How to prepare for Startup Interviews?

You are an experienced tech professional. On any given weekday, you open your LinkedIn or your personal mailbox, and there it is. "Hello from Google!", "Hiring Sr. SDEs at Amazon", "Meta would love to Talk", if you have a decent LinkedIn profile, you are bound to receive these messages from FAANG companies. There is plenty of material online about how to prepare for FAANG interviews. If you are an Engineer, you would practice LeetCode, study system design, prepare STAR format answers etc. If you are a Product person you would practice case studies, perhaps SQL etc.

But, let's say, you wake up to a different kind of email in your mailbox. "Come Grow with us at {Startup Name} YC W/S 20xx". Let's break it down. YC is Y Combinator, a startup incubator. Many of us have heard of the successful startups that graduated out of YC such as AirBnB (Winter 2009), Dropbox (Winter 2007), and Doordash (Summer 2013). Hurray! You have been approached by either an alumnus or the current cohort of the coveted Y Combinator.

Let's see the email contents then.

Hi {Your Name}!

I am Richard Hendricks and I am a co-founder here at Pied Piper, a leader in high-efficiency compression algorithms. My other co-founders are Guilfoyle, Dinesh, and Jared. Together, we have plenty of experience in Silicon Valley. We recently graduated from YC and have strong investor backing from Erlich Bachman.

We are looking at hiring our first Fullstack Engineer and talking to other YC startup founders, your name came up. Your background in Web Development at Hooley is of particular interest to us.

I know you may not be looking right now, but in case you are curious about Pied Piper, I am happy to chat over a coffee and tell you about the amazing things we are building here. Looking forward to it!

Thanks, Richard

Prima facie, this looks like a genuine approach from a well-heeled startup co-founder. Is it though? Let's break it down. Crunchbase would indicate some positives. They have raised 5.2 Million in funding. Pied Piper is indeed a startup in compression algorithms, not sure if they are a leader - that's a tall claim. However, they never were at Y Combinator, leave alone graduating. So that's a lie - yikes! And who is Erlich Bachman? Definitely not a well-known VC firm such as a16z, Khosla, Sequoia, or Battery Ventures - perhaps a celebrity angel investor?

Next comes the part about You. Their email appears as though you have been singled out and approached because some other founders said nice things about you. But, you are at a giant tech company Hooley. There are 10s of thousands of Web Developers at Hooley and 100s at least whose friends are YC Startup founders. If you are not one of them, this could very well be an email blast to all Web Developers at Hooley - or heck even to those at Google, Facebook, Amazon, and so on. So this email is not about you.

This particularly fishy email aside, you may be curious about what the startup interview process entails. How many rounds, how to prepare, and how to evaluate the eventual offer. These are all great questions to have. Before diving further, I recommend reading my first article on the series on Startups, "Should you join a Startup?". I wish I had an organized process initially when I started interviewing. I happened to interview at 30+ Silicon Valley startups in the last 6 years. Through that process, I have observed a few patterns. Hindsight is 20/20 and I want to share my clarified vision with you. Some spoilers, not all interview processes are alike. Also, there isn't always a rational reason behind conversion aka selection vs rejection. And, surprisingly or unsurprisingly depending on your preoccupation, they are relatively easier (Startup founders with a high bar, please keep the hate for later).

The flowchart below is a summary of the steps involved, we will go over each of them in detail in the following sections

1: The Background Check

Unfortunately, the email example above is the reality of some Startup approaches. Typically, a Background Check is one of the final steps in getting hired. But as a first step, you oughtta do one of your own verification on the prospective Startup.

What are your resources for the Background Check? Any upstanding Startup would have a Crunchbase profile. As an example, we are going to go through the profile of a recently funded startup Pomelo. I do not work there or in no way have been associated with Pomelo as of this writing. In fact, this is the first time I heard of them (from Crunchbase's latest funding list). This will be an unbiased review.

The website looks polished and beautifully designed. Outlines what the product is about in a clear way. See the Funding Amount of $75M, which sounds substantial, what's more impressive is its Seed round! But there is a catch, the $50M out of this funding is Debt Financing. I am not a Financial expert, but I would advise against going to Startups with significant Debt Financing. That said, it is common for Fintechs such as Pomelo to use Debt Financing as an "investment" to fund the product/service they offer to their customers - in this case, money transfers.

Next, I would check the profiles of the co-founders. The CEO had raised $382M in their previous venture "SingleStore" formerly MemSQL - a popular Cloud Database product, also a YC alumn. This is a stellar leader to work with! Although, for extra credit, you may want to check why they left SingleStore.

Next, check some material online about the company, specifically customer grievances, BBB reviews etc. Read about competing products in comparison reviews. This gives you a good idea about product market fit and the addressable market size.

Check out their engagement on social media. It is pertinent for a Startup's success that they interact with their customers. E.g. For SaaS product Startups, check interactions with developers on Reddit, Discord, and Twitter.

In the case of Stealth Startups, you will often want to talk to insiders and get some idea about their product market fit. My tip is to not entertain a Stealth unless you know someone who works there already and vouches for the Startup - you can take a chance though if the CEO is stellar, as we saw in Pomelo's case. Strong Leaders with a track record, secure funding from investors who believe in the leader and stay with the company.

2: The Hiring Manager Call

Try to get on a call with the Hiring Manager early on in the process. The Recruiter may lay down a process that involves a screening round, which is likely an exercise with an IC at the Startup. But you push for talking to Hiring Manager first, if that Hiring Manager is a C-level, so be it.

Definitely ask a lot of questions to the Hiring Manager. viz.

• How long have they been at the Startup?
• Where were they prior?
• How do they know the Co-founders?
• What is the team composition now?
• How do they plan to grow the team?
• What are the most pressing challenges?
• How long is the runway?
• What is their management style?

If the Hiring Manager has been at the Startup since its inception or a majority of its existence, it's a good sign. If they were at a large Tech company and they left that job to come here another positive sign. If they have worked with the co-founders before and wanted to continue working with them, big plus. If they want to grow the team but want to maintain a high bar and allow people to learn on the job, excellent. The team is non-existent, you will likely be the first hire for this team, not a bad thing - but do you have the Body of Work to take on something like that? The challenges should not be "funds", "resources" or "tech debt", but rather specific. e.g. We need to build a streaming service but we don't necessarily have WebRTC experience, so we like you. If the HM says, funding is not a problem, our co-founders have raised a substantial amount and we have a long runway - great. You have done the Background Check, so this is a cross-verification of those numbers. Their Management Style should be of Autonomy and Empowerment, rather than that of top-down enforcement.

3: The Interview Scheduling

Parts of this section will perhaps get esoteric for non-Engineers, but there are nuances that are common for all Startup interviews.

When the recruiter outlines the interview steps with you, note them down, in fact, ask them to email them as a bulleted list to you. Some startups, waver from their own process, trying to insert another "round". It is not worth your time to go through a screening, then a 5-hour onsite, only to be told, sorry you didn't get to talk to Jason from Customer Success, we need another 45-minute slot with you. Politely refuse and walk away. A startup that doesn't have its interview process together, doesn't have its s*it together.

A word of caution, for those really "early-stage" startups, where you meet the co-founders at a coffee shop (or at Burning Man). If they are hiring you as a co-founder, that's a separate level that I have not unlocked yet, so I can't talk about it. But only under those circumstances, you can really jive with the co-founders at the spiritual level and decide to join them. Otherwise, for all practical purposes, you are going to be an employee and employees get hired via interviews that happen in an office setting.

Startup founders who are going like "if you can't deal with the dynamic nature of our interviews, you probably can't deal with the uncertainty that startup work entails". Yea, perhaps I don't want to deal with "uncertainty" before I am offered. And hey, I am putting my career and life on the line here, so at least get your act together.

Once again, when scheduling interviews with Startups, ensure that you ask about each unit in detail. viz.

• Would I need to share my screen for this interview?
• Would I need to go over a product I built in my past job?
• Should I come prepared with a slide deck to go over my past project?
• Would I need specific tools installed on my laptop for this coding interview or is it just coderpad?

