In the 100th episode of NBC’s 30 Rock, the mentor-mentee relationship between Jack Donoghy and Liz Lemon is at a cataclysmic crossroad. Jack, played by Alec Baldwin, is re-evaluating his decision to take Tina Fey‘s Liz Lemon under his wing. Concluding the relationship is weighing him down, he decides to move on, then imagines the consequences of not stopping Liz from moving in with her deadbeat boyfriend. Guessing they’ll get married and move to Jacksonville, Florida, he’s aghast. “Jacksonville?!” he cries, “Her hair can’t handle that humidity!” With that, he rushes to his mentee’s aid, re-affirming his status in her perpetually conflicted life.

Not all mentors are as dedicated to their mentee’s intractable tresses, but many stories attest to the impact of these relationships on one’s professional — and personal — paths. Far from being one-shot deals, mentees report turning to a variety of mentors over the course of their careers, each offering something new and valuable that helps one to grow and succeed.

Just ask Keesha Rosario. In 1988, at the age of 11, Rosario was matched with business executive, author and mentoring expert Patricia Barbato, as part of Big Brothers Big Sisters’ mentorship program. But what started with personal motives eventually evolved into a professional engagement that continues 20 years later. In fact, upon graduating from university, Rosario struggled looking for work. Barbato’s mentorship — in the form of advice and ongoing support — proved invaluable. “I called her a lot. She got the ball rolling,” recalls Rosario. Barbato’s connections and assistance resulted in Rosario securing her first marketing position, a job that laid the foundation for future opportunities.

So positive was the mentorship experience, Rosario decided to pay it forward, taking on a mentee of her own. “I’ve been able to help her make choices by asking the right questions, being supportive, coaching.” She emphasizes that the choices have to remain in the mentee’s hands. “It’s not about controlling the situation but letting it ride and ensuring that the ball keeps rolling forward.”

An asset for your career

What is it about mentorship that creates so many believers? “Mentoring is about having a cheerleader in your court, a motivator, someone to help build self-confidence and self-esteem, and help you make choices,” states Rosario. For those starting out, it’s good to set yourself up early in your career, adds Barbato. It’s a way of taking your career into your hands, being proactive. Whether it’s within your job or outside of it, mentorship can help you attain skills and wisdom you may not get elsewhere.

Rob Drynan would probably agree. President of MacLaren Kiindrid, a new communications practice focused on social benefit, Drynan came on board after spending six years as the executive director of Camp Oochigeas, a position intimately rooted to his experience with mentorship. It began when his grade seven teacher, with whom Drynan enjoyed a good relationship, showed up at his father’s wake. The mentoring relationship grew organically from there. “I talked to him about issues and challenges and he gave me his two cents,” says Drynan. “He’s got more years than me and more experience so he gave me some guidance on my life,” he adds, explaining how, in many ways, the former teacher took on the role of father figure, too.

And his professional advice proved equally providential. When Drynan was searching for a meaningful volunteer experience, his mentor — with years of experience in camping — directed Drynan to Camp Ooch, suggesting he’d be good at it. He was right. One thing led to the other and Drynan was soon at the organization’s helm.

It was there that he met his second mentor, the past chair of Ooch’s board. Drynan turned to him for guidance because “he had a very deep understanding of the organization, was well respected and could provide me with lots of insight.” That was almost eight years ago and the two still meet when possible. As Drynan transitions into his new role, leveraging his advertising smarts with nonprofit know-how, he speaks highly of his mentor. “He was a great help throughout my career,” he says, explaining how he clarified Drynan’s strengths and weaknesses, helping him figure out what he wanted to do next.

How to make a match

Evidently, Drynan found mentors that suited his needs but how does one ensure their relationships are equally successful?

“You need to feel they have something to offer you,” says Barbato, be it personal, professional or something related to their experience or even leadership style.

“Find someone who is as different from you than you can imagine,” advises mentoring veteran, Wayne Stewart, whose experience includes developing a mentorship program for the University of Calgary and a coaching program for EDs, Executive Directions.

