If I generate insights about my medical condition using ChatGPT, should I share the output with my doctor?  Should I upload it to my healthcare portal? 

Also: Is there a way to enter my whole medical record into ChatGPT and have it come up with tests I should take?  If I do that, is my medical information not protected enough?

— Russ A., Marblehead

Dear Russ A.,

These are outstanding questions, and you are clearly a proactive “patient.” The medical arena offers some of the most promising and beneficial ways artificial intelligence can help us humans. But there are still loaded mines to navigate, mainly for confidentiality and accuracy (not nothing!). I will gladly offer my personal opinion here, but have sourced two experts who deal with these questions every day: Waichi Wong, of Boston Medical Consulting, and Emilia Javorsky, director of the Futures Program at the Future of Life Institute.

Both agree that AI is an excellent tool that democratizes medical information and enables folks to learn more about their medical needs. But as Javorsky—who describes herself as an AI advocate and ethicist—puts it, “ChatGPT is not a doctor, and general purpose LLMs [large language models] like ChatGPT have not been cleared by the FDA as medical devices for diagnosis.” In other words, there is zero guarantee that what ChatGPT shares with you is accurate. Still, AI is a good way to translate complicated medical jargon into words that anyone can understand. So, sure, ask ChatGPT (or Perplexity, Claude, Gemini, etc.) for medical insights, but make certain that you use that material as a conversation starter with your human doctor.

As for uploading that AI-generated data into your healthcare portal…hey ho, not so fast. The issue with artificial intelligence is that it can be Just. Plain. Wrong. If you upload your AI findings to your portal, future providers could get confused and misguided by erroneous information. That’s a big deal! Now, if you feel there is low risk of a fiasco like that, Wong advises uploading a brief summary with a short list of questions. “Practically,” she says, “many portals have message length limits, and clinicians may not have time to read a long attachment.”

Regarding entering your entire medical history into ChatGPT for guidance on tests and diagnosis; how cool would that be? The short answer is yes, someday that will be the case and AI is tracking toward that by the nanosecond. But today? AI has some hurdles. First, there’s a possibility that it will recommend tests that are not necessary. “Lab interpretation is context-dependent—reference ranges differ by laboratory, and small deviations can be clinically meaningless,” Wong says. “Physicians interpret results in the setting of the whole clinical picture and decide whether a borderline abnormality is truly important.” Additionally, while cost can be, of course, a factor in deciding what tests a patient receives, so is the risk of false positives. “Such findings then require follow up testing and procedures that are often not risk free, meaning patients take on risks without benefit,” Javorsky says.

Finally, on your question of whether your medical information is protected if you share it with ChatGPT: In most cases, it’s a big fat no. Doctors are bound by HIPAA, a U.S. federal law that prevents a patient’s medical information from unauthorized disclosure. Your records are confidential, and you have legal rights if HIPAA is not honored. Big tech companies abide by no such law. In fact, your shared medical record and personal identifiers could be used to train future AI models. No problem with that? Go for it.

Previously: How Can AI Help My Senior Mom Communicate Better?

Welcome to “The Salty Cod,” a monthly column in which humorist Steve Calechman grapples with uniquely New England dilemmas. 

God, I hope not, because I screwed up big time. I grew up on the course, right at the top of Heartbreak Hill, and watched pretty much every race during my childhood, and nothing, not the chance to eat a lot of pasta or run by my own house, ever made me want to do it. Then again, not everyone who grows up in Winthrop becomes a pilot.

And that’s fine. We don’t have to do or like all sports. And marathons, especially, are nothing to trifle with. You can’t just show up at the starting line on a whim. You gotta run a lot. You gotta run outside in January. And you never hit a downhill and get to coast for a mile. It really is all you.

Some of us are happy to be on the sidelines and remind you of just that. Think about it, runners. I know you feel you’ve done something medal- and massage-worthy at the end, and maybe you have. But without the crowds, that Monday is just 26.2 miles on concrete. Are all the splits and intervals and lost toenails still worth it? Now think about what those fans are going through. Standing—most likely sitting—for three, four hours, cheering “You got it!” over and over and over again, meaning it each and every time, even making the effort to occasionally decipher your shirt in order to say, “You got it, Mike!”—all while not spilling a drop of their chili. Sometimes it’s also drizzling, maybe a touch chilly, and they still don’t quit. Who’s the marathoner now?

