Vulnerability in the executive suite: Teachers' top lawyer leads with his heart on his sleeve

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On a Monday night in early June with a Toronto Raptors’ championship on the line, the Oscars among the in-house legal crowd was also happening, and Jeff Davis, rubbing his head and snapping his fingers, knew he had to keep it “going.” He had just won Counsel of the Year, a tremendous honour, no doubt, but in that moment, one that demanded some brevity in his remarks.

The chief legal and corporate affairs officer at Ontario Teachers’ Pension Plan stood at the podium, looking out at a room of 600 lawyers and senior executives, from blue chip law firms and corporations, gathered at the Fairmont Royal York Hotel for the 15th annual Canadian General Counsel Awards.

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After rifling through the requisite thanks, with humour and charm, he dove right into a weighty topic, turning what could have been yet another brief acceptance speech, at yet another black tie affair, into something that has been echoing around corporate Canada ever since.

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You’ve helped me survive the darkest moments of my life

“I carry all of you in my heart everyday,” Davis said, addressing his friends inside and outside the workplace. “You have stood beside me through everything. Through all the fun and exciting and joyful moments, including tonight — but, more importantly, you’ve helped me survive the darkest moments of my life.

“You helped me struggle through depression, loneliness, disconnection, deep-rooted shame — the human struggles we all suffer through, but are scared to talk about.”

It was a profoundly intimate moment, played to a full house, and it showed the top lawyer at a $190-billion pension fund to be human, vulnerable and all-too-real before an audience of high-achievers drawn from a community where leaders have traditionally been typecast as invincible, where betraying weakness is tantamount to a character flaw.

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But times, as they say, are changing, and maybe Davis, with a heart-on-his-sleeve approach, is at the forefront of the shift, a 21st-century pivot away from the Alpha-boss archetype, to a more rounded image of what a leader can be. One whose messy, complicated, fragile parts don’t need to be hidden, who can build an effective team centred upon the belief that vulnerability — that is, showing one’s authentic self at work — isn’t a sign of weakness, but a key element to building organizational strength.

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At the very least, Davis started a conversation. Since the speech, he has received two invitations to speak from law firms and scores of messages thanking him for his words, while impressing upon his peers, including Ken Fredeen, chief counsel at Deloitte Canada, that an emotional suit of armour is not necessary to succeed.

“Lawyers are expected to be tough, to work very hard, to never fail — we are all about winning — and the consequence is you wouldn’t necessarily want to talk about being in a vulnerable state, because historically that’s not what people did,” Fredeen said.

Fredeen is 60, and of a generation, as he describes it, that was taught to push through problems, not speak of them, and where the boss retired at 65, stereotypically dropping dead from a heart attack the next day.

“Having a great leader like Jeff talking about being vulnerable, it’s wonderful,” he said. “It is a model that you can be vulnerable, and be successful. Too often, here in the legal profession, and not just the legal profession, we hide our vulnerabilities from others, and that is not necessarily the real us.”

Bringing the private self into the office sphere isn’t merely balm for the soul, it can be good for business.

Studies have shown that workers want leaders who are approachable, whom they can trust and connect with. Trust fosters openness, and openness, in theory, creates an environment where, for example, all aboard can celebrate when things are going great, but also feel comfortable talking to their leaders, questioning ideas or sharing their struggles when things are going sideways, either on the whole, a particular file or in an individual’s private life.

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“We can often connect concepts of authenticity and sincerity to notions of vulnerability,” said Geoffrey Leonardelli, an associate professor at the University of Toronto’s Rotman School of Management. “Meaning when our leaders have expressed their own challenges in life, we see them as being more real people, and coming from a place of experience that can give them an appreciation for the struggles others go through.”

So what, exactly, was Davis going through, and why did he decide to give the speech he did, when and where he did?

Eight days after the CGCAs, the 49-year-old lawyer was in his 12th floor office in northern Toronto, dressed in jeans and a T-shirt, and, well, being vulnerable, speaking candidly about the darkest moments in his life he referenced the week before.

When our leaders have expressed their own challenges in life, we see them as being more real people

Geoffrey Leonardelli, associate professor at the University of Toronto's Rotman School of Management

Davis was a whip-smart associate at Torys LLP in Toronto in his younger days, one who dyed his hair with platinum streaks and asked for six months off so he could move to Miami Beach, Fla. There, he met a woman and got married “for about a minute,” which in actual time translated to about 10 months.

Davis remarried a few years later. Marriage number two was going to be the perfect version, the one with the kids and the house and the happily ever after. Only it wasn’t very happy.

Within six months, the relationship was toxic. He hung on for a few years, but he knew the marriage wasn’t right and was going to end, and that thereafter he would be that guy: the lawyer in his early 40s and already twice-divorced — and, as he points out, who wants to be that guy?

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“I spiralled,” Davis recalled. “I tried to isolate myself. I felt embarrassed.”

