They say you should go find a mentor.

They say that it’ll be great for your career, for your personal life, for your work/life balance.

They say it’ll open doors, it’ll expand your network, they say it will help you grow and succeed and stuff like that.

But no one ever actually says how to find one

So there’s so much stuff out there about finding a mentor. I’ve read a lot of it, and it’s mostly BS clickbait stuff, those kinds of articles that say what you need to do but not how to do it and that are the same as every other article on the topic. I hate those articles. So I’m gonna give you some real advice that will actually help you in real life.

1. Figure out what you want

The obvious but apparently not-so-obvious first step. We have a tendency to jump into something because we hear that’s what we’re supposed to do, so we do it, but we don’t really think about why we’re doing it or what we want to get out of it.

So make sure you think about that. Ask yourself these questions:

  • Why do you want or need a mentor?
  • What do you want to get out of it?
  • What are your professional goals in the near future?
  • What is your definition of success?
  • And most importantly, what do you need from a mentor? What kind of commitment and time do you need from them? How big of a role do you need them to play in your life?

You don’t have to have this all figured out. No one has it all figured out. But you need a good idea, because otherwise no one can help you.

I like to write stuff like this down because it helps me think through it instead of just having some vague notions in my head. But we’re all different.

Once you know the answers to these questions you’ll be in a much better place to look for people who could help you. After all, we’re trying to find the perfect mentor here. If you take some time to figure this stuff out, the rest of the process will go easier — and take less time.

2. Look for people with your ideal job

Don’t just think of people you already know of. Or people who are famous in your field, or those “thought leaders.” You can reach out to those people — and you should — but they likely don’t have time to take on more commitments. (Though it never hurts to ask.)

If you find people who aren’t famous and in-demand, people who fly under the radar, they’ll be much more likely to a) meet with you and b) develop a relationship with you. Because not only will they have more time to spare, they’ll be flattered. Part of finding a mentor is to make them feel awesome. One day you’ll be in their shoes and want to return the favour. 

Look for people you may not know about. There are a lot of places you can look and it depends on your industry and role. What you really want to find is a “booster,” those people who love helping others. It’s not always evident off the bat, but there are plenty of people who genuinely want to help out others who are at the start of a path they are much further along in. 

This one time I found the ultimate booster. I reached out to her (mentioning a mutual connection) and asked for a coffee date. She immediately offered up all of these connections and resources and continued to offer me advice and support long after our meeting. I saw her do the same with a ton of other people, as well. She’s just that type of person, and that’s the type of person you want to find.

It’s also good to look for people with similar hobbies and interests. It’s much easier to break the ice and to bond with people if you both love swing dancing or skiing or football. Which leads to the next step…

3. Know everything about them

Now you’ve made a list of possible mentors you’d like to reach out to. It’s time to research them. Thoroughly. Don’t just look at their LinkedIn and Twitter accounts. Look at their Facebook and Instagram, their website, their company, their company’s products, and most importantly, you want to read or listen to every piece of content they’ve released. Yes, that’s time consuming, but there are three reasons for this:

  1. If you want to find the perfect mentor you need to know a lot about them both personally and professionally;
  2. You’ll have some specific things to mention when you reach out to them and you’ll have some good questions to ask when you do meet them. Plus you won’t ask stupid questions. This is important;
  3. You’ll know how to compliment them, and you might find some ways you can help them. Which again leads to the next step…

4. Get some ideas of how you can help them

Relationships aren’t a one-way street (duh). Especially in the beginning you’ve got to build up some goodwill. You can’t just put your hand out expecting help and not give any in return.

If you’re in the beginning of your career this can seem impossible. You don’t have any connections and you have much less knowledge and experience than your possible mentor. After all, that’s why you want their help.

It’s time to get creative. One of my favorite ways to help is to critique a part of their product. For instance, once I did a breakdown of Rdio’s onboarding flow. It was just for fun, but I ended up meeting their growth product manager who asked for a meeting so I could give them feedback on growth possibilities within the product. I wasn’t as experienced or as knowledgeable as them, but I was able to offer a some meaningful feedback and a different perspective and they appreciated that.

