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Both sides benefit from a top-flight mentor relationship.

By Jill Coody Smits


Say you’ve just graduated from school and don’t know where to start. Or perhaps, as a professional, you’ve been hanging onto the ladder’s middle rung so long your fingertips are primed for a climb up El Capitan. What you need is a sage consigliere, a guru for getting it done. Lucky for you, it’s National Mentoring Month.

“Mentors are essential because we’re all victims of living in our own heads, and it’s critical to have a third party give outside perspective  on things we struggle with,” says organizational psychologist and executive coach Michael “Dr. Woody” Woodward. Without that honest and informed feedback, he says, it’s easy to “get wrapped up in your self-talk and for beliefs to get in the way.” 

As Shakespeare’s self-talking characters have taught us, it’s not always wise to soliloquize, and airing thoughts to a mentor can help us uncover strategies and ideas we may never have considered. And while Macbeth might have benefited from a fair and knowledgeable sounding board on a murderously different level, there’s something in it for both sides of a professional mentoring relationship.


Those Who Can, Do. And Teach.

When D’Wayne Edwards started out in footwear design more than 20 years ago, he had a lot of talent but little formal education. One of six kids growing up in a single-parent home in Inglewood, California, Edwards was fascinated with drawing sneakers. In high school, he won a Reebok design competition, fueling his dream to become a footwear designer. Design school was not in the budget upon graduation, but he balked at advice to forget footwear and focus on a career in the military or fast-food restaurant management.

Instead, he attended night school and lucked into a life-changing job as a temp at shoe company LA Gear.

Fully aware of his good fortune in landing the gig, Edwards made himself known as the kid who put shoe sketches in the suggestion box. Six months and 180 drawings later, company founder Robert Greenberg rewarded Edwards’ determination by hiring the 19-year-old and taking him under his wing. Today, Edwards credits his mentor with paving his way in the business. “He was running a major company and gave me a start. I asked a lot of questions, and he always had an open door.”

Edwards still feels Greenberg’s influence every day. There are the little things—like getting an idea recorded the moment he has it and reading industry news each morning. And the big ones—like valuing hard work. Edwards says Greenberg’s crazy work ethic “taught me that no matter how important you become, there’s another level of effort required to stay there.”

Eventually, Greenberg left LA Gear to start Skechers. Edwards followed him there and, by age 28, had launched his own brand. 

In 2000, Edwards was lured to Oregon by Nike, where, in 2007, he achieved high-top immortality when he became one of only six people ever to design an Air Jordan. 

In 2011, he gave it all up to open Portland-based Pensole Footwear Design Academy and become a full-time mentor. Edwards says, “I had reached the peak in my industry, and my calling was to provide the pathway I didn’t have and to open the door for the next generation of talent.”

That calling to help people achieve their dreams is another thing Edwards learned from Greenberg. “I want him to know the opportunity he gave me in 1989 is living on today through the students I’m reaching.”

That legacy of mentorship is definitely alive at Pensole. Edwards describes the four-week program as “a farm system” for the footwear design industry. So far, the system is more Boston Red Sox than Bad News Bears, sending up more than 60 former students to work professionally for brands like Nike, The North Face, Under Armour, and Adidas. Win-win-win.


Mentee, Know Thyself

As the more than 600 kids who apply for every 20 slots at Pensole can attest, securing a quality mentor is no easy feat. In fact, some experts say mentorship is on the decline. In their book Rebooting Work: Transform How You Work in the Age of Entrepreneurship, Maynard Webb and Carlye Adler suggest that ever-shrinking employee tenure, increasingly burdensome workloads, and a fiercely competitive job market are making traditional mentorships a scarce commodity.  

That doesn’t mean finding one is impossible, though, as long as you know where you want to go and have the gumption to find the person to help you get there. Depending on your circumstance, Woodward says, the right player might be within your own company if they can “help you understand the politics, history, culture, and traditions of the place.” While some of that can come from your boss, “it’s important to find someone who can give you off-the-record perspective,” he says. 

If that person runs with a pack above your pay grade and your company doesn’t have a formal mentoring program, Woodward recommends volunteering for cross-functional workgroups that allow you to interact with otherwise inaccessible colleagues.

But don’t fret if finding a mentor within your workplace is unrealistic. Woodward says a guru can be anyone who helps you assess whether your routine is on a roll or in a rut. Are you a female writer, a Hispanic engineer, a food-truck entrepreneur? Woodward suggests seeking out special-interest groups and joining local chapters of professional organizations. 

If these avenues are dead ends, there is always what might be called the “Hot Pursuit” strategy. That is, do some research on your industry, focus on key players, and doggedly pursue them—in a nice way. Sending a message via LinkedIn, for example, may, in a kinder, gentler form of cold call, yield a connection.

Wherever you look, Woodward says it’s key to find someone who will be “open, honest, and direct.” The flip side of seeking honesty is being tough enough to take the advice to heart. He says, “If you’re not willing to hear it, there is no value in the relationship.”

Or relationships. Woodward says that the mentor capable of counseling you in a nonprofit work environment won’t necessarily be the person to guide you through freelance nation. “I hear people talking about having a mentor, but it’s important to think about multiple mentors that fit with the circumstances in your life.”


There’s a Right Way and a Wrong Way

Imagine receiving an email with the subject line “INTERESTED IN YOUR EXPERTISE.” The sender addresses you as “Dear professional,” expresses a desire to secure you as a mentor, then proceeds to ask for more information about your work and how you might help them succeed.

While that all-caps flattery may lure you into opening the message, you’ll soon decide a mentee who doesn’t bother to learn your name isn’t likely to be worth your effort. 


“You need to demonstrate your potential, make a good impression, and [show] that you’re worth getting behind,” Woodward says. “They have to look at you as someone who is going to listen, take feedback, and do something with it.” 

In choosing who to mentor, Edwards says he’s most interested in those who prove they are willing to work. He tells his students, “There will always be people who are more talented than me, but no one will outwork me.’” 

His best tip, though, is the most fundamental one. “Early on, I saw the value in asking and receiving. Some people don’t even ask.” 


What’s In It For Me?

Of course, you can’t have the Karate Kid without Mr. Miyagi, which means those with enviable skills must find worth in sharing their hard-earned wisdom. As it turns out, there are reasons aplenty. 

For those in senior positions, Woodward says, “It’s a good way to get perspective. It’s a way to be reminded of what it’s like to start out. It’s also a way to give back.”

But there’s more to it than fulfilling some karmic professional obligation; you may just learn something. Edwards says his students often remind him he doesn’t know everything. “This industry is young and current. When I’m mentoring, I’m learning from them as well, so I see it as a trade.”

Don’t take on a protégé just to say you have one, Edwards advises. “Not everyone is cut out to be a mentor. It’s something people like to say they are,” but it can be counterproductive if handled poorly.



So maybe it’s time to consider whether a mentor can help you launch or make it to the next rung. If you do find yourself in a symbiotic relationship with a knowledgeable colleague, remember to keep a good thing going.

As Edwards relates to each of his students, “I wouldn’t have achieved all of this without guidance, so I challenge them to mentor not one, but two, so it keeps multiplying. That’s what it’s about. If it stops with you, the chain ends.”


Jill Coody Smits is an Austin, Texas–based journalist. Find her online at blueseedcommunications.com.


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