Wendy Cox Was Leaning In Before It Had a Name

Before “leaning in” became a movement, Wendy Cox was carving her path in law and finance—navigating challenges with humor, resilience, and a sharp strategic mind. From her early days in litigation to her current role as Director of Personal Trust and Chief Fiduciary Officer at Greenleaf Trust, Wendy has embraced reinvention and leadership at every stage of her career.

In this conversation, Wendy reflects on pivotal career moments, the lessons she learned from breaking into male-dominated spaces, and the power of knowing when to stand her ground to ensure she walked away with the last $20,000.

Tell me a bit about your role at Greenleaf Trust. Are you working on anything exciting right now?

I wear three hats at Greenleaf Trust. First and foremost, I’m a Trust Officer serving our clients. I also have the privilege, along with others, of leading our Trust Officer Team, and I serve as the Chief Fiduciary Officer for Greenleaf Trust.

The exciting news is that on January 1, we received our national charter, making us a nationally chartered trust bank. That’s a big deal, because it allows us to serve clients nationwide, especially in Florida, where we already have a strong client base. We’re focusing on the Naples area since many of our clients call that home. Right now, a lot of my work involves helping with the regulatory transition that comes with this expansion.

Do you have a pivotal moment in your career, and if so, how did it shape your career trajectory?

Early in my career, before I worked at Dykema, I practiced regular insurance defense and business litigation. One of my coworkers passed away suddenly at a young age on Thanksgiving Eve. I spent the entire holiday weekend preparing for a trial set to begin the Monday after Thanksgiving. The trial settled on the courthouse steps Monday morning, and I had this moment of clarity: This is not the life I want.

I didn’t want to drop dead at 45, having missed my children’s lives. My daughter was very young at the time, and that’s when I decided to pivot to trust and estates. That decision led me to Dykema, where I reinvented myself—and I’ve been reinventing myself ever since.

Dykema was a wonderful firm, especially in its support of women. I would never work for any other firm. While at Dykema, I did a lot of probate litigation, but, by my early 40s, I knew I couldn’t spend the next 25 years fighting over the china.

One of my all-time favorite stories from that time: I was in a partners’ meeting when the police called me and the opposing counsel (who was a lovely man). My client and her sister were holding onto either side of their mother’s purse, refusing to let go, and the police wanted to know how we wanted to handle it. It was just crazy behavior. Now, when people tell me their story, I’ll share that example to encourage them to avoid probate litigation.

I noticed you went straight from Dykema to a leadership role. Did Dykema help prepare you for leadership in banking and wealth management?

At Dykema, I led a client-focused team, which was a great way to dip my toe into leadership. At that time, we only had Michigan offices and one Chicago office, so I led this team that spanned multiple offices. If you can lead lawyers, you can lead anyone—lawyers are like herding cats!

When I transitioned to the banking industry, I faced differences in communication. In law, everyone communicates in a very straightforward way. However, there are about 15 different communication styles outside of law, and, especially in a leadership role, I had to learn how to adapt.

In your role, it looks like you work closely with attorneys and other professional advisors. Can you recall a time when an outside advisor—whether a lawyer or another professional—really stood out to you and made a lasting impression? What did they do differently?

One of the most fun aspects of my role is working with my lawyer friends, including those at Dykema. Not all lawyers are created equal, but when you work with a great firm or a great attorney, it is so collaborative.

One of the most significant learning curves when moving from the drafting side to trust administration inside a bank is realizing how much process is involved. The best moments are when I can sit down with an attorney and problem-solve. If they say, “Here’s what we’re trying to do,” I can respond, “If we do it that way, I’ll have to open 14 accounts. Maybe let’s try it this way instead.” That kind of creative problem-solving is so rewarding.

Recently, we collaborated with a grantor and his attorney to create a trust that would support his son, who struggles with substance abuse. We worked together to make it both protective and practical. Most of the time, when families need a corporate trustee, it’s because they need an independent third party to help navigate a difficult situation. That’s the part I love, that gives me joy—helping people and making a real difference in their lives.

With ongoing discussions about dismantling the Consumer Financial Protection Bureau (CFPB) and potential shifts in financial regulations, how do you see these changes impacting fiduciaries and wealth management professionals? 

As trust officers, we have three core responsibilities: client care, fiduciary excellence, and purposeful growth. Regarding fiduciary excellence, we follow both the letter and the spirit of the law because that protects our clients and our organization.

We always say: We’re going to make mistakes. Mistakes happen. But if we make a mistake, we fix it, and we fix it right away. That’s our guiding light. So, no matter the regulatory environment, we always focus on doing what’s right for our clients.

Have you faced any barriers or biases in your career, and if so, how did you overcome them?

Greenleaf Trust and  Dykema are both excellent in that regard. In my first week at Dykema’s Detroit office, Bill Fisher came into my office and said, “We understand you need to pick up your daughter in Troy by 6 p.m. We don’t want you barreling up the freeway, risking life and limb. Can you stay later if we plan ahead?” I said, “Absolutely.” I’d leave at 4:30 every day unless we discussed otherwise, and many times, work later in the evening. It was never held against me. They even wrote in my reviews that I was always available and did great work. Eventually, they made me a partner. That kind of support was rare in the industry then, and I was lucky to have incredible women role models at Dykema, like Kay Felt, the firm’s first female partner.

Of course, I’ve faced barriers elsewhere. I was often in rooms where I was the only woman and significantly younger than everyone else. I remember one negotiation where all the men were cracking off-color jokes and then apologizing. At the end, there was $20,000 left to allocate, and they asked, “Who should get this?” I leaned back and said, “I think I should get it.” When they asked why, I replied, “Because I’m the cutest one here.”

They laughed but didn’t give me the money right away. I playfully stood my ground—and I got the $20,000. Sometimes, leaning into my differences and having a sense of humor got me a long way. Sure, it was uncomfortable to speak up at that moment, but I knew I wouldn’t get anywhere by throwing a fit.

A wonderful mentor, Marsha Woods, once told me, “If you’re reasonable and fair 98% of the time, a well-placed fit can do wonders.” That advice has served me well for 30 years. If you’re tough and demanding all the time, people will think you’re difficult. But if you’re strategic and choose your moment, it gets attention when it matters.

You’ve already spoken positively about Dykema. Is there anything else that you remember fondly or other memories you would like to share?

Dykema was a great firm, and they were great to me. I have nothing but fond memories of my time at Dykema and the people I worked with. I had an entire posse of women who are still my close friends! The support I received wasn’t the industry norm, and I’ll always appreciate that.

I had great mentors like Marsha, who took me under her wing early in my career. Now, I’ve realized—I’ve suddenly become old! People call me for advice and mentorship. So, it’s my turn to pay it forward, just like the women before me.

Funny story: My first day as a banker was the day Lehman Brothers filed for bankruptcy. I was sitting in orientation thinking, Wow, this was a terrible career decision. But it all worked out in the end!

Greenleaf Trust is a comprehensive wealth management firm with specialized disciplines in goals-based wealth management, trust administration, and retirement plan services. 

This conversation is part of an ongoing series. If you’re a Dykema alum and have an interesting story, we want to hear from you. Please email alumni@dykema.com.