How to Convince Someone You Admire—but Have Never Met—to Mentor You

Five years ago I was living in a cramped three-bedroom apartment in East L.A., trying to build two startups simultaneously with no clue what I was doing and no seed capital. I had very little income, no connections and, frankly, no friends. Nevertheless, I was determined to find a way to become successful.

I had recently attended an entrepreneurship conference and bought a DVD profiling young millionaires. One of the lessons from that DVD was to find a mentor—that is, a person who currently is where you want to be, who can take you under his or her wing and show you the ropes.

I hadn't really made an effort to network with other entrepreneurs up until that point, so I couldn't just call one up and ask for an intro. So, I carefully crafted a series of emails and follow-ups to all of the young millionaires profiled in the DVD I was watching!

Not only did I get responses, but I impressed one of them enough to agree to mentor me. This individual guided me when I needed it and eventually granted me access to her incredible network. I have since started, scaled and sold five companies.

The key to my success was simple. I didn’t want to blend into the crowd of others like me who I was certain were going after the very same entrepreneurs, so I set 8 simple rules for myself, as follows:

1. Do your research.

Before you seek out a mentor, know which industry you want to learn about, and in what way. Then, come up with a shortlist of people you’d like to target—and do your research on each. See if you can find their bios online; look for articles written on them; and check out their LinkedIn profiles.

When you do reach out, make sure your research is apparent. This attention to detail will show your prospective mentor that you’re not just blanket emailing a ton of people at once—that you actually want to learn from him or her specifically.

2. Don’t be desperate.

Many people seeking a mentor will resort to begging. They’ll talk about how they don’t know what they’re doing, how their company is failing, or whatever other negatives they think will demonstrate their need for a mentor.

However, just as a bank won’t loan to somebody who’s broke as they don’t want to risk not being paid back, successful people won’t mentor somebody they feel they can’t make an instant impact on as they fear wasting their time.

3. Show that you’re a self-starter.

You need to remember that the best mentors out there will often be the toughest to get.

To give yourself the best chance of success, demonstrate that you’re not starting from complete scratch, that you’ve made it pretty far on your own already.

If you're an entrepreneur, for example, you've might explain that you've already got a business plan or spent a significant amount of time getting to know the industry. If you're a career changer, you might show that you've taken some classes on the topic. If you're looking to climb in the field in which you currently work, you might describe what you've done so far.

4. Demonstrate self-confidence.

Successful people were not always successful, but most of them were confident—even early on in their careers or entrepreneurship—in their ability to learn and become successful.

In your communications with your potential mentor, your ability and passion to make things happen needs to be apparent not just in what you say and do, but how you say and do it.

5. Establish specific, low-pressure terms.

Asking a successful entrepreneur, “Will you mentor me?” is akin to a man asking a woman he’s never met to marry him. He's much more likely to be successful if he instead has a nice conversation and asks if he can call her sometime.

Approach a prospective mentor in the same way.

Don’t flat-out ask them to be your mentor. Instead, let them know that you really respect them and have learned a lot from what they’ve done, and then start with one specific question that shows you’re actively working on building your own empire. Get your first positive response, and then go from there—slowly.

6. Don’t create work for them.

When starting to work with somebody you want to mentor you, make it known that you’re aware how busy they are and how valuable their time is. Then propose something as simple as a 15-minute call once per month when their schedule permits.

7. Showcase your implementation.

There’s nothing more encouraging—and more flattering—to a successful businessperson than someone showing them how much they’ve learned from them, how they’ve implemented it, and the conclusions and next questions they’ve come to as a result.

After you ask your first question or two, don’t even think about asking anything else until you’ve implemented the advice they’ve given you and can show it.

8. Show your gratitude.

By and large, if you’re asking a successful person to give you their valuable time, you need to acknowledge that you understand that they are making sacrifice on your behalf.

While you likely don’t have much to offer them at this point, you can remember to thank your mentor each time you talk. But also show your appreciation in a unique way now and again, perhaps with a gift around the holidays or when they help you with a particularly challenging problem. I prefer something like Edible Arrangements as it shows how thankful you are without sending an inappropriate message.

Travis Steffen is currently the founder of UP (upshare.co) and one of the founders and VCs sharing their insight at MentorMojo, an entrepreneurial e-learning platform. Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs.