Why You’re Approaching Startup Interviews All Wrong

Do you remember your very first job interview?

If you’re like me, you walked into McDonald’s and realized just how freaking weird it is to wear a tie in there.

But even if your first interview was at a classier establishment, I’m guessing your attire was pretty much the same


Because we’ve been trained from an early age that job interviews are a game you play based on your interviewer’s rules.

You dress up, you memorize clichéd answers to clichéd questions (“I guess my biggest weakness is that I just work too darn hard…”), and you wait until you’ve been asked a question to speak.

I mean, what other way is there really?

The Startup Way

Well, there’s the startup way for one.

And no, the startup way isn’t the same old corporate way, just on beanbags instead of Herman-Miller.

Because if you think about it, startups are like Bizzaro Superman. Sure, they put out a nice façade of organization and polish, what with their slick videos and carefully-pruned social media accounts. But underneath that corporate veneer is a seething cauldron of total chaos. Which all bubbles over when it comes to interviews.

Because whereas a typical big company’s interviews are carefully stage-managed by a giant HR team, complete with standardized questions to ward off discrimination lawsuits, startup interviews are like the Wild West.

As in:

  • Startup Founder: “Hey, do you mind interviewing this guy in five minutes?”
  • Dude by the Water Cooler/Kombucha Dispenser: “Umm… OK. What do I ask him?”
  • Founder: “Just roll with it. Y’know… whatever feels good!”

Which means that, if you happen to be “this guy” and you’ve spent the last week working on your clichéd answers, you’re kinda screwed.

Because what happens when your interviewer says, “OK, so tell me something about yourself?”

Or: “Hey, what can you do for us?”

Or even: “Uhh… that’s all I got. What else do you want to talk about?”

Uh oh. When are you going to get a chance to work in that suave answer about your so-called weakness?

And startup founders are the worst at this. Because they both want to be involved in every hiring decision (“This is my baby!”) but also have the least amount of time to prepare for interviews.

So their interviews are often one-question affairs: “Hey, do me a solid. I gotta run to a meeting in a sec… just tell me why should I hire you.”

Which is why preparing for a startup interview like you would a big company one is such a recipe for disaster. Because instead of being rewarded just for studying for the test, as you have been all your life, you’ll be on the spot to define and prove your own value.

The Opportunity

While the thought of leaving behind the cozy confines of “Tell me about your biggest weakness” can be intimidating, you should see it for what it really is: A frickin’ huge opportunity.

Because now, for the first time in your career, you’re freed from the shackles of the HR team’s boring, safe questions. And most importantly, you’re freed from your own boring, safe answers that never helped you stand out from the competition anyway.

Instead, you now have a chance to actually lead the interview conversation, to take it where you want to go. Because when your startup interviewer says “OK, so tell me something about yourself,” that’s a conversational hole wide enough to drive a Mack truck through.

And so, instead of throwing out some milquetoast big company answer focused on yourself (“I just want you to know that I’m a highly motivated team player”), how about you focus on what the startup needs?

And what does the startup need?

Put simply: Someone to solve their pain.

It could be that no one’s followed up on their delinquent customers in months so now they’re bleeding red. Can you get those customers to pay up?

It could be that their once red-hot growth has leveled off and their investors are getting nervous. Can you pour gasoline on their user numbers?

And it could even be that they just need someone to solve the various crises that erupt on a daily basis (did I mention how crazy Startup Land is?). Can you be their oasis in the midst of the startup storm?

Because if you can be the Advil to their Existential Headache, you’ve got yourself a job. You just need to follow three simple steps to make your case.

Step 1: Understand the Pain

While each startup has its share of misery, to paraphrase Tolstoy, every startup is miserable in its own way. So rather than guess at what’s going on inside, it’s far better to just ask.

And while that might feel really intimidating (“So… umm… what do you guys really suck at?”), here’s a relatively painless alternative approach:

  1. Go to LinkedIn and run an Advanced Search
  2. Set the Company to your target startup and the Filter to “Former”
  3. Find someone who’s left the startup really recently (ideally from the team you want to join)
  4. Use EmailHunter to guess their current email
  5. And send them this exact email:

Subject: How was STARTUP?


I’m considering applying for a role at STARTUP but saw that you just left there.

