You know that awesome woman you met at a networking event—or that author you stalk on Twitter—who you just totally admire?

Wouldn’t it be great if he or she was your own personal career mentor—the person who could impart concrete industry knowledge and help you make better informed decisions whenever you needed it most?

Yep. If only it was as easy as walking up and asking: “Hey, will you be my mentor?”

Unfortunately, asking so bluntly is generally a futile approach to having an established professional agree to be your mentor. I mean, just look at J.D., who spent full seasons chasing after the reluctant Dr. Cox and asking him to be a mentor (shout out to Scrubs and Zach Braff fans!).

But here’s the thing: Even though he never got a firm “yes,” Dr. Perry Cox progressively grows to fill the role of J.D.’s mentor over the years as their connection grew. How did he do it? We spoke with folks who have had firsthand experience in successful mentorship and found out exactly how to establish a connection without being too formal.


1. Follow Them on Twitter

Twitter is brimming with smart, accomplished folks in your industry, and following and even engaging with your favorite thought leaders is a great way to get on their radar. And once you are? When you ask a specific, well-thought out question, the odds are in your favor of getting a response.

Andrew Legrand, an attorney at law, tried this approach a few years ago. “While in law school, I found a local lawyer on Twitter, and followed him for a while before I had the courage to contact him,” Legrand says. “Fortunately, he was easy to approach, and I never had to ask him to act as a mentor—it just happened.”

This is a flawless approach for mentorship. If you can create a rapport by reaching out in small ways over time, you can build a natural relationship—that could turn into a mentorship—without ever having to ask. (For more on this subject, check out Lily Herman’s tips for interacting with people you admire on Twitter.)


2. Be Generous With Your Time

In any part of your life, a good first step toward a lasting, fruitful relationship is generosity.

Ray White is on the board for the University of North Texas Professional Leadership Program, which recruits more than 160 mentors and mentees each year, and has mentored folks who have gone onto become successful entrepreneurs and executives. His advice? “Offer to help out on any projects they have, offer to help with their favorite charity,” he says. “It is easier to give than to ask, and it establishes a good foundation of mutual benefit.”

Of course, there’s a fine line between being generous and being creepy—you should only offer your time and expertise on things you’re truly interested in. But if you see that a contact sits on a board of a nonprofit you’ve been interested in getting involved with or donates to a cause you care about? That’s a perfect way to forge a real connection.


3. Exude Passion in What You’re Doing and Pursuing

You probably already know that established folks have no time for demotivated couch potatoes! So, show people that you’re the opposite by going out of your way to talk about your work passionately in everything you do.

For instance, say you’re doing an informational interview with someone in your network you’d love to learn more from. Seize the limited time you have by coming prepared with though-provoking questions and common topics that interest you both—it’ll be much more likely that the other person will want to continue the conversation after your initial meeting. Or, say you’re emailing someone who heads up a professional organization you’re part of about an upcoming event. Adding to that email a few thoughtful new ideas or intriguing articles related to your job is a great way to exude your passion.

Keep in mind that the last thing you want to do is reach out to someone to simply stroke his or her ego. “As a mentor myself, I'm not looking for flattery, I am looking for someone who is serious about what they do,” says Dr. Gayle Carson of Carson Research Center, who has appeared on ABC and NBC and in the Wall Street Journal.


Bonus Tip: Pursue More Than One Mentor

Another essential point White mentions is that you can and should have more than one mentor “because each has their own strengths, and you don’t want to take too much of any one person’s time.” In other words, don’t put all of your mentorship eggs in one basket, and keep a look out for a variety of strong, successful professionals you could learn from.



Fact is, most people have had some type of help on their way to success—and most are willing to return the favor. But it’s important to remember that the best relationships are never forced. If you work hard to build connections, reach out casually (but strategically) over time, you’ll likely find that some of those acquaintances naturally turn into strong mentor figures.


Photo of coffee meeting courtesy of Shutterstock.