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Finding My Fighting Words: How I Learned to Have Uncomfortable Conversations

I had 50 painfully uncomfortable conversations with strangers to practice being assertive under pressure. Here’s what I learned.

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I’m sitting alone in a coffee shop in Manhattan and I’m about to become the most disliked person in the room. First, I’m going to interrupt the man reading quietly near the window and ask for a sip of his latte. Next, I’m going to ask the line of people waiting to pay if I can cut to the front of the queue. And before I do any of this, I am going to lie down on the dusty, coffee-stained floor — eyes open, slowly counting from one to 20 — as the rest of the room looks on in uncomfortable, visible disapproval. This is how I chose to spend my last vacation. Here’s why.

Growing up, all I ever heard about was “EQ.” It was the mid-’90s, and psychologist Daniel Goleman had just popularized the concept of emotional intelligence with his 1995 bestseller of the same name. Now emotional quotient, or EQ, was becoming the latest buzzword to describe this new form of smarts. Unlike IQ, which tracked conventional measures of intelligence like reasoning and recall, EQ measured the ability to understand other people — to listen, to empathize, to self-regulate, and to appreciate. My mother, an elementary school principal, prized brains and hard work, but she placed a special emphasis on Goleman’s new idea. To her, EQ was what separated the good students from the great after they left the halls of her school. It was the elixir that transformed ideas and intellect into impact and influence. She was determined to send my sister and I into the adult world with as much of this elixir as possible, and she led regular dinner table conversations on the subjects of empathy, communication, and patience to do so.

But when I finally began my first full-time job after graduation — an early employee at a fledgling tech startup — something was missing. Sure, EQ mattered: It was crucial in clinching the interview and integrating quickly into a small, tightly knit team. But before long, I began to notice a second elixir swirling around in the back pockets of some of my colleagues. It gave their opinions extra weight and their decisions added impact. It propelled them into positions of credibility and authority. Strangest of all, it seemed like the anti-EQ: Instead of knowing how to make others feel good, this elixir gave people the courage to do the opposite — that is, to say things that others did not want to hear.

This was assertiveness. Psychologists conventionally define assertiveness as the healthy middle ground between passivity and aggressiveness, but in practice, I found that it boiled down to the mastery of a single skill: the ability to have uncomfortable conversations. Assertive people — those with high “AQ” — can comfortably engage in the sorts of conversations that make many of us squirm. They ask for things they want, decline things they don’t, provide constructive feedback, and engage in direct confrontation and debate. While the top performers at our company varied widely in terms of personality, gender, and introversion/extroversion, they all excelled at these types of tough talks.

In fact, the more time I spent in the working world, the more I felt I could map everyone I interacted with according to their levels of EQ and AQ.

The four types of people I encountered at work.

Those with low EQ and low AQ were the “grumblers.” Difficult to work with and unable to speak up for themselves, grumblers turned to gossip and passive aggression to deal with others. Creating a toxic environment wherever they went, they generally encountered a low ceiling in their personal and professional lives.

Those with high EQ but low AQ were the “people pleasers. While well-liked and collaborative, people pleasers struggled with conflict and saying no to others. Like the grumblers, they also hit a ceiling, passed over by managers and steamrolled by friends and family for not having the guts to have tough conversations.

Those with low EQ but high AQ were the “assholes.” Blissfully unaware of or uninterested in social graces, assholes ruthlessly told you what they thought without fear of or concern for how it made you feel. Assholes could sometimes buck the EQ trend and rise remarkably high on their AQ alone, but most eventually hit a ceiling, albeit a higher one. Peers whispered that they were hard to work with, and they were excluded from the best professional opportunities and personal relationships.

Those with high EQ and high AQ were the “respected leaders.” These people were likable and great to work with, but also knew how to say no, ask hard questions, and share constructive feedback—and to do so in a way that was firm and respectful. This is where most of us want to be.

Turning the mirror on myself, I landed in the top-right quadrant, but just barely. A lifetime honing my EQ helped me empathize with those around me, but it also left me overly sensitive to situations where I had to say or do things that might make others unhappy. While I didn’t avoid conflict, I was always frustrated by how much my mental machinery would degrade when I had to say or do something that could upset someone. Engaging in heated debates and providing negative feedback were the hardest for me. My thinking would get cloudy. I’d stumble through my words or use too many of them. After the conversation was over, I’d be frustrated by how poorly I had conveyed my message and feel emotionally drained from the experience. Compare that with the people I respected the most — our CEO, say, or my mother — who seemed to be able to maintain clarity of thought and speech in even the most uncomfortable situations.

