How to Approach Your Dream Mentor

A good mentor can dramatically alter your career. Oprah Winfrey credits longtime mentor Maya Angelou with igniting her ambition. Richard Branson’s drive to shake up the airline business was fuelled by mentor Freddie Laker. Steve Jobs’s legendary obsession with design thinking came from dialogues with his early mentor Mike Markkula.

Research suggests that working with a mentor (or mentors) can make you more effective in your work, confident in your abilities and happier with your career — all while increasing your earning potential. There are plenty of less tangible benefits, too: As Dragons’ Den star Arlene Dickinson put it in a 2022 conversation with fellow entrepreneur Anthony Lacavera: “One of the best benefits I’ve had from a great mentor is the ability for me to sit back and take a breath, to listen to what they’re telling me and not get so overwhelmed by the obstacle in front of me that I can’t see a way forward.”

That likely all sounds terrific. But how exactly are great mentor/mentee relationships formed? What’s involved in finding, approaching and securing a mentor who can help you elevate your performance? Is it simply a matter of chance, of circumstance — or of having the chutzpah to ask? Or is it a process best tackled with thought and care?

Smith Business Insight contributor Deborah Aarts spoke with expert Smith School of Business alumni — all experienced mentors and all erstwhile mentees — to prepare a playbook.

Be strategic

First things first: Before you approach any potential mentor, you need to do a bit of homework. “It’s important to start by taking the time to reflect and set intentional goals,” says Mary Elms, director of career education and coaching at Smith’s Career Advancement Centre, which encourages aspiring professionals to work with mentors as a best practice. “That means asking yourself three questions: What do you want out of the relationship? How do you want to learn? And why is it important to you?”

A few variables to consider: Are you looking for guidance on your long-term career trajectory (e.g., learning what it takes to get from where you are to the C-suite), or for advice on navigating a more immediate matter (e.g., taking on a new role in a different department)? Do you want help brushing up your skills (e.g., delivering effective presentations), refining your style (e.g., becoming a servant leader), or establishing habits (e.g., improving your time management)? Would you like your mentor to be a sounding board who helps you work out problems, an arbitrator who helps you gut-check your ideas, or a tough-love challenger who pushes you out of your comfort zone?

You might want to answer “yes” to all the above questions — but it’s in your best interest to prioritize. No mentor can help you with everything, and certainly not at once. “When you map out the most important qualities you need in a mentor, you can be a lot more strategic in approaching one,” Elms explains.

Be realistic

Once you’ve set your strategy, you can start considering who might be able to help you.

The good news is that mentors can be found everywhere. You can look within your workplace: to your manager, yes, but also to a colleague in a different department whose skills you admire, or a peer who overcame a challenge like one you’re experiencing. Mentors you work with carry the benefit of knowing the nuances of the organizational culture you’re operating within, and they often have at least some understanding of your own abilities and accomplishments.

Beyond your nine-to-five, you can scour LinkedIn for individuals — ideally, those with whom you share connections — who have forged instructive or inspiring career paths. You can volunteer with alumni chapters, community groups and industry associations to meet folks with experience and a proven inclination to pay things forward. And you can lean on social and family connections. External mentors offer fresh perspectives, unbiased advice, and, often, a safe forum to air sensitive concerns you might not be able to table with colleagues.

Elms advises you to make a long list of potential fits and then triage based on who best lines up with what you hope to gain. Here, she says, it’s important to be realistic. You may dream of being mentored by someone in the C-suite — just think how great that would look on your CV! — but not only is a top boss unlikely to have heaps of time to spare, he or she may also be a few decades and salary bands past being able to provide relevant advice to you at your career stage. Furthermore, you can never assume you’ll find one person who can check all your boxes, much less someone interested and available. “You want to find a good match that meets your key, must-have criteria,” Elms explains. “But it doesn’t have to be the perfect match.”

Be specific 

How you ask someone to be your mentor will depend on your relationship. If it’s a colleague or contact you see regularly, you can bring mentorship up in conversation. If it’s someone you know less well — or not at all — a cold email or LinkedIn message is appropriate. The medium matters less than the message, and on that, experts agree: Clarity is your best virtue.

“You need to be specific when you are approaching a potential mentor,” affirms Lucie Jeffers, a former chief strategy and people officer who provides advisory and consulting services in the HR space. As someone who benefited greatly from the guidance of mentors throughout her career, and who has since mentored many others, Jeffers has learned that if you’re asking someone busy and successful to give their time and expertise, a vague “I’m looking for a mentor, will you do it?” won’t cut it.

“If you are reaching out to me, tell me why,” Jeffers says. “What are you hoping to get out of it? What specific skill are you looking to grow, or what advice do you hope to gain? You need to clearly articulate what interests you and why you think I can help you. Because you’re asking me to make a pretty big commitment, and there’s a good chance I absolutely want to help you, but I need to know you’ve done some work first.”

Here’s a checklist of sorts: Be explicit about what you hope to learn from your mentor. Put forward as much detail as you can about the face time you’d like — say, for a half-hour Zoom call, once a month, for six months — so the recipient can assess the time commitment involved. And commit to setting an agenda for each meeting, to showing up on time and to tackling action items between.

If this seems like overkill, consider this: Most would-be mentors have a lot on their plates and are unlikely to agree to anything whose scope or purpose is undefined. It’s like the difference between a neighbour asking you “Can you do me a favour?” and asking you “Can you help me move a couch on Saturday afternoon?” Specificity arms your audience with enough information to make an informed response.

Be respectful

While many mentorship experiences end up being reciprocal — in that mentors often learn a great deal from their mentees — few begin that way. The reality is, you’re asking someone very busy to add an unpaid task to their to-do list, and that warrants a degree of deference. “Mentees often underestimate the magnitude of their ask,” explains Jill Nykoliation, an executive coach and former marketing agency CEO with a rich and varied range of experiences as both a mentee and a mentor.

Would-be mentees often also assume that their role is to simply become a vessel for their mentor’s bequeathed wisdom, which Nykoliation says couldn’t be farther from the truth. “Being a mentee is not just about receiving information,” she explains. “You have to be super active. You have to be insatiably curious. You have to be like a keener in class: asking questions, coming prepared, doing the work.” Most mentors want — or need — to see some evidence of that drive before they’ll agree to get involved.

For these reasons, your outreach to prospective mentors should contain as much proof as possible that you won’t waste their time. Demonstrate that you’ve done some research about who they are. State what you admire about what they’ve accomplished and articulate some of the questions you’d like answered. Show that yours is a well-thought-out appeal, not a cookie-cutter request.

Keep your tone professional — no emojis, no typos, no “hey” salutations — and reinforce that you appreciate their consideration. “If you approach me too casually or carelessly, it’s a fast ‘no,’ ” Nykoliation says. It’s less a breach of etiquette, she explains, and more a red flag that you might not approach the work, and the relationship, with the respect it deserves.

Be courageous 

If this all feels a bit daunting, well, it can be. Asking someone with more power and experience for help is an inherently vulnerable act, which can feel uncomfortable. But if you’ve thought it through and treat the process with care, the experts agree you have little to lose — and everything to gain.

“Approaching a mentor is intimidating, but keep in mind that we’ve all been in that seat before,” says Lucie Jeffers. “If you don’t ask for what you want, you’re never going to get it. Sure, you might hear ‘no’ from 10 people, but when you get that one ‘yes,’ it can really change your trajectory. So don’t be afraid to shoot your shot.”