We all are. Is it the classic definition of one? No. But there are a lot of ways to be part of something. Sometimes it’s hoofing it. Sometimes it’s yelling supportive stuff at people we don’t know. But the thing we have in common is that we both willingly keep coming back because it makes us feel good. If it didn’t, we wouldn’t. “It’s not rocket science,” says Jeff Brown, psychologist for the Boston Marathon’s medical team and author of The Runner’s Brain.

It’s the basis for most traditions and rituals, and it’s a way to make something feel like ours. So no, you don’t have to run to be a part of the marathon. Now, a question for you, readers. What’s one of your traditions that could only happen here, one you wouldn’t miss for all the pasta in the world?

This article was first published in the print edition of the April 2026 issue, with the headline,“Do I Have to Run the Boston Marathon to be a Real Bostonian?”

Got a question for the Salty Cod? Send it to editor@bostonmagazine.com.

Previously: What Should Boston’s Official Smell Be?

First: Congratulations on being a wonderful daughter. The fact that you are asking these types of questions already tells me that you are a thoughtful, loving, and forward-thinking caretaker. Having recently gone through this with my own mom, I know how wildly stressful (and sad)  this time can be. She’s compromised physically, likely mentally, and that’s frustrating for everyone, but especially her. Artificial intelligence, though arguably problematic in some ways (job loss, bias, privacy), can be a savior for the elderly and their caretakers. The senses that are dimming can, in effect, be augmented—even replaced—by AI. With that in mind, let’s tackle your questions one by one.

How can she use AI to get news and information?

First, although this is an AI advice column, here are some human thoughts: This is the time of life when all that matters is that your mom is comfortable. If it’s easier for her to watch the news on an old-school TV at full volume,  let her.

There, I said it.

For poor hearing, “smart” hearing aids are a thousand percent revolutionary. They use AI to analyze her sound environment, separating human speech from background noises. There’s also key voice-activated equipment that can help her access news and other information. Amazon Alexa, Google Nest Hub, and Apple’s Siri were created to work with natural language. Seniors don’t need to understand complicated technology—they can chat the way they would with a friend. These devices can share the day’s news and weather; look up information instantly; play favorite music and TV channels; and remind users about medications or appointments. Wendy Stevens, a Boston-based guerrilla AI marketing expert, suggests starting with two or three simple commands to build confidence. Alexa, tell me today’s headlines. Siri, play Frank Sinatra. When is my Social Security check arriving? You get the point.

Finally, ZVOX AccuVoice soundbars or Sereonic wireless portable TV speakers are good options to further amplify audio for easy listening.

If your mom’s hearing continues to decline, reach out to the American Speech-Language-Hearing Association ProFind, which is the national credentialing resource for speech and hearing experts.

How can she use AI to communicate with family and friends?

Again, this is all about the “no-hands” approach. Find the right voice-activated device (Alexa, Siri, Google Nest) to assist. Alexa, call my daughter, Gwen. Hey Siri, email my doctor for an appointment. Then, she will dictate the message that she wants to send. It’s that simple.

Video calling is another awesome option. The ViewClix Smart Frame doubles as a digital picture frame, showcasing family photos, but can be set up to automatically answer calls from approved contacts. CallGenie can connect with your mom’s TV, and displays the video call on a large screen. And, there’s Komp, which is a large screen with a single on and off button. Family and friends can send images, messages, and calls in a private app.

For in-person socializing, many apps employ AI to instantly transcribe spoken conversation into text on smartphones. Hint: Increase the font size for even more accessibility.

How can I ease elderly people into the tech world?

If your mom is interested in learning, CyberSeniors.org is a fantastic resource for seniors. There are classes, help lines, and community groups devoted to helping the elderly learn about AI. In fact, every Thursday at 2 p,m., seniors can drop into a Zoom session to ask any tech-related question.

Additionally, there are AI companions or social robots created specifically for the elderly. ElliQ, for example, is a small, friendly-looking robot that can initiate conversations, answer computer-related questions, play music, and generally act as a chatty friend.

Bonus Tip: The Password Stumper

Now, you did not ask for this, but I remember receiving several phone calls a day from my mom asking me to help retrieve yet another forgotten password. There are various digital and safe “vaults” that store all pertinent information with one, and only one, master password. RoboForm, Dashlane, NordPass and 1Pass are a few password managers that range from $2.39 to $7.49 a month for subscriptions.