And there was another thing that kept me low on the AQ spectrum. Somewhere in my twenties, I’d lost track of my own introverted tendencies and let them snowball into moderate social anxiety, specifically when it came to approaching strangers. It felt like another unintended consequence of doubling down on EQ. Anytime I had to approach someone I didn’t know — at a trade show, networking event, or social occasion — my empathy would kick into a sort of broken, distorted overdrive. I’d instinctively imagine the person I wanted to speak to being annoyed or uncomfortable with my overture, feel a spike of anxiety at this imagined reaction, and more often than not, I’d bail. It felt like a dirty secret: I regularly spoke at conferences in front of hundreds of people, but I’d break into a sweat if I had to approach a single person in the crowd.

This was a problem. Whether negotiating for a car or for venture capital, providing honest feedback to a romantic partner or a business partner, I knew that a stronger stomach for uncomfortable conversations would be necessary to get the things I wanted out of life. I became fixated on finding a way to move up the AQ spectrum.

The big idea

EQ is notoriously hard to improve. Socializing is a complex symphony of subtle cues and interactions, and getting better means learning to play an ensemble of new social instruments, often all at once. In contrast, improving my AQ felt like a much more manageable task. Instead of an orchestra, assertiveness felt like a single important, imposing instrument: the courage to tell people things they may not want to hear. This was good — I figured if I could just improve on this one skill, I could knock my AQ up a few notches.

In theory, AQ felt easier to improve than EQ. But finding opportunities to practice it was a challenge.

The problem was that meaningful improvement of any skill requires deliberate practice, the intensive form of practice coined by K. Anders Ericsson, the grandfather of expert performance psychology. Deliberately practicing a skill means setting a target just outside your comfort zone, crafting exercises that enable you to work repeatedly toward that target with intense concentration, and then, once you achieve it, raising the bar and repeating the process. A tennis player working on their backhand does not casually play games with friends, hoping to improve; they set a target, load the ball machine, and work the backhand — focusing intensely on every swing, observing the output, and adjusting their technique as they go.

But there was no obvious ball machine for uncomfortable conversations. Providing friends or family with unsolicited “feedback” might be a fast way to practice, but I’d likely be left with no one to share my findings with once it was over. Waiting for real conversations to emerge organically was an option, but I reckoned that I only had about 10 really hard ones a year. Worse, most of these conversations snuck up on me, with no time to prepare beforehand or reflect meaningfully afterward. This left me with perhaps two or three opportunities a year to really focus and deliberately practice the skill. At that rate, by the time I got in the 40 or 50 reps I thought I’d need to make a meaningful improvement, some of the best years of my life would be over.

This was when my gears started to turn. Could I build a ball machine for uncomfortable conversations? Could I create exercises — more realistic than role playing but safer than experimenting with real relationships — that simulated the key skills I wanted to develop? And could I wrap these exercises into a sort of personal bootcamp, which concentrated lots of practice into a short period of time, in order to accelerate my progress?

Building the bootcamp

I set out to create a bootcamp for uncomfortable conversations. Here’s how I did it:

The exercises

I created two types of exercises to develop my AQ: uncomfortable negotiations and unusual conversations.

Uncomfortable negotiations involved entering into negotiations at flea markets, where I would offer vendors unreasonably low prices for their wares — generally 25% or less of the retail price. The negotiations would follow a specific script, where I had to make the offer and then remain silent, maintaining eye contact until they replied. If they declined, I had to firmly repeat my offer, followed by the same silent stare. If they declined a second time, I thanked them politely and went on my way. The goal was not to get a discount but to practice saying things to people that I knew they would not want to hear. This worked, sometimes too well: since the crafts on sale were often painstakingly produced by the people I was negotiating with, my lowball offers did not just discount the price — they discounted the creative output of the vendors themselves. As a result, my negotiation partners were not just disinterested in my offers, but often visibly insulted by them.

Unusual conversations involved approaching strangers and saying or doing things that, while unthreatening, were downright weird. I began with easier challenges — asking someone on the street if they had a stick of gum or if they liked my shoes — and increased the intensity of the weirdness over time. By the last day, I had to ask a stranger for a sip of their drink, convince a tourist in the park that I knew them, and ask a line of people at a Starbucks to cut to the front without justification.¹

The intent was two-fold: First, I hoped that by approaching strangers with highly uncomfortable requests, it would stretch my comfort zone, making more conventional approaches feel less daunting by comparison. Second, I guessed that the ability to take social risks — to be okay with other people thinking I was a bit weird — might be a prerequisite for the ability to tell people things they may not want to hear. If I were right, increasing my social risk tolerance would act like a rising tide, lifting all my other assertiveness ships along with it.

