The Art of Listening: What I Learned from Women

Illustration by Benjamen Purvis

Legal Lessons: Views from the Judge

There is an old line in the movie business: “Funny is money.” The best teachers I’ve ever had were both amusing and smart. I remembered their lessons better than any others; their wit remained in my brain. I met Suzanne years ago, when she was the divorce attorney for one of my best friends. When the divorce became final, my friend had a cocktail party to celebrate the occasion. The first thing Suzanne said to me after hello was, “Do you know the best tribute a woman ever gave to her husband?”

“No,” I answered.

“The best tribute, in my view,” she said, “was the present I gave my husband for his 40th birthday. He’s a big Democrat,” she went on, “and to surprise him, I went to Providence, Rhode Island, and had a picture of a donkey tattooed on my left butt cheek.”

“Really,” I said.

She smiled. “Really. I have a picture of it.” She smiled again. “I got up on our little office Xerox machine bare-butted.” She opened her tote bag and pulled out a sheet of paper. There was the donkey in black ink.

“I’ll never forget you,” I told her.

“That’s my point,” she said. “Get people’s attention. Particularly since there were very few women in any law schools in America when I got the ink.”

Since then, we’ve been good friends. Over the years, I referred many of my clients to Suzanne for legal work, primarily divorces. She is selectively profane, often to underscore practical points. She does not suffer fools well but unfailingly gives smart, practical advice, direct and unconventional, always effective. Unfortunately for me and her many clients, she was named a judge by the governor and ended her career on the bench of the Superior Court.

Here is some of her advice to me about many things that all smack of her knowledge of human nature and the often-absurd behavior around us.

“You know what quality is the most difficult to find in American society today?” she asks. “I think it’s common sense. Everyone is afraid to cut through the nonsense. No one wants to make the effort to simplify things. Well,” she says, “I’m the grit in the oyster shell. It’s my destiny. And I like simple. For instance, often, divorce comes down to the fight over who gets the pink plastic cup in the bathroom.”

Wake Up: A Lifetime of Lessons from Smart Women, published by TidePool Press, is currently available to purchase at your favorite online booksellers, including Bookshop. / Photo via Getty Images

Early on in our friendship, I asked her, “Is everything a contest with you?” She looked at me as if I were an idiot. “Hey, what’s the matter with you? Every day, if we’re good at what we do, we go to war. Did you ever hear of the battle of the sexes? It’s eternal. Thousands of years of history. Only today, it’s out in the open. Not so many years ago, the man of the house gets up and goes into the bathroom: clean towels, clean socks to put on, underwear, shirts, all there. He comes down to a hot breakfast and he tosses his wife the keys to the car. ‘Take me to the train, honey, and take the car for a service. Standard lube, no big deal, you can probably wait while they do it.’ He goes off to work, has interesting people with him for lunch, has lots of give and take. His wife picks him up at the train. She has dinner cooking, and when they get home, she tells the kids to be quiet because ‘Daddy needs to unwind.’ The husband was a king. What a life. Now it’s all changed. Let me tell you what’s wrong today: If I were a guy, I’d fight to the death not to give this up. Stripping all the crap away, that’s why the fight is out in the open. The poor bastards are confused, and they resent giving up the greatest deal on Earth. But they’re losing.” She told me all of this 25 years ago.

Here are some of Suzanne’s guidelines and advice on legal and life matters—all of which have helped me shape my views of behavior. I would not have a business life anywhere near as successful as it is without the perspective I could only learn from women.

1. “Even if you’re a nuclear physicist, you still need human interaction. And remember, in that interaction, the most important quality is a sense of humor. Because people are really terrified of each other.”

2. “We are not practical people; we believe what we see on the screen. I have handled hundreds of divorce cases, and I know that marriage is something you have to work at every day, like constantly negotiating a peace treaty. American men won’t believe that you cannot just marry for love.”

3. “Never overlook the obvious in dealing with people on any level. Tip O’Neill once asked a woman in his district if she voted for him.

‘No,’ the woman said to the longtime Congressman.

‘Why not?’ asked the surprised O’Neill.

‘You never asked,’ the woman answered.”

4. “Talk to people you need something from as if it’s their problem; as if they’re a person also. I call an assistant to an eye doctor, for instance (eye doctors being a class of people who can only fit you in after Labor Day, 2025), and tell them, ‘You sound like the only really intelligent person I’ve talked to all day. Well, thank God, because my eyeballs are falling out.’ Somehow, you involve them by complimenting them. No one else does it, and we all want to be stroked.”

