Mutual Mentorship

▶ Watch the original lecture

Mastering the Gift of Mutual Mentorship

Startup Secret: Mentoring is a gift. At its best it’s not one-way; it’s mutual. It’s a gift you enjoy giving and a gift you enjoy receiving, and if it isn’t turning out that way, you’ve got to change it.

Two ways to look at it: do you have this gift (are you already a gifted mentor), and do you give this gift? Mentoring is very rarely something paid for; that’s consultancy. Nobody I’m aware of is paying for this, so the question is how we really get the most out of the gift. I have zero answers and lots of questions, so this is a subject we explore together. This is one of the hardest classes I run, because it’s the hard soft stuff; you’re not walking out with three answers to action immediately.

Why do people come to a mentorship session? To find and get a mentor; to learn how to approach someone and get a relationship going; to be more creative about all the different ways a mentor can help (many people’s lists are too short); to maximize the time and output with a mentor; and, again and again, to make it mutually beneficial and a real relationship rather than something transactional, where you just ask a question, they respond, and weeks later you have another. Mentors come to be good at what they’re doing too, because it’s a two-way street. A good word for it is exchange: an exchange of value, and it should be fun, because relationships don’t last if they’re not fun and enjoyable. One mentor put the exchange differently: somebody gave help to me, and I’d like to exchange that not by giving it back to them, but by giving it to somebody else. So it’s exchange and pass along.

How to make use of mentors is something we don’t get taught. It’s an assumed skill: supposedly if I get a mentor, they must know how to mentor me, and I must know how to receive it. In fact that’s not the case, which is why this became one of the most popular things I’ve written, with tons of feedback.

I’ll give you three skills from a framework. They’re not the only skills; they’re examples to get us discussing how to get the most out of our relationships. In a nutshell, the three skills are QED: Questioning, Establishing Fidelity, and Deciding (taking advice mindfully).

Skill One: Questioning

Do you know how to ask for help? We all think we do. One founder, closing her first fundraising round, described reaching out to former professors: “I send an email: ‘Hi Professor so-and-so, hope you’re doing well, I took your class, I was remembering such and such and it came to mind as I’m trying to do this thing, and I’m wondering if we could meet to discuss XYZ.’ It’s never the first sentence that says ‘I need help.’”

That’s going about it the right way, because it’s less transactional. It opens with catching up and referencing prior history (the class), building the relationship. Remember, mentorship is a gift, and how often do we give gifts to people we don’t like? Start by building a relationship. If you ask for help from somebody you don’t get along with, it’s actually really hard to receive the gift, even if you respect them, whether it’s basic chemistry or cultural differences.

Now the question itself. Between “Should the answer be A or B?” and “How should I think about this problem?”, the open-ended question gets you the most help. Ask the most open questions you can, and fess up to the fact that you don’t know. It’s the most powerful, disarming, and engaging thing when somebody says, “I have no clue about this, I wonder if you could help me think about ABC.” I immediately think I’ve got an open-minded person who wants to learn. By contrast, “Do you think the answer is A or B?” gives me no context; even if I say A and think A is right, it might be completely wrong for them. When one founder asked “What are fair terms for an investment?”, that’s a decent starting question, but it’s not fully open, and it assumes terms are the most important thing about fundraising. An even more open question came from the group: “What do I need to know about the fundraising process?” That establishes priority and urgency, and opens up things you haven’t even thought of yet. We don’t know what we don’t know. The biggest challenge in mentoring relationships is that people start with a very specific idea of what they need to ask, when they may not even have the context for whether it’s the right or most important thing.

Why questions and not answers? If I could just give you all the answers, how would that do? Open-ended questions bring out lots of different things, leading to brainstorming and getting to the actual kernel of the issue, versus putting it in a box before you even start.

Don’t take the road already traveled. There’s an enormous temptation, even after starting with open questions, to lead down to a single answer. Suppose you finally get to “raise your Series A, and here’s how much.” The first thing to do is check: is this appropriate for you, no matter what anybody tells you? Even the two best mentors on the planet don’t have all the answers for their mentees. Who’s going to know more about your potential business, me or you? I hope it’s you. Who the hell is Michael Skok to give you an opinion about whether it should be seed or Series A, even with all the experience in the world? I’m not you. As one mentor, Matt, put it: “I wouldn’t tell you what to do. I’d try to get you to go through the steps that might be part of my process, without saying at each step how I would resolve it.” And even if you think the mentor is dead right and it feels right to you, ask this question: “What were the sets of things that led you to that conclusion?” Because if you just take the answer, you’ve learned nothing. You might have made the right decision, but when the mentor’s not there for the next decision, you have no framework, you didn’t learn their thought process. Great mentors won’t take the first answer from their history, because Albert Einstein said it best: “We cannot solve the problems ahead of us with the thinking from the past.” You’re trying to be your own original, innovative thinker. So the last question is: “What would I do differently? How would I innovate around this?” That’s usually what leads to breakthrough thinking.

