As you’ve probably guessed from the title, the past two months have been a whirlwind of interviews — back-to-back meetings with recruiters, coding challenges, and the constant weight of anticipation. Before this, I’d only gone through 4 interviews in my life, and one of those was for a waiter position. Interviewing is never easy, but I’d been fortunate to face rejection only once — and that one still haunts me.

It was my first job rejection, and it stung. I thought I’d nailed it, even telling my wife, who was my girlfriend at the time, that we should start looking for housing near the office. Then, the call came — and it knocked the wind out of me.

“Hey Chesong, how are you? The team loved meeting you, but unfortunately, at this moment, they’ve decided not to move forward.”

I tried to tell myself it was okay, but that night, sleep wouldn’t come. No matter how hard I tried to push it away, my mind kept circling back to the same question: What did I do wrong? Desperate for closure, I sent a thank-you email to the hiring manager, clinging to the absurd hope that they’d reply with, “Actually, we were wrong — we’d love to hire you.”

That email never came. But that’s a story for another day.

Ironically, I’ve given hundreds of interviews throughout my career. I always knew the process could be stressful for candidates, but looking back, I realize I never fully grasped the gravity of it—until now. It’s like being told how much it hurts to step on glass. You can imagine the pain, but until it happens to you, no description truly prepares you.

This time around, I found myself on the other side of the fence. I’d heard from colleagues and seen headlines about how tough the job market was, but how hard could it really be? I wasn’t fresh out of college; I had experience, battle scars, and a track record to prove my value from day one. I’d co-founded a company that was acquired, started a new division at a multi-billion dollar company, and held key roles in large tech firms. Many people would kill to have those credentials on their resume.

I initially applied to five well-known companies, expecting a recruiter’s call in a matter of weeks. Instead, I was met with silence. I panicked. Pre-pandemic, I was confident the recruiters would have reached out to me first, but this time felt different. So I did what many of us do in uncertain times—I created a spreadsheet. Not just to track the companies I applied to, but to document every step of the process, including my reflections and feedback.

Now, I’m excited to share what I’ve learned from this journey—insights I didn’t expect to gain and areas where I discovered I still need to grow.

Here’s the breakdown:

  • I applied to 80 companies: 33 small, 19 medium, and 28 large. I categorized them by estimated headcount—though it was more art than science.
  • Out of those 80, I never heard back from 43 companies. Not even a rejection email.
  • Ten companies sent rejection emails, stating that my resume wasn’t a good fit, despite my belief that I had strong alignment with the roles.
  • I went through 27 phone screens with recruiters or hiring managers to assess fit. Of those, 5 ended with no further progress—sometimes because the ’nice-to-haves’ in the job description were actually requirements, or the position was filled or closed.
  • For the remaining 22 companies, I had technical coding rounds, and I performed poorly in 7.
  • I made it to 11 final rounds—the last step before an offer could be made. I canceled 4 final interviews due to existing offers I knew the company couldn’t match or because I saw better opportunities elsewhere.
  • In the end, I received 7 offers—hovering around a 70% success rate, which I don’t think is terrible.

Reflecting on the process, I noticed an interesting pattern: the companies I didn’t receive offers from were the ones where I had final interviews earlier in my job search. As I interviewed more, my answers became sharper, my storytelling more succinct, and I developed a better sense of what strong answers looked like. My background gave me countless examples of facing challenges, mentoring colleagues, and navigating tight deadlines, but I quickly learned which experiences resonated more with interviewers.

By my fifth interview, I began to recognize patterns in the questions and frankly, many of them started to feel repetitive. This familiarity helped me improve as I moved from one company to the next.

But the point of this post isn’t to celebrate my successes. It’s to share the lessons I’ve learned through this process and how I’ve grown as both an interviewer and an interviewee, and how this experience has shaped the way I approach the entire hiring process.

Here are my lessons:

Interviewee: Lessons Learned

1. Prioritize companies you’re okay being rejected from

Practice makes perfect, right? When I first started applying, I thought, why not shoot for the stars right away? But after a few early stumbles, I realized start with companies with lower risks. It’s like going to the gym. You don’t lift the heaviest weights on day one; you work your way up. With each interview, I got better at navigating tough questions, learned where I needed improvement, and gained confidence. Sure, there are paid services that offer mock interviews, but why pay when you can learn firsthand or ask a colleague for a favor?