GKW, I hope these suggestions help absolve you and your mom of any AI stresses. That way, you can focus on what counts: Spending quality time with your beloved mother.

Previously: What Are Some Useful Lifestyle AI Apps?

Dear Salty Cod: Why do so many apple cider doughnuts not taste like apple cider?

Another autumn, another attempt to visit an orchard and not over-pick. As you fail spectacularly once again, the thing that makes it all better is the promise of that doughnut at the end. Yet after waiting in that long line, when you finally take a bite…well…it’s not really that apple cidery.

To address this seasonal betrayal, the Cod reached out to two experts: Nathan Kibarian, owner of Desserts by Nathan, and Marissa Rossi, pastry chef at Northern Spy. The culprit, they say, is that the cider likely hasn’t been reduced. On its own, it’s watery and thin. The former can prevent the dough from frying well; the latter makes it too weak to compete with the spices, sugar, and oil. As a result, the cider flavor gets buried, relegated to backup vocals, handclaps at best.

Buying one at a bakery or farmstand might up the odds of finding something cider-forward, but Kibarian and Rossi would still go with an orchard. And of course, that’s where you’re going anyway, because it’s not merely about buying a doughnut. It’s about doing the walking, picking, and mild sweating to justify putting down one, two, probably three-plus doughnuts. The cider is also most likely made in-house, and you have the best shot at getting a hot doughnut, and a hot doughnut makes most problems go away.

If you think you can tell cider concentration just by looking, well, you’re a fool. You certainly could ask, “Hey, do you reduce?” but only if you want to get mocked by the teenage employees as soon as you walk away. There are, however, some signs you’re getting a good doughnut. It should be fluffy and the size of, you know, an actual doughnut—a four-biter, as Rossi says. Anything smaller is a letdown; anything larger has to take a longer oil bath.

You also don’t want to see any greasy shine, Kibarian says, and Rossi will look to see if any sugar remains on the outside. The sweet stuff is hygroscopic, a fancy way of saying it’ll draw out moisture, then dissolve. No sugar means dryness, so your next move is to stare at the menu board, make your best “can’t decide” face, and let people go ahead of you, because you will wait for the next batch to come out.

Got a question for the Salty Cod? Send it to editor@bostonmagazine.com.

See also: Where to Find the Top Cider Doughnuts at Greater Boston Farms and Orchards

Previously: What’s the Deal with Foliage Drives?

One morning this summer, I burst through the doors of the Tesla showroom at the Prudential Center, announcing my arrival with authority.

“Hello!” I said. “I am interested in a Tesla.”

The young salesman looked up. “All right,” he said agreeably.

I should tell you that my proclamation about being interested in a Tesla was not, technically speaking, 100 percent truthful. In fact, it’s probably more accurate to say I was not really interested in a Tesla at all.

To begin with, I’ve never been a Car Guy. I mean, I drive a car—my wife and I own a pair of Hyundais—but, as that make suggests, I don’t feel the need to possess the coolest, shiniest ride out there. What’s more, when it comes to new technology—say, an automobile that runs without gasoline—I’m a late adopter. You all work out the kinks on whatever gizmo or gadget has just been invented; ping me when everything is running smoothly.

Of course, my biggest reason for not wanting a Tesla is the fact that, after his DOGE hijinks, I loathe Elon Musk with the white-hot intensity of a thousand lithium batteries. That I’m not alone in this feeling—that Tesla has been suffering sales-wise because of it—has provided me just a tiny bit of solace.

Given all of the above, why was I nonetheless standing in a Tesla showroom, expressing my interest in one of Musk’s vehicles?

Simple. For the previous couple of weeks, I had been interviewing some of Boston’s finest negotiators about the finest points of negotiating, and I had a sudden epiphany: The combination of Musk being desperate to sell cars, and me not having the slightest interest in buying one, made me think I’d stumbled into every negotiator’s dream: serious leverage.

The very lack of wanting a Tesla was going to let me get one, super-cheap. The sales guy asked what model I was interested in. I briefly considered saying the hideous-looking Cybertruck, until I realized there’s a difference between not wanting something and legit having to set yourself on fire if you actually get that thing. So instead, I told him I liked the Model 3, Tesla’s sleek little sports sedan.

“Do you want to do a test drive?” he asked.

