Why It's Hard To Predict Success
Why It's Hard To Predict Success
How perceptions distort our view of who might be good, the importance of having a fast and objective feedback loop, and my new initiative for 2023
Many years ago, we hired two new customer success managers who couldn’t be more different. “Taylor” sailed through the interview process. He was charming and well-liked by everyone he met. “Pretty sure that guy will be running the whole organization in less than a year,” one exec said to me.
“Amelia” on the other hand, couldn’t have been more different. It was surprisingly hard to describe her personality. Because Amelia was super low key. She didn’t say much, and seemed to prefer hanging out in the background listening to everyone else talk. “Amelia seems oddly quiet for someone in a customer facing role,” one colleague remarked. “Not sure how long she’ll last here.”
That’s because our startup was hands down the most unforgiving work environment I have ever worked for. If you weren’t good at your job, you’d be shown the door quickly. I’d been working there for less than a year, but in that time saw more employee departures than I ever did at any other job.
And I used to work in Biglaw!
That context about the atmosphere helps explain how this narrative—that Taylor would do well, and Amelia would struggle—took hold quickly. Among everyone. High turnover would lead to fast promotion opportunities. Taylor was the golden child—and it made sense that he would glide his way up the org chart. And Amelia, who seemed like she might underperform—would struggle to hold on to her job. Right?
Wrong. Amelia ended up outperforming Taylor by a mile. Within a year, Taylor was on his way out of the company. And by then Amelia became one of the company’s most valuable employees, beloved by customers, her peers, and the execs.
Watching how this all played out helped shaped the way I view the corporate world today.
Being underestimated
I’m proud to say that I wasn’t completely caught off guard by what happened. Because just a few months earlier, I had the same experience. I’d been in Amelia’s shoes. When I joined the startup as an entry level sales rep, they didn’t think much of me. “Don’t worry if you get fired,” they said. “The sales game, it’s not always fair.”
I think what they were trying to say in a nice way, is that I was likely to fail. Because as a smart, well-educated Asian American lawyer, who looked like an introvert, I might not have what it takes to be good at sales. I was relatively quiet around new people, didn’t follow sports obsessively, and hated small talk.
A colleague once told me that she was surprised when she found out I was a salesperson. “You seem more like a product guy,” she said.
It’s crazy how big a role perceptions
play into success in the corporate world. Like I always knew it mattered. I just thought it only really mattered for senior managers, like when they talked about “executive presence.” What I didn’t realize was how much it mattered even as you moved down the org chart.At a startup, perceptions still matter. But compared to large organizations, they play a much smaller role. The feedback loop is much faster at a startup, and you find out quickly if people are legit (or not). Perceptions quickly give way to reality.
In my first year of sales I outperformed every single person on the team by a wide margin. I made double or triple the number of cold calls as my competition, and spent my free time getting up to speed on our product and customers. So hard work did help me stand apart from my peers.
But the thing that really made a difference? It was the fact that my job was in inside sales.
The fairness of inside sales
For most of history, sales took place in person. You would show up to someone’s office and talk about sports, the weather, or whatever. Maybe at the end you would make a soft pitch. It was “relationship selling” and you were selling your own personality and image just as much as you were selling your company’s product.
At some point someone figured out it could be more efficient to sell software remotely.
All you needed to do was train sales reps in an office, and give them a phone and tell them to smile and dial. It was a high volume, transactional job. Traditional sales reps and traditional buyers hated it. It just seemed so engineered.Yet at the same time, by removing from the equation what the sales rep looked like sales became more fair. Prospects treated me more fairly—they didn’t stereotype me because of my race or what I looked like. In person, I might be a quiet Asian guy who doesn’t know how to talk about sports. But on the phone, I was a sales commando, who knew the pitch cold, and could speak intelligently about the product, the market, and the customer.
Measuring performance became more objective too. You couldn’t rely on your looks or conversational skills to look like a successful rep. The bosses could just check your results. Inside sales created a real opportunity for many of us to play on a level playing field.
Overcoming how people perceive you
In the end, how I was perceived didn’t end up hurting me. My results showed up on the dashboards and in conversations with prospects and customers. I was promoted, eventually. I was lucky because there was a fast, objective feedback loop.