I created 25 variations of each exercise, or 50 in total.² If I was averaging two or three opportunities for deliberately practicing uncomfortable conversations in the course of my normal life, I figured this would amount to about 25 years of life experience.

The grand gesture

I knew that doing these exercises would be scary and hard, so I leaned on a trick I learned from Cal Newport — the “grand gesture.” The idea is to tie a hard thing you’ve been meaning to do to something significant that breaks you out of your normal routine. J.K. Rowling booked stays in the Balmoral Hotel for $1,000 a night to help her complete the final book in the Harry Potter series. Bill Gates took “think weeks” at a cabin in the countryside to undertake deep thinking, away from the draws and distractions of everyday life.

I took a week off work and flew from my home in Toronto to an Airbnb in East Harlem, a neighborhood of Upper Manhattan in New York City. Committing a nontrivial amount of time and money to the trip, combined with the reassurance that nobody there knew me, gave me the extra boost of intention to overcome the fear and complete the exercises. It also allowed me to structure the exercises as a bootcamp, so I could accumulate my 25 years of practice in only seven days.

The structure

Fear loves discretion. En route to social events, I’d often promised myself to step out of my comfort zone and talk to strangers. But “talk to strangers” is a vague goal — Who is a stranger? How much talking do I have to do? — and given this wiggle room, my anxious brain would expertly craft credible reasons for why approaching people was impossible, or irresponsible, or a bad idea, and I’d bail.

But take away this discretion — turn “talk to strangers” into a predetermined plan for the number of people you must approach and the specific questions you must ask them — and your brain’s deceptive power in the moment is neutralized. All the reasons you couldn’t or shouldn’t do the thing you were planning to do shrivel away, leaving behind only the bare bones of the thing that is holding you back — the fear.

For this reason, I spent months before traveling to New York wrapping structure around the trip. I mapped out all the flea markets in the city and the dates I would visit them. I created detailed plans for the exercises I had to do each day, including scripts of what I had to say and spreadsheets to record what happened. The idea was to leave no space for discretion when doing the scary thing, so that when I was in the moment, it was just me and the fear.

One of the spreadsheets used to track the exercises. Columns C onwards were filled in after completing each exercise.

Lying on the floor

In addition to the conversations I had prepared, I started each day of the bootcamp with an extra exercise I’d read about from fear-facing expert Tim Ferriss. Every morning, I’d enter my local coffee shop, and after ordering my drink, I’d force myself to lie down on the floor in the middle of the store. For 20 seconds, with no explanation or advance warning, I’d lie there — eyes open, silently counting to 20 — as the rest of the café looked on in confusion. Then I would get up, pick up my coffee, and go about my day.

It was an extremely weird thing to do, and each time I considered it, my social defense system would go into overdrive, firing every reason it was impossible or unreasonable or unsafe. Feeling the alarm bells go off, putting them aside, and doing the exercise anyway was a great way to start every day of the bootcamp with a small victory of courage over cowardice and set the tone for the rest of the day.

Starting the day practicing extreme discomfort on the floor. I asked the (at this point, bewildered) barista at the coffee shop to take this picture on the last day of the experiment.

The secret

Despite the large amount of time and energy I was investing into the trip, I told no one about it. My friends, family, and co-workers knew I was taking an unusually long holiday in New York, but that was it. I did this to avoid chickening out: Research shows that telling others about something difficult you want to do triggers many of the same emotional sensations as actually doing the thing. These sensations can then erode your motivation to actually achieve your goal — because by telling people, you’ve already obtained the identity you were striving for. To mitigate this risk, I kept the whole thing a secret until I returned.

The important caveat

During the bootcamp I often felt anxious or uncomfortable, but I never felt unsafe. Part of this came from a set of ground rules I followed — avoiding doing the exercises at night, for example — but another part came from something I got for free: the fact that I am a white man. My privilege afforded me the ability to deliberately place myself in situations that could have turned confrontational without fear of repercussion or physical violence. While the intention of this essay isn’t a commentary on race — anyone can have difficulty with uncomfortable conversations — it is important to acknowledge that were I not a white man, the world may have reacted differently to these behaviors. Sadly, the reality today is that it is not always safe for everyone to embark on a journey like mine.

