Interviewing for a job often is a daunting experience. It may commonly be described as a two-way selection process, one in which the candidate is evaluating the company as much as the company is the candidate, but the somber truth is that outside of the most highly sought-after segments of the talent pool, the balance of power resides squarely with the hiring company and the candidate has little leverage until the moment a job offer is presented. This seemingly is especially true in Silicon Valley, where each job opening routinely attracts hundreds of applicants and it is not uncommon that the candidate simply never hears back from the company in the case the interview is deemed unsuccessful at any point along the process, without even a notice of rejection, let alone being provided an explanation or feedback of any kind. Basic decency and decorum can seem to fly out the window once the company makes the determination you are “not a fit,” which effectively translates to “henceforth a waste of time,” simply an undesired byproduct of an essential process, to be discarded as quickly as possible.
But every once in a while, as is the case with life in general, an exception comes along that runs against the grain of your learned expectations. It shows you the extraordinary does exist and offers a reminder that much of what happens in this world lies on a distribution, despite the seeming tyranny of what occupy the regions of central tendency. While it won’t negate the broadly observed norms, the reminder that excellence exists in almost all domains of human activity sometimes is enough to sustain one in a journey that is full of pitfalls and trials, providing the inspiration that helps keep alive hopes and aspirations even when the objective and dispassionate prognosis appears far from welcoming. Interviewing with Stripe, the payment startup, for me, was such an example.
My very first interview with Stripe started off quite inauspiciously. It was a phone interview with the recruiter, and after spending some time to explore and discuss both my background and that of the job, he let me know that my skillset probably was not as good a match for what the hiring team was looking for as initially thought. In retrospect that sort of upfront candor might have been an early indication of the caliber of the organization that was to be revealed more fully later on. But the remarkable thing that happened after he uttered that assessment was that he wanted to refer me to another recruiter, for a different role which he thought presented a better match. This was something that quite literally had never happened in my experience, admittedly a small sample as it may be – a recruiter that not only was well-versed enough in another position for which he was not recruiting, was empowered enough by the organization to make that kind of an autonomous referral decision without consultation, but also, probably most impressively, cared enough to take on such an initiative when I was deemed no longer useful for his immediate need, which was to fill the position at hand.
The subsequent interviews, for the new role, went more smoothly, uneventfully in the best sense. Over the course of the ensuing few weeks, in succession, I had a phone call with the new recruiter, a Zoom video call with the head of the business unit for the role (who was based overseas), a writing assignment, and in-person coffee shop chats in San Francisco with the said head of the business unit who happened to be in town that week and also with the hiring manager. All of that led to culminate in an on-site round of interviews with 7 individuals that lasted over 4 hours in January of this year at the San Francisco headquarters of Stripe.
In retrospect, it is clear I did not perform as well on the on-site interviews as I should have. What was unique about Stripe was the interview questions were actually provided in advance – the recruiter arranged a call with me prior to the scheduled date to go over the questions one by one. Gripped by the notion, somehow, that interviews are just conversations, however, I did not spend a lot of time preparing specific answers for those questions. Looking back, I now think a big part of the reason why was hubris; I have a tendency to think I enjoy all conversations, and proceeded to draw the conclusion in my mind that conversations I enjoy in an interview setting therefore must also be good interviews. The mere fact that I was ready to enjoy the interviews, in their natural, unscripted, conversational formulation, was, in a way, enough preparation. But once the on-site interviews began it became apparent the interviewers were pressing for a higher level of specificity in the answers than I was prepared to give in the course of a casual conversation. I could feel the inadequacy of my answers resulting from the lack of deeper considerations given to them in advance, and I simply was not good enough to get to the level of detailed thoughtfulness on the spot. As I was ushered out of the building after the interviews concluded, I recall feeling a sense of regretful uneasiness creeping in. Almost compulsively, I remained hopeful, but far from confident. And surely enough, a few days later I was informed that I didn’t get the job.
