Dear Mom: What Does a Mentor Look Like?
Signe Brewster

What does a Mentor Look Like?

Meditations on tech across generations

Dear Daughter,

I’ve never spotted a mentor, except in hindsight. I am glad you are actively on the lookout for mentors, at this early stage of your career.

At your age, I still cherished my independence over everything else. I so wanted success to be based upon some objective measure of merit: Something everyone had to earn the hard way, with grit and determination, solo. Mentoring, to me, had a whiff of brown-nosing and the old-boy network to it.

As a result, I consciously avoided seeking any guidance from professors or early supervising attorneys. Much less my own mother, an entrepreneur in her own right.

I did try to be a mentor early in my career, when asked by one of those programs that pair promising young Fortune 500 women with executives. None of them resulted in the relationship I envisioned. For the most part, to me, each mentee seemed to be looking for me to show her the easy path through the jungle, rather than showing up wielding a machete.

My true mentoring relationships grew organically in the context of the work at hand.

Here is what I know about what a good mentor looks like.

A great mentor admires the problem

I once asked a counselor what I should do when I can see that someone I care about is making a mistake. “I can’t just sit there and do nothing,” I said.

“Admire the problem,” was her reply.

This sums up the essence of a good mentor. Listen actively, reflect, draw out the factors affecting the decision, and let the mentee have the privilege of letting the answer dawn on them.

Of course, as a mentor, you get to be your authentic self, as well, which for me includes occasional impulsive bouts of brainstorming and unsolicited advice. There is a lot of room for this, as long as the listening part is actively cultivated.

It is so rare in this world to find an experienced person who can help another find clarity. “When you want wisdom and insight as badly as you want to breathe, it is then you shall have it,” Socrates said. The mentor’s job is to bring oxygen to the room, giving the mentee a healthy place to wrestle with difficult decisions.

In admiring the problem, we honor the essence of the other person, and allow them to see that they are the one uniquely equipped to make decisions about their own lives.

As the mentor, your best questions are reflective and open-ended:

“What do you see as the key risks and opportunities?”

“That sounds difficult — what is your instinct?”

“What would be your ideal outcome?”

“How can I help?”

Had I approached my mentee from the formal executive program in this spirit, we would have been guided to a rich and rewarding relationship. Instead, both she and I assumed I was there to solve her problems for her, during our monthly one-hour meetings.

Paraphrasing Socrates, good mentoring is the kindling of a flame, not the filling of a vessel.

In seeking a mentor, look for the listeners.

A mentor observes the truths about you

Performance reviews have always been inadequate and a missed opportunity, in my experience. Generally, they have tended to be something to simply be survived by both the boss and the employee, rather than the tremendous opportunity for insight they could be.

Enter the mentor. The most valuable mentors in my life have given me what performance reviews did not: self-awareness.

Having a trusted person who can see the unique risks and opportunities presented to you — at the intersection of your talents and shortcomings and a given opportunity set and corporate culture — is priceless.

I often think of Donna, the partner I worked for in a large, San Francisco-based law firm, right out of law school. A trailblazing woman in the male world of corporate deals and financial transactions, she was feared by the associates for having “impossible” standards. Some of her partners were inclined, obliquely, to disparage and attempt to marginalize her. I believe it was because of her immense talents, and her unwillingness to stop being “uppity.” By that, I mean effective, powerful, and only as self-effacing as an average lawyer. She insisted on being herself in a world that sought to knuckle her under.

She did not look like a mentor, with her sixties-holdover style in the halls of commercial power.

As a young attorney, I was free to seek out assignments from any partner — a free agent, by and large. Conventional wisdom would have been to hitch my wagon to part of the power structure, the guys who looked the part.

Despite her reputation, I gravitated towards Donna.

Looking back, I recognized that she modeled what I could aspire to become. To be respected, and, when the occasion called for it, feared, even. A force in my own right, with my own hard-earned empire.

Donna was tough with me and perfection was the goal. By holding me to the highest standards, and expecting me to get things right on my own, she gave me the theory that I was far better than I imagined myself to be. When I inevitably screwed up, she skipped the criticisms and moved me immediately into corrective action.

She also gave me the insight, on the fly, that if I didn’t grab my chances and learn some basic survival skills, I would end up being less than I could be.

“You only have one strategy,” she said one day, when I told her how I was going to handle a situation. “You are a Mack Truck.” I didn’t understand this criticism; I so valued my Iowa straight-shooter values.

Law firms can be brutal places. When Donna grabbed me, I was on my way to confront a partner who had inserted a criticism of me into a performance review. It was disguised as a compliment. Another partner, charged with conveying my review on behalf of all the partners I worked for, cringed as he passed along the offending comment: “Her work is excellent and clients love her, but the work demands must be hard on her, because I know she is a good mother and must want to work part-time.” I was being accused of a thought crime — lack of commitment — the dreaded “C-Rap,” as we associates called it. It derailed many associates’ journey toward partnership.

I thought my plan to confront the partner immediately and directly was perfect. “You will just drive him underground,” Donna said. “You need to develop some peasant cunning.” I scowled at this suggestion. “Don’t prove his point,” she admonished.

