How to find — and keep — the best professional mentor you'll ever have

by Sam Dewey
March 23, 2016

More often than not, finding success in your professional and private life isn’t just dumb luck. Success takes tenacity, grit, and sheer hard work. They’re gristly qualities, but having a mentor — a familiar face in your corner celebrating your wins and counseling your losses — makes them each a bit easier to chew.

Finding the right mentor for your professional development, however, can be tricky. You’ve got to find someone in the right domain who can empathize with your struggles and fuel growth toward whatever professional direction you’re headed — someone with whom you can communicate effectively and from whom you can extract real, iterative value.

Someone,

COO and President Dev Mukherjee said, who can stand besides you in a substantive, decades-long relationship.

Mukherjee is a business professional with years of experience on both ends of the mentorship teeter totter. We sat down with him for advice on how to find the perfect mentor and tips on how to manage the mentor/mentee relationship.

Understanding the difference between a mentor and a coach.

Mukherjee said one of the key steps to finding a mentor is to understand exactly what it is you’re looking for. There’s a marked difference, for instance, between a mentor and coach, and identifying the roles and responsibilities of each can help to better set you on your path.

“I think of a coach as a good manager — someone who is assigning work but is also going to help you get better at that work,” he said. “A mentor is someone who’s thinking more about the person — and for the long haul.”

Because of the long-term nature of the relationship, conversations between the professional and the personal tend to blur. For that reason, it’s important to...

Find someone outside of your organization.

It’s always a boon to have an outsider come in with a fresh, unbiased perspective on a problem at work, free from office politics or personal agenda. For that reason (among others), it’s a good idea to seek mentorship with someone outside of your department or organization.

“It’s very hard for a manager or direct boss to mentor someone who works for them directly, because you’re balancing on-job performance with what's good in a broader context,” Mukherjee said. “For the individual — it can be hard to share things with someone who’s going to write a performance appraisal in a month.”

That’s not to say former managers or bosses can’t make great mentors. They can — and do — in part because of their familiarity with your performance, professional history and goals, personality, and private life. This is important, Mukherjee said, because building a fruitful relationship with your mentor is all about…

Embracing intimacy.

The connection between a mentor and mentee is different than most other relationships you’ve likely built in your life. Mentorships are chock-full of charged serious conversations, pointed questions, and thinking seriously about areas in your life for personal and professional growth.

“For really great mentorships, it’s a very intimate relationship,” he said. “You’re having to disclose stuff you might not disclose to everyone you work with or bump into on the street.”

Because of the unique space the mentor/mentee relationship occupies, it’s important to consider things like whether or not you like each other personally, share the same values, or communicate effectively. But before you even get to that point, you’ve got to...

Know where you’re going and who can help get you there.

Even the most compassionate, insightful, and motivating mentor will prove ineffectual if he or she doesn't have a clear idea of who you are and where you want to go. It’s up to you to provide a mentor, in more or less words, with a roadmap of what you want and need out of the relationship.

“Before you even start, you need to have some awareness of what domains you want to have a mentor in and also what sort of person you have worked well with in the past,” he said. “Is it someone who’s unlikely to give you direct advice but is more reflective? Is it someone who is brutally honest?”

For instance, if you’re a female CEO and founder of a young software company, you might be looking for someone with advice on the unique struggles that may lie ahead you — like dealing with seed-stage VCs, scaling a software company of your make and model, or dealing with sexism from employees in the workplace. Once you know the types of things you're looking for, you can start thinking about…

How to approach the right mentors.

There’s no smoke or mirrors behind finding a good mentor. It’s all about connections, mutual interests, and shared experiences — but unfortunately, there’s no “Tinder for mentors.”

Instead, Mukherjee said it’s as simple as approaching them politely and professionally. Send them a message on LinkedIn or ask them a few questions after a panel discussion. From there, ask for easy, natural next steps — like asking to grab coffee for 15 minutes to get their perspective on a problem you’re facing.

“There’s nothing stopping you from approaching someone you admire or appreciate,” he said.

The best mentorships grow organically, so don’t try and force a relationship on a leader you admire. Strong mentorships are built over time, and part of management includes…

Knowing when to stay in touch, when to say thank you — and when to move on.

It’s important to maintain communication with a mentor as your career progresses. If you’ve landed a good one, she or he will likely hold you accountable for the goals you’d set during your last meeting. A mentor might check in to see how you’re progressing — but a good mentee will be forthcoming with updates, new questions to ask and problems to tackle, and a “thank you for the words of wisdom” thrown in for good measure.

But those check-ins, Mukherjee said, may take some time.

“It’s a different type of relationship when you’re pushing them to think about or do something uncomfortable,” he said. "When you've had an intense discussion, there may be a long period of time before you hear from them again. If you have had any value — and hopefully there will be value — you should make sure that you at least say thank you.”

Because mentorships can span an entire career, there’s no need to feel pigeonholed into a particular relationship or two. Mukherjee said it’s beneficial to have multiple interlocutors for various areas of your professional and personal life. They're your go-to shoulder for support, and if a relationship is no longer valuable, you should consider other options.

“There’s no financial contract,” he said. "If it’s not working, move on.”

Images via Shutterstock/LinkedIn.

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