Rosario can relate. She was once assigned a mentor who was “the complete opposite of me”. He was strong in all areas she wasn’t, which proved beneficial. “He also called it like it is,” she adds. “A mentor needs to be very honest with you but you also need to be very honest with yourself.”

Stewart’s long list of mentees includes the mayor of Calgary, Naheed Nenshi, whom he meets once a month. He’s also had experience on the other side of the divide, having turned to mentors much of his life, with the most prominent, Grant MacEwan, former mayor of Calgary and Lieutenant Governor of Alberta. He adds that some of his mentors today are younger than him but no matter, they share wisdom he wouldn’t otherwise have access to, like instructing him on matters of the arts or technology.

Where to look

Once you’ve decided you want a mentor, where do you look? First off, says Rosario, “You need to be humble and be able to ask for help, whether in your own workplace or another organization.” Keep in mind, she adds, you can have different mentors for different phases in your life. Case in point: Rosario has found additional mentors as a member of the board of Big Brothers Big Sisters, one of whom is helping her with cash-flow planning.

Barbato echoes her mentee matter-of-factly: “Here’s my motto: as many people as often as possible.” She also suggests that people see their bosses, co-workers and informational interview prospects as mentors with a view to grow, gain skills and insight. “The important thing is to reach out to contacts, find someone to talk with who can give advice or counsel.” Even meeting for a 45-minute coffee can result in gaining knowledge that changes your whole perspective.

Look within your own network first, offers Drynan. “But you need to challenge yourself on the definition of a mentor.” Your first instinct may be to look for obvious contacts in your field, but it’s best to broaden your horizons, he adds. “My grade seven teacher doesn’t know anything about advertising but he knows a lot about life, so I could learn a lot from that side of things; I find that very valuable.”

There are a number of online sites as well as social media avenues such as Linkedin you can try. Then there are your natural networks, which Barbato claims young people simply don’t use enough of. You need to realize what you already have, she states. And let’s not forget the benefits — albeit frightening for some — of cold calling, a personal favourite of hers.

Managing expectations

In setting up a mentorship relationship some ground rules may be necessary. For Drynan it meant understanding what his Ooch mentor could and couldn’t help him with. For one thing, he wouldn’t be his advocate when it came to the board. “What we talked about with regard to the organization was closed on my side and his, which was really valuable because then I could open up and talk about stuff I couldn’t necessarily talk about with my board members or staff.” And, he adds, “There’s a real value in setting up expectations upfront.”

It’s not about formalities; it’s about having a conversation to determine you’re on the same page. Stewart cautions not to set out all the parameters at the beginning, using his mentorship with the mayor as an example of how you just need to be constantly checking-in. “If this gets to point where this is not of value, we quit.” He says you should lay out how often you will meet, ensuring this is convenient for the mentor.

Barbato believes setting a three-month time frame is reasonable. “If you say there’s an endpoint it gives everyone a way out,” she explains. And the various criteria — including goals, objectives and what you’re trying to get out of mentorship — should be pinned down at the beginning. That way “you both know what they are contributing to the relationship; it’s the only way to have success.”

Moreover, the relationship should be reciprocal, says Drynan. “I would want to know they have some form of vested interest in me, that there’s some reason they want to be engaged with me and that they have knowledge and experience that can be a benefit to me.”

Interestingly, mentors often laud the beneficial mutuality of these relationships. Stewart relates how when he’d visit MacKewan in his retirement home the last few years of his life, MacKewan’s parting words would always be, “I am so glad you dropped in, I’ve learned so much.”

Always be sure you’re not approaching a prospective mentor with the goal of leveraging their connections or in pursuit of another objective that crosses the mentoring line. “It probably won’t work out well cause it’s short-lived and pretty superficial,” says Drynan, explaining that while his mentor has exceptional connections, he’s always cautious about what he asks him for, thereby ensuring he doesn’t jeopardize the relationship.

Drynan also cautions that you only get out of mentorship what you put into it. “I would never go to a meeting unprepared, but I’m always willing to go with whatever direction and just listen.”

Elisa Birnbaum is a freelance journalist, producer and communications consultant living in Toronto. She is also president of Elle Communications and can be reached at: info@ellecommunications.ca.