Julia Hensel: What first sparked your interest in becoming a lawyer?
Barbara Connly: My father was a district court judge, so I grew up seeing his career firsthand. He primarily handled criminal matters at Dorchester District Court, and I always found his work fascinating. We were alike in many ways, and I admired what he did.
I was also much stronger at reading and writing than I was at math. Writing is an enormous part of being a lawyer, and I have always loved it. Because of those influences, I was drawn to law school from an early age.
After college, I took a year off and worked at a law firm. Then I applied to law school and met my husband on the very first day.
Julia: Was it love at first sight?
Barbara: It was interest at first sight, at least for me!
We have now been married for 31 years and have practiced law together for 26 years, so I suppose it was meant to be.
It is interesting to look at how my life evolved. My father first introduced me to the legal profession. Then I married someone I met in law school, and we eventually built a legal practice together.
Julia: You began your career on the insurance-defense side of personal injury litigation. What did that experience teach you?
Barbara: Insurance defense is the polar opposite of the plaintiff’s personal injury work we do today.
It was a valuable way to begin my career because I learned how cases are evaluated and handled from the defense perspective. Now, as a plaintiff’s attorney, I understand what is happening on both sides.
I used to joke that inside every insurance-defense attorney is a secret plaintiff’s attorney waiting to come out. On the plaintiff’s side, there is more freedom in how you practice. You are not tied to billable-hour requirements or required to run every decision through a series of people.
As plaintiff’s attorneys, we determine the strategy, decide what steps need to be taken, and continually move each case forward.
I highly recommend learning both sides of whatever type of litigation you practice. We are almost always dealing with insurance companies, and my defense experience helps me understand how they are analyzing a case, assessing risk, and making decisions.
I have now practiced on the plaintiff’s side for 26 years, and I can honestly say I prefer it.
Julia: What led you and your husband to open your own firm?
Barbara: Greg and I were both working at insurance-defense firms. He had always wanted to practice independently.
Greg is very independent-minded. He served in the Marine Corps as a JAG officer, so he was accustomed to responsibility and leadership. He wanted to run his own practice.
We opened the firm in 2000, when our children were one, two, and four years old.
When we look back now, we wonder what in the world we were thinking. We were opening a business, becoming responsible for our own health insurance and finances, and raising three very young children at the same time.
But we did it.
We have now put all three children through college. They are grown, living independently, and building their own careers. The firm created so many wonderful opportunities for our family.
Greg always remembers that his mother made the first telephone call we received on the day we opened. She lived in western Massachusetts, and she was our only caller that day.
Over the years, however, clients continued to find us, and we are incredibly grateful for that.
Owning a firm is difficult, but it is also rewarding. I always say that the best thing about being the boss is that you are the boss, and the worst thing about being the boss is that you are the boss.
Julia: What has made the work rewarding for you?
Barbara: Work is still work. They do not call it fun for a reason.
You do not have to be in love with every part of your job. But as long as you like it and it creates more positive opportunities than negative experiences, you are in a good position.
We genuinely like what we do.
Personal injury work allows you to form very close relationships with clients. You meet people during an extremely difficult period in their lives, and you learn a great deal about them and their families.
That human connection has been very rewarding. We are 26 years into operating the firm, and we are still here and still married.
Julia: Your clients’ reviews reflect how much you care about them personally. Is there a case that has stayed with you?
Barbara: Years ago, we represented a wonderful family whose disabled son had been seriously injured at the residential facility where he lived. He eventually passed away.
His mother had been extraordinarily close to him and was devastated.
We pursued the case, and it eventually went to mediation. The mother attended with us.
During the mediation, the owner of the residential facility asked to address everyone present. He offered a profound and sincere apology for what had happened to her son.
I had never seen anything like it.
Defense attorneys do not typically encourage their clients to stand up and apologize. This had not been an intentional act, but it had been negligent.
The mother began to cry.