This is also why I don’t recommend a single mentor. Mentors are usually good in one respect or another: some at a personal level (team building), some financially, some in your marketplace, and those are very different skills. There’s nothing wrong with multiple mentors, as long as you can manage the synthesis. Take as many as you can afford the time and energy for and are comfortable synthesizing; multiple viewpoints generally give much better answers. And bounce answers off a group: “Tom’s steps led him to say Series A, but would you have taken those same steps? Maybe not. Tell me why not.” That gets brainstorming going.

Close your eyes and imagine you have absolutely nobody to ask the next really important question in your life. What are you going to do? Nobody will be better armed to figure it out than you.

On getting unstuck. When you’re stuck, ask: Where can I get the best help? A good mentor is a pointer to resources; even if they don’t know, they might know a person who does, because a big part of mentoring is networking. Use LinkedIn; I purposely keep my network open. Then ask: is this one-off help (you just need the answer once) or continuous help (something you’ll constantly need, like hiring)? One founder looking for a CTO to help map historic Palestine and destroyed villages, and another looking for senior engineers, both eventually saw that hiring is a repetitive problem. If someone could either hand you your first engineer or teach you how to hire and assess engineers, take the teaching, because you’ll never stop hiring; hopefully that first engineer even brings more engineers. And what should you do with any answer you get? Figure out why they came to that conclusion: the path they took, the networks they tapped, their assessment methods, their diligence process, how they interviewed and qualified people.

The same applies to networks. Mentors often bring networks, and networking is the number one reason many mentees want a mentor, especially somewhere like the Middle East or DC where it’s all about who you know (one team got to the Smithsonian and the founder of the Palestinian telecommunications company that way). But even then, ask: how did you build your network? If the mentor disappears, you can’t access their network, and their contacts from 12 years ago are out of date. I built my network by being very systematic: in every business I was specific about which segments I went after, which CIOs I wanted to know, the groups they worked with, and how we built that. I’d far rather teach you how I did it than give you names.

Three tips when you’re really stuck. First, get your mentor to figure out where you’re stuck, and reframe. You might think you’re stuck on “I can’t find the CTO,” but ask why you’re hiring the person. In a board meeting, we had to let go someone in a critical role, and the whole focus became rehiring them. We changed the question: what’s the priority right now, building the product or getting it to market? We realized we had enough product; our real challenge was customer success, and one of the founders was really good at product management, so we changed the spec and filled it internally. We changed the construct. Mentors help by asking questions that seem irrelevant, especially about framing. As Matt said, “Usually when you’re thinking about a problem, you have some context you imagine the problem to exist within, and often the problem is better understood by taking a broader view, a higher level of abstraction, or asking something stupid like: is that actually a problem, or is it a good thing?” When we get really focused, we get stuck physically in a certain mode in the brain, and we need somebody to pull us back and reframe. Second, find a way not to get into that place again, because if you keep getting stuck in the same place, it’s frustrating for your mentor. Do a debrief: “How did you get stuck this time, or the time before? What were the series of events?” Is it a pattern? A mentor’s job is to get to know you and understand how you think (pictorial, logical, free-form), and to bring in someone who thinks differently from you. Third, everybody has a base need to problem solve; in a startup, day to day it’s problem solving.

Skill Two: Establishing Fidelity

The second most important skill is interpreting the information you’re getting and understanding how to apply it, and being open enough that when your first reaction is “eh,” you tamp that down and go, “Wait a minute, I need to be more open, the world is bigger than what’s in my head.” How you receive advice matters to the mentor: “That doesn’t apply to me” is deflating, a loss of energy. “I don’t think that applies to me, but I really don’t know, and I love that you shared it. Perhaps you could tell me how you think it might apply” is energizing.

