Opinion: How asking strangers for sips of their coffee helped me navigate difficult conversations
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Silicon Valley's conservative folks often censor their ideas for fear of others' negative reactions. But what if we could train ourselves—like athletes for a marathon—to develop skills for uncomfortable conversations? Well, Daniel Shiner's done exactly that, and explains his unique “bootcamp” experience in Medium's Human Parts blog.
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 …
[But after graduation, I realized I was missing] 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. …
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? …
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. …
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. …
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. … [I]t 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. …
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. …
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. …
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. …
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. …
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.
Read the whole thing here (behind paywall).
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