Interviewing at a startup

2014-06-18 by Jason Freedman
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I was talking with a friend of mine who is making the jump from an advertising agency at a big company to marketing role at a startup.  She had loved the work she was doing, but she hated being at a big company.  And thus, the jump to a startup role.

Within a few weeks, she had one company that she really liked and that seemed to like her back.

I asked her how she was doing in the interview process and she said, “I’m actually still trying to get an interview.”

“That’s weird.” I told her.  “I thought you had already met with them a few times.”

“Well, I grabbed coffee with the founder, and I had dinner with the team last night, and then we went to a bar together.”

I chuckled.  She was clearly confused with the whole matter.  I told her, “Look, you just made it to the third round”



Another quick story before I really dive into this blog post.  We had a gentleman over to interview for one of our account executive positions at 42Floors.  He had strong experience leasing SF office space:  great resume, great cover letter, did well in our initial phone screen.

When he walked in the door, we could hear the clacking of his shoes on our hardwood floor.  He was dressed impeccably in a suit that probably cost more than my first car and was carrying one of those leathery-thingys that seemed to exist only for the purpose of being carried during interviews.

I stole a glance to a few of the people from my team who had looked up when he walked in.  I could sense the disappointment.

We’re all happily wearing blue jeans and sneakers.   It’s not that we’re so petty or strict about the dress code that we are going to disqualify him for not following an unwritten rule, but we know empirically that people who come in dressed in suits rarely work out well for our team.

He was failing the go-out-for-a-beer test and he didn’t even know it.




So what’s going on here?  I don’t think this is just a case of startups having peculiar dress needs.  I also should say, I don’t think that our startup is unique in its preferences.  Most startups take the building of their culture very seriously, especially when the culture is still new and quite fragile.

The suit on this guy was a reminder that he would be importing someone else’s culture into our’s.  It’s not like this guy was born with a suit on.  He had learned through his “big company” experience that suits, nice watches and those leathery-thingys were an important part of presenting himself.

At one point during his interview with me, I told him he could take off his tie and jacket and loosen up a little bit, and he acknowledged that he felt a little out of place but said that, “you can never overdress for an interview.”

Well, dude, no, actually you can overdress for an interview and you just did.  Of course I didn’t say it.  And we didn’t decline him based on what he decided to wear.  We declined on him because he wasn’t a fit for us in many other ways.  The suit was just the early give away.




If you’re jumping into a new job, regardless of whether it’s a startup or a big company role, it’s your responsibility to learn their cultural norms.  The reason everyone knows to wear suits to interviews at big companies is because you practiced it during your college interviews and had it reinforced every time you walked into a company where you saw everyone else wearing suits.

So this little post is a just a little heads up that when you see a startup filled with people in jeans and t-shirts, it’s not only okay for you to wear jeans and a t-shirt, it’s probably much, much better.

Here are a few other tips to help you get off to the right start.



Tips for interviewing at a startup


Dress appropriately

Don’t overdress, don’t underdress.  And it’s totally fine to ask someone before you come into the office what appropriate dress means.

Keep your schedule flexible

We love to bring people in for short interviews. But if you WOW us, we’d love for you to stay.  Sometimes we’ll have a thirty minute interview extend the rest of the day and into the evening.  We don’t mandate it, and we don’t ding you if you have other plans.  But when it works out organically, it’s a nice thing for everyone and it moves the process along much faster.

Use the product and use the competitor’s products

In a startup everyone is obsessed with the user experience.  So you should definitely come in knowing the ins and outs of how everything works, if for no other reason that it will stimulate a bunch of questions you might have on why certain decisions were made as well as lead you to that golden interview moment when you offer up a good idea that resonates.  For bonus points, you should become a super user of all the competitors.

Read the startup’s blog

That’s where you get to see how the founders think.  And for bonus points, read the blog back to the early days so you can ask questions about why they made certain decisions.  For more gold stars, read the blog of the competitors as well.

Find some way to delight and surprise

I like to give an example of how we always give out chocolates to anyone that tours an office space because we always like to delight and surprise our users.  It’s awesome when candidates for a job do the same.  My friend Shawn just brought organic heirloom carrots and a 6-pack of Sightglass coffee to an interview as a gift.  That’s awesome.

Follow the normal processes set out on their Jobs page

Most companies have some sort of applicant tracking system, so if you’re interested in a job make sure you’re doing exactly the things that you’re supposed to do; that way you won’t get lost in a bunch of email exchanges.

The normal process is necessary but not sufficient

You need to do some things that are unexpected because in a startup scenario the unexpected is usually appreciated.  My very first startup interview as a business school student, I showed up with a product spec – something cool I thought this company should do. It took me an hour and it was, in the end, totally off base, but it at least show a sense of initiative.

Find someone to give a warm intro

If you don’t know the founders, go through each person on that company’s team page and see if you have someone in common on LinkedIn or Facebook.  If the person you have in common will give you an amazingly warm intro, then ask him.  If it’s anything less than amazingly warm, then you should probably skip it.




Hope that helps!  Happy job hunting!



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About Jason Freedman

Entrepreneur, Co-Founder at 42Floors, Co-Founder at FlightCaster, YC-alum, and a Tuck MBA

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  • Alejandro

    Great article, thanks for sharing!

  • sonal

    I disagree with the way candidate dresses up for the interview. We have found great engineers at our company(a startup) from a guy wearing star wars tshirt(with torn up jeans) and another one wearing a super formal suit with a briefcase. If this contributes to even 1% to the filtering criteria for the interviewer, then I believe they do not have a hiring process.

    After all, from where did the norm that sneakers and jeans are more appropriate clothes for startups came from.

  • Rob

    I wore a suit to my first interview at my current startup, not because I thought it was a suit sort of place (I knew via research that it was not), but because I wanted to show respect and convey a sense of seriousness towards the role and the companies’ goals. 7 years later we’re still doing amazing stuff and growing like a weed, and I like to think that had I have not taken the extra 10 minutes to put on that ill-fitting off the rack Macy’s suit, my destiny would not have been the same. A good fit culturally would have been able to adapt to the scenario and gel with the team, whether clad in a 3 piece suit or a toga.