The three keys to a successful mentor-mentee relationship | Advertising Age

“Experience is a hard teacher because she gives the test first, the lesson afterward.”  —Vernon Law

This is especially true of business leadership, whose career path is shaped by trial and error and where much of the learning comes after the fact. Mentoring can play a crucial role in accelerating the development of future leaders, equipping them with the wisdom and tools to bypass many of the pitfalls.

A great mentor is akin to a great coach—they should not be afraid to hold a mirror to a mentee and provide brutally honest candor and advice, no matter how uncomfortable this may become for either party. But, all too often, mentorship becomes an exercise in career cheerleading rather than the delivery of hard truths.

A great mentor-mentee relationship is based on three tenets:

A deep bond of trust
A mentee has to believe in their heart of hearts that they want, and need, to improve and that the mentor’s only motivation is to make them better. Without that underlying psychological safety net, the relationship is doomed. As such, all mentor-mentee relationships are deeply personal as well as professional. Unlike a manager, a good mentor understands the key driving forces of the mentee’s life outside of their professional responsibilities (e.g., their spouse, dog, parents, fears, etc.), including both their assets and vulnerabilities. Likewise, a mentee is far more likely to commit if the mentor opens up about their own mistakes and weaknesses, past and present.

Unbridled candor
Helping people understand their superpowers (their exceptional skills/capabilities) is a critical step towards providing guidance. Having spent more than 20 years supervising thousands of employees, I’ve found that up-and-coming talent generally falls into two camps: those that over-index on self-confidence and under-index on self-awareness; and those that do the exact opposite.

Over-confident mentees don’t know what they don’t know. That’s where the mentor comes in. To an extent, the mentee has to be broken down before they can be built back up. Tools like 360 reviews and role-play scenarios can help them understand how they might have handled particular situations better.

Conversely, under-confident mentees don’t realize that their superpowers are far stronger than their weaknesses. In this case, the job of the mentor is make them realize they possess talents that are near impossible to teach adults (e.g., humility, compassion, inspiration, positivity), whereas their weaknesses tend to be skills (e.g., P&L management, negotiation training, management training) that are highly teachable.

A few years ago, I approached a mentee with a step-change promotion opportunity. What happened next was eye-opening to me. She grilled me as to why I thought she was qualified for this leadership position and explained all the reasons why she might fail. Although she accepted the position, for the next year her self-doubt hindered her ability to fully succeed in her job. (I subsequently learned the term "impostor syndrome".) 

Interestingly, and unsurprisingly, I’ve found far more success mentoring those blessed with tremendous self-awareness but a shortage of self-confidence than the other way around. The reason is simple. Those will high self-awareness are more likely to be open to feedback and have an innate willingness to learn. But when lack of self-confidence is so acute that it breeds defensiveness, it can derail a rising star in the making.

The journey is the reward
My college-age son was a pretty good basketball player growing up and an eventual high-school star. We traveled to a lot of spring and summer tournaments, where frequently I would see parents lose perspective on the games—they would focus solely on the outcome rather than enjoying the journey as their sons they battled with failure and adversity, and celebrated team and personal success.

The best relationships span years, if not decades. In mentoring, like parenting, there is no end zone where you spike the football and do a touchdown dance. Mentorship is a commitment to helping each other over time (mentees also have much to teach mentors). It's the gift that keeps giving. So, forge a deep bond, be brutally honest with each other and enjoy the journey.

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