20 Job Interviews

February 10, 2022
10 min read
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Let me confess a ridiculous fact: From June 2020 to August 2021, I interviewed with 20 companies.

At my weakest, I sent over 200 cold applications through company sites and LinkedIn. It felt productive, but it was fruitless. In hindsight, I did it to keep myself busy.

I’ve had my brain picked. Spoke to a dozen recruiters. Had conversations with leaders and so-called decision-makers. Was ghosted a handful of times (not uncommon, yet sadly accepted). I would meet every executive in the company (HR, marketing, product, brand, design, ops). They said they’d follow-up, then I would see a job posting on LinkedIn — with my language as their job description. Funny. 

I would get as far as interviewing with every single person on the team, and at the very end, receive an email that said these words.

I am impressive! But alas…

Because the employer said I wasn’t a fit, was too senior for the role, or not what they were looking for, none of which are failures, denial worked in my favor. A handful of people followed up months later to confess that many people quit and internal org was being restructured. 

“See?” I told myself. “It had nothing to do with you.” Yet in desperate moments, it felt good to believe it was all my fault for not getting the job because that gave me an excuse to stay in place.

What I did learn from this experience is akin to a child babbling before learning to speak. By doing so many interviews for various kinds of roles and companies, I practiced talking about my core skills, what I can bring to the table, and how I think about the challenges ahead. It also made me get clear on what I would not do, no matter how much money was offered. 

All of this was a good experience. Where else in your life do you engage in this kind of negotiation? 

Reinvent the job interview process

What’s missing from the “future of work” conversation is how absolutely horrendous and outdated the job interview process is. Out of the 20 conversations I had, only two experiences – both from warm connections – were memorable. The interviews were conducted with thoughtfulness and transparency, from pay range to expectations to the deeper issues within the company, and the recruiter was able to share a compelling vision for where they wanted to go. 

Some say that is a good ratio; I say as an industry, there is an enormous opportunity to do better. Talent recruiting isn’t viewed as important as design or engineering, but I think bigger companies are slowly realizing how necessary it will be in the future.

The workplace is fundamentally changing, with challenges intensifying, so the practice of acquiring talent is ripe for transformation. The problem, I've noticed, is that most recruiters are clueless. Either they aren't brief properly or they don't know how to spot talent, how to speak to talent, or how to look at a portfolio.

Big tech companies with lots of money win the talent market because they can offer insane salaries and have the halo effect of being popular/famous/successful. They got a legal team that can expedite your travel visa. And my friends in their 30s and 40s — with a kid on the way — want to be comfy.

But if you aren’t at the level of the Yankees or Los Angeles Lakers — if you aren’t Stripe, Google, Apple, a16z — you’ll need to be persuasive and show leadership and outline career growth and the promise that it’s worth working there. Especially for younger talent, if your company is not known, they’ll think, “Well, this might not look great on my resume. My other friends are working at ‘cool’ companies.” You’ll have to win hearts and minds, not just offer salary and perks. 

The games job seekers played in the past are not the games of the future. Everything from retirement plans to where you’ll buy a home to the kind of workplace you want to be in is all open for change. This changes how people see themselves at a company.

Overall, I think many people read outdated books and the wrong articles on what to do in a job interview. Some people treat it militarily. Others treat it like a quick coffee meeting with an old friend from out of town. It is a strange game of chess. A bait-and-switch of which mask we’re going to put on. Do we speak as if we’re already on the team? Or are we playing a game just to get our foot in the door? Does authenticity really pay off?

Don’t make my mistakes

Rejection after rejection — especially if you’re already burned out — makes it exhausting to stay resilient in your job search. The self-defeating thoughts slither in: “Maybe you aren’t as good as you think you are.” “Maybe you should change your career.” (Like that’s easy?)

One of the worst things to do is what I did: Apply to jobs to get out of what you’re in. This is reactive and your desperation becomes visible even through a Zoom window.

You should apply for jobs because there is a faster train headed toward where you want to go and the opportunity cost is greater. Because you are no longer earning and learning. Because you realize you’re jaded and need to get out to save yourself from hating your craft. 

The smart scenario is applying for jobs when you’re already content. 

Because when another company is genuinely interested in you, you have leverage. You already have a job, so it’s the company’s objective to pull you away from that one by offering something better. You can go back to your job and say, “I got this offer. Can you beat it?” If they do, you win. If they can’t, you still win, because you have a better offer elsewhere. 

When you hate your job and want to move on to something else, it’s a different game. You’ll take anything because you believe that anything is better than the toxic shitstorm you’re in. But what if the next job is even worse? You’re alone, with no allies, in a worse situation. Compound that with burnout and a slew of other personal issues.

The best advice I got from a friend was to figure out how to make my situation less shitty. Be realistic and honest about the fact that you have no leverage right now. You can’t quit because you don’t have 3 to 6 months of savings, so you’ve gotta work. How do we make the situation better, for now?

