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Welcome to "The Startup Solution." I’m Heidi Roizen from Threshold Ventures.
I don’t think any successful person makes it truly and completely on their own. If you ask pretty much any leader whether they had help along the way, they’ll usually bring up someone who gave them critical advice at an important juncture, or championed them somehow, somewhere along the way. Sometimes, that person was their teacher or professor. Sometimes, it’s been a boss or community leader. But it isn’t always a more senior person coaching a younger person. It could be what I call a ‘fellow traveler’ – someone you know through work or school or some other group who’s at the same stage of life that you are but knows something you don’t. It could even be someone younger than you.
In the Threshold Venture Fellows program at Stanford, one of the benefits we provide is to pair each Fellow with an alumni mentor. In some cases, these relationships have turned into career opportunities or even ongoing friendships. But sometimes they don’t click, and they fizzle out. Not every pairing is perfect, so I don’t expect everyone to end up with a deep connection. But in a couple of the situations I’ve heard about, I think it’s been more the case that the mentee had a lack of understanding about how to actually be a good mentee.
So that’s what I want to tackle today. Because seeking out and engaging mentors is not something you only do as a student. I’ve sought out mentors my whole life, and I continue to do so even now. And particularly for entrepreneurs, I think that mentors can make a meaningful difference in your and your company’s ability to succeed.
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The word “mentor” has been around for thousands of years. It was first used by Homer in the Odyssey when Odysseus leaves his son with someone named Mentor to serve as his guardian and teacher. So, being a mentor is a well-established construct. But what about being a mentee?
Well, the fact that the word “mentee” is not even a legitimate word in most dictionaries gives us a clue that being a mentee is not as well-established as a practice. And yet, for most of the mentor/mentee relationships I’ve been involved with, the success of the relationship depended on the mentee doing the bulk of the work to build and maintain that relationship – rather than just waiting around to be called and soaking up whatever wisdom comes their way when that happens.
Like any relationship worth having, the mentor/mentee relationship requires work at every step. And the first step is to find and recruit that mentor. So, let’s start there. I’d suggest you begin by looking right around you at the people you already work with.
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Some of the most productive mentoring relationships I’ve had, both as a mentor and a mentee, have formed around some mutual activity or work product. In some cases, the work product itself is the topic for the mentoring, for example, a more senior exec coaching a direct report through a product launch. But mentoring doesn’t have to be constrained to the work product itself. I’ve generally found that the people I admire, say, good people skills or good analytical skills, can be great mentors for how to develop and apply those skills in areas other than the immediate task at hand.
Outside of your actual job, there are still plenty of other places where there’s some sort of ‘work product.’ Activity clubs, nonprofit organizations, and, of course, schools are all great places to look for those fellow travelers who may have skills or insights that you want to learn from. And you might be surprised to hear me recommend getting involved with trade associations, too. Some of the people I’ve met by being active in the software and VC trade associations have become some of my most important mentors and business associates.
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For you entrepreneurs, fellow entrepreneurs a few years ahead of you can make great mentors – and you might be surprised at how open many of them are to talking with you. I think that’s why accelerators are so popular: more than just the funding and the structured learning, they provide the opportunity to connect with and learn from other entrepreneurs.
But even if you’re not in an accelerator program, there are plenty of other ways to connect with fellow entrepreneurs. Conferences – like Fortune Brainstorm or TechCrunch Disrupt – can be great places to connect with other founders. Platforms like Meetup have plenty of startup events and communities for you to join. Startup Grind, which has been around for almost fifteen years, has communities in many cities around the world that focus on bringing entrepreneurs together. Founder Institute and Indie Hackers are two other organizations that I’ve heard great things about from founders looking to meet up with others. And don’t forget to look around the coworking space you work in, as well as the innovation centers or tech hubs that may be sponsored by your communities or local governments.
If you’re in a more isolated location, you can also look into virtual communities. LinkedIn has a near-infinite number of groups, so you can probably find one that fits your needs. There are also Slack channels, like Founders Network or Techstars Open Network. And, of course, there’s Reddit, where there are subreddits focused on entrepreneurs and startups. And if you’re a college alum, there are probably some organized mentor programs available through your alumni organization.
Of course, mentors don’t necessarily have to come from a group or formalized activity. While I think it’s easier to form a relationship around a work product or shared activity, you can also just start from scratch. I’m a huge fan of hunting for potential mentors on LinkedIn – where it's relatively easy to find out about people who are ahead of you on the roads you want to travel, whether those are particular industries, companies, or even specific job functions.