5. “If you can tell a joke, you’ll always sell more tomatoes than anyone else.”

6. “When I interview young women, I don’t just want them to work 70 hours a week. I want them to have a life. I want to hire a social person with street smarts. I also check her for grooming; her hair has to be clean and her clothes neat, clean, and pressed. Like it or not, appearances are how we judge people at first blush. All pitches to a jury, for instance, are a sales job.”

7. “When you pick lawyers, relate to them, don’t react to them. I want to relate, to be the key; otherwise, it’s going to be an unsatisfactory relationship. I want answers to questions they wish I’d ask. It’s stupid to say you only want a female attorney, or that you only want a male attorney. You can tell in five minutes if your potential lawyer is truly willing to listen to you and if you relate.”

8. “When I prepare for trial, I shut my door, forbid all phone calls, sit for two hours, and think about the case, think about what’s important, and think about what the other lawyer is doing. Because I focus on the real issue…I want the jury to give my client money.”

9. “Check rates at the start of your problem. Don’t wait for your first bill. Ask what everyone in the law offices receives: paralegals, associates, partners. And find out approximately what the feeling is about the overall cost of doing your job.”

10. “Find out if your lawyer is on any big case at the time you consider retaining them. Prior commitments can put you on the back burner.”

11. “Don’t overreact. If all I want is a man to tie a slipknot, I don’t have to go to bed with him.”

“I had a young associate years ago who easily got hot under the collar,” she goes on. “He was very smart and, when angry, made it obvious that he was contemptuous of most other people’s opinions. No one likes to be made to feel inferior or stupid. We all have enough problems with self-esteem not to have disdain heaped upon us. My young associate went over the top, losing his temper over certain rules and regulations that he perceived to be idiotic and ‘making zero sense.’ And he sounded off to several back-office employees who viewed their behavior as just doing their jobs. One of them came to me and said, ‘Who the hell does he think he is?’

I brought my young associate into my office.

‘People have long memories for abuse,’ I said to him. ‘You lose control over something fairly routine, and it does several things. You lose credibility with your coworkers. And you plant a seed with people that you’re a bully, and they will find a way to punish you in the future. People who interact with you at work, in garages, in restaurants, plumbers, carpenters…if you’re arrogant with them, they can screw up your life. Anger plants the wrong seeds in others.’”

Suzanne’s advice applies to the people who insist on switching tables endlessly in restaurants, who change hotel rooms on a whim, and who want every hint of garlic removed from the sauce. And also for people who want to sell all of their U.S. stocks because of problems in Malta or the fluctuation of the Chinese yuan. These are the people who react to headlines with either panic or euphoria. In this regard, Suzanne has also told me, “When you’re hot under the collar, take a deep breath, step back, and say, ‘If I throw a hissy, how much can it damage me?’ Inflating relatively small matters can hurt you.”

12. “My advice to men is to learn to talk of personal things and lose the eternal guy mode of ‘show no weakness.’”

13. “Expect the worst from people, and you’ll never be disappointed.”

Suzanne called one day recently to talk about the stock market. After chatting for a while, I asked her if she had seen the press coverage about a female state senator’s son arrested for having a wild party at his mother’s house while she was away on vacation. There was liquor and drugs present, and all the kids were in high school. The senator was controversial and in the news a lot. Suzanne went on. “As a matter of fact, the newspapers called me to comment,” she said. “I told them I’d give them a reaction if they printed it exactly as I stated. They said they would, and I told them, ‘It’s got nothing to do with the senator. Don’t you know that all teenage boys are assholes?’”

Her practicality and irreverence have given me insight into the legal profession. When we met, I really had no experience with lawyers, except for the person who helped me with my first house purchase. One of her main lessons to me resonates in any legal transaction I enter: “Make sure your lawyer understands human nature, in all its forms. Then they can get into the heads of their opponents.”

Recently, I asked Suzanne, “How come you and I are such good friends? Why me?”

“Well,” she answered, “you appreciated that I was different from the usual lawyers you had encountered. You laughed at my jokes. You enjoyed being with me. But most of all…you listened to me. That’s what men need to learn more than anything else. Listen to us.”

