Skip to main content
power points

The best mentors push us. They are often not nice, but they are always in our corner (even if it may not seem like that at times).

That assessment from Bonnie Hammer, vice-chair of NBCUniversal, who also happened to mentor Meghan Markle in her Toronto acting days, runs counter to the widespread belief that the ideal mentors are gentle, supportive souls. Yes, many mentors are kind and can be helpful. But the mentors we are likely to remember stand out for being challenging rather than supportive.

“Good mentors are like cheerleaders. Great mentors are like coaches. But the best mentors, the ones who change our lives (or at least our career trajectories) are like drill sergeants. The first two can help us win a game. But it’s the challenging mentors – the drill sergeants we encounter – who prepare us for battle and help us to win the war,” she writes in her new book, 15 Lies Women Are Told at Work ... And the Truth We Need to Succeed.

She points to a photojournalism professor in university who threw her out of class when she turned up one Monday with mediocre photos, after a weekend focused more on a date than her assignment. After showing other students the photos and calling them “pure junk,” he told her not to come back until she had images worth his and the class’s time. “I was humiliated. But I never gave him less than my best again – and in the process I discovered my eye was even better than I’d thought,” she recalls.

Media mogul Barry Diller was often demanding and sometimes demeaning when he was her boss. He questioned everything she did. She even painted his last name in capital letters on the six-foot punching bag she used for her weekend kickboxing classes so she could take out her aggression on that representation of him.

One weekend, they sparred continually by e-mail about a show she was trying to get approved for the Sci-Fi Channel. He pushed her to explain her logic and back-up plans in detail. Finally, four words came back from her boss: “Your argument wins. Go.” She had assumed he didn’t like her but realized she just wanted him to fight for her ideas tenaciously, intelligently and passionately. “When he asked me questions, he wasn’t telling me I was wrong – he was hoping to be convinced that he might be,” she writes.

The kind of mentoring she is praising tends to be organic rather than organized, the result of chemistry between two people. But most mentorship today comes from bureaucratic programs instituted by human resource departments, which she feels are wary of a mentor who tells us hard-to-hear truths. “What HR department wants to be on the hook for facilitating a relationship that is by its very nature difficult, even combative?” she notes.

But sometimes, she insists, we need to be pushed and prodded so we can learn what we’re capable of. In particular, she feels women are losing out on such challenges with mentoring formalized and niceness the name of the game. At the same time, she stresses that while challenging mentors are often our bosses, not all challenging bosses are mentors. “There is a difference between someone who is trying to grow and stretch you and someone who is trying to break you,” she says.

Seek mentors but don’t make it a big deal so the long-term commitment doesn’t seem overwhelming to them. Just ask to have a coffee and come armed with thoughtful questions. That’s what Meghan Markle, now the Duchess of Sussex did, when hired for the television show Suits. She would reach out to Ms. Hammer with positive, well-thought-out questions, from building the depth of her character and role, to how to more fully engage with the director, to – when Prince Harry came along – how to navigate security concerns without inconveniencing everyone else. “She had the humility to seek out my opinions – rather than demand advice or favours – and she was smart enough not to overstep,” Ms. Hammer writes.

Quick hits

  • To persuade somebody to do something, ask for a commitment in the future rather than right now, Phill Agnew, who hosts the Nudge podcast, recommends. He points to a study that found when students were asked to tutor others in the current school term, they only committed on average to 27 minutes per week, but that rose to 85 minutes when asked to tutor in the next term. People commit more in the future than they do in the present.
  • Executive recruiter Gerald Walsh has found when candidates don’t immediately know the answer to a question, they often start to ramble, making them seem unfocused. If you are uncertain about what is being asked, it’s fine to ask for clarification. If you understand the question but need a moment to think, he urges you to take a brief pause to gather your thoughts and structure your response more effectively.
  • Good things happen when you put yourself in rooms where you don’t feel like you belong, advises venture capitalist Sahil Bloom. Those rooms are all around you, he insists, but your fear of being “found out” holds you back.

Harvey Schachter is a Kingston-based writer specializing in management issues. He, along with Sheelagh Whittaker, former CEO of both EDS Canada and Cancom, are the authors of When Harvey Didn’t Meet Sheelagh: Emails on Leadership.

Follow related authors and topics

Authors and topics you follow will be added to your personal news feed in Following.

Interact with The Globe