I was devastated, but this is the point from which I was led to Stripe revealing itself to be a truly unique, unconventional company in the most unexpectedly wonderful ways. First, the recruiter offered to schedule a call so we could review the decision. I was pleasantly surprised to be given such an unusual opportunity, so I took him up on it. During the call he relayed some useful feedback, though it is clear in retrospect that I got too excited to be on such a call and spent way more time talking than listening to what he had to say. But importantly, the conversation helped me come to a realization, in concrete ways, that I was a much worse interviewee than had previously believed myself to be. It prompted me to ex-examine my natural tendencies in the ways I think, talk, and engage with others in conversations. When I shared this revelation with my wife, she was more than happy to supply additional pointers in areas of my failing.
The fact that the recruiter – and by extension the company – was willing to engage with and spend the time and effort on someone deemed to be “not wanted” was an enormous departure from everything I had experienced previously. Frankly, it was the kind of thoughtfulness and generosity of goodwill that I never expected any corporate entity to possess or display. I knew I had been rejected, but now I wanted Stripe even more, and I couldn’t let myself just give up. So I did something quite silly: I sent an email to the CEO. Fortunately Patrick Collison, Stripe’s CEO, lists his email address on his personal website. But I had no idea if the email would actually reach him, or if he would read it if it got to him, or if he would respond in any way. The overwhelmingly realistic outcome was that nothing would happen, and I knew it. It was a desperation move, one you are able to make only because you have nothing to lose.
Then, I got an email from the recruiter. He asked if I wanted to speak with the company’s chief risk officer – the job I interviewed for was a risk function – for reasons that were not entirely clear. He mentioned I might want “a bit more closure,” but I didn’t want closure; if anything, I wanted to keep the door ajar as much and as long as possible. He also said that the meeting was optional, with “no pressure.” Perplexed yet intrigued, I took up the opportunity to speak with the executive. She began the call with something to the effect of “I know you reached out to Patrick.” I had reached out to everyone I had interviewed with to solicit feedback, and since the name “Patrick” didn’t register right away I processed it to mean one of the interviewers. But about 5 seconds later I realized there was no one named Patrick that I had met, and then it hit me that it must be Patrick Collison, the CEO. My email to him was why this call was happening, which the chief risk officer confirmed when I asked her in disbelief. I was stunned. Having taken place almost a half year ago, much of the details of the call is a blur. But I recall distinctly her asking why Stripe should hire someone like myself. Most improbably, it seemed, this might be a second chance.
I had written to Patrick the CEO with a proposition: I offered myself to be a counterfactual data point in an evaluation of Stripe’s hiring process, after learning that Stripe’s credit card fraud detection system lets through some transactions which its algorithms flag as likely frauds in order to determine whether they turn out to be true positives or false positives – thereby evaluating the algorithms themselves – in a process called “counterfactual evaluation.” When the chief risk officer asked why I should be hired, I reiterated that proposition: the case I was making was not about my own merits, but the willingness on Stripe’s part to apply counterfactual evaluation to its hiring process, to determine whether I was a false positive (incorrectly rejected) or a true positive (truly no good) by letting me join Stripe, without a bias to either outcome. I couldn’t tell if I was making any headway with this argument, but we soon ran out of time and she had to go to another meeting.
In the end, the outcome of my interviews did not change and I remain not an employee of Stripe. But out of all the job interview experiences I’ve had in my life, the one with Stripe stands out as singularly remarkable. When I shared my story with a friend she was so impressed that even though she wasn’t looking for a new job, she said she still might apply to Stripe just for the experience. Today Stripe has earned a reputation as one of the best embodiments of the ideals of Silicon Valley – a place of inventive and ambitious companies that not only come up with new, innovative products and services, but also new, innovative ways of how companies are run. My first-hand experience with Stripe’s hiring process left a deep impression and I remain, to this day, inspired. Certainly, not everything was perfect – some interview questions, perhaps unavoidably, seemed contrived, and it’s unclear how much better Stripe ultimately is than other companies at shaping the interview process so that it is an effective and reliable predictor of the performance, broadly defined, on the job. But its openness, willingness to deviate from procedural norms – indeed, possibly, not to have deeply ingrained and inflexible procedural norms – and above all, the basic decency of treating all who come through its doors, however briefly, with thoughtful courtesy and respect are well deserving of my awe. Yours, I hope, as well.