How to Ask the Best Questions at a Startup Interview.

Jared Wolff · 2017.3.27 · 12 Minute Read · engineering

Interviewing at a hardware startup, especially early stage, is a different experience. Founders often have no protocol or rubric for bringing on talent. They will often make a decision by a combination of how they feel about you as a candidate but also your past experience. This is a bit liberating because you don’t necessarily have to be the best technically as long as you can show that you’re providing extreme value.

So, what is extreme value? What can you provide that no one else can? Seth Godin’s Linchpin goes into detail about this process. The biggest takeaway from that book is that you should take a step back and look at yourself as a candidate for a job and also a functional piece of society. What are the things you are good at that no one else can come close? Or what things can you be the best at that, when it came to a deliberation between candidates puts you on top?

For me, when interviewing at the first startup I ended up working at, it was a combination of the niche/self taught skills of circuit design and the skills I had learned on the job during my internships at Apple and Cisco. The activities I did on the side for fun were often the biggest reasons why I was hired where I was. As an engineering candidate, big companies like Apple and startup companies alike will look at what your passionate about or where you will add exponential value before hiring you. All the extra formalities like dressing nice etc. are just icing on the cake.

I’ll reiterate the above because it’s important. If you’re just coming out of school and you’re looking for an engineering job in startups or in technology people will look at your side projects. If you have none, your peers with side projects have proof that they are passionate will completely outshine you.

Sometimes interviews don’t go your way.

After college I was really hell-bent on getting into Apple. I had an in at the time as I already knew many people on the hardware team but after a series of failed interviews and filled positions, I knew that those dreams would be squandered.

I failed mostly because I was horrible at technical interviews. I remember sitting with one of the senior members of the iPhone team and I confused clock jitter with clock skew. Needless to say, that interview didn’t last much longer after that blunder.

For some reason though, my calling to California was still very strong. I started branching out my search into very niche job postings on websites I really admired. These were the days before Indeed or Angelist existed or even what LinkedIn is what it is today. While I started poking around these specialized websites that may be looking for hardware talent, I happened to come across Adafruit’s job posting (Currently down for some reason as of this writing) area where there was a posting for now my first official post-college startup, Sifteo.

There are, of course, other reasons why someone may want to hire you. I, at the time, had very flashy resume with some of the biggest companies on it. I can attribute getting the first interview to the fact that I had worked at Apple. Without that on my resume I doubt I would have gotten a call back as fast as I did. Jeevan, the CEO of the Sifteo, reached out to me about 5 minutes after sending my initial email. I was completely flabbergasted and humbled to say the least!

Do the opposite and interview the interviewer

As I alluded earlier, interviewing at a startup can be sometimes a special experience. It’s usually very informal and generally no one knows what they are doing unless they have a track record of success or running companies in the past.

In light of this dangerous ignorance, I’m going to make a suggestion that may not make sense or that you may be afraid to do: interview the interviewer.

What exactly does this mean? As I mentioned, at startups, you may be potentially be working with people who don’t have the work experience to lead people or just flat don’t have any work experience at all.

Before getting started though, you should be aware of some of the legal formalities that you may need to go through before continuing. Typically more informed startups will require you to sign a non-disclosure agreement. What does this mean? This means that you’re signing a document that states you will not disclose any information that has been shared with you regarding the business and technologies of the startup you’re interviewing for. This is a great way to for the company to protect themselves but also your ticket to ask about more pertinent and not publicly known aspects of the company.

Here are a few bullet points about what you should be checking during an interview. You can inject most of these questions at any point in time. Remember these questions are used to form an overall impression of the company, where they are and where they are going and how you fit in the picture.

You’re checking for viability.


Guess what, startups may sound magical but the proof is in the pudding. What are the technologies and methodologies that are going into that startup? Are they things that exist today? I would consider it a red-flag that no one at the company has a grasp on how the technology works or even if it is scalable.

Some simple questions to ask to poke at this issue include:

How does this technology work?

If they can’t answer it, find someone in the company that can. If that person can’t. You’re in for a world of hurt if you decide to move forward.

Caveat, if you are the person that needs to know most about this technology, and you feel comfortable with the challenge, disregard this red flag. The thing you should be worried about is whether or not the founding team will listen to you when it maters the most.

What is your plan on scaling this technology?

If they don’t understand the nuances of tolerances, calibration, and testing in the manufacturing processes. Dig into what they know about what it takes to bring a product to market.

There is a caveat here: Just like the earlier question, if you are interviewing for a very early position, and the interviewer listens to what you have to say about implementing or scaling the related technology you’re in a good place. Founders will never know 100% about everything, that’s why they’re hiring you in the first place. THe most important thing is that they listen and try to understand your expertise in your field of work.

Ask to see the proof of concept.

The interviewer should be able to tell you about the proof of concept, how it works and where it falls short of what the goals are with the final product. No engineering project is perfect and those imperfections have to be known very early on to deliver a fully polished production product.