Sometimes people need more than financial compensation. They need answers. They need to hear that another person understands their loss and recognizes what they have endured.
I do not even remember the final financial result of that mediation. What I remember is the weight being lifted from that mother’s heart when she received such a meaningful apology in front of everyone.
It was incredibly moving.
Julia: Do many clients struggle with the idea of bringing a claim?
Barbara: Almost every new client who sits across the table from us says, “I am not the kind of person who pursues litigation.”
We understand that.
Most people are not naturally inclined to bring a lawsuit. But they have been injured through no fault of their own because someone else was negligent.
Negligence does not have to be intentional. But now the injured person may be dealing with hospital bills, medical appointments, lost income, physical pain, and a family that is also suffering.
I always explain that this is why insurance exists.
If someone walks up my front steps and falls because one of the steps was loose, I have insurance to respond to that situation. When an injured person brings a claim, it is generally handled through insurance.
There is a deeply human and emotional element to personal injury law that commercials and advertisements do not always communicate.
Julia: Beyond practicing law, what have you learned about operating and marketing a firm?
Barbara: Marketing has certainly been a learning experience because lawyers are not naturally marketers.
It is difficult to translate what we do into an advertisement or commercial.
When we began practicing in Massachusetts in the 1990s, lawyers generally did not advertise. It was considered improper or uncouth. Most firms obtained business through word of mouth.
Lawyers might advertise in a legal publication or a local newspaper, but television and radio advertising were uncommon. That began to change as larger national firms entered the market.
We started the firm before the internet became central to business, so adapting to digital marketing has been a significant learning curve.
We are somewhat old-school. For a long time, clients simply found us through personal recommendations.
Julia: How do you feel about artificial intelligence becoming more common in legal work?
Barbara: I am torn.
As a plaintiff’s attorney, you should know your cases better than anyone else. We handle cases involving serious injuries and enormous volumes of medical records. I want our attorneys to know those records inside and out.
I do not want artificial intelligence writing our demand letters for us. First, it is often obvious when something has been written that way. More importantly, reviewing and writing about the records is how you truly learn the case.
Greg has always believed that if you understand the details better than the other side, you have a significant advantage.
An attorney in our firm personally reviews the client’s medical records. When we encounter something we do not understand, we research it and consult appropriate experts.
We want to know every case thoroughly. That level of preparation matters.
Julia: Are you seeing clients use AI to develop their own legal arguments?
Barbara: Absolutely.
But I always explain that while someone representing themselves does not have to pay an attorney’s fee, hiring an experienced lawyer will generally increase the value of the case enough to account for that fee.
In Massachusetts, the standard fee in a personal injury case is commonly one-third of the recovery. In my experience, a qualified attorney can often obtain at least that much more than a person would obtain on their own.
Insurance companies immediately recognize when someone without legal training is representing themselves. It is almost like the person has a bell around their neck.
The adjuster may try to resolve the claim very quickly, and often for far less than it is actually worth.
Hiring an attorney changes how the insurance company views and handles the case.
Julia: You and Greg have successfully operated a firm together while also raising a family. How have you made working with your spouse successful?
Barbara: People often tell me, “I could never work with my spouse.”
I tell them that if you can get along with your spouse in front of other people, you can probably work together.
In some ways, working together can help a relationship. You are interacting in a professional environment, so you learn to communicate with each other cordially and respectfully.
I sometimes joke that I work for Greg at the office and he works for me at home, although I do not think that is entirely true.
Even though we share an office, we spend more time emailing one another than sitting together face-to-face. Much of our day is spent talking with clients, employees, and other attorneys.
One thing I have come to appreciate is seeing Greg work with clients. He has an incredible ability to explain complicated legal concepts understandably.
The law often provides extremely complex answers to very simple questions. Part of our responsibility is translating those answers so clients can make informed decisions.
We always tell our clients, “You are the boss. We are here to advise you.”
