In Conversation
How an Intergenerational Convening Led to a Co-Mentorship
In Conversation with Maddie Freeman and Jaspal Sandhu
Maddie Freeman and Jaspal Sandhu are co-mentors who developed their professional, intergenerational relationship at a convening hosted by Hopelab and the Arthur M. Blank Family Foundation. This event brought together young leaders and funders to explore the opportunities and challenges in youth mental health. Maddie, the founder of NoSo, is dedicated to educating young people about social media’s addictive design and its impact on mental health.

Frequently asked about their co-mentorship — from its origins and how to start one, to potential pitfalls — Maddie and Jaspal address these questions in the following conversation.
This content has been edited for clarity and length.
Question 1: What does it mean to be a co-mentor?
Maddie: Sometimes I’ll be talking to my sister or friends on the phone, and I’ll mention that I have a co-mentorship meeting later. They’re like, “What is that? You mean mentor, right?” And I explain that it is different – that we mentor each other. People are always a little caught off guard. But at the same time, they think it’s really cool because we’re so used to having a mentor who is always older and tells you what to do all the time. And usually, there is no reciprocal energy.
I’ve found a lot of value in being co-mentors with you (Jaspal) because we share expertise in different areas. That stems from a mixture of lived experience as well as education and also work experience. And there are my own entrepreneurial experiences as well as my experiences as a young person growing up with social media impacting my day-to-day life. That’s a lot of different perspectives! Co-mentorship, to me, means the fusion and the blending of different experiences in life and being able to support each other in different ways regardless of age or expertise. Co-mentorship is the ability to be equal parts of a whole.
Jaspal: Co-mentorship is really about the relationship and getting value out of it. To really do co-mentorship, you have to do it in a way that’s not about checking a box or showing other people that you did it. It’s not a transactional relationship, it’s multi-directional. It’s really about the value that we are getting out of it, not the value that we’re showing to other people.
Co-mentorship means the fusion and the blending of different experiences in life and being able to support each other in different ways regardless of age or expertise. Co-mentorship is the ability to be equal parts of a whole.
Question 2: Who needs a co-mentor?
Jaspal: In our space – youth mental health and well-being – I am inclined to say almost everybody needs a co-mentor. However, I think there is a difference between who needs a co-mentor and who might be ready for a co-mentor. I don’t know what makes people ready or not ready, but if somebody is not ready to accept the role of a mentor or to accept they need a mentor, I think it is not going to work out. Co-mentorship has to be driven intrinsically from the heart and the mind that the two people want it to happen, that they’re seeking it out, that they feel like it’s right, and that they see the time is now.
Maddie: I think everyone needs a co-mentor. I think it’s helpful for young people and adults, especially within mental health. A lot of organizations are very focused on youth and their offering being youth-centered, but there’s not as much bringing youth to the table as there could be. For an adult, having a co-mentor who’s younger can be such a catalyst to really deeply understand young people’s needs. As a young person, especially one like me who has their own organization, having someone who has professional experience creating and leading organizations helps me grow my organization. I feel like it’s really a two-way street and young people and adults can really benefit from having a co-mentor.
Question 3: Do you have any strategies or approaches a person can utilize to initiate and cultivate a co-mentorship connection with someone they admire or respect in their chosen field or area of interest? How do you find a co-mentor?
Maddie: That’s a good question. I feel like we got really lucky because the incubator where we met was a good spot to get to know each other. It was a good time to establish a connection and vibe and, at the same time, hear each other’s intentions and goals for the future within the work we do.
I think setting an intention in your mind to scope out a co-mentor at a conference or professional event could be a good starting point. You could even use co-mentorship as an icebreaker question: “Hey, have you ever heard of a co-mentorship?” and see where that goes. Intentionally going into spaces and seeing if anyone fits a match for you.


Question 4: What are the key challenges or obstacles that can arise in intergenerational mentorship relationships, and how do you recommend addressing or overcoming them?
Maddie: That question was a little hard to answer because we haven’t had any conflicts. We’re also not super deep into it yet. There’s always the chance of unequal support—one person taking too much time and energy from the other. One co-mentor could feel like they are not getting much out of the relationship, and that the other person is benefiting more.
Jaspal: Looking back, I think if we had, what I’ll call “a business relationship,” meaning that Hopelab and No So November were working together in a contractual way, that might have complicated our mentorship relationship. Things can always change over time, but there was no expectation that this mentorship would lead to a partnership. If we ever get to that point, we’ll navigate it.
Maddie: I like what you said about not having a formal partnership when we started our co-mentorship because I agree. We’re working towards similar goals in terms of mental health and well-being for young people and we’re also in separate bubbles that aren’t always bleeding together. Because of that we’re able to take that outside perspective with each other and support each other with our similar missions. That’s been something that has allowed us to get a lot out of this relationship.
Question 5. Do you have anything else you’d like to add?
Jaspal: I’m really grateful you participated in the convening we hosted with the Arthur M. Blank Family Foundation. We were looking for exceptional young leaders in youth mental health, and it was really clear why you were recommended to attend. Every time you show up in any of the spaces I’ve shared with you, you show up with a lot of authenticity and integrity. I know those words get thrown around a lot, but what I appreciate about you as a person, as a leader, and as my mentor is that integrity comes first. You speak to the things that are important, not just what is in your interest or the interest of your organization. You’re about doing the right thing first.
Maddie: That means so much. It makes my heart feel so warm and full. I feel like a big reason we really connected is that I feel that you share those same values and that you’re authentically yourself no matter what room you’re in and no matter who’s around you. I’m so grateful that we’ve gotten the opportunity to connect, and it means a lot that you speak so highly of me; I hope you know I feel the same way about you.
Key Takeaways
Jaspal and Maddie offered some tips and best practices that are helping their co-mentorship thrive.
A co-mentorship thrives on intention and regular communication.
Maddie and Jaspal meet every two to three weeks, with sessions lasting 40 to 60 minutes via phone, Zoom, or in person when they are in the same city. They alternate the focus of each meeting—one session addresses Maddie’s needs, while the next centers on Jaspal’s.
While there’s no single formula for a successful co-mentorship, this approach works well for them. As you consider these takeaways and reflections, you may find yourself ready to embrace the role of co-mentor.
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