Dale Sherman – Allstate

A first job rarely becomes a lifelong career—but Dale Sherman was lucky enough to find the right fit on his first try. Mere months after graduating from the University of Illinois College of Law, he stepped into the Chicago office of Allstate and has remained there for nearly three decades.

“Something people hear me say a lot is ‘Fortune favors the generalist,’ and that’s certainly been true for me,” Sherman says. “As a generalist, I got to try a lot of different roles without switching companies. I strongly believe that being a generalist makes you a better lawyer and leader.”

In 1995, he started as a staff counsel attorney for the insurance company, which has a global network and serves customers across Canada and the U.S. He quickly moved up the ranks to senior trial attorney, and by 2000, his hard work had clinched him the position of lead counsel. Five promotions later, in May 2019, he became the vice president and assistant general counsel.

Dale Sherman | Vice President and Assistant General Counsel | Allstate

Confidently leading its claim litigation practice, Sherman’s team improves the company’s loss cost accuracy by millions of dollars each week. At the company’s year-end on September 30, 2022, Allstate’s revenue reached nearly $51 billion.

He manages nationwide defense matters, ranging from coverage challenges and appeals to declaratory judgment actions, bad faith disputes, class actions, commercial lawsuits, and occasional real estate disputes.

He also conducts due diligence on potential acquisition targets and, as such, played an important role in Allstate’s $4 billion purchase of National General Holdings in January 2021. Accordingly, one of his focuses for 2023 is completing the integration of lawyers from the home, auto, personal and commercial insurance company.

“We’ll all be under the same tent, with everyone reporting to me, and I’m excited that our team will now have the benefit of a wide array of experience,” Sherman says. “We’ve all been conducting similar work, but they’ll bring a new approach, giving us all a wonderful opportunity to learn from one another.”

Ensuring a learning legacy in insurance

Learning, mentoring and sharing knowledge is a guiding force in Sherman’s career regardless of whether he’s working with new employees or veterans.

“I try to mentor in the moment, whether people realize it or not,” he says.

He likes asking open-ended questions, especially to lawyers who are new in their career or new at Allstate. For example, one of his team members may ask, “I’ve never seen a bad faith allegation of this kind, how do I handle it?”

Instead of providing a direct answer, Sherman will ask the colleague to think about possible outcomes and return with a solution. He makes sure to ask such questions one-on-one, so the person can think without fear of judgement from other colleagues. He says this is especially important when integrating new employees as a result of mergers or acquisitions.

“They’ve been doing things a certain way, and many have years or decades of experience,” he says. “Yes, we provide them with documents explaining our standard operating procedures and so forth, but I want them to feel comfortable applying their previous knowledge and expertise at Allstate—as that’s beneficial to them and those of us already here can learn from their new perspectives.”

Although not officially part of his role, Sherman also formally mentors a group of 12 individuals from outside his team and outside the company. He meets with them for about an hour over lunch either once a month or once every two weeks depending on circumstances and their needs.

“With my team and mentees, sometimes they’re on the right path, and I can just assure them of that, so they build their confidence and become autonomous instead of depending on me,” he says. “Sometimes they do get stuck and, even then, I offer a different perspective instead of simply saying ‘this is what you should do’ because that doesn’t offer any chance to learn.”

While he’s led many kinds of teams—court room lawyers, litigation managers, counselors, claims professionals, administrators and paralegals—over the past 27 years, he says that lawyers are the most challenging and fun to mentor. Attorneys have strong opinions and are trained to argue with him, he explains to Vanguard with a laugh.

“I also learn a lot from mentees, which is why I think it’s so important to keep an open mind and stay humble,” Sherman says.

Investing in talent

For Sherman, learning and working together successfully goes beyond discussing work matters. That’s why he’s made it a point to treat his claim litigation team like a family—this includes new hires and the people he’s been integrating into the team due to acquisitions.

“When people are comfortable and the work environment is fun, then they are their strongest selves and give their best contributions,” he says.

For instance, he tries to make fun of himself in his updates at the beginning of meetings to loosen the mood. He says because the work is so serious, he finds it healthy to take at least five minutes out of a 30- or 60-minute meeting to discuss personal lives and favorite shows. He’s also happy to answer any questions and share his expertise, especially as he’s not a specialist in just one field of law.

He’s also a generalist in his hobbies and passions. When he isn’t boxing and weight training, he can be found headbanging at a metal concert or chatting up Styx’s drummer, with whom he grew up. The father of three teenage children also enjoys hosting charity events, working as a DJ and attending standup comedy shows.

Yet, his main passion has remained teaching others and learning from them in return. As he explains, he didn’t achieve anything solely on his own but had wonderful mentors—and wants to carry on that legacy.

“I want to develop and support the next wave of talent,” Sherman says. “The further I advance in my career, the more I realize how important sharing my knowledge is, so that others can emulate my successes—and as for the mistakes? Well, the best mistakes to learn from are someone else’s, so my mentees have a lot to learn from me!”

View this feature in the Vanguard Winter IV 2023 Edition here.