What Happened

I completed the bootcamp this past October. The trip was extremely impactful, mostly in ways I didn’t expect. Here’s what happened:

It was grueling

The bootcamp lived up to its name — it was grueling. I woke up every morning dreading the day ahead, cringing at the list of uncomfortable conversations I’d have to have. I spent large chunks of time sitting in flea markets or on park benches with my head in my hands, working up the courage to initiate a conversation that my internal social compass told me was an extremely bad idea. The experience felt a bit like binge-watching Curb Your Enthusiasm, but instead of Larry David saying painfully awkward things to strangers, it was me.

In fact, the most surprising part of the experience was how violently my body and brain would revolt when I pushed myself to act like Larry. When I would offer an unfair price to a flea market vendor or ask a line of polite people to cut to the front of the queue, the shock to my system was intense. I felt a wallop to my nervous system as intense as physical pain, and after the experience was over, I felt as drained as though I had just gone for a hard run. After each exercise, I needed nearly 40 minutes to regain the energy to get back in the ring for the next one. And the pain I felt when acting like a jerk didn’t decline much, even after repeating the exercises over and over again for a week.

This is probably a good thing. The things I was doing were explicit violations of the social contract: making unfair bargains, asking for things I didn’t deserve, or generally acting unpredictably with others. These are things that I could force myself to do as one-off experiments but are not behaviors I ever want to get used to doing. It was fascinating — and frankly, reassuring — to experience that I probably never could get used to doing them, even if I wanted to; the electric collar of our human instincts is just too strong to overcome.

But it worked

While I never acclimatized to acting like a jerk, the exercises did translate to a meaningful boost to the skill I set out to improve — my ability to have uncomfortable conversations. Since returning to Toronto, I’ve found myself significantly more capable navigating conversations that I previously would have fumbled. In the months since I’ve returned, I’ve provided tough, constructive feedback to direct reports without stumbling through my words. I’ve advocated for controversial strategic decisions to strong-willed colleagues and prevailed. And I’ve approached countless strangers — some for practice, some for important questions or introductions. The results have been overwhelmingly positive. My ability to influence has increased, and my personal and professional relationships have improved. AQ really is a superpower.

I think the boost to my AQ has come from three key changes that occurred over the course of the bootcamp. The first is a heightened awareness of how my brain and body react when I engage in a socially uncomfortable interaction. By repeatedly triggering my own anxiety, I’ve learned to recognize the physical and mental sensations that reliably come along with it: the heat and tension in my chest and temples, the images of the expected rejection that play on my mental movie screen, and the emotional pang urging me to avoid, agree, or do whatever is necessary to restore harmony between myself and the person I’m engaging with.

Previously, these sensations would occur beneath the blanket of my subconscious, triggering an automatic flight response without any opportunity for my rational brain to intervene. Now, I can usually catch these sensations as they occur, providing me with a precious few seconds to consult my rational brain before my animal instincts react. This brief window is just enough time to ask myself whether my reaction is justified and, if not, to regain control of the machine — to reset my eye contact, organize my thoughts, and effectively deliver the message I was intending. This improved awareness is probably the biggest driver of my AQ gains thus far.

This new awareness is complemented by the second change: a more realistic expectation of how people will react when I engage with them. Historically, hanging on a bulletin board in the deep recesses of my subconscious was a memo that read: PEOPLE ALWAYS WANT TO BE AGREED WITH AND LEFT ALONE. But my experience in New York proved that wasn’t true.

Most strangers politely engaged with even my weirdest requests: The man in the coffee shop agreed to let me try a sip of his drink (I declined), the tourist in the park kindly engaged in my investigation of how we might know each other (we didn’t — he was from Australia), and not a single person in the Starbucks line rejected my request to jump ahead. Of course, the responses of cautious strangers are not perfect predictors of how people will respond in real-life interactions, but the upshot still matters: My projections for how people will react to being approached or challenged are often much worse than the reactions actually are. Now when I ask my rational brain whether the thing I’m about to say will upset the person, I’m much more likely to get the answer right.

Unusual conversation #17: challenge a stranger to an arm wrestle. This university student kindly obliged, warning me that he wasn’t any good at these things. Then he demolished me.