Ensure you have NDA before you share your past work and also before they talk about their work. Don't let them have you come to a coding interview with a laptop that they expected to have a menagerie of tools installed. Ask them to give you one or share the configuration, recommend them to give you a docker config file so that you can replicate their setup.

If you have the Body of Work and you are not trying to fake or oversell your abilities, the interviews themselves should be a breeze for you. Startup Interviews, focus on your ability to do the job you are getting hired for. They may still ask you the deeply conceptual, fundamental questions such as Top Sort or Red-black Tree traversal, but the overall emphasis will be on how you can solve real-world, project-sized problems.

4: The Take-Home Test

They often times give you a take-home assignment. This assignment needs to be submitted in a given time and based on which you would advance to the next stage or get rejected. Upon receiving the test, it can go two ways. Either you take one look, another deeper look, and realize this is not something you can do. Good job on that Startup's part to construct a test that filters out this quickly - efficient, not wasting either party's time. The other possibility is that you are confident that the test is in your wheelhouse and you get to solve it.

This is where things can get tricky. Sometimes, the assignment is perhaps too large that you can't complete it in 2-3 hours. You don't want to spend a day on an interview assignment. Keep in mind, that the test is perhaps calibrated to grade the performance for a 2-3 hour-long effort. A longer effort may produce a highly polished version, but they may very well reject you because although you showed great intent, you can not be graded as your output is too long to read. Clarify firsthand what are the specific outcomes expected out of the test and the expected time it should take.

A word about setup. If the assignment doesn't build with the instructions provided or if the unit tests they supplied are not running, point it out to the recruiter. This is why always attempt the test on a weekday afternoon rather than late evening or on weekend. You will get a response that can help you proceed. Don't jump to business logic development before first building and running unit tests.

5: The Interviewers

There are two personas of Startup interviewers. The ones that are looking for "culture fit", meaning can I work with this candidate, more like, can I hang with this candidate? The other category is, "skill fit", meaning can this candidate actually do this job and the many other jobs that will fall on their plate? So it's a bit like a video game, you don't know what kind of Boss is waiting for you at a given level.

Remember that you are not trying to impress the interviewers. You would need to convince them. Your Background Check on the Startup that you have performed prior to the interviews will enable you to ask insightful questions, gaining you points on the "culture fit" scale. Whereas, your Body of Work will get you through the "skill fit" check.

A word of caution about "obnoxious" or "intimidating" Startup interviewers. Sometimes someone being too friendly, is borderline uncomfortable in an interview setting. Unfortunately, unlike large tech, you would sometimes encounter unstructured, unfiltered Interviewers in the Startup world. There is no easy way to deal with them. But I would recommend reading this book by Zach Wong about Human Factors. It talks about personality types, how to identify them and how to interact with them in a professional setting in order to succeed in your project. In this case, your project is the Interview and you have encountered a difficult Interviewer, dealing with whom takes practice, but this book is a great guideline. The key is to keep the focus on the Interview and keep the conversation moving. And of course, if it gets too uncomfortable, walk out. You don't want a co-worker who pushes your buttons to a level that you can't last a 45-minute interview with them, this startup is thus rejected, by you!

6: Evaluating the Offer

You have conquered the Interviews, you have made a name for yourself in that Startup already because of your fantastic performance on the Take-home Test, heck even the CEO is eager to meet you. So they generate an offer. I talked about Startup Offers my previous article in the series "Should you join a Startup?". TLDR: Do Not Take a PayCut! This is the point in time where you should request for a demo of the product, especially if it's already not live. Remember that you are going to be an investor in this Startup, so you need to vet it like one.

If it all looks good, the numbers that is, if the people seemed reasonable, the leaders are influential and can be counted on, heck yea. May be you want to join this Startup. It's not about the idea or what you will work on, I mean it is at a cerebral level, but at the surface level, you need to watch your six - and that's your career and your life. So choose wisely my friend. Until then, Leet Hard! I am kidding, build your Body of Work, share your projects.