Bola Oyesanya: Managing Director, Head of the Law Firm and Professional Services Group, J.P. Morgan Private Bank

“I take a daily dose of vitamin G for gratitude,” says Bola Oyesanya. “It’s intentional. I make sure to remind myself how fortunate I am to be here and be able to do what I love.”

It’s a fitting metaphor for how Oyesanya moves through both her career and her life: with deliberate optimism, an eye for other people’s strengths, and a belief that gratitude is an everyday practice.

We first profiled Oyesanya in 2018. Since then, she has changed firms and stepped into a new leadership role. She shares the lessons she has learned in stepping into a leadership role at a market-leading firm, the lasting legacy of her mother, and why caring will remain an essential leadership skill, no matter how much AI changes the landscape.

Scaling Up

When we last spoke with Oyesanya, she was a mid-level executive at a different firm. Today, she is a Managing Director at J.P. Morgan, where she has spent the past three years leading the Law Firm and Professional Services Group.

What drew her to JPMorgan was the scale of the opportunity. “It was the allure of doing this with a bank of this brand and stature,” she says. “The opportunity to serve clients on this scale was too good to pass up.”

Today, she leads a team of bankers and specialists serving the wealth management needs of professionals in the legal and professional services industries. Her group supports clients across the balance sheet, from investments and estate planning to liquidity and financing.

“Our clients are sophisticated but incredibly busy people,” Oyesanya says. “Most of their time is spent focused on their own clients. My team’s job is to be the ones thinking about their finances, so they don’t have to.”

For Oyesanya, the role is “a happy marriage” of everything she has studied and done: law, banking, and now leadership.

Fighting Adversity With Optimism

Speaking of challenges, Oyesanya’s perspective on adversity has been shaped by experiences that tested her both personally and professionally. Years ago, she was diagnosed with cancer and survived it. Last fall, what was supposed to be a routine mammogram led to a biopsy and a second diagnosis.

“Everything comes to a grinding halt,” she says of receiving the news.

What carried her through was a combination of faith, family, and friends. Her manager and HR told her simply to take the time she needed and not worry about work. “Being in an organization where you hear that, it puts your perspective in the right place,” she says. “And my team really rallied around me.”

In the aftermath of her second diagnosis, a friend’s words crystallized something for her: “You fight adversity with optimism.”

Oyesanya came back from treatment with a small plaque on her desk that reads Grace and Gratitude. “There’s always room for grace,” she says. “There are things that may go wrong, but how we approach them, what we say, can still leave a positive impact.” More than ever, she says, “I’m filled with a sense of grace and gratitude.”

The experience has also made her more intentional about how she leads. She believes in the mantra: work hard, play hard. When she takes a vacation, she truly steps away, and she encourages her team to do the same.

“It’s informed how I choose to be intentional day to day and how I bring that same intentionality to my colleagues, peers, and the team as a whole.”

Her Mother’s Secret

That intentionality has deep roots. Oyesanya traces much of it to her mother, who passed away in 2019 but, she says, left her with a legacy she brings to work every day.

“My mother died with a secret,” she says. “Each of her children thinks they were her favorite.”

One of eight children herself, Oyesanya says her mother made each of them feel uniquely valued without making the others feel less so. “What she did instead was to celebrate everybody’s strengths.”

Oyesanya carries that lesson into her own leadership.

“I’m very intentional about celebrating and cheering my team on and playing to everybody’s strengths.”

One of her favorite desk items is an applause button, given to her by one of her bankers before she went into surgery. It captures the culture she tries to create: “Everybody knows they will have their day of applause. And when you know your day is coming, it’s easy to cheer for someone else.”

What AI Can’t Do

Asked what skills will matter most for future leaders, Oyesanya doesn’t hesitate. “The one thing AI will never get is caring. That’s a human trait.”

In a business becoming increasingly high-tech, she believes the human side of leadership will only become more important.

“AI will never be able to emote like we can. That’s where we need to spend a lot of our attention, showing that care. That’s how we earn business, that’s how we keep business.”

She sees the same principle at work in leadership and retention. “Showing a team, as a leader, that you care, more than anything else, is the number one retention tool.”

That philosophy extends beyond her own team. She recalls interviewing a candidate who arrived late and visibly rattled after helping his mother open her store that morning. Rather than let him carry that anxiety into his next interview, she sent him to straighten his collar and tie and start fresh. “I’m the only one who knows you were late,” she told him.

He later thanked her on LinkedIn for the moment. “That caring, showing up, and making an impact in people’s lives, I hope those are the things I’m remembered for.”

For Oyesanya, legacy is something considered in everyday decisions. “I always ask myself: long after I’m retired, what would people say? What would people remember? Keeping that legacy in mind helps inform decisions and not make shortcut decisions.”

Staying Present and Dancing in the Kitchen

Two unlikely mentors have also shaped how Oyesanya stays grounded. One was a mailroom clerk, whose calm she once asked about. “I don’t focus on the things I cannot control,” he told her.

“It seems very simple, but it was profound,” she says. “Markets rise and fall, portfolios fluctuate, there are countless things we cannot control in the course of a day, but we sometimes allow them to really determine our moods.”

The other was a shoeshine man Oyesanya encountered in an elevator after an exhausting day. When he asked how work was going, all she could manage was a deep breath. “Work doesn’t finish,” he told her. There would always be more to do tomorrow.

The line changed how she leaves the office. Rather than carrying home everything left unfinished, she takes stock of what she accomplished that day before turning her attention to her family.

These days, she finds her own ways to step away and recharge, including dancing in the kitchen.

“If you wait to find the right time for fun, honestly, you will miss a lot,” Oyesanya says. “Don’t wait until a vacation before you take five minutes to decompress and celebrate. Find a moment to pat yourself on the back and remind yourself how great you are, because each of us is phenomenal in our own way, and we should celebrate who we are.”

By Jessica Robaire