I know that you must be crazy busy in your new role but would love to pick your brain about your experience. Just let me know if you have 15 minutes free during any of these times over the next few weeks:






The advantage of this approach is three-fold:

  • Former employees have no skin in the game, so they’re fully free to dish
  • Everyone loves to talk about their experience (especially when they’re not worried that you’ll hit them up for a job)
  • And you make it super easy just to say “Yes” – no scheduling muss or fuss

And then once you get a chance to chat, you can figure out their former employer’s biggest pain point with a single question: “So, what do you think was the biggest thing holding them back?”

Step 2: Solve the Pain

Now that you know where your dream employer is hurting, it’s time to put together a solution. And rather than reaffirming your corporate lameness with a PowerPoint deck, I’d just lay out a simple one-page plan.

Call it your 21-Day Action Plan, including:

  • Here’s what the problem is
  • Here’s exactly what I’m going to do in the first week
  • Here’s exactly what I’m going to do in the second week
  • Here’s exactly what I’m going to do in the third week
  • Here are the results you can expect by Day 21

For example:

  • Problem: It feels like your growth is awesome but you haven’t figured out a way to monetize and you’re running out of runway
  • Week 1: I’ll interview our highest-engagement customers and come up with three hypotheses for what they’d be willing to pay for
  • Week 2: I’ll build out super lightweight prototypes for each of those hypotheses
  • Week 3: I’ll go back to each of those customers with the prototypes and will ask them to put down money on the spot in exchange for a big discount as a pilot customer
  • Result: You’ll have $10K+ in guaranteed revenue, plus, most importantly, you’ll know which monetization direction to focus on scaling

Step 3: Communicate the Solution

Now, while you may be feeling mighty special right about now, just know that all your hard work counts for absolutely nothing until it’s sitting in your future employer’s brain with a direct connection to you (“You know who was really great? That Plan Guy.”).

And so, as you might imagine, how you communicate your awesome idea is everything.

Here’s what not to do: Go back to studying your clichéd answers, tuck your ideas in your back pocket, and pray that you get a chance to show them off.

Because that’s a recipe for sitting at the bar, post-interview, going: “WTF just happened? How did we end up talking about why manhole covers are round for two hours???”

Instead, here’s exactly how to play the perfect hand:

  • Ask your point of contact to tell you everyone who’s scheduled to interview you
  • Look them up on LinkedIn to learn a little bit about their backgrounds (school, former companies, interests)
  • Again, find their emails on EmailHunter and send them this message:

Subject: Plan for CHALLENGE


POINT OF CONTACT tells me that I’ll be interviewing with you next DATE, which I’m really excited about given SHARED INTEREST.

In particular, I’ve been thinking a lot about CHALLENGE and how that’s a really tough nut to crack. As such, I’ve put together a plan that I’d love to love to share with you.

Looking forward to discussing next DATE!


(Note: Don’t attach the plan! You want to whet their appetite and build the suspense… 🙂

  • Then, at the outset of the interview, reiterate your excitement to share the plan…
  • …Which will guarantee you a shot to do so, during which you say the magic words: “Here’s exactly how I’ll tackle this challenge.”
  • And finally, you attach the plan to your thank you email as soon as you get back to your computer

Now, of course, you should be prepared for lots of pushback. Any time you throw out something concrete, a current employee is going to be tempted to tear it down based on their insider knowledge (“But we’ve already tried that!”).

But instead of getting into a fight, just roll with the punches (“Wow, that’s great – I’d definitely want to spend Week 1 adjusting my plan based on what’s already been tried.”). Because the ultimate efficacy of this approach doesn’t come from the details of the plan itself, but from the fact that you have a plan.

Because all things being equal, startups want someone who can come in and hit the ground running. They don’t have months to train you or hold your hand. Instead, they need results – and they need them know.

So if you were in the middle of the startup maelstrom and had to choose between two strong candidates – one who has a great answer about their weaknesses and one who has a great plan of action – who would you choose?


And that’s exactly why it’s time to change up your startup interview game.

Because this isn’t McDonald’s. You don’t need to wear a tie. And you definitely don’t need to wait until spoken to in order to win this job!

Jeremy Schifeling is the Founder + Chief Nerd of Break into Tech, a site that helps anyone launch their tech career – no coding required! Click here to get the free, step-by-step guide to answering any tech interview question, based on Jeremy’s experience hiring for and winning jobs at LinkedIn and startups.