I’m not even saying “listen,” because listening implies you agree or are taking it in. Sometimes just record it, write it down, even if at that particular moment you can’t take it in because you’re wound up in your own way of approaching things. A number of times I’ve written something down thinking it was a waste of time, then came back with a little more context or experience and finally understood it. And how often do people say, “Oh, I thought you meant ABC”? Don’t leave it to chance. Confirm right away what they actually meant. “Did you mean this?” “Hey, I don’t think that really applies to me, but could you tell me how you think it applies to me?” is also a way of confirming and getting more out of the advice.

One mentee asked how to balance being humble while still showing you’re competent, so the mentor wants to give you information. You don’t want somebody formless, without goals or objectives, asking random questions; you want questions that move things forward and lead somewhere, so the mentor feels you value their time. But I’d still encourage you to start by saying, “I don’t know where this might lead, but I feel this question is important.” Give your mentor a sense of what you’re trying to achieve, be clear about your purpose, so questions have context. That’s framing, or context, or giving them a model, and it helps a lot.

I call this second skill establishing fidelity: active listening, recording, and confirming what you heard. You have a very important responsibility to understand whether you’re receiving this right. An easy question: “Did I hear this right? Did you mean this?” You’ll both instantly validate whether there was fidelity in the conversation. The number of times people just skip on (“It doesn’t seem important,” “I’m not sure I heard it right, but it doesn’t matter”) is a waste of each other’s time.

A live example: someone had read my Wall Street Journal article on mentorship. When I asked what he took away and he described it, I just established fidelity. I found out that an article I spent time writing years ago actually got the message across; for all I knew it didn’t, in which case it was useless. Fidelity is also a living thing: an answer that applied at one point in time won’t always apply; the world changes. Don’t forget to go back and recheck with people as things evolve. If you asked about fundraising, you’re not going to raise funding all in one go that lasts forever, so understanding the whole process is more valuable than the answer to one Series A question.

Skill Three: Deciding (Taking Advice Mindfully)

The third skill, and I think the most important, is thinking about what advice you should actually use. Should you use all the advice you get? No. Filter carefully. I’m amazed how often people feel that because someone famous, high-profile, and inspiring told them something, it must be true. They don’t know you, and in most cases those famous people are less likely to be at the grassroots with you, knowing what you’re actually doing. Ask: does this apply to your situation right now? Does it work in the way you’re working today? How might it be different, and how might you improve it? What’s your own secret sauce, even if it’s just salt and pepper?

One mentee kept getting told, “You should be the Getty Images of this domain,” and couldn’t let the advice go even though it didn’t make sense and wasn’t where they wanted to go. What to do? Ask why: “Why do you keep telling me I should be the Getty Images? You’re emphatic about it; you believe this. I haven’t understood why it’s so important to you, but it clearly is, so tell me why.” Even if you don’t agree and decide not to use the advice, you’ll understand their thinking and maybe extract something. And remember the difference between recording and acting: there’s nothing wrong with recording everything a mentor says without acting on it, and coming back to it later. The worst thing about mentorship, and I’ve been there, is putting in a tremendous amount of energy to help somebody who isn’t even capturing it. By contrast, seeing someone really take it in and make notes, even if they can’t fully act on it yet, inspires you as a mentor.

Startup Secret: Don’t ever take advice blindly. Take it very mindfully. This is your life; you are making the decisions for your reasons. My number one premise as an investor is: it’s your business. I might be making my investment, but it’s your life that you’re investing in building a company, so you’ve got to decide whether this is the right advice for you; nobody else can. Think about gut decisions: how many have you made that were fantastic, and how many terrible? Even with the greatest advice, step back and ask what feels right. I’ve very rarely made a good decision when it didn’t agree with my gut. And here’s why it matters: if you don’t believe in something, how much energy will you put behind it? When somebody gives you advice you really believe in, that just feels right, you bring a different level of energy and conviction, and you’re more likely to execute on it. That’s part of taking advice mindfully.

To summarize the three skills, QED: ask the right kinds of open questions to frame what information you want; establish fidelity (did you hear it right, and why was it given); and take it mindfully, deciding whether it really applies to you. There’s nothing worse than answering the wrong question well, and QED is designed to avoid that, constantly iterating to make sure you’re answering the right question.

Mentoring is a gift, a wonderful gift, and it’s not one-way; it’s mutual at its best. Develop it as a skill, because mentoring, and being mentored, is a skill like anything else.