Virtual Mentoring Conversation Starters

Virtual Mentoring Conversation Starters

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by Laura Francis

August 25, 2020

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Millions of us are working from home now due to the coronavirus pandemic. As we juggle video calls for work and homeschooling our kids, we shouldn’t lose sight of how we can stay connected with our professional networks. Virtual mentoring has become a lifeline for many people.

For those new to the process, here are conversation starters to help you get to know your mentee or mentor through a virtual connection.


Questions Mentees Can Ask

1. Have you mentored anyone else?
This question will help you assess the person’s experience as a mentor and can lead to a conversation that digs into their views on mentoring, what role the mentor should play, what they expect of you as a mentee, and so forth. This type of understanding plays a key part in building a solid relationship with your mentor.

2. Why did you want to become a mentor?
This is a great question to ask someone because it gets to the heart of their motivations. Were they nominated or otherwise asked to be a mentor by someone else because of their job role or experience? Do they want to give back to those around them because they empathize with people and recall what it was like to need a helping hand? There could be multiple reasons why someone agreed to be a mentor; understanding why can help you better understand what to expect.

3. Tell me a little bit about your experience with [state your goal/mentoring topic].
While many people may think they must have the master expert as their mentor, you may find that a relative newbie is a good fit for you if you are also just starting to learn about a topic yourself. You want to find someone who can recall what it was like to be in your shoes and who can help you trek along your learning path. And consider this: If they recently walked that path, they may provide some good advice that an expert could have forgotten.

4. What was your biggest aha moment when you were learning about [state your goal/mentoring topic]?
This question allows you to discover what excited this person about the topic at hand and what their learning journey was like. Their aha moment may also be a great learning moment for you and become a point at which you and your mentor can start a profound conversation.


Questions Mentors Can Ask

1. Why do you want to learn about [state your goal/mentoring topic]?
This question will help you uncover the mentee’s motivations for mentoring. Do they want to improve a skill area that they hope will lead to a promotion? Are they deeply interested in a topic area and want to expand their knowledge? Do they have a work issue they want to address? No matter their motivation, it is helpful to learn more about it so you can be prepared for what they want from you as a mentor (which leads us to the next question).

2. How do you hope that I can help you?
Each mentor brings with them a unique background, point of view, skill set, and so on. Why did this mentee specifically seek you out? What do you offer that they are hoping to gain? Asking about this up front can help you set expectations with the mentee as well as identify any boundaries that you may feel are important.

3. Is this your first virtual mentoring relationship?
This question allows both of you to share your history with mentoring and can help you formulate what the relationship will look like. Perhaps one of you has had a virtual mentoring relationship before and can provide some tips on how to navigate that. Or maybe both of you are new to this process and can discuss what you expect of one another as part of this relationship.

4. What obstacles have you overcome to get where you are today?
You will get to learn about your mentee and their life journey with a question like this. It can reveal what areas they found challenging in their work (and possibly in their life in general), and it can create a wonderful opportunity for you both to open up to one another about yourselves. That candor can help build trust between you, which is critical for any mentoring relationship but even more so for one virtually taking place. Now is absolutely the time when you should be brave in mentoring.


Use these questions as a starting point for your mentoring relationship, not the endgame. Engage in open conversations with one another and see where it takes you. This is your relationship and you can shape it however you want.


Laura Francis is Chief Knowledge Officer for River, a mentoring software company based in Denver. River was acquired in 2020 by MentorcliQ, the leader in employee mentoring software, and River will operate as a wholly-owned subsidiary of MentorcliQ.  Laura has been with River since 2000 and was part of the team that launched the first-ever commercially available online mentoring software in 2001. She has more than 20 years of experience focused on mentoring, writing, thought leadership, and strategic innovation.


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