He felt as though he couldn’t tell anybody, but what he felt most of all was a consuming sense of shame. Naturally, he did what anyone back in 2012 would do: he Googled “shame.” Up popped a TED Talk by Brené Brown, a University of Houston shame researcher who defines vulnerability “as our most accurate measure of courage,” as “the birthplace of joy, of creativity, of belonging, of love.”

Davis, a hug-your-pals-when-you-see-them type of person, was hooked. He watched more videos, he read, and he gradually revealed at work what was happening in his personal life, not self-indulgently, or willy-nilly, or with all the gory details, but when the moment fit.

He found his sense of shame evaporating, while the colleagues he confided in often responded to his story with a story of their own.

It took him a few more years to understand that all the talking and sharing, as well as his ideas around vulnerability, weren’t just a personal thing, but a professional call to arms, that there was not just a mere place for them at the office, but a measurable, meaningful value in having them there.

“Over the years it has bled into my working style and how I relate to my team,” Davis said. “Where it has become almost programmatic — that this is what we do here, this is our strategy — was probably in late 2017-2018.”

Don’t be fooled. No matter how warm, fuzzy and beneficial a more open, authentic, bring-your-whole-self-to-work culture sounds, there is still a place for your tough-guys/girls-don’t-cry boss, according to Leonardelli.

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“It is still a prominent model,” he said. “I associate it with what we might describe as a command-and-control model, wanting a firm grip on how things run, and that comes with an authoritative perspective and ideology, and a might-makes-right and my-decisions-need-to-be-followed kind of logic. There are times when that is necessary.”

In other words: the alphas aren’t dead yet, though they may want to consider becoming a composite, a Frankenstein of the c-suite, with all the necessary steel to deflect the slings and arrows, but also an understanding that perhaps the best way to optimize a team dynamic is to be viewed as a true teammate by its players, instead of a remote overlord.

What makes Davis a true man of his people, among a team of 80, is that he doesn’t just prattle on about vulnerability, or have it written into — and it is — Teachers’ corporate affairs strategy, he walks the walk, a quality Rossana di Lieto, chief compliance officer at Teachers’, admires.

Di Lieto joined the pension fund five years ago, after stops in a few different places, including an 11-year stint at the Ontario Securities Commission. As a leader among the other leaders she had known, Davis stood out as “unique.” (Another colleague referred to him as a “unicorn.”)

She gives an example from 2018. She was five minutes away from giving a presentation to the board when she received word that a family member had been diagnosed with stomach cancer. Her impulse was to go ahead, because that’s what senior executives do — they power through. Davis offered her an out, but she insisted, so he wandered away for a minute before wandering back.

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“Let me do this for you,” he said.

She relented, and in that instant she understood it was okay, and knowing it was only enhanced the trust she had in Davis and the rest of her colleagues.

“You know everyone on that team is really going to be there for each other, and it’s genuine,” di Lieto said. “It doesn’t feel forced. It doesn’t feel contrived. It is coming from the heart.”

On the professional side, it translates into Davis’ colleagues feeling comfortable questioning him, disagreeing with him, arguing with him and convincing him of the error — if there is one — of his ways without self-censoring. It is about being vulnerable, sure, but it is also about the bottom line.

You know everyone on that team is really going to be there for each other, and it’s genuine

Rossana di Lieto, chief compliance officer at Teachers’

In person, Davis radiates warmth and, at root, he is honest, since part of being vulnerable means being able to acknowledge when one of your brilliant ideas is a flop. Like the time he created an internal email address — clarifyjeff@otpp.com — and gave it to everybody in his division so they could send him questions. Nothing was sacred. Everything would be anonymous. It was going to be great.

“I didn’t get one email,” he said, laughing. “Not a single one.”

Some of his other ideas, like talking about vulnerability while accepting an award, have turned out much better. He wrote his CGCA speech on the Friday afternoon before the awards, on the screened-in porch of the Long Island vacation home he shares with his current wife, Darien Leung, and his stepdaughters, Tessa and Gracie. The couple married in 2017, and live in Brooklyn. Davis has found his happy ending.

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“The girls came into my life about five years ago, and you know what kids are like, they’ll say anything, like, ‘Oh, you are losing your hair,’ so they hold you to your authentic self,” he said.

Leung is a partner in Torys Manhattan office, a native New Yorker, a day older than her husband, a friend since 2003 — and a speaker of plain truths, which include kidding her husband about his frequent use of the v-word.

After Davis finished a draft of his speech, he showed it to Leung. He wasn’t sure if the more personal bits were the right fit, or if, in a room full of power brokers, he should risk putting them out there for all to see.

“She said to me, ‘This is who you are, this is what you believe in, this is what you practice — you wrote those words for a reason – and I think you should say them.’”

So he did.

? Email: joconnor@nationalpost.com | Twitter: oconnorwrites