How To Use Virtual Mentoring To Get Unstuck

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Tamara Franklin



Many successful people rely on mentors to help them reach the next level. Bill Gates seeks advice from Warren Buffett. Oprah Winfrey was mentored by Maya Angelou. And if you want to take it waaay back, Socrates mentored Plato, and Plato went on to mentor Aristotle.

Virtual mentoring activities

So, whenever you feel unsure of your next move, seek out someone who has done it before to guide you. 

Thanks to technological innovations that would likely blow Aristotle’s mind, entrepreneurs can now get advice from experienced professionals anywhere in the world from the comfort of their home. This makes it easy to find the help you need when you need it.

What Is Virtual Mentoring?

Virtual mentoring refers to any mentoring activity that does not occur face to face. 

Virtual mentoring involves an experienced individual providing guidance and advice, and can be an ideal solution for busy entrepreneurs who might not have the time to meet with a mentor in person.

Today's communication tools, including Zoom, Google Meet, telephone, email, and direct messaging, open up this style of mentoring to more people.

Benefits of Virtual Mentoring

Virtual mentorship can be a game changer for entrepreneurs, whether you’re just starting out or trying to scale your business. It can also do wonders for your employees and help establish a learning culture. Here are a few ways virtual mentoring can help you and your staff excel.

Higher retention rate: Mentoring can help employees stay motivated and cultivate a supportive team environment.

Closer relationships: Communicating openly and honestly fosters authentic connections between colleagues. Mentors and mentees who meet online can develop a sense of mutual respect and understanding.

Silo-busting: A virtual mentorship program can help break barriers between employees from different departments or offices. Mentees who might feel uncomfortable interacting with senior executives can communicate through emails, Microsoft Teams, Slack, or Zoom instead.

More authentic matches: “One of the top benefits of virtual mentoring… is that it helps individuals create more effective mentor/mentee matches," says Alyssa Wright, CEO at fundraising consultancy Wright Collective.

“If you’re able to curate partnerships across several offices and locations, the pool widens to allow more strategic and thoughtful relationship building. I’ve seen this enhance skill development time and time again, versus limiting mentoring opportunities to one physical location and pool of employees who may possess similar skills and cultural conditioning.”

Examples of Virtual Mentoring

There are many ways to implement virtual mentoring in your business. Try one or all to see what works best for you and your team.

One-on-one virtual mentoring

The most common type of mentorship. You schedule regular video chats with another entrepreneur who is accomplished in your field to discuss your goals, barriers, habits, and more. To implement virtual coaching within your company, you could pair new hires with experienced employees as a part of the onboarding process.

Virtual mentoring groups

Mentoring doesn’t have to be only one-on-one. You can set up virtual mentor groups that meet regularly to discuss common challenges and share lessons and tips. Group members can set goals, help each other achieve their targets, and offer accountability.

Virtual employee resource groups

You could design mentoring programs focused on uplifting specific underrepresented groups in the workplace, such as for employees who are LGTBQ+, caregivers, veterans, or female. Workers from various backgrounds would meet virtually as a cohort and discuss common experiences and share advice. 

Limitations of Virtual Mentoring 

Difficulty in forming a connection

While virtual mentoring might benefit some people who are uncomfortable in real-life social situations, it could also be detrimental to others. People who value body language when communicating may struggle or feel awkward if they don’t get enough eye contact.

“When you’re sitting next to someone, it’s a lot easier to feed off their energy and create a strong rapport. That level of connection is harder to establish virtually,” shares Jessica Brown, an entrepreneur and book editor. 

How to make it work: Encourage mentoring sessions on video calls instead of over the phone whenever possible. Try icebreaker games and social times (e.g., virtual coffee) to help your mentor and mentee get to know each other. After the first two sessions, check back with the group to see how things are going.

Lackluster chemistry 

Sometimes, mentors and mentees just don’t click. Having an ocean between them can make it worse: There’s just something about awkward long pauses on a video screen.  

How to make it work: A mentor pairing should reflect on why they feel the chemistry might be lacking, but they shouldn’t be forced to continue the session if they don’t feel it fits. 

Set up templates and procedures for how mentors and mentees can resolve issues. In this case, encourage an honest evaluation and discussion, and make it easy to rematch the pair to other colleagues. 

