Get Your Mentors to Respond

The most important part about getting in touch with possible mentors or future employers is getting them to respond to your email. The only way they are going to respond is if your message provokes them to do so. You have to give them something to work with, especially when you consider the fact that they have tons of emails coming in every single day that get immediately deleted and disappear into oblivion. Your email shouldn’t meet that same fate.

I provided an example of an email that I sent in the original Hijacking Mentors section, and I want to expand on that a bit. That email was a result of hundreds of emails that I’ve written that were met with no response—it took me a long time to write outreach emails that actually converted, and even longer to get to a point where I could teach it. Here are a couple tips to write better emails that convert:

Have a purpose.

What’s the goal of your email? Do you want a phone call? Ask them when they are free for a short phone call. Do you want to ask them a question? Ask them a question in the email. Do you want to meet them for coffee? Ask them when they are free for coffee.

If the goal isn’t clear, it’s really difficult for them to respond and help you out. It’s just confusing to get an email that has no end. What was the point? As they say in sales, a confused buyer doesn’t buy.” Don’t confuse your target.

Start with a unique question.

Starting with a really unique or specific question is a great way to reach out to thought leaders, authors, or executives in your space. This works for a couple reasons, but mainly it’s because people want to take care of as many emails as they can when they open their inbox. If your question is a relatively interesting but simple question to answer, the hope is that they’ll take a couple minutes to respond to it and get it taken care of.

If your question is good, people will remember it. I had emailed Ryan Holiday months before I met him for the first time, and when I did meet him months later, he was on tour for a book release. He still remembered the question I had asked him months before, and even noted to me that it was a memorable and unique question.

Several notable examples that I have asked to various influential people:

What did brilliance mean to you when you were graduating high school versus what it means to you now, or has it changed at all?

How did you internally develop into a thought leader (or whatever you may call your celebrity-like status) and how did you have to grow as a person as you became more and more widely known?

When you started out with the Vignellis in the outset of your career, what was the first thing that you distinctly remember that made you understand that they were top-tier professionals? (Asked to Michael Bierut, who worked with Massimo and Lella Vignelli in the beginning of his career. Shows I did my homework.)

What was it like when you were just getting started in graphic design and really decided that this had to be a living for you? How did you go through that transition?

Leverage your age.

If you’re under 18 or still in high school, mention this in your email. It seems cheap to use your age to get people to respond to you, but it works. Mention it in passing, but don’t be afraid to mention it. If you’re 35 and asking a question about executive leadership, it’s not that exciting. If you’re 17 and asking questions about executive leadership, that’s a whole different story. Use it.

Create context.

How did you decide to reach out to this person? Let’s say you want to send an email to one of your favorite authors (who hopefully isn’t too famous and therefore you have a good chance of being able to email them directly). Tell them the story of how you found out about them, which books you’ve read by them, and what you thought about them. Tell a story, even if slightly exaggerated, about why you decided to reach out to them. Here’s an example from an email that I sent to Ryan Holiday. (He responded and I’ve spoken to Ryan multiple times since.)

Ryan, I bought the Daily Stoic a couple weeks ago and I’ve loved it ever since I got it. My parents even have it on their kitchen counter and read it every single day. It’s a wonderful thing to share between us all and talk about rather than goofy news or office politics or school. I’ve read a bit about you on your site out of curiosity and your articles are great and I love what you’re doing.

I can’t just show up in somebody’s inbox with no explanation as to why or how I got there. If they don’t recognize my name, and I don’t know them personally, that makes it all the more imperative that I create context before I go on asking them any questions or asking to speak to them on the phone. This explanation is key, and also makes sure that your target knows that it’s not a generic spam email. If it’s even remotely close to being copy-and-paste spam, they will not respond.

Do your homework.

Don’t show up in someone’s inbox to ask them a super basic question that could’ve been answered on your own by doing your research. This is the number one way to get someone to immediately delete your email—if you cared so much to get the answer to your question answered, you would have looked it up for yourself and found out…but, you didn’t. Deleted.

If you don’t know the person that you’re about to reach out to, do some research beforehand. Look up their company, and figure out what exactly they do in your field of interest. If they are famous and have done interviews, listen to those interviews and read the articles that have been written about them.

It’s much easier to reach out to people who you have already at least heard of, or to executives at companies that you are familiar with. You should know about their company, and if they’re a public individual or figure of any sorts, you should know them well enough to ask good questions.