I paused. I recognized an attempt to undercut my leverage when I saw one. I’d take the Model 3 for a quick spin and like it, and the tiny thing in your brain that makes you want stuff would make me want a Tesla.

“I’m good,” I said firmly. “Can we talk numbers?”

He asked for information. Color? Red, I said. Buy or lease? Buy, I replied. Time frame for financing? I went with 48 months.

He nodded and told me today was my lucky day. Between now and the end of the month, Tesla was offering zero percent financing on all purchases.

He typed some stuff on his computer, then swung the screen around for me to see. He could have me in a new Tesla for less than $600 per month.

My left eyebrow arched. (Okay, not really. But I’m trying to conjure this moment in cinematic grandeur.) That was actually cheaper than I imagined. Still, I’ve played the car-buying game before—my 2019 Elantra didn’t purchase itself, folks—and I had a few tricks of my own.

“So…any chance you can come down a bit?” I asked.

He nodded, understanding my request. He told me that with the zero percent financing, the only way to lower the monthly payment was by lengthening the financing period. Was I interested in that?

I could see we were playing hardball. I quickly pivoted to a different strategy, hoping to throw him off-balance.

“What kind of deal can you give me if I just straight-up pay cash for the car?” I asked.

He looked at me, appearing somewhat pained that I didn’t understand what he was telling me. He tried again: The cost of the car, he said slowly, was the cost of the car. I could pay it all at once or spread the same amount out over several years. But the price was the same.

It was right then that I began to realize—and a Google search later confirmed—what I suspect Car Guys, and most of America, and undoubtedly you, savvy reader, have known for some time: that Musk and Tesla don’t haggle over the price of their cars, the way almost every other car company does. Buying a Tesla is no different than buying a pair of pants at Old Navy. There’s a price. You pay it.

That realization quickly set off a second one: The massive leverage I thought I had in this negotiation? Well, I didn’t have it at all. Because there was, in fact, no negotiation. I’d inadvertently fallen prey to one of negotiating’s classic blunders: being unprepared.

I sat quietly for a moment, hoping my steely silence might break down my worthy adversary and have him slashing thousands off the cost. It did not. And so I rose and shook the young man’s hand vigorously. Then I walked out of the showroom, somewhat crushed that I wasn’t going to be a player, at least not today, in what I’m pretty sure is a new Golden Age of Negotiation.

That Elon Musk doesn’t bargain when it comes to Teslas, I understood later, is probably the true cause of his spectacular breakup with Donald Trump—because the current occupant of the White House is a guy who essentially sees all of life as a negotiation. Tariffs on our trade partners? Peace in Ukraine? A new Air Force One from Qatar? Bending Harvard to his will? As Trump likes to put it, it’s all about who holds the cards.

You undoubtedly have your own feelings about the president, but hate him or love him, it’s pretty undeniable that his way of running the country has put the biggest spotlight on negotiating that we’ve seen since the 1980s, when Trump wrote—or, you know, at least might have read—his first book, The Art of the Deal. And for all my antipathy toward the guy, I don’t think that’s necessarily a bad thing. Because while it’s pathetic to view all of life as a negotiation, life is nonetheless filled with negotiations—lots of them—from consumer purchases to business deals to relationship give-and-take.

It was in hopes of elevating my game in all of those areas that I reached out to some of Boston’s top bargainers: A Harvard Business School professor with a bestselling book. A top divorce lawyer. A wheeler-dealer in the State House. And a hockey union official who at one point might have served as mayor of Boston.

What did I learn? Well, my Tesla misadventures notwithstanding, there are absolutely steps you can take to give yourself some better cards at the negotiating table. In fact, think of what follows as the Seven Golden Rules of Negotiating in this, our new Golden Age of Negotiation.

Just don’t expect them to help you get a deal on a Tesla. That’s not happening.

Rule #1: Easy there, tiger—try not to be so nervous.

The Harvard Business School professor I mentioned above is Alison Wood Brooks. Earlier this year, Brooks, who’s won several teaching awards at HBS, published a bestseller called TALK: The Science of Conversation and the Art of Being Ourselves. As the title suggests, the book smartly uses academic research to help readers sharpen and deepen the way they conduct conversations. (Rule number one: Take time to prepare for a conversation, including making a mental list of topics you want to talk about.)