Technical issues

Technological glitches can be time-consuming and frustrating. Nobody wants to reboot their computer during the middle of an important session.

How to make it work: Both parties should ensure they have a stable internet connection before starting the session. They should also plan for backup options if one of them experiences an interruption in service, such as switching to a mobile video chat app or making phone contact. 

Zoom fatigue

Spending all day on video calls can be exhausting and may cause you to feel less engaged than if you were face to face with your mentor.

How to make it work: Mix things up! For example, opt for a phone call one day. Or, if the weather's nice, video chat with your mentor while you are on a walk. You can also experiment with virtual reality meeting technology for a change of scenery. Lastly, if you happen to be in the same city as your mentor, try the occasional IRL meet. 

Virtual Mentorship Best Practices

Clarify rules of engagement

Virtual mentorship often requires more focus on getting the logistics right. 

Decide how often you’ll communicate, whether you’d rather do so via synchronous (e.g., video-based platforms, phone calls) or asynchronous (e.g., emails, instant messages) methods, and what times of day would be best for each party. 

Consider what feels comfortable for both sides — for remote workers, be flexible about scheduling meetings around other responsibilities like caring for family members or homeschooling children.

Stay focused during meetings

To succeed with virtual mentoring, the mentor and mentee must be fully invested. Demonstrate your interest and commitment by showing up on time, eliminating distractions, practicing active listening, asking smart questions, and appreciating each other’s time. 

Discuss as a pair whether you should record your sessions. On the upside, it will eliminate the need for constant note taking and allow both sides to be more engaged in the conversation. However, it could make your conversations less relaxed if one party is nervous about being on a recording. 

Give and receive feedback

One of the most important aspects of being a mentor is providing honest and actionable advice and guidance. And if you’re being mentored, don’t be afraid to ask for feedback on how you are doing, and give your mentor feedback on how their guidance is helping you.

Is their mentoring style effective? In what ways have you incorporated their feedback? Are they communicative, responsive, and reachable? Actionable feedback to and from your mentor helps both parties get the most of the practice.

Virtual Mentoring Activities

One-on-one mentoring activities

One-on-one mentorship programs must focus on the mentee’s development; here are some activities that can help them grow:

  • Check-Ins: Talk to your mentor about a positive and negative experience of your week and allow them to offer advice on how you did or how you could have done better. 
  • Q&As: Ask thoughtful questions about your mentor and their life experiences to learn from their successes and mistakes.
  • Skill Development: Ask your mentor to run a mini-workshop on a skill they have that you'd like to learn or improve on.
  • Career Mapping: Have your mentor help you map out the steps needed to achieve your ultimate career goal.
  • Job Shadowing: See if you can shadow or accompany your mentor as they complete tasks like pitching a business idea to potential investors or attending a board meeting. 
  • Project-Based Learning: Ask your mentor for the opportunity to work on a project you are curious about. 
  • Current Events: Discuss with your mentor current events within the industry or the world, and get their insights on how they see current trends impacting the future. 
  • Storytelling: Wright suggests incorporating storytelling activities in mentoring plans. “You can start with simple questions like, ‘What legacy do I want to leave? What can I learn from the work ahead? What are the best and worst things about my leadership style? How can I do better?’”

    For an additional benefit, Wright recommends drawing pictures, making collages, or sharing photos that help tell your story in a creative way. “Incorporating art into mentoring activities enhances critical thinking and can support entrepreneurs psychologically, improving memory and inspiring resilience.”

Peer mentoring activities

If you implement a mentorship program in your company that pairs employees of similar rank or positions together, try some of these tactics:

  • Elevator-Pitch Sessions: Have mentees help each other craft elevator pitches for their ideas through brainstorming, feedback, and revision.
  • Problem-Solving Sessions: Encourage mentees to meet regularly to discuss solutions to workplace challenges.
  • Knowledge Sharing: Give mentees the space and time to share skills and knowledge and help each other learn new skills.

Group activities: 

Group mentorship programs are great for feedback, knowledge sharing, and community building. Some activities to try:

  • Masterminds: As a mentor, meet with your group of mentees to explore different options for growing your business or reaching other specific professional goals.
  • Team building: Identify common objectives and work toward them by brainstorming and solving problems together.
  • Current events: Stay informed by reading news stories about your industry or position and share what you’re learning with the group.


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