2. Research the company (really, do it)

I know, it sounds obvious, but it didn’t hit me until later that each company has its own set of challenges and their interview questions will likely reflect those. For example, I applied to a travel company, and their system design questions were focused on that industry. So yes, they might throw in a “Design Twitter” curveball, but they’re often testing how you think about their problems. The more you know about what the company does and cares about, the better you can tailor your answers. You wouldn’t pitch a spaceship to a food company, right?

3. You can do everything right and still be rejected

This one hurts. It’s like preparing for a big race, running your best time, and then getting disqualified because the wind was too strong. I had interviews where I felt like I nailed it only to hear, “You lack UI experience” or “We’re moving in another direction.” It’s frustrating, but sometimes rejection has nothing to do with your abilities. Maybe the interviewer was having an off day, or maybe they felt threatened by your expertise. Either way, remember that once you’ve done your best, it’s out of your hands.

Interviewer: How I Will Be Better

1. Genuinely want candidates to succeed

Looking back, I didn’t realize how much it matters. As an interviewer, I was focused on checking boxes: Can they solve the problem? Do they know the trade-offs? But I wasn’t thinking about the pressure the candidate might be under. Now that I’ve been on the other side, I realize how much it means when the interviewer is rooting for you. Even saying something like, “I’m here to help if you get stuck,” can ease the nerves. I wish I had been more encouraging. Interviews are stressful enough without feeling like you’re on trial.

2. Be interested in the interviewee

There were a few times I felt like the interviewer was mentally checked out—like when one interviewer actually stepped away to pack for vacation mid-conversation! It made me think: as an interviewer, was I always fully engaged? If someone is giving me their time, the least I can do is show up 100% and really listen. A good interview is a two-way street; it’s not just about grilling the candidate.

3. Don’t ask questions that won’t get you the signal you need

This one is key. I was once asked to build a UI in Storyboard when all my recent experience was with programmatic views. The irony? The company didn’t even use Storyboard! So why test me on it? I remember asking for help, and the interviewer responded with, “I can’t help you; it’s been years since I used Storyboard.” That left me baffled. If the tool doesn’t reflect how the team works, don’t make it part of the test. Instead, focus on what truly matters.

Takeaways

1. Small companies can move as fast—or slow—as large ones

There’s this myth that small startups move faster than big companies, but I didn’t see a clear pattern. Some small companies dragged their feet, while others moved at lightning speed. The size of the company doesn’t always correlate with the speed of the interview process.

2. Big companies can spoil you with tools and infrastructure

At my last big tech job, we had amazing internal tools. I never had to think about encoding or decoding JSON because our platform team had built tools to handle that automatically. Then, in interviews with smaller companies, I was asked to write that code myself. It’s a reminder that while big companies can make you feel like a rockstar, they can also shield you from some of the day-to-day challenges that other companies face.

3. Veteran interviewers make for a smoother process

I quickly noticed a difference when interviewing with people who had been at the company for years. They were calmer, more methodical, and had seen every permutation of how a candidate might answer a question. In contrast, newer interviewers were sometimes unsure, or even gave confusing feedback that threw me off. It’s clear that experience matters on both sides of the interview table.

4. Be prepared for specific library or tool questions

One time, I was asked to build an app that plays a video, but I completely blanked on the library name. (Spoiler: It’s AVPlayer.) I should have expected it, but in the moment, my brain froze. Lesson learned: be ready for specific tool or library related questions, especially if the company’s work focuses on a niche area.

5. You’ll never be 100% prepared—and that’s okay

No one is perfect, and that includes me. One thing I’ve learned from going through interviews is that there’s always more to learn. Whether it’s sharpening coding skills or revisiting techniques you haven’t used in a while, the key is to keep learning. I’ve worked in environments with highly developed tools that automated many tasks, and I found myself getting rusty in areas like building APIs from scratch. But recognizing those gaps is the first step in improving. Remember, it’s a marathon, not a sprint—don’t try to cram everything into a single month.

Regardless of the outcome of your interviews, treat it as a valuable experience to learn and grow from.