Brooks has studied conversation broadly, but she’s also an expert on a particular type of conversation: negotiation. (She teaches a popular course on it at Harvard.) As we chat via Zoom one morning, she offers a wonderfully simple definition of what a negotiation is. “It’s two or more people who disagree, seeking to reach agreement,” she says.

Earlier in her career—“I was just a baby grad student,” she laughs—Brooks did some fascinating research on the role emotion, specifically anxiety, plays in negotiations. “Humans feel anxious when there’s uncertainty,” she explains to me. “And there’s uncertainty in a negotiation because I don’t know what I’m going to do, and I don’t know what you’re going to do when we’re interacting.”

It turns out that uncertainty does more than just give us a queasy feeling in our stomachs; it also makes us lousy dealmakers. In her research, Brooks found that because people who are feeling nervous just want this whole fricking thing to be over with, they frequently make lower first offers, respond more quickly to the other side’s offers, and exit negotiations early. The result: worse outcomes. Bad deals.

So how can you avoid the negotiating jitters? Well, simply slowing the process down can make a difference—don’t be in such a hurry to get things over with. But even more helpful is the strategy Brooks recommends for conversations in general: Put in some prep time (that might’ve saved me in the Tesla showroom). Can you anticipate what the other side might do? Can you anticipate what you might do in response?

“I think the main takeaway from a negotiation course is the value of preparation,” she says. Which, conveniently enough, leads us to…

Rule #2: Figure out what game you’re actually playing.

There has been a lot of research about negotiating over the years, with experts generally dividing dealmaking into two different types. A “distributive” negotiation is your classic zero-sum battle—there’s one piece of pie left, and you and I are going to haggle over who gets it.

An “integrative” negotiation, by contrast, is all about collaboration—one person’s win doesn’t come at the expense of the other. It also involves multiple elements of debate, and everyone gets something in the end: maybe a piece of the cake, or the small amount of milk left in the carton, or first dibs the next time there’s cake.

Circumstances obviously dictate which type of negotiation you’re dealing with, but so does your relationship with the person on the other side. “If it’s a stranger you’ve never met before and your chances of seeing them again are zero, that’s going to make it feel more transactional and much more like a fight—you’re going to care less about being a jerk to each other,” Brooks says as we continue our conversation. “Whereas, if there’s any chance you’re going to see that car salesman again, or that diplomat, or stay married to that person, you should be looking to make it more integrative.”

As a general approach, you want a negotiation to be as integrative as possible; the more moving pieces there are, the more creative you can get in crafting a deal—and the more likely you are to win on the things that really matter to you. So ask your negotiating partner: Can we think more broadly here? Are there other things we can put in play that might end up benefiting both of us? What TV show will we watch while we eat our pie, for instance? Who’s cleaning up afterward? Who’s baking the next pie? (By the way, these questions work better for pie than for, say, negotiating with Russian foreign minister Sergey Lavrov. Although everyone does like pie.)

Another way to categorize a negotiation is whether or not you absolutely have to have a deal. Jennifer Koiles is a well-regarded family law attorney based in Salem, and when she and I talk one afternoon, she tells me that the necessity of an outcome is one of the things that distinguishes, say, a divorce negotiation from a business negotiation. “With a business transaction, you have two willing negotiating parties who understand they want a deal,” she explains, putting the emphasis on want. “With divorce, if you don’t reach an agreement, you’re still getting divorced and you’re still going to be entered into a contract, one you might not be happy with.”

That fact tends to make people in the latter scenario much more realistic when they come to the table, she notes. So think about the question ahead of time. Do I need a deal here, or just want one? If it’s the latter, you can go bigger and bolder with what you want.

Rule #3: Know your endgame, period.

A few days after I talk with Alison Wood Brooks, I find myself wandering through the eerily empty Massachusetts State House. The legislative session has wrapped up, and most pols have gone home. About the only one who seems to still be toiling away is Democrat Aaron Michlewitz, who chairs the House Ways and Means Committee and has led negotiations on seven state budgets.

Michlewitz invites me into his cavernous office, and we start gabbing about negotiating.

“You know, I think it was coming from the North End and growing up in a neighborhood where everything is a negotiation of some sort,” he says when I ask where he learned the art of dealmaking. “You’re fighting for whatever little space you can have in that small neighborhood. That upbringing kind of prepared me for a life of politics, but also for a life of negotiating.”