More than anything else, that’s the lesson from women men need to know…

“Listen to us…”

Romance and the Train Test

There was a famous bar in Harvard Square in Cambridge called the Casablanca, affectionately called the “Casa B.” You didn’t want to see it in the daylight, a serious, dimly lit bar that, for a long time, had wicker seats for two: a padded cushion with a wicked wicker overhang that covered two people, like a carriage cover shielding a baby from the sun. Make-out seats. They had a great jukebox as well, playing everything from rhythm and blues to the Great American Songbook to Édith Piaf, Mel Tormé, and Duke Ellington to Broadway show tunes to cuts from student productions like the Hasty Pudding show. I met Olivia at the Casa B, hanging out with friends of mine.

Olivia was at Harvard Law School, one of the very few women there in the 1960s. We ended up that night singing along with the jukebox—show tunes, karaoke before it was invented—and we started dating. The first James Bond novels were just becoming popular, and I was hooked on them. One night, I was picking Olivia up at her dorm, excited to see her—the first rush of romance, so much unknown, one of the best things in life, the discovery phase.

I was on time, but I waited for her for half an hour, watching the other guys waiting also, their dates coming down from their rooms
saying, “Sorry, sorry. Hair dryer broke. My folks called. Studying, forgot the time.” They’d all be happily, shyly nervous, then out into the night. Olivia smiled her way into the reception area. “Sorry, sorry. But it’ll be worth it.”

It seems parking a car in those days was never a problem. I had a Volkswagen Bug and paid no attention to legal or illegal spaces; just stick it in somewhere and be an optimist. I unlocked the Bug and immediately saw a wrapped package on the driver’s seat. “How the hell did this get here?”

“The fairies probably left it,” Olivia said, completely unsurprised.

“The car was locked.”

“Open it.”

Inside the package was a black wool-knit sweater, like a varsity sweater. On the front, a knitted red “007” in block numbers. Olivia was smiling a secret little smile like a Bond heroine. “Live up to it,” she said.

She was late meeting me because it took her a little longer than she thought to jimmy open my door. She had knitted the sweater herself, one of the best presents I ever received.

I can’t say she loved me. But she believed in kindness and, as she told me, “Always be a surprise to people, and never really show ’em your hole card; keep a little in reserve for yourself.” I’ve taken this to heart, realizing that no man I’ve ever met would give me this advice. And in a “007” sense, Olivia would have been an excellent spy.

At one point that fall, we both had reasons to go to Manhattan. “Let’s take the train,” she said.

“Bus is cheaper.”

“Nope. The train. Trains are romantic. In four hours, a train trip is the single best way to find out if there’s really something in the relationship. You’re locked up with each other, and no one can get away.” On the journey, she taught me the hand signals that traders used to transmit orders on the old American Stock Exchange, which started outdoors originally with men signaling with hand movements to buy and sell stocks. The exchange was nicknamed “the Curb Exchange” because when it was founded, the members operated outdoors, literally on the curb. And I told her about the wild characters I’d met during my own Wall Street training program.

When we got to Grand Central, she hugged me and said, “Well, it’s workin’ so far.” I guess we both passed the train test. I still use this in relationships, and the best compliment I can give anyone is, “You’re never boring.”

“You want to really test a relationship, take a four-hour train trip, no devices, just two people seeing if they can make the trip without boring each other.”

The Money Game: Finding Your Niche

My friend Kathleen loved the financial markets years ago and believed she could become an effective stockbroker, now called “wealth manager.” Even 25 years ago, female stockbrokers, or financial consultants, were rare in the industry. At our office, we did not take trainees, but our firm had another office in the city that trained new brokers. I pleaded Kathleen’s case to our regional manager, telling him how effective she had been running several small businesses of her own and how the future should probably be much brighter for women in finance. The regional manager thought it would be a good idea and arranged an interview for her at another office we owned in our city. She interviewed with Fat Freddy, which is what we called the office manager who used to pass out beer to his troops every day when they passed certain benchmarks in commissions. They even carried beer illegally in the Coke machines. It was often party time at Fat Freddy’s office. She called me after her interview.

“What did Fat Freddy say?” I asked her.

“I heard him on the phone as I waited outside his office,” she said. “He was talking to some honcho in New York, and he said, ‘If Spooner thinks he’s gonna shove some broad down my throat, he’s got another thing coming.’” He didn’t hire her. But I pushed, and she did get into one of our suburban offices, where within eight months she became the biggest producer of business in that office. I used to mail Fat Freddy proof of her accomplishments. He never answered any of them, but I got an enemy for life, and I was happy to have him as an enemy.

