I failed 3 job applications; Here's what I learned

Tips and mistakes to avoid when applying software engineering jobs at top tech

It is the layoff season and some of us may need to dust off our interview skills. I've carried hundreds of interviews in the past few years to hire the best talent but I've also spent a significant time on the other side of the interview table as a candidate.

Today after 23 years, I have a relatively high level leadership position but it wasn’t always like this. As an introvert in a world that’s optimized for extroverts I had a long and painful learning curve.

Like most people I’ve failed more interviews than I made. Sometimes I walked out, most of the time, I was rejected. In this post, I will go through my top 3 favorite interview lessons hoping to shorten the learning curve for some of you who may be in the job market.

Disclaimer: I linked the name of the people that I had a great experience with (for recognition and appreciation). I also do acknowledge the risk of oversharing and accept the consequences because I believe as an industry we’re better off having more transparency. If you want to share your experience without being personally identifiable, I highly recommend Glassdoor and Blind. Those platforms however have rules against how much information you can share and how long you can write. I wanted to pack these 3 together because there’s a theme here.

Datadog

Let’s get this out of the way: I ❤️ Datadog!

I believe one can tell a lot about the people behind a product just by using it. As we’ll see, Datadog didn’t disappoint.

Back in 2019 I’ve been their user for 3 years. I had great interactions with their sales engineer Misiu and sales executive Philip. As an engineer obsessed with performance, great UX and fantastic documentation I was inspired by their work and could totally see myself working at Datadog. Datadog leads the pack and won many awards!

OK, enough about Datadog. It’s starting to sound like a sponsored post 😄

If I recall correctly, I applied for a senior Node.js position to work on their OpenTelemetry and dd-trace open-source project. My team heavily depended on dd-trace. I had investigated their code extensively due to some bugs and had some ideas for improvement.

This was around the time I had learned Golang enough to feel confident using it as the weapon of choice, but my background was 8 years with JavaScript. Datadog agent was in Golang, so I saw the Node.js job as a chance to get my foot in the door and gradually shift to work on the agent.

My first point of contact was with the sales executive who referred me to their talent acquisition. The recruitment team were friendly, quick and the process was one of the best I had seen. In less than 1 week from the application, I went through the phone screening and tech screening.

Then I met my to-be team lead for a technical interview. Nice young engineer based in New York. He talked about the challenges they are facing and all of it sounded good. Their dd-trace relied on monkey-patching the Node.js API so I talked a bit about my ideas for improvement. Then he asked my opinion about working with the Node.js core team to introduce performance hooks that would allow APM (application performance monitoring) and enable OpenTelemetry integration in ES6.

I’m paraphrasing here because I don’t remember the details from 3 years ago. At the time I considered myself well-versed in JavaScript and had read both the good parts and bad parts.

The infamous JavaScript books

So, I knew it well, but not well enough for the bar they were aiming for. They needed a JavaScript master AND C++ developer who could contribute to Node.js core on DataDog’s behalf. They needed a specialist. Alas, that wasn’t me. I had worked with frontend, backend, serverless, mobile, even graphic design and UX. But not exclusively with Node.js core. I knew how to make a product e2e but my understanding of the event loop wasn’t beyond what you could Google and read on blogs.

I was rejected for that position but still got kept in the system. The feedback was that they liked my attitude, but my skill level didn’t match expectations. When I’m hiring, I go for “Hire for Attitude, Train for Skills”.

I got to meet Alison who scheduled me with Marcus (this is not your average Marcus, he’s one of the founders of the company that developed the JRockit). He too knew a lot about performance and hinted on a new project (at the time) that would dramatically improve performance monitoring at the JVM level.

Unfortunately, they wanted a JVM pro (or someone who is at least interested to become one) but I kissed Java goodbye when Oracle bought Sun and had no intention to go back. I was deemed unfit for that position too.

I was constantly amazed by the amount of brainpower and talent that DataDog has amassed and my respect for their brand grew even more. This reveals that their success is less of an accident and more of a deliberate plan backed by hard work.

Key takeaways

• I got to meet people behind my favorite product and had many inspiring conversation

• I learned that my talent and skill profile is generalist, and I should not waste time on specialist positions

• Datadog job site

• Read more Datadog interview on Glassdoor

Spotify

OK, this is gonna look like it's going sideways but bear with me. 👌

It is hard to work in the Stockholm software market without ever bumping into someone from Spotify. You may bump into people from many famous brands without ever knowing but Spotify is different. With a strong employee branding, proud identity, and loudspeakers on full volume, you're sure to know if you had the pleasure to meet someone from Spotify.

I had my share of experience until I got a chance to work closely with Patrick who had been an EM and PM at Spotify.  Patrick’s narrative was more balanced. We used to talk a lot about the Spotify culture, how it evolved over time and lessons learned. Later I briefly got a manager who was an agile coach at Spotify and tried to rub some of that goodness on our team before throwing the towel.

