should choose someone who is close enough to your industry and functional area so that very quick, even shorthand explanations will do, and they can immediately dive in and understand your primary challenges and goals.
3. Can this person give actionable advice? Have they told you something in the past that you’ve been able to apply right away? Are they a good teacher? Do they share tactics, or do they generalize? If they don’t recommend specific actions to take, then pause. They might be too senior and removed from the day-to-day work. You might be better off with a skip-level above you than an executive.
4. Does this person seem present and focused? Great mentorship requires undivided attention. Sure, everyone is busy, but in the past, has this person listened to you with intent? Do they give you or others their full attention when they’re in listening mode? Or are they looking at their phone? Do they interrupt?

Depending on which side of the equation you find yourself, ask the relevant set of questions. This can help to pare down the list of people you’d consider working with. Once you hone in on a few who might fit the bill, consider sending them a version of the other list of questions (i.e. if you’re a mentee, send them the list of mentor questions).

They don’t have to tell you their answers. Frame it as some thoughts to consider before entering into a more regular arrangement. It will make you appear and feel prepared — and set strong expectations. It might also disqualify suboptimal candidates who won’t make the investment you’re looking for. If questions are answered positively on both sides, it’s very likely you’ll have a productive match.

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