Finally, surviving the bootcamp has resulted in a newfound confidence to initiate uncomfortable conversations in the first place. My experiments at the extreme end of the AQ spectrum have increased my social risk tolerance, making normal, run-of-the-mill awkwardness seem almost blasé. Once you’ve asked a line of impatient New Yorkers to get your coffee before theirs, summoning the courage to provide respectful feedback to a co-worker feels a bit like a layup. The old adage about your comfort zone is true: The further you stretch outside of it, the more it stretches to meet you there.

…Sort of

Shortly after returning from New York, I was called into a meeting at work to discuss an urgent issue about a project I was responsible for. The organizer of the meeting — a peer in another department who was known to have a short fuse — was concerned about the issue and demanded that one of my teams drop everything to fix it. When I surfaced my concerns with this plan — the team had already committed to another deadline — he lost his cool, exploding into bluster and dismissing my concerns in irritated exasperation. The room tensed up, and everybody looked to me for how I would react.

This was the moment I had been training for — head-to-head conflict with an aggressive opponent — and the perfect opportunity to flex my new AQ muscles. But I was shaken by being yelled at, hurt by his condescending tone, and in the moment, I stumbled. Instead of observing my own discomfort, consulting my rational brain, and then calmly and respectfully voicing my disagreement like I had practiced, I reacted too quickly, responded too agreeably, and ultimately downplayed my concerns. After the meeting was over and my head was clear, I realized this was a mistake and had to schedule a time-consuming follow-up meeting to relitigate the whole issue. I had failed.

I wrestled with early failures like this one a lot in the first few weeks after the trip. I had put everything I had into improving my assertiveness. I flew to New York City. I had a lifetime of painful conversations. I spent every morning on the floor of a hip East Harlem coffee shop, publicly humiliating myself. And still, I wasn’t as assertive as I wanted to be. What did this say about the impact of the trip — was all of that discomfort for naught? Or more precisely, was the optimistic philosophy underpinning the entire exercise — that deep-seated aspects of our character are as pliable as a tennis swing — naive? Was I stuck the way I was?

I eventually found the answer hiding in the words of my own question. If I, a novice tennis player, signed up for a weeklong bootcamp to improve my backhand, I wouldn’t expect to return home ready to dominate at Wimbledon. That would be ludicrous; everyone knows that mastering a skill takes years, even with intensive practice. So if I was modeling my assertiveness training on traditional athletic improvement, why was I expecting the results to be any different?

Put more scientifically, in constructing my bootcamp, I had recruited the first half of Ericsson’s research on expertise — that with the proper application of deliberate practice, humans can get good at anything. But when extending that theory from acquiring a technical skill like a tennis swing to a social skill like assertiveness, I forgot to include the second half of Ericsson’s findings: that mastery takes a tremendous amount of time.

“Expert performers,” writes Ericsson in Peak, his 2016 opus on how great people become great, “develop their extraordinary abilities through years and years of dedicated practice, improving step by step in a long, laborious process. There are no shortcuts.”

In other words, far from invalidating my philosophy, the bootcamp — and my experience in the weeks and months that followed — have cemented it, albeit with a sobering dose of reality. Our abilities, be they motor skills like a tennis swing or social skills like assertiveness, are profoundly malleable, with enormous upward potential and a ceiling we don’t know and can’t predict. But skills are skills, and there is no weeklong exercise or secret hack to short circuit the path to mastery. There’s only one way to get there — and that’s to keep setting up the ball machine.

Special thanks to Rachel Kattapuram, Jamie McDonald, Jamie Shulman, Zack Belzberg, Eli and Alex Gladstone, Noam and Yael Pratzer, Talia Schlanger, Geoff Gualano, Liam Kearney, Vanessa Chung, Mark Shiner, Laura Shiner, and Micah Vernon for reading early drafts of this essay.

[1] I got many of the ideas for the unusual conversations from Jason Comely’s Rejection Therapy game, designed to help players get more comfortable with rejection by asking strangers to do things they will almost certainly decline.

[2] Because of logistical challenges, I only ended up having time for 21 uncomfortable negotiations. I made up for it by having four extra conversations with strangers to ensure I hit my total of 50 conversations. These extra conversations included several normal conversations, such as asking people where they suggested I visit in the city or where they purchased their laptop case. I realized that by having exclusively weird conversations with strangers, I was at risk of conditioning myself to expect others to respond negatively to my advances. Balancing out my unusual conversations with a handful of normal conversations felt like a healthy way to ensure I didn’t finish the bootcamp more uncomfortable than I started.

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Daniel Shiner

Daniel Shiner

I love building and learning new things.

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