I ask Michlewitz who was the best negotiator he ever saw, and he tells me former Boston Mayor Tom Menino, who gave him his start in politics, was a master. One, Menino understood how to use outside perceptions to drive an issue. Two, he played a long game. “You don’t stay mayor for 20 years by not building long-term relationships,” Michlewitz says.

When our conversation turns to particular tactics, Michlewitz points to something that might seem basic, but that many people overlook: You have to know what you want in a negotiation—not just in a general way, but in a very detailed, specific way. That’s because, almost by definition, negotiating means you’re not going to get everything you’re looking for, so you better have a clear set of priorities. What’s a must-have? What’s a nice-to-have? What’s something the other side can have?

When it comes to the state budget, Michlewitz figures that out by talking to his colleagues in the House. “Probably close to 150 members come in here and advocate for their priorities,” he explains. “You get a sense of what the themes and priorities are within the membership. And then you try to craft something that’ll capture that as much as possible.”

Now, this doesn’t mean you have to schedule 150 meetings with yourself before your next negotiation, but it is smart to sit down and list, in order, what’s meaningful to you in a particular deal. Let’s say you’ve gotten a job offer. Is salary the most important thing? How about time off? The ability to work from home? Your title? Rank them in order of their importance to you—and then be realistic.

You know who agrees with this approach? Another former Boston mayor who knows something about negotiating. “You usually have to give up some of the things you want in order to get an agreement,” says Marty Walsh, who calls me one day while working on a deal in his current gig as head of the NHL Players’ Association. “Now, you might have to give things up that you weren’t intending on giving up. But I think the real important piece is to be a good listener, and don’t be so reactionary, and try and keep an open line of communication with the other side.”

Ah, yes, the other side. That leads us to…

Rule #4: Chat first. Negotiate second.

The fact that you might have to give something up is a reminder that you’re not the only one in this relationship who has needs. The other side has a priority list just like you do, and the more you understand what’s on theirs, the more likely you are to be able to get what’s on yours.

The best approach is simply to ask. The one thing all the experts I spoke to agree on was the benefit of sitting down and talking with the person on the other side before you officially start “negotiating.” This doesn’t mean securing a conference center and bringing in translators and notetakers; it can be as simple as asking that car salesperson what’s going on at the dealership right now. The benefits are two-fold: One, you might learn about an issue you hadn’t even thought about. Second, it can help build trust and rapport. “There’s been some cool research recently that says you shouldn’t only be talking about the issues you need to negotiate,” Brooks says. “The approach should be more, this is a relationship and a conversation.”

What you’re searching for are what Brooks refers to as superordinate goals. “It’s like, hey, we’re all here because we care about our employees,” she explains. “Or, we care about having an ethical business transaction.” (Or perhaps: I know we share a love of pie, Mr. Lavrov.)

In addition to the issues, the more you understand about the style and personality of the person sitting across from you, the better off you are. “It helps to know, does this person have to have the win?” Koiles says. “If they do, how do you give it to them so you’re not compromising your own position?”

It can even help to know whether they like to laugh. “Like some attorneys, I can be very sarcastic,” Koiles says. “It can work really well, and it keeps the temperature down. But I know that if I do that with some attorneys, it will skyrocket the whole negotiation in two seconds.”

Rule #5: Get some easy wins on the board early.

Yes, in some ways, this rule might seem counterintuitive. Why put time and energy into topics it’s easy for you to find common ground on if you’re just going to start throwing coffee mugs at each other when the going gets rough?

But in practice, focusing on the simple stuff first can actually help you reach an agreement on the tough stuff later. “I think people are more likely to negotiate on the fifth issue when they know they’ve already agreed on the other four,” Koiles says.

Marty Walsh concurs. A couple of years ago, when he was Secretary of Labor in the Biden administration, Walsh served as the mediator in negotiations between railroads and the railroad unions. “I suggested they take the most complicated issue and save it for the end,” he tells me. “Because sometimes if you can resolve all the other issues, it’s like freeing up a logjam.”

Indeed, momentum can be crucial. In that same negotiation, Walsh brought the parties together and told them to settle in for a marathon session. While the two sides had been talking for nearly a year, they’d been doing so in shorter meetings. That made it tough to get traction. “They had been negotiating for months and months and months on the contract, and they couldn’t get anywhere,” Walsh remembers. “And then, in the matter of like 14 hours of negotiations, we got a deal done in the room.”