You’re checking for how well the CEO knows the company finances

The finances of an early stage company are the lifeblood that gives you a reason to be there. Without money, generally, people have less of a reason to stick around and do the work. Here are some questions related to finances that you definitely should ask during your interview:

Burn Rate

What is your burn rate?

The burn rate of a startup is the amount of cash that is being spent per-month. If the CEO or money person cannot answer this question this is a huge red flag. There is an inherent risk of joining a startup company because there is a limited amount of money. It’s extremely important that the CEO is making choices to ensure that they’re successful with the cash they have.

How much money do you have in the bank?

Similarly to the burn rate question, this question directly relates to how much cash is in the bank. Interviewers that dodge this question either don’t know or they’re hiding something. Be wary of a CEO who won’t share this information with you. Remember, despite what other people may tell you, your livelihood depends on working and getting compensated for it.

Remember, there are always risks with joining startups. Not every startup will be a pretty picture and they often almost fail before becoming big. These questions should raise your awareness about what the risk/reward scenario is should you join this company.

How many people do you plan on hiring?


Can open a can of worms and really determine where the CEO’s head is at. Are they focusing on the small short term wins or are they talking about how the company will be 80 people in one year? If they’re doing the later, it’s most likely that they’re turning the crank on the hype machine a bit too much. Every CEO will hype up their company, (who wouldn’t!) but they need to be grounded in reality.

In either case, do they have the experience to lead this amount of people? Ask them about their track record and if they have managed teams in the past. Alternatively, a good CEO will hire people who are great at these things. If you can, interview someone one tier lower on the org chart to gain insight about this.

What are your immediate goals financially?

Similarly to the question related to knowing the burn rate, what does the CEO foresee as the financial future of the company? Will they run off of venture money (debt) for several years? Do they aim to be cashflow positive by the end of the year? There are different situations that may require different strategies. For instance, startups may want to push into the market and grab a big share before making any money off the market whereas some companies may want to make money as soon as possible. This depends on the risk tolerance of the CEO and what the investors are looking to do.

Snapchat is a good example of a product that didn’t focus on making any money (until later on with paid for customized filters, etc.). To this day I don’t think they are focusing on it. Time will tell if these ::quote:: long game ::endquote:: strategies really work. In my opinion, they’re just a fuzzy way to puff up companies and sell them to bigger companies or the public for top dollar. Remember, founders often have shares of stock that cost nothing or extremely low so they want a payday just as much as the next guy. Sometimes though, the chase for greed backfires in the worst way. Just look at the news about Uber these days, not so good is it?

Know your risks but don’t be picky


One of the most amazing things that a startup offers is that fact that you are the person who is solely responsible to produce the work that is required of you. If you don’t get it done, tough nuts get it done. No one else around you will magically take these tasks off your plate and complete them for you.

Additionally, you get the opportunity to take on as much responsibility or as little as you want. This is the place where you are able to learn the most about the operation of a company as a whole and gain insight to how marketing, software, hardware, design all come together to make a product experience. You can’t get that working at [Insert Big Company Name Here].

Even if you get perfect answers to all the questions above, sometimes things will go wrong. Startups fail all the time and sometimes for reasons out of anyone’s control. Remember this before going to sign your paperwork. That’s why I advocate for anyone who works in a startup to have 6-8 months of expenses save in an account they don’t touch should things go awry.

Get in the door

My final point related to startup interviews is that they won’t always work 100% the way you think. Companies, because they are restricted by the cash they have, will low ball your salary and they will attempt to hire you on as a contractor for a certain amount of time. I have personally advocated hiring new folks as contractors before hiring them on full time and have been a contractor myself. It’s mutually beneficial because you get the chance to work at the company and meet the people but also get paid something why you figure out whether you can all co-exist in the same room together.

A typical contracting period can last anywhere from 3-6 months. I highly recommend, especially if you need health insurance, to aim for the 3 month point. Three months is a good number because by then you should be fully up and running, understand the engineering challenged and know everyone on your team well.

So, things may not seem to rosey or even attractive at first glance. Remeber the opportunity is there but there are alway opportunities down the road. Take a step back to determine what you really want as a professional. Are you willing to get paid less for maybe a short amount of time? Are you willing to take a chance on some scrappy startup with five employees?

Red pill or the Blue Pill I leave it up to you…


Startups can be an interesting experience. You will likely not regret working for one but expect to work hard and get shit done. It will become very apparent when you aren’t getting your work done because there is no one else around to do it for you.

Be wary of the startup hype machine and ask questions to make sure that the company is on track. Remember you want the best experience working there as your coworkers and leaders do. If you can already foresee it to be a miserable experience, don’t bother joining and move on to the next opportunity. Your future self will thank you later.

Photos are Creative Commons. The originals can be found here, here, here, aaand here.

Last Modified: 2020.3.7

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