If you’re going to take this route, I’d recommend seeking out people who are not the super-famous, super-senior, super-followed people. Instead, find people who are maybe three to five years ahead of you. Their experience will likely be more immediately relevant to you, and they’ll probably be more accessible and responsive to you too.
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To initiate a relationship on LinkedIn, you can start by following them, reading what they post, and reacting to their posts. I’ve ended up meeting some great new people over the last year who’ve done just that with my podcast posts – so I’m living proof that it works.
Of course, moving from a loose association to a mentoring relationship is going to take a few more steps.
I think the best next step with any prospective mentor is to ask for something easy that can be accomplished in one short meeting. Why? Because neither you nor your potential mentor have any idea at first whether this might be a relationship you’ll want to continue. In fact, I think it’s rather off-putting when someone I don’t know emails me out of the blue and says, “will you be my mentor”? I mean, that’s a big ask and how would I have any idea whether I’d want to make a big commitment like that to a total stranger? It’s much more likely that I, or any prospective mentor, will say yes to a short and easy ask with no future commitment.
For example, you might ask something like, “I see that you’ve worked at both a small startup and Google, and I’m currently facing a decision to go either the startup route or join Google myself. Would you be willing to spend 15 minutes with me to share how you weighed those same options?"
Notice a few things about this request. It’s very specific, so the person you’re requesting time from knows exactly what you’re asking about and why you’re asking them, in particular. The time request is very short, which also makes it easier for someone to say yes! And the request is only for one interaction, not an ongoing commitment, so again, easier for someone to say yes to.
Some people are responsive directly on LinkedIn. Some people, like me, have overflooded inboxes on LinkedIn, so you’ll have to find some other way to reach them. And sometimes people don’t answer at all. If that happens to you, don’t feel bad about it, don’t take it personally, and above all, don’t let it stop you from trying with other people. This is a lot like sales prospecting, and any good salesperson will tell you that it takes a lot of outreach to get even a single response.
So, keep trying. And at some point, someone will say yes. Which means, it’s time to do more homework.
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It’s time to learn more about the generous person who said yes so that you can make whatever time you have with them as productive and hopefully enjoyable as possible – for both of you! Luckily, this isn’t that hard to do because most people have a pretty detailed digital footprint out there, between LinkedIn and other social media platforms, as well as websites and such about the companies they work for. So, spend some time digesting all that information about your prospective mentor – that way, you don’t have to spend precious meeting time on stuff you could have already learned in advance. Plus, this will help you organize and refine the questions you want to ask in that first meeting. Believe me, the person you’re meeting with will appreciate that you took the time to make the meeting efficient.
Next, and as I’ve said in prior episodes – make yourself easy to help. Remember, they’re doing you the favor, so don’t ask them to do extra work, like reading something ahead of time. I think it’s fine and even desirable to send them a few sentences about yourself, as well as a link to your LinkedIn profile. In fact, that information is usually part of what gets a person to say yes to a meeting. But don’t load them up with more than that.
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It’s also up to you to make the meeting as easy as possible for them to actually do. You should be the one to travel if the meeting is in person, to a location of their choosing. And you should fit their time schedule, not ask them to fit yours. You should keep the length of the first meeting short. Oh, and you should show up on time. I hope that’s a given. I had a person show up 20 minutes late for a 30-minute meeting with no excuse. As you can guess, that one didn’t go too well.
And on the topic of time, don’t assume that the prospective mentor has the time to run longer than what you asked for. Bring the meeting to an end on time proactively, so that you don’t put them in an awkward position of having to cut things off.
I’d also recommend trying to meet in person if possible. The real world still has advantages that aren’t as fluid when you’re online. That said, if your prospective mentor isn’t local, or simply prefers Zoom, that’s not a deal breaker in my book. In my life today I have a number of relationships with people that I’ve never met in person, and we both still manage to get something out of it. So, it can work.
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When it comes to the actual first meeting, the biggest mistake I’ve seen people make is that they talk about themselves the whole time – maybe out of nervousness, or to give a lot of context, or just to try to impress the prospective mentor. And then, they run out of time before they even get to their questions, which makes the whole meeting feel like a failure. And let’s be honest. Have you ever met a new person who spends all the time you have together talking about themselves? It’s not a great way to start a relationship.
The people who have impressed me the most in the first meetings were the ones who came well-prepared and asked the most engaging questions and follow-up questions. I’m an advocate of that famous expression, “it’s better to be interested than interesting”. In fact, I have a game I play sometimes that I’d encourage you to try. When I'm at a dinner party, I challenge myself to say as little as possible about me. And instead, I try to get the person next to me to talk by asking lots of questions. If you try this yourself, I bet you’ll actually find it hard to do, I mean, we’re all so used to talking about ourselves. But I’d also bet that if you’re successful, the person sitting next to you will enjoy the experience and come away thinking that you are a great conversationalist.