Michlewitz agrees that time is an underrated factor in a negotiation, something he’s become more strategic about over the years. “I’ve learned to understand the difference between what a hard deadline is and what a soft deadline is,” he says. It’s also worth asking yourself whether your position strengthens or weakens as time passes.

Rule #6: Stay cool when they try to rattle you.

No two negotiations are alike, and neither are negotiators. Some come across like your best friend; others prefer to mess with you. You’ll know you’re in the presence of an over-the-top hardball player by looking for a few telltale signs:

1) He or she issues ultimatums—this is a take-it-or-leave-it offer.

2) He or she says no to your proposal but doesn’t counter with one of their own.

3) He or she uses an obscure platform called Truth Social, where they say things like, YOU KNOW, I’M BEING TREATED VERY VERY BADLY…NO ONE’S REALLY EVER SEEN ANYTHING LIKE IT, IF YOU WANT TO KNOW THE TRUTH.

If your negotiating position is not particularly strong—say, you’re bidding on a house and there are 10 other offers—there may not be a lot you can do. This is a good time to ask yourself if this a must-have deal or something you can walk away from.

But if your negotiating position is relatively equal to that of the person across from you, recognize these moves for what they are—tough-guy tactics. Don’t let them faze you, and try not to get angry. “Things can get personal really quickly,” Walsh says. “But you try not to let it get personal, because you might walk away from the table frustrated and angry.” And that doesn’t get you closer to a deal.

When things get tense, Brooks offers a strategy she learned from longtime Patriots chief operating officer Andy Wasynczuk, who became her colleague at Harvard Business School. “He used to say one of the strongest things you can do when someone is mad or disappointed is to reframe it as shared sadness,” she explains. “Say something like, ‘We’re both upset that this isn’t working. What do we both care about?’ Instead of sitting on opposite sides of the table and fighting, you’re sitting on the same side of the table and untangling a puzzle together.”

It’s a fantastic tactic, and it makes me wonder if, during my Tesla non-negotiation, I should have sniffled and wiped a tear from my eye. Just sad, Mr. Tesla Guy. Just sad…

Rule #7: Ink it, don’t just think it.

Okay, let’s say you’ve worked through the whole process above: You didn’t get anxious. You made the negotiation “integrative,” not “distributive.” You knew what you wanted and what your opponent wanted. You started with the easy stuff, and that helped with the hard stuff, and when Mr. Lavrov started banging his shoe on the table, Khrushchev-style, you didn’t get angry, you just expressed heartfelt disappointment.

Still, there’s one more step. “I think it’s really important, once you’ve reached an agreement, that you are writing it down together,” Koiles says, putting an emphasis this time on together. “Not a full contract; just bullet points so that everyone leaves the meeting with the same understanding.”

That makes sense. Even in the Golden Age of Negotiation, who wants to sit down and start all over again?

In retrospect, it might have behooved me to master all of these rules before I’d gone into the Tesla dealership. Then again…

A few weeks after my Tesla visit, an email from Tesla popped up in my inbox. My eyebrow arched. (Again, not really.)

I opened it. “Get $7,500 Off Upfront,” the email said in large bold letters. What was this? An effort to jump-start—all right, maybe just start—negotiations?

It continued: “The federal tax credit takes $7,500 off the purchase price of your new Model 3, Model Y, or Cybertruck at checkout, so you get the same features, technology, and five-star safety rating for less. Eligible buyers must take delivery of a qualifying Tesla vehicle on or before September 30, 2025.”

I sat for a moment and looked at my screen. That’s a lot of money. Why hadn’t the Tesla sales guy mentioned the tax credit to me when I was in the showroom? Of course, it quickly dawned on me why Tesla was bringing it up now. The federal tax credit was about to disappear under Trump’s “One Big Beautiful Bill.” Tesla wasn’t negotiating with me; they were negotiating with time itself. The company that had built its brand on never haggling was now in full panic mode, trying to move inventory before their customers lost a $7,500 incentive.

It was a perfect example of Rule #2: Figure out what game you’re actually playing. When I’d walked into that showroom, Tesla thought they were in a position of strength—cult-like demand, Musk mystique, take-it-or-leave-it pricing. But they’d failed to recognize they were actually in a race against the political calendar. The “non-negotiable” price was suddenly looking a lot more attractive, courtesy of our Dealmaker-in-Chief’s policy reversals.