This was when the Spotify model was hot. So, cargo culturs from across the planet were adopting it as the ultimate solution to all their dysfunctions. Jeremiah did a nice piece here if you’re interested. Anytime someone says, “the Spotify model” I can’t help but to think of this Karl Marx quote: "If anything is certain, it is that I myself am not a Marxist” (context).

Speaking of the father of communism, here’s the Spotify manifesto which is probably one reason behind the strong employer branding.

Note: I noticed the effect of employer branding is stronger on those who have just this one big brand in their CV, or their majority of their career has been at one company. Those who have experienced a few big brands are much more open-minded, modest and down to earth.

So, I had an idea what Spotify feels like from the inside and more importantly why I'd never work there.

Never say never! 😄

Fast forward to 2019 and an ex-colleague of mine who had recently joined Spotify invited me for a tour of their new office at central Stockholm. I worked close by so I figured it wouldn't hurt. I was curious.

I'm glad I went. It was jaw dropping. Every detail was stylish, thought through and to be brutally honest a bit like a golden cage. You can take a virtual tour here. Free food, regular hackathons, games, I don't recall everything, but one detail stuck with me: a VR room! Yes, a room fully dedicated to virtual reality… at a music streaming company! It was every bit obvious that they had money to burn. But how? Spotify hadn't been profitable for a long time. Artists have been complaining about how little they get paid. Some say, “all PR is good PR”. I don’t agree. To me it didn’t add up and wasn’t ethical. A VR room?

I don’t know if it was the magesty of their office or the free food my ex-colleague offered on behalf of Spotify; I ended up talking to his manager because they needed someone with my profile. Nice and friendly lady but I managed to make it awkward. I suck at hiding my thoughts (guess it's obvious to my readers 😅). The best strategy I came up with is to be me and shine my silliness in full glory!

Still touched by the VR room, I asked her what she thought about the artists who are not paid fairly. I don't remember her answer. Some corporate politically correct mumbo jumbos. The semi-interview ended with me saying that I'm interested in a staff engineer position. At the time I was working at Staff Engineer capacity without officially having the title. A promo was on the way, but I figured if I’m going to join Spotify, it has to be with a title bump or else I have to start from scratch and build a case, which could easily take a couple of years.

A few days later their TA (talent acquisition) set up a call. She said they like my profile but for a senior engineer position, not staff engineer. So, I politely declined.

I emailed my ex-colleague to see what's going on and whether he can get me some feedback from his manager who met me at their office. She wrote that she assessed that I don't “talk like their staff engineers”. I understand. One doesn’t question the whole business model of the company on the first interaction! 🤐

Key takeaways

• If you go in with negative prejudice and your heart is not with the company, it'll leak out during the interview. Don’t bother applying to a company you don’t resonate with. (But it’s totally fine for interview practice)

• Practice, practice, practice. Having a friend interview, you are one thing, going to an actual interview is another. There was one year I did 20 rounds of interviews and in total I think I’ve been at least to 60-80.

• Don’t miss an opportunity to be promoted while applying. This time it didn’t work, but at my current job I got promoted from Staff to Sr Staff when changing jobs.

• Don't take rejection poorly, especially if you're in a small market where people are connected. Reflect on what went wrong and move on.

• Spotify job site

• Read more Spotify interviews on Glassdoor

Shopify

This story started a decade ago. I was at the TicTail office back when they were a tiny Swedish startup. I won a silly competition called “CSS in the dark'' (basically you’d try to style a few divs to match a JPEG template without seeing the monitor).

After the event, I ended up talking to their founder and CTO who was hiring. I wasn’t interested. My problem? The office was too far. Now before you judge me, I have to say something about Stockholm's geography. Stockholm is composed of 14 islands. The most pragmatic way to connect these with public transportation is a star topology centered at TCentralen. I lived at the polar opposite side of town, which would translate to 2 hours commute per day, unpaid! Plus, I had a history of missing the change stations, so it'd occasionally add up to 45 minutes to that time. So, I politely declined.

Fast forward to 2020 and TicTail was part of the Canadian giant, Shopify, led by Tobias Lütkte, the second richest man in Canada (2 years later, 11th, after a layoff).

I was gearing up to leave Sweden. After elaborate research we decided on Toronto, Canada. The full reasoning can wait for another post but what I did was to reach out to my contacts on LinkedIn who were based in Toronto. Remember that CTO from a decade ago? He kindly replied and put me through the process for Shop Pay. Having worked at Klarna and living cashless for quite some time, I knew a thing or two about the domain and user experience.

My recruiter wasn’t the friendliest. She tried her best, but you could say she’s not passionate about the job (or me, it could be either or 🤣). It doesn’t matter but if you’re an employer reading this, please get your first impression right.

Every company has their own process. What was new to me at Shopify was the “life story” part. It’s documented here under “The process”. I was basically sitting for 1 hour talking to her about my life journey while she was taking notes. It was a bit unusual to say the least. I don’t know how my non-professional life would be relevant to the job, but hey, it was a data point they were gathering.

They also did an online reference check which is way deprecated in any company worth their salt (basically they send an email to someone you introduce to fill out a form about you). I called a friend and we got that sorted.