We may recommend whether to accept or reject an offer, file a lawsuit, or proceed to the next stage, but the final decision belongs to the client.
Our job is to make sure the client understands everything at stake: the offer, any medical liens, the attorney’s fee, the risks, and the possible outcomes.
Greg is exceptionally good at turning legal language into simple terms, both for clients and for juries. Having a front-row seat to that has been a joy.
Julia: Are there any practical rules that have helped you work together?
Barbara: We established one rule very early.
Our work requires a tremendous amount of writing, which is one of my favorite parts of practicing law. I love reading, researching, and writing.
We agreed that if Greg’s name were going on a document, he would have final approval. He could edit anything I prepared if he was signing it.
If my name were going on the document, I would have final approval.
We have followed that rule from the beginning, and we still use it today.
It provides clarity. It does not really matter who makes every decision, but it helps to know whose decision it ultimately is.
We can also read each other’s minds during meetings. Occasionally, one of us calls the other “love” in front of a client, and then we have to clarify that we are married!
Julia: Does working together make it difficult to leave work at the office?
Barbara: We occasionally discuss work at home, but we do not talk about it constantly. Fortunately, we have many other things to talk about.
Working together has also set a positive example for our children. They were able to see us cooperating, building something, and supporting each other professionally.
We also understand the demands of each other’s work because we see them firsthand. Not every spouse has that opportunity.
Sometimes I can sit back during a meeting and think, “Wow.” Greg is extremely intelligent, and it is remarkable to watch him take a complicated legal situation, analyze it, and reduce it to something understandable.
Julia: What advice would you give someone considering opening a firm?
Barbara: I enjoy this profession because I am constantly learning.
My favorite thing is receiving a brief or motion from the defense, opening a completely blank document, and eventually turning it into a 12-page legal analysis. I love the research and writing process.
Opening our own firm also gave us freedom.
Because clients can reach us on our cellphones and we can access our work remotely, we can often work from different places and at different times.
That flexibility was especially important when our children were young. We were able to attend their soccer and football games, coach their teams, serve as Scout leaders, and participate in their activities.
Leaving at three o’clock because practice began at four might not sound significant, but when your children are young, it matters enormously.
I do not think we would have had the same opportunities if we had remained at larger firms.
I was also able to work part-time while the children were very young so I could be home with them in the afternoons.
Now we are empty nesters, and it all feels as though it went by very quickly. I am waiting for grandchildren so I can do it again and help my children while they are working.
Julia: Has that flexibility continued as the firm has grown?
Barbara: Yes. We do not believe people have to sit in the office from nine to five simply for the sake of being there.
Some employees work from home. The important thing is that the work gets done and that everyone understands their responsibilities.
Plaintiff’s attorneys also generally do not operate under the same billable-hour model as insurance-defense firms, which has been freeing.
Today, Greg and I can sometimes leave at noon on a Friday and go skiing for the weekend.
Owning a firm presents challenges, especially because we are responsible for the finances and every other part of the operation. But the freedom has been valuable for our family.
Julia: What mindset helped you and Greg handle the demanding years of building the firm and raising children?
Barbara: Do what needs to be done.
If the work is difficult, the day is going to be long, or you have a trial and need to work all weekend, put your head down and do it. Do not spend all of your energy complaining.
There will be another weekend. There will be another opportunity to rest and enjoy yourself.
Be fully supportive of the time and effort required, especially when you are in your late twenties and thirties and trying to establish yourself professionally.
For years, Greg left home before the children woke up and returned after they had eaten dinner. I did not question it or complain because I understood that what he was doing supported our family.
I was working part-time when the children were very young, and we were completely aligned about what each of us needed to contribute.
It becomes easier over time because you gain experience. You become more familiar with the work and do not have to reinvent the wheel every time.
People can become so anxious about everything that needs to be completed. Sometimes the answer is simply to begin.
Take it one day and one task at a time. Put in the time, do the work, and keep moving forward.
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