Mutual Mentorship (Mentor–Mentee Relationships)
The Mindset: The best mentor–mentee relationships feel like true partnerships. Both parties are actively learning and invested in one another. Mentorship is an ongoing gift, not a transaction.
Foundations of Mutual Mentorship:
- Relationship First – Build trust and shared understanding.
- Gift Exchange – Mentors offer suport and guidance for learning; mentees bring fresh perspective. There is mutual learning and gratitude.
- Skill Development over Answers – Great mentors create independence, not dependence. Great mentees ask questions like “what am I missing?” or “what do I need to learn for myself?”
The Q.E.D. Framework:
Q – Questioning – Focus on open-ended questions that deepen understanding.
E – Establishing Fidelity – Confirm clarity and check for mutual understanding.
D – Deciding What to Apply – Encourage reflection as to what really applies to you before taking mindful action
Use this framework as the operating system for your mentoring conversations.
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Mutual Mentorship: Mentor–Mentee Relationships
Building the Relationship Organically
Before you can extract value, there has to be a relationship. How do you develop one organically, especially with people who aren’t that accessible, without it feeling artificial or like you’re just using the person? There’s a power asymmetry between mentors and mentees, and at the beginning the mentee often has to give more. In the real world it’s rough.
The key is to remember it’s a gift, and you don’t give gifts to people you don’t like, so find people you’re connected with, where you have some history, and build the relationship first. The other side matters too: if you ask for help from somebody and it turns out you don’t like them, receiving that gift is really hard even if you respect them. So if a relationship seems forced right away, there’s an issue. As one mentor put it, it’s like looking for a girlfriend or boyfriend with a checklist of 20 things: if you cross people off for missing a few, you miss out on all the other stuff. It should be fluid, natural, almost instantaneous, so they’ll want to help you. Get outside your building and go talk to customers, potential partners, and suppliers; some of the best mentors are people you’re trying to get to know.
Make Your List: What Does a Great Mentor Do for You?
If you’re going to find a great mentor, you’d better know what you’re looking for. What makes a great mentor? The audience’s list: knowledgeable; a good listener (given everything about open questions and hearing you, this is very important); domain expertise relevant to what you’re building; a great network; personally relatable, someone you like (the need for a relationship); honest (you have to trust them); invested, meaning they care about your project and what you’re trying to accomplish; and accessible (what use is a mentor you can’t keep connecting with?).
So the first thing to do when looking for a mentor is make your list of what your mentor will be to you. I’m amazed how many people looking for a mentor haven’t made their list. Job one: write down what you’re looking for, be really explicit. Even if that list never physically appears, you’d better have it in your head. Some things you can research yourself: if domain matters, Google it, that’s your job; don’t ask them whether they know about medical devices.
The Mutual Contract
You’ll never find a mentor who meets everything on your list unless you’ve worked with them for years. As one mentor honestly said, a list “can close you off from realizing value or beauty or the experience of where you actually are.” So have a dialogue and set expectations together. A great mentor immediately has that conversation: “I know you want Jesus Christ Superstar, but unfortunately I’m just mortal Matt. None of us is perfect or will have your whole list, but here’s what I bring to the table, and had you thought about these other things I also bring, would that be useful to you?”
One of the first problems in the mentor–mentee relationship is that there’s no contract; it’s not made mutual up front. You don’t sit down and have that discussion, so you have no idea what your expectations are of each other, and you start off mismatched by definition. It doesn’t have to be a formal conversation (in reality it’s very informal), and you don’t literally go through a list, but in your head you’re checking: does this person feel accessible, honest, like someone who’d get invested?
What do mentors look for in a mentee? First, that you showed up to a hard, abstract class like this, where you’re not walking out with three actionable answers. Second, that you were paying attention and engaging: “Michael, I’ve observed your A, B, and C, and I think I’m looking for A, B, and C. I also think I need D, E, and F, and I know you don’t have that, but maybe you have G, H, and I that I should be thinking about.” That’s a great conversation to approach a mentor with. I try to understand where someone is coming from, what they’re looking for, whether I’d be a fit and could really help. Remember it’s a gift, and the best thing about a gift is when it’s received by the right recipient who really appreciates it.
A Mutual, Safe Relationship, and Regular Check-Ins
We haven’t mentioned one word, but I bet it’s on your list: safe. A good mentor–coach relationship with a mentee is safe. You should be able to tell them anything: your worst fears, your greatest challenges, and those moments of darkness, because that’s where you come out.
Startup Secret (from my own first mentor, who reminded me of it over lunch just two days ago): things are never really quite as bad as they seem, but they’re also very rarely as good as they seem. A good mentor helps you see that. When you’re frustrated and down, they help you realize it’s probably not as bad as you thought, so take a deep breath, come back tomorrow, and reframe. And when you’re carried away with enthusiasm (you got your first customer and believe the next hundred will be just as easy, which is unlikely), they temper your enthusiasm and keep you realistic.
How do you know you’ve got a good relationship? Ask the question: is this working? Regularly. If you’re a mentor and don’t feel you’re doing well, ask the mentee, “How could I help you more? What might be a better way? What didn’t work?” And flip it: if you’re a mentee and it’s not working for you, say, “I’m not sure this is working for me; I’ve got these questions; how could we improve it?” This leads to a simple recommendation: record and review regularly, agree on check-ins, whether once a week, once a month, or daily. This business of checking in and asking how it’s going is really important. We’re trying to get to a mutual relationship where feedback is enjoyed by both of you and you both want to learn.
And how do you let a mentor know you had an aha moment? Ideally in person. It’s so rewarding for a mentor to hear, “I went away, thought about what you said, had this aha moment, and now have the confidence to go do something with it, and it feels right.” That’s what gets me out of bed in the morning. It’s a huge win-win, a flywheel of positive reinforcement.