After that first meeting, and regardless of whether you want to continue the relationship or not, you should follow up with a prompt thank you note. It doesn’t have to be formal, in fact I prefer email to a card or handwritten note, because it’s easier to respond to that if I want to. It’s best to do this within a day or two of the meeting while you’re still fresh in the other person’s mind. If you want to continue to build a relationship, you can add something like, “I really appreciated the advice you gave me, and I hope you won’t mind if I reach out again once I’m farther along. And if there’s anything I can do to be helpful to you, I’d love to repay the favor.”
Why that? Well, first of all, it’s never wrong to offer to be helpful. But also, other than asking if it’s okay for you to be in contact again, there’s no other ask.
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What would be wrong at this point, and what happens more often than I’d like, is that there’s an immediate ask for something more, say forwarding the person’s resume to one of my contacts or referring them to a job opening in our portfolio. And unless I specifically offered to do that in the meeting, this feels like a step too far, like the person just used the meeting with me to get something. And that’s just not a great feeling for starting a relationship.
I know some people disagree with me on this topic, and I’ve met plenty of people who use meetings like this to advance their own agendas with no regard for the other person. But from my experience, that’s just short-sighted. Do you want me to help you once, or do you want me to always want to help you? If it’s the latter, then you’d better spend some time building that relationship first before you start asking for things.
Which is why in my book, the only appropriate ask is about taking a next step towards building a relationship. Hopefully, they’ll say yes. And each time you meet, if you take the same approach of being respectful, prepared, accommodating, and grateful, they’ll continue to want to meet. And ultimately the relationship will build to the point where an ask would be appropriate.
But even when you reach that point, always approach asking for a favor in a way that allows the other person to say no gracefully. Remember, it’s ultimately not about any individual ask; it’s about having a relationship, and giving a person a comfortable out can preserve the relationship even if they don’t want to do the thing you asked about.
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Ultimately, building a relationship with a mentor is no different from building any other relationship. The best ones are built on trust, honesty, and mutual respect. Being open about what you’re not good at and what you want to improve on will help your mentor to better help you. And in every subsequent meeting, telling them about how you used some of their advice and what came of it will, at a minimum, show them you were listening. But even more, it will make them feel good about having helped you – and more likely to want to keep doing that.
I also want to bring up some seemingly “little stuff” – that may sound unimportant, but it all adds up and contributes to the other person’s feelings about you. If you make a commitment to meet, honor it, be on time, and respect the endpoint. If your mentor emails you, respond as soon as possible. And if they ask you for something, deliver it on time and make it your best work.
And I’ll say it again, expressions of gratitude go a long way. I’m not saying you have to write a thank you note every time you meet, but trust me, it feels a lot better to keep helping people when you know that they appreciate the help.
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Here’s one last thing I want you to consider – and that is, what can you do for your mentor? I think everyone can think of something they can do for another human being, regardless of each person’s seniority or resources. I’ve had mentees cook me dinner. One bartended for an industry event I was hosting. One went through all my social media settings to make sure I was protecting my privacy properly. And one millennial helped me understand the current trends and memes of their demographic that I was too embarrassed to ask my kids about.
I’m not saying you have to do stuff like this, but I do think that finding ways to make the other person’s life better will lead to a stronger relationship. It’s optional, but on the flip side, not only can it be helpful, but it can be really fun, too.
I suppose I can boil all this advice down to one high order bit, and that is that I think it’s primarily the mentee’s job to make relationships work. And if you approach each potential mentor relationship with this in mind, it'll lead to far more success than sitting around waiting for the phone to ring. So, look around you, pick one person who might have something to teach you, and take that first step — send the email, ask for the coffee, or even just comment on their LinkedIn post. Because the best way to get a mentor is to start acting like a great mentee.
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Thanks for listening to this episode of “The Startup Solution.” I mentioned a lot of resources in this episode, so to make it easier for you, I’ve linked to most of them in the show notes. I hope you’ve enjoyed the show, and if you have, please share it with someone who you think would like it too. I’m Heidi Roizen from Threshold Ventures.
I mentioned a bunch of organizations and resources in this episode, so here are the links to them:
And finally, here are first-person narratives on learning how to be interested, not interesting. There are similarities – but there’s something to learn in each one of them: here, here, here, and here.