This is the thing about our current Golden Age of Negotiation: The rules are constantly changing, usually at 3 a.m. via Truth Social. From Tesla scrambling to beat policy deadlines to CEOs racing to curry favor at Mar-a-Lago, everyone’s negotiating—not just with each other, but with an entire system in flux. Tesla’s email wasn’t really about generosity. It was about desperation disguised as opportunity. They just weren’t calling it negotiation.

I looked again at the email. $7,500 off—money that will soon vanish thanks to the stroke of a presidential pen. Don’t get me wrong; I still didn’t want the car. But the newfound flexibility from Tesla was a beautiful thing to behold. In fact, walking away empty-handed had been the best move I’d made in years, because I’d learned the most important lesson in negotiation: The person who needs the deal least usually wins. Now I had both the knowledge and the right approach to jump-start my next (real) negotiation. Game on.

---

The Handshake

Get this wrong, and you’re done before you start. Aim for firm but not crushing—you want to convey confidence, not audition for the WWE. A limp handshake suggests you’re already defeated, while a bone-crusher screams insecurity. Think business meeting, not arm-wrestling match.

Your Face (and Theirs)

Eye contact shows you’re engaged, while a genuine smile and occasional nods signal that you’re looking for win-win, not total domination. Meanwhile, touching your face, furrowing your brow, or pursing your lips telegraph disagreement louder than words. The key is balance: projecting positivity and openness while simultaneously reading their facial expressions for the same cues. If they’re suddenly touching their eyes or their expression goes sour, you’ve hit resistance. Time to switch tactics.

Your Body (and the Space Between You)

Four feet of personal space is the sweet spot—close enough to connect, far enough to breathe. Lean in slightly to show interest, keep your hands visible and your limbs relaxed and open (hidden hands suggest hidden agendas; crossed arms suggest you’re already checked out). If they suddenly push back from the table or lean away, you’ve lost them. Time to recalibrate.

Quit Twitching

Most important: Stop fidgeting! That bouncing leg, constant chair adjustment, pen-clicking, or handwringing tells everyone you’d rather be literally anywhere else. Confidence is stillness. Control your nervous energy, and you control the room.

Before you bring in the Boston theme—a noble desire, by the way—the name has to work as a name. It needs originality, personality. It’s got to be theirs. When you yell it across a park, seven dogs can’t come running, which is just another way of saying that we have enough Bellas and Lunas.

To get a winning name, you gotta think, discuss, cross stuff off lists. And above all, the kids do not get final say. It’s a good teaching moment that not all of their ideas are gold. (We also have enough Shadows.)

Now to make it Boston. We have tons of possibilities, some so obvious as to be overlooked. The biggest? Dunks. It’s quick, strong, needs no explanation, and will get a constant response of, “Can’t believe I missed that,” but you’ll need to get on this early because it has the possibility of becoming like Charlie and Jack.

If you want to honor our long, storied history, then go with Norm, Lilith, or Coach. If this isn’t resonating, your first to-do item is to watch Cheers. But under no circumstances can you pick Sam. (See Luna and Bella.)

Sports could be seen as too easy, too hack, but it’s still a good source of the great and unsung. For the Celtics? Hondo (John Havlicek), Russell (Bill), or Bird (Larry). The Bruins? Doakie (Gary Doak), Schmautz (Bobby), Sweeney (Don or Bob), or Chief (Johnny Bucyk), the latter allowing you to constantly say, “How ya doin’, Chief?”—the ultimate Boston display of concern. Patriots? John Hannah gives maximum boy/girl flexibility with his last name and nickname, “Hog.”

The Sox well is deep, but dig a little deeper and consider Boomer (George Scott), Pudge (Carlton Fisk), Tiant (Luis), Carbo (Bernie), or, most especially, Freddie Lynn (Freddie Lynn). If you want to be totally innovative, something we love to do here, well then, it’s Monster. Give the pooch a green collar, and the story is told. If you want a little more bite, Stubby, acknowledging where you end up buying your tickets. Or you could go with Obi, a classic Boston nickname (O’Brien), which in this case could stand for Obstructed View Seats.

Actually, any name that ends in “er” has legs, because you can/should spell and say it with an “ah.” Which leads to another ridiculously awesome choice: Chowder. Full name would be Chowderhead, and in more casual moments, Chow.

And finally, if you’re adopting two dogs at once, there’s only one option: Wicked and Pissah, which would be, well, you know.