Exercise, sleep, hold boundaries (haha), or simply say no. This will help alleviate the day-to-day. The goal is to get your mind into a better place where your self-talk isn’t overcharged with rage and self-loathing. It is to realize that a job is just a job — you can always change it — and to mindfully choose where you want to invest energy. (Watch this video by Elizabeth Gilbert on job vs. career vs. vocation.)

For me, it was cycling. Fifteen-mile bike rides before I opened my laptop cleared my head and allowed me to embrace anything, from pointless meetings to three-hour conversations. Heavy weight lifting helped me get the frustration out of my body.

Changing a job will not solve your problems. You have to change the story in your head. And that takes time, space, friendship, meditation, journaling, exercise.

But look, if you’re like I was, sending an application every day, spending more time on LinkedIn than any other site, I feel for you. Slow down. This is a marathon. 

What I tell my friends

Open, vulnerable conversations with your friends about salary, equity, the job description, etc. will be the most clarity-inducing practice. 

Nothing is as reassuring and hope-giving as having candid conversations with friends who are either experiencing what you are going through or have gone through it. 

Here’s what I tell friends and what friends have told me (YMMV).

1: Expect nothing — I often found myself disappointed after conversations with a company and had to understand why. It’s because I placed this company on a pedestal. They are “known” I’d say. “Famous.” “Successful.” Avoid these phrases. What is the job? Are they paying you what you’re worth? Are there interesting problems to solve? Will you grow there? Do you like the people that you’re working with? Do you have a life outside of work? Are you inspired by, or feel like you can learn from, the people around you? Focus on those. 

2: Always err on the side of being genuine — Sometimes I am too open. Too honest. Too quick to share a spicy opinion that, on a few occasions, offended the person interviewing me. On the flip side, if I wasn’t myself and got the job, my true self would eventually show, and I’d get fired. Being yourself and not getting the job is not a failure. Both parties win. 

3: “Full transparency” is never full — Negotiations in job interviews often feel like the Wild West. Who’s gonna draw their gun first? It’s all so pedantic sometimes. If companies could show their cards thoughtfully, they would get better talent. But instead, they attempt to play poker to get the most out of a person for the least amount of money and resources. If you feel like you’re being transparent, but they aren’t, run. Why work for people like this? Imagine what else they’ll hide from you.

4: They need you — This is a fact to always remember, especially if you’ve proven that they need what you have. If they had their shit together, they wouldn’t be talking to you. Remembering this will become a source of confidence. But don’t be arrogant – you still need the job.

5: No company has their shit together — No company is perfect or ever will be. Every company, to some degree, is a shitshow. You must assess the level of shitshow behavior. Experience in various industries will help you fine-tune your intuition. Early in your career, you’ll believe that in order for a company to do great work, it must have a great culture. Flawless processes and no siloes. This is naivety on steroids. A company can be an absolute shitshow and, inadvertently, they’ll still ship great work. That’s because they have extraordinary talent. Experience will prepare you to ask the right questions, spot red flags, or detect patterns. 

What I would tell recruiters

Recruiting is going to be as hot of a job as community building became five years ago. I can imagine someone with a strong network and a good talker to be a linchpin at companies. They know the language, they know people.

No matter what companies did before the pandemic to earn talent, they need to throw away the old playbook.

I’ve dealt with two kinds of recruiters. One sees talent as a buffet. The other sees it as a tailor-made suit. The buffet recruiter is cranking out meeting after meeting. Filling their schedules and pretending to be busy. They have a script of questions and stories. Often, these people want senior talent, but deserve mid-level at best. 

The person who wants to tailor an opportunity for you that fits like your favorite hoodie focuses on you as an individual and tries to match you to someone on their list of clients. They ask sharper questions. Often, the conversation contains a level of candidness that perks up my ears. They know their shit.

So many of the recruiters I spoke to in the last year would only focus on surface-level checkboxes, like salary expectation, title, remote or in-person, etc. I get that those are important, but for senior talent, for people like me, that is maybe 20% of the conversation. We know typical salary numbers. Our friends are making more. Junior hires are naive and can be won with salary and full-time remote. For top talent, the other 80% is leadership. It’s storytelling. It’s persuasion. It’s the people they meet. It’s how the talent assesses your culture after interviewing with a dozen people over the course of 3 to 6 months. 

Big famous successful companies most likely have top talent already. Those people know people. A recruiter can easily 10x their output by developing relationships with the existing notable talent and tap into their networks.

As I'm drafting this, I received a recruiter email from a company that I spoke with in the past. They're talking to me as if I didn't do 6 rounds of interviews last year. Did they forget that they handled the interview process like amateurs and ghosted me? Are there no notes? This templated, scattershot approach is the reason why companies will not get top talent. This disconnect between senior leaders at the company and recruiters is shockingly bad.

If recruiters can actually show up like a real fucking human being and speak candidly, thoughtfully, and be genuinely curious about the talent’s background and how their skills can contribute to an exciting mission where they can contribute and learn, you’re already ahead of the competition.

The real talk? Pay 20% above market rates and give people four-day workweeks and they'll probably join instantly. But no one wants to say that out loud.


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