When Kathy started in the investment business, she chose her clothes each day as if she were going into battle, selecting suits of armor: power suits. For three years, she battled to find her niche, her specialty, where she could separate herself from the crowd. After a few years of this struggle, on a gutsy move, she went on trips to the Far East, on her own dime, hoping to interest Hong Kong and Taiwanese businessmen in investing in America’s markets. She was heavy on the gold jewelry then, and the diamonds, and the South Sea pearls. Because Kathy figured the richer she looked, the greedier she would make the Chinese gentlemen. One Taiwanese man who owned shoe factories asked her a question in Mandarin. An interpreter listened and said to Kathy, “Mr. Wu admires your jewelry. He wants to know if you received these as presents or bought them for yourself due to your success in managing money.”

“Tell him I bought the jewelry myself,” she said. The interpreter translated, and Mr. Wu smiled. Kathy did not get the business and later asked a host about it.

“Ahhhhh,” said the host, “Mr. Wu thinks that a really smart person would be able to get such glorious jewelry as gifts from others and invest her own money that she made.”

“But he asked such an impolite question,” Kathy said. “I know that the Taiwanese are much more subtle than that.” Her host nodded. “It’s probably because Mr. Wu was educated in the United States and got into bad habits. He went to Yale.”

After Taiwan, Kathy threw herself into products strictly recommended by her firm, products that mostly crashed and burned. Then she had a brief foray into options, then bonds, then international mutual funds. Through all of these metamorphoses, Kathy never felt that she was in control, never felt that she had found her specialty. One day, after walking through a picket line the Teamsters had set up in Chicago outside the restaurant that was the model for “cheeseburger, cheeseburger,” she had an epiphany.

“Unions,” Kathy thought. “I’ll pitch the unions.”

Through some family connections, Kathy had a strong entrée into several public employee and local teachers unions. By this time, she had determined that she couldn’t run money herself. She was a marketer. She could bring the clients in, then she would farm the management of the monies out to assorted professional management firms in various disciplines (international, emerging growth, large blue chip, etc.). The fees the investors (unions) would pay would be split between Kathy’s firm, the investment advisers…and Kathy. She would be the quarterback, allocating the union funds between various managers. With other people actually managing the money, ideally, she would be free to go out marketing to new clients. She would never have to be in the office, and the fees would come rolling in, good markets and bad…evergreen. But money always draws a crowd, and union pension funds can contain tens, if not hundreds of millions of dollars in assets. So there is hot competition among investment people to pin these monies down for themselves and their firms.

Kathy has high energy, and she is honest. “I was recruited to pitch a number of accounts, in competition with others,” she said. “In five competitions, I was told that my presentation was brilliant, my slideshow the best, my overall performance the most professional. But I finished second every time. Second out of six, five, three competitors. But second, I’m an optimist,” she told me. “I always thought, ‘Next time, it’s me.’ Well,” she went on, “next time, it’s a $50 million pension fund for the benefit of a relatively small carmen’s union, you know, the guys who run trolleys and buses. I’m up against three other firms, and the pitch is in some Italian restaurant on the South Shore, the kind with the melted wax on the Chianti bottles and fried calamari for $3.95. Cocktail hour goes on for two hours, and I’m drinking club soda with olives in an old-fashioned glass so the boys think I’m throwing back the martinis. At dinner,” she went on, “I’m sitting in between two very nice guys. The man on my left talked to me about nothing except his children and my children. The man on my right only talked to me about my schools, his schools, and the decline of education in America. What unnerved me somewhat was the conversations on their part seemed almost rehearsed, both formal and forced. The only natural thing anyone said to me was said by the man on my right, who told me, ‘Never say no to seconds on veal Parm, Kathy. You never know when you’ll be in a position in life when you ain’t even offered firsts.’ Then he apologized.”

Kathy told me that after dinner, she and two others, both men, gave their presentations for the possible management of the pension plan. She was the only one with a slideshow, performance projections, and choices of various investment managers. During Kathy’s performance, she glanced over at the president of the union. He was slumped down in his chair, his head back, his mouth wide open, snoring away.

At the end of the evening, the man on her right at dinner escorted Kathy to her car. He had finished several grappas and was wobbly in the parking lot. “You remind me of my daughter,” the man said. “Uh-oh,” Kathy thought, “here it comes.”

“The truth’s sad sometimes. You gave the best presentation by far,” he said, “but you’re never going to get the business.”

“Why not?” she asked, her arms suddenly very tired carrying her presentation materials.