That’s why when I first met Taylor and Amelia, I knew to discount what I saw and felt. Because they were just perceptions based on what’s valued in the hiring process. Yes, Taylor did seem really good with people, and did seem like the kind of person who would do well in the role. And yes, Amelia did appear to be someone who would not do well in a customer facing role, and might shy away from difficult conversations.
But you know what? Maybe not. Maybe the traits that made for a successful customer success manager weren’t immediately visible on day one.
Within weeks of their start date the picture became clear. Taylor wasn’t very good. He spent his days “pretending to work” although he did always make himself “visible” to the managers. Amelia spent nights and weekends studying up on the product and understanding customers, and worked incredibly hard. And it showed.
The difference between the two became immediately obvious anyone who listened in on their conversations with customers. And eventually, to the whole company.
Over time, Taylor’s charm wore off. Meanwhile, Amelia’s confidence began to grow as her knowledge with the product, familiarity with customers, and respect within the company grew. It was almost as if she became a completely different person.
At least that’s how it felt. That’s how perceptions work, I guess.
The best people are hidden in plain sight
In large organizations, who the “best” people are is always viewed through the lens of whoever is in power. A senior exec once confided in me that he had reservations about one of our talented sales managers because that manager “wasn’t polished enough.” We were a tiny startup with a few dozen employees. Was “polish” even in the top 10 list of things that mattered? If the sales manager’s team was happy and produced results, shouldn’t that be enough?
Many executives are political animals who are better at acquiring organizational power than driving business results. That skillset is important in large mature organizations—like Fortune 500 companies or Biglaw firms. But in exercising influence, they end up relying on existing power structures that rely on outdated stereotypes.
Which penalizes many employees who are talented at driving business results. Because they often don’t look or act like we expect. And these misperceptions or stereotypes or whatever you call it is hurting individual employees—can you imagine the impact it’s having on the business as a whole?
Finding tomorrow’s winners
I haven’t figured out exactly what to do with these thoughts. I know the world isn’t always fair, and that maybe I have a naive view of how things work. But at the same time, my desire to run towards “fairness” led me leave the law and stumble into a weird corner of the world, at the intersection between law, technology, and new media.
And in this tiny little corner, I think I can have an impact.
So far my attempts to have an impact are embarrassingly small. My first one was to join the tech startup scene selling e-discovery tech to try to disrupt the legal industry. After building up some career capital,
I ended up at a high impact startup I'd always admired, working for an executive I'd always admired. And over time, I’ve built up an audience on social media, where I regularly raise awareness (through jokes) about the legal industry’s lack of diversity, its resistance to technology, and the persistence of outdated values.I'd like to do more. So as head into 2023 I plan to expand to new and unfamiliar territory. One of my most promising experiments
is to focus on investing in early stage startups. It's not just about the money—I don't think returns are all that great especially what's happened to tech valuations this year.For me, I see my investing activity as a way to help me get a glimpse into a different part of the corporate world I don’t fully understand. And maybe, just maybe, if I’m lucky—my choice to look past perceptions will enable me to find tomorrow’s winners early. It’s my way of putting some skin in the game behind what I say I believe.
What kind of startups will I look for? Probably those in the legal industry to start, since that’s what I’m most familiar with. What can I contribute? Just a small check, since I’m not rich. Yet. But I do have other things to give, like expertise in selling/marketing technology to lawyers, and a small but loyal audience on social media.
My ultimate goal is to find the Amelias of the world. And then empower them. Because my twelve years in law & tech, and all of my experiences working on the front lines tells me that there are many, many more of them out there.
Wish me luck.
I use the word perception here, but “stereotype” works equally well
If you’re curious, check out this detailed history of the rise of inside sales
Just because the feedback loop was objective doesn’t mean it was based on metrics alone. Sales veterans are expert at making their numbers look good. For example, some are bad at sales but good at cherry picking the best leads so it looks like they have higher conversion rates. Having a strong feedback loop requires a holistic view of performance, which means sometimes you need to rely on anecdotal data from a range of perspectives.
Some of my work can be found on this Substack, but also elsewhere. E.g. Don’t Waste Your Time Collecting Golden Tickets
I do a lot of experiments, often without much planning, research or a deep understanding of the end goal. I like to call it “farming for luck” and it’s what led me to become a content creator, which I described in How My Failed Solo Practice Set Me Up For Success Years Later