You could also just do some work from them. This varies widely depending on your field, but the basic gist is the same: find something about their product that could be better. Then create that thing. If you think their UI could use some improvement for a feature, redesign that feature. Or write some code. Or run a small (and free) marketing campaign. Or make an introduction to someone else they might find it valuable to know. It doesn’t have to be some crazy huge thing, and it shouldn’t be. It should be small in scope, just enough to be valuable.

5. Reach out: how to write a great cold email

Obviously warm intros are ideal here, so search high and low for any common connections. But often they aren’t possible, especially if you’re starting out in an industry or if you aren’t part of the “inner circle.” So cold emails are fine. And they actually work, at least in my experience.

Here’s what you do:

  • Have a specific subject line;
  • The email should be as short as possible. Ideally less than 5 sentences. I also like to break it up into short paragraphs, even if it’s only once sentence. It’s much easier to read that way;
  • Basically say: “You’re awesome, and I want to be awesome like you.” I once sent a cold email to Sean Ellis and this is what I said: “First off, I wanted to thank you – I stumbled upon your blog a few years ago and it really helped me understand what I wanted to do in my career. It’s always great to find someone who approaches things so deliberately and writes so clearly“. This is a thinly veiled “You’re really cool. I want to be cool like you“. I then briefly introduced myself and stated my ask in just one more sentence. He responded within one day. (I was asking him to come speak at a private event, and he said yes);
  • Make a specific ask, like I did. At this point when looking for a mentor it’s best to ask for a 30 minute coffee date. It’s a small commitment and a good threshold for people who don’t want to help you;
  • Provide them with possible times. This is just a matter of respect. They’re busy and they don’t want to go back and forth suggesting times. Tell them a few time windows you’re available, something like: “I’m free Tuesday and Wednesday mornings and Thursday afternoon this week and next.” Oh and when they do say yes, send them a calendar invite immediately.

6. Be awesome and smart and likeable

Be so awesome that they want to spend more time with you and want to shape you into an even more awesome person and then you can conquer the world together. Or something like that. Here are some ways you can be awesome:

  • Prepare ways that you can help them;
  • This could be something you already did, like in step 4, or just think of some ideas you can bring up in the meeting. You don’t want to come empty handed;
  • Ask good questions. Yes, there are stupid questions. 

If you’ve researched them you’ll know what this means. Here are some ideas of questions you can ask:

  • What new trends are you seeing in the industry?
  • What will change most dramatically in next few years?
  • Best lesson you’ve learned on the job?
  • Most valuable experience at your company?
  • What skill or trait that has helped you succeed?
  • What can I do to set myself up to succeed?
  • What do you wish you’d known when you were my age/in my position?
  • If you were me what would you be doing to maximize your chance of breaking into the industry?
  • Any resources you can suggest?
  • What do you read to be good at your job?
  • What projects have you done for your company that you felt added the most valuable?

(Obviously you should incorporate these a bit more naturally into your conversation.)

  • Have a specific ask;
  • There needs to be some point to the meeting or else neither of you will get anything out of it;
  • Invoke the Ben Franklin effect.

This idea was popularized by Ben Franklin, like, forever ago. Basically, he found that when someone did him a favor, they would be more willing to do favors in the future. By helping someone once you’re putting in an investment. And you want to follow through on the investment — after all, you wouldn’t have helped them if they weren’t worth it. This is subconscious — it’s a form of cognitive dissonance.

Being awesome shouldn’t be as overwhelming as it sounds. Remember that everyone struggles with insecurity and nervousness, no matter how awesome them seem on the surface. Be genuine and friendly and you’ll do great.

7. Follow up

The next and most important step is to follow up. Here’s what you should include:

  • A specific thing or piece of advice you got from the meeting;
  • If you mentioned any resources or articles send those along;
  • Follow up on anything you offered to help them with;
  • A question to keep them engaged so that they’ll email you back. 

If you do these things, it’ll eventually work and you’ll find the perfect mentor. It may take some time but it’ll be worth it. And when in doubt, just remember Philip Seymour Hoffman and Patrick Fugit in Almost Famous. That relationship was beautiful and it developed naturally:

Don’t just ask them to be your mentor, that’s super awkward. Instead, build a relationship and a rapport based on how they interact with you. Ask for their advice and help and offer your help in return. Give and take. Eventually, the relationship will grow and deepen and you’ll land the perfect mentor.

Boom.

Jessie Wood


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