“Because twice a year, we go away for board meetings. We play golf, we drink beer, we gamble, and we shoot the breeze about life, you know what I’m saying? You are never going to come in first, and that’s the sad truth.” After that debacle, she decided she needed to get out of the suburban office and move into the city. She interviewed a manager in the other firm’s Boston office. He said to her, “What do we need with a woman from the suburbs around here?” She stayed with us, and they moved her to an in-town branch.

Kathy never quit on anything in her life. So she thought back about what the union man had told her, and she thought about her career and where her focus should be. The next week, she went to a baseball game with her husband. Seated right in front of them was a whole section of nuns, drinking Cokes, eating hot dogs, cheering the hits. After the third inning, Kathy elbowed her husband. “That’s it,” she said.

“What is?” he asked.

“The nuns!” Kathy exclaimed. She was off to the races, calling on various charitable organizations and orders around the country and very successfully establishing her niche. “Where else can you do a good job for people financially and, after every phone call, get the blessings of the Virgin Mary called down upon your head as well?”

Kathy, like almost all of my women friends, mentors younger people coming into, or thinking of coming into, their professions.

Here are some of her observations that she passes on to others seeking her experience:

1. “I’m old-fashioned. My Dad ingrained in us: Stay together. In the summers, all my brothers and sisters (eight of them) stay in the same community and see each other constantly. I can’t wait for summer every year. When I tell friends about this, both old and new, they universally say, ‘How horrible.’ That’s because, in my experience, many families cannot stand each other. In my case, they’re my rock; it’s what I count on, that close therapy once a year. Most people never have it.”

2. “Because of this family orientation, I had to choose a career carefully. I was 38 years old and had been a housewife for 18 years when I decided to get a job. Can you ‘have it all’? Well, I knew I probably only had a 25-year job life, and probably the corporate life would be impossible. So I chose something—financial services—where I could mix home and career. Because you never know how your kids are going to grow up and what extraordinary needs they might have. As a financial consultant, you essentially work for yourself, no matter whose name is on the door. As you start out in life as a young woman, pick a career that can build in a potential family life and try to make it something as comfortable as possible. But bear in mind, if you go this route, it will be the job and the family. Period. You will be forced to sacrifice a social life and even friendships.”

“Staying connected to old friends who you most treasure is difficult, but you must free yourself to do it, even if it’s sending birthday cards and being organized about these dates.”

3. “It may sound hokey, but I read some motivational books. But mostly, I read with history in mind so that I can learn about the past and not be so surprised about the complexities of human nature. The motivational stuff I read because I want pull-ups in life and not pull-downs. Pull-downs just sap so much energy. But it’s from history that I learn how little changes in our hopes and fears.”

4. “When I first went to work, I believed blindly in everything I heard and in everything that management spouted. I thought I had to rely on others. This was a big mistake when I realized that, fundamentally, I was smarter than so many of the so-called experts. The big lesson: You cannot rely on anyone else’s opinion. What has been the biggest change in the financial industry has been how much more professional it’s become. Leadership used to be the seat of the pants and the ‘buddy business.’ Those days are long gone.”

5. “Anything is achievable if you are willing to pay the price. This sounds so simple. But most people don’t recognize this price—what it takes to become an astronaut or an Olympian, for example. I suggest, if you are young and have ambitions and goals, that you keep a notebook and write down the positives and negatives of all the important moves you might make. It won’t eliminate surprises, but it can help a lot in the decision-making process.”

6. “Here’s how I try to differentiate myself from others, from the thousands of financial consultants out there. I present myself as being my client’s advocate; I’m the family physician if you will. I provide advice beyond investments, and I call this ‘unrelated business services.’”

7. “What kept me going in business is the motto I developed when I realized how inept so many people in management were. It gave me faith in myself to keep going. And every time I saw examples of inefficiency and even stupidity at upper levels of organizations, I would say, ‘There’s hope for all of us.’”

Only a woman could teach me to look at life through different prisms, to anticipate the real future, not just material comforts.

Kathy’s notion of what she would have to sacrifice when she went into finance woke me up. No man I ever knew thought about this when going to work, never thought about the “tradeoffs in life.” We just plowed ahead, wanting to prosper, have toys, vacation in the sun. Never tradeoffs. Only a woman could teach me to look at life through different prisms, to anticipate the real future—not just material comforts.

“Think about what you’ll have to sacrifice to achieve what you want in life.”

First published in the print edition of the July 2024 issue with the headline, “The Art of Listening.”