Then it came to salary negotiations and although my salary would almost double compared to Sweden, my life standard wouldn’t improve, all expenses considered.

Their mobility package was nice: they would pay a moving company to pack my sh*t and deliver it at a sotrage in Toronto. Meanwhile a legal team would fix the visa and residence for me, and my family and the company would pay for the family trip to Canada. 🍁And they’d provide 2 months free accomodation till I find a place.

The catch? If I get fired or quit during the first year of moving to Canada, I would have to pay back all the expenses for the nice mobility package. As it turns out Shopify did do a layoff later, so I consider it an a** saved!

I didn’t have to wait for all of that though. I could start working from Shopify’s Swedish office right off the bat till the visa is sorted out. In Sweden, I’d be getting paid a Swedish salary which was computed from my Canadian salary.

Those who’ve read my salary negotiation strategy know that I don’t put all eggs in one basket though. In parallel, I started the process with Discovery networks (through a connection) as a backup plan. Unlike the Shopify recruiter, Ana from Discovery was super nice and over the course of the interview I really felt guilty for not being too serious. Discovery had a great recruitment team, and they really get the first impression right.

As it turns out, I joined Discovery with a better pay than what Shopify would offer in Sweden. Part of it was my gut feeling, part of it was practical reasons that has nothing to do with Shopify.

This one wasn’t technically a rejection but goes to prove that building options puts you in power to choose your destiny.

Key takeaways

• Join meetups and silly competitions. Network with people. You never know what doors they can open.

• Reach out to your network for advice and help

• Read through the terms of your contract. In this case, a friend with more experience told me it’s rather unusual for the employee to have to compensate the mobility package if they get fired/laid off.

• Never apply for 1 job. More about that on my salary negotiation strategy

• If you have the luxury of options, don’t ignore the gut feeling

• Shopify jobs

• Read more Shopify interviews on Glassdoor

Pro-tips

The job market is tough. Gergely did a good piece recently (🔒paywalled). TLDR; it’s the employers’ market and the bar is higher now. With the rapid advancements of AI, it is just the beginning for all practical purposes.

I sincerely wish this post will help you be more prepared, but I want to close with a few high-level takeaways:

• Our life on this planet is limited. Pandemic, war, climate, AI, … it feels like the threats never end but remember that every crisis is also an opportunity. Assess, Adapt, Act.

• If you haven’t, get a copy of Who Moved My Cheese (or watch this crappy animation on YouTube). That book is more relevant now than ever.

• There’s no failure. There are just lessons to learn. There are only two ways to learn: 1. make your own mistakes, 2. learn from the mistakes of others.

• Never take anything for granted. You may have a job today, but you never know when you’ll be back on the market again. Build options already. It is 10x easier to find a job while you’re already employed. My experience complies. Don’t waste that multiplier.

• For all 4 companies mentioned in this post, networking opened a door. I can’t stress this enough: if you want to guarantee your career, make sure to build connections and keep those links alive. You never know where someone ends up and what doors they can open for you. Also, if someone reaches out for help, do your best to open a door for them. It’s tough times, we could all use a bit of help.

• Note the “declined politely” part. You don’t want to burn any bridges even if you have no intention of working for that company again. The reason is because people move across the industry, and you never know where they’ll be when you’re in the job market again. I usually elaborate with honest reflection because a particular position is not a good fit at the time. More about feedback in an upcoming article.

• Instead of wasting time mass-applying for jobs, use your time to learn what’s hot in the market and apply deliberately where you want to work. Use Glassdoor, Blind and a few reddit groups like r/careeradvice and LinkedIn job ads to learn about the job market and companies. Choose with open eyes. Read the career site of the company. Many good companies (all 3 in this list) have enough detail about how their process looks like.

• When you get a job, be kind to candidates. Everyone applies with a lot of hopes and dreams. If you reject them, give them some feedback (in a future post I’ll discuss how to give feedback on the spot).

• Every time you’re rejected by something good, you’re actually being directed to something better. If you go in with this attitude, it’ll help to see rejection as a step toward success. Feedback and reflection are critical for it to work.

• If a company is interesting, apply even if it’s not 100% matching your criteria. The least that can happen is to practice interview in a real setup. The best thing that can happen is that you learn something new, and they actually are a match. You never know till you try, and the more you try the more you learn.

• If you screw up an interview, most companies don’t want to see you for a grace period (usually 6-12 months). However, they are obliged to remove all your personally identifiable information per your request. I live in the EU so after a failure, I request data erasure according to my GDPR rights, but there are similar rules across the world. Read about your right to be forgotten (or forgiven!).

• Interview is a sales and negotiation situation. There are many books in this domain that can help to both present yourself better but also get your worth.

• Companies are not charities. They have every intention to maximize profit by paying you less than the value you create. So do your homework and go prepared.

If you don’t want to subscribe, I’d still love to hear your feedback. Here’s the comments on HackerNews and here’s on LinkedIn. I liked DataDog’s reply there.