It is still a weak spot, my wanting to approach every person and every problem head-on. My instinct that the shortest distance between two points is a straight line is often off-base. Because of Donna, I work to pause before this response, and think about what will be effective in a given situation. Sometimes, the best route is circuitous.

I found a way to be effective with the problem partner, through the proper channels. The partner in charge of associate development, who delivered the review to me, was the right place to start, as he knew how to get the sentiment removed from my file and how to raise the subject with the offending partner. Had I simply marched into the offending partner’s office to confront him, I would have given him anecdotal evidence that I lacked judgment; the dreaded “J-Rap.”

When looking for a mentor, find someone who sees you and isn’t afraid to tell you what she sees.

Third, a mentor can vouch for you

Be on the lookout for respected senior folks who can vouch for you.

I once came into a company as CEO just after one faction of the board of directors had ousted the previous CEO in an ugly public proxy battle. During the battle, as a member of the board, I was working to try to resolve the conflict between the CEO and the board members who opposed him. I had a lot of brutal conversations with Charles, the chair of the independent committee of the directors, which was backing the CEO. Sometimes, the conversations Charles and I had gave off more heat than light.

Charles was a pedigreed director, serving on the boards of big banks and companies. He had seen a lot of crisis situations, and he had the trust of a large group of activist shareholders of my company. I was worried how Charles and I would mend fences.

I had parachuted into a tough situation. The company developed, built and operated power and steam cogeneration plants. It was a male bastion, with large industrial customers and hostile local electric utilities battling the innovation and competition the company brought to the power industry. The company had been run into the ditch during the proxy fight, and I inherited the mess of major litigation with construction vendors and customers, debt in default, plant operational problems, and flagging employee morale.

The shareholders were screaming bloody murder. A week into the job, a major shareholder from a vulture fund set up a conference call with Charles and me. The subject was the stock price. It was in the tank. He gave me what in the distressed asset world passes for a “pep talk” — expletives strung together, end on end, riffing on his views of my inadequacies.

When he came up for air, Charles jumped in: “Is that what you are worried about, that Julie can’t turn the company around?”

For purposes of this letter, I will condense the shareholder’s verbose and colorful response to a “yes.”

Charles did not miss a beat. “Julie is a pro,” he said. “The best in the business.”

After that short phone call, I was able to deal with the activist shareholders on my own. Charles became one of the most valuable mentors imaginable. He had perspective on the pitfalls of leading through crisis, and the specific land mines of my strategies. He made himself available whenever I called, even when he was on vacation, from the satellite phone on his boat.

Most importantly, he vouched for me.

I wouldn’t have spotted Charles as my future mentor. I couldn’t imagine, having been on the other side of a very protracted controversy, that he would even want to speak with me. The fact was, when we were adverse to each other, Charles recognized that I had the toughness and the industry skills and leadership traits needed to turn the company around.

When looking for a mentor, find someone who will vouch for you.

Most importantly, a great mentor gives you a theory, so you can learn

As a leader, I find myself returning to the words of W. Edwards Deming, the great leadership and quality guru. One of his basic insights is that “experience by itself teaches nothing…without theory, there is no learning.”

The mentor’s greatest gift is not an answer to a question. It is the right questions, and a framework for thinking about the problem. You need a theory to learn.

I have found that books can perform this critical mentoring role. They can offer theoretical frameworks that give you hooks on which to hang the insights experiences offer. Go to the leadership section of a bookstore and grab a bestseller that catches your eye. Most recently, I found a treasure trove of profound advice in Difficult Conversations, a book written by the folks at the Harvard Negotiation Project, the same folks who wrote Getting to Yes, the famous book teaching interest-based negotiation. Difficult Conversations chronicles the reasons why those afflicted with the human condition often can’t get to yes. The Harvard team studied the limits of Getting to Yes for 16 years to crack the code. It turns out that emotions and identity get in the way of win/win outcomes — and the book goes on to provide a framework for dealing with the reality that our rational thoughts are a thin veneer over our roiling emotional interior lives. Arguably, the book makes the case that men should not be allowed in business — they are too emotional.

Peers can be mentors, too. In one of my startups, we didn’t have a development budget, and we purposefully built a team that had senior industry experts and entry level professionals, with no middle management. We decided to try out the idea that peers can mentor each other. Every month, a junior team member would pick out a Harvard Business Review Article and lead a discussion at a brown bag lunch in the office. Team members from different disciplines brought insights to one another. That is mentoring at its finest.

In order to benefit from a mentor, you have to be a great mentee. In my experience, the best mentees find the folks whose shoulders they can stand on in order not to repeat the mistakes of the mentor. They actively acquire the wisdom of others. A great mentee considers her time with mentors precious. Work hard, organize and cogently present your quandaries and options, and find ways to make the relationship one of give and take. Involve yourself in active planning to implement the mentor’s advice. Above all, as a mentee, pair your seriousness of purpose with a ready laugh at your own foibles.

Ben Franklin said “tell me, and I forget; teach me, and I may remember; involve me, and I learn.”

Both your life and the mentor’s will be richer for the relationship, far beyond the obvious, immediate career benefits. So, keep your eyes peeled for those who listen to you, speak the truth to you about you, believe in you so they can vouch for you, and those who take the time to give you theories, so that you can learn. Work has its dark moments, so offer the same to others around you. In the words of Yoda, “be a candle, or the night.”



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