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Would You Pass a Job Interview With Jack Dorsey?

The Betts Team
January 22, 2020

Do you ever get nervous during an interview?


Everyone does!


It’s nerve-racking stuff, especially if it’s your first time. But what if we took things up a notch – what if I tell you that your interviewer is Jack Dorsey?


He’s the co-founder of Twitter and has a net worth of $4.4 Billion. So it’d be safe to say that this guy has a real knack for leadership and management. He knows a lot about entrepreneurship; he dominates social media and runs a tight ship in the workplace. He is also an ace at programming, law, real estate, managing large organizations, publishing and more. And despite all that, Jack Dorsey’s also got some major hippie cred.


Can you tell where we’re heading with this?


Dorsey’s also a tough nut to crack when it comes to hiring – he’s very demanding. So imagine what you would feel as you walk into a room and the interviewer introduces himself as Jack Dorsey. It would be nerve-racking, for sure. But here’s a fact: if you can impress him, you can impress anyone, that’s for sure. We asked around to find people who have been in his presence and know his style. Here are some questions he might ask, and possible answers for you to practice. You never know when you’ll encounter an interviewer as demanding as Jack Dorsey, so having a sense of how to handle these questions can prepare you for any tech interviewer you may face.

1. Why are you here?

Dorsey has said that this is the number one question he always asks in interviews. He’s one of the most successful entrepreneurs of all time, and would have high expectations for this answer. You need to be careful. Interviewers like this are looking for purpose, drive, and passion – they wants to know if you’re hungry for the same stuff they’re obsessed with.


This points to a universal best practice for job interviews: Try to get a sense of your interviewer’s personality, and match it in your answer.


You might not know this, but Twitter started as a podcasting startup. His other startup – Square – was launched because his friend was trying to make a sale and wasn’t able to accept credit cards as payment.


Jack likes fixing things and that’s what he looks for in a candidate. So if you’re applying for a sales role, he’s looking for someone who can sell a hairbrush to a bald guy and that too after selling them a hair-growth formula. If you’re that passionate about sales and can prove it to him, you’re good!   Oh, and if you tell him what he’s doing wrong and back it up with a solid argument that makes him scratch that “hippie beard” of his, you’re going to make the impression of a lifetime. But don’t get too cocky!

2. How many times have you said no?

This is a tricky one. If he asks this in a job interview, don’t say a number! Demanding interviewers who ask this question are really trying to find out if you’re a risk-taker.


Jack Dorsey has founded multiple companies over the years. That inherently takes a whole lot of risk – but he took it and came out on top on the other side. As he once said: “What I’m proud of is that we did get proof of concept and we did show people, we kept taking risks.”


Another way he could ask this is, “Would you go all-in on a hand of poker if you were certain you had a losing hand?”


He wants to hear that you believe in something so badly that others start gravitating towards you.


There are times you think you’re going to fail, but you’re willing to push through those times and keep moving ahead. Of course, real-life examples are necessary. He’s a smart guy, and will probably be able to tell if you’re faking it.

3. Are you still in school?

He probably wants a resounding yes – even if you’re employed full-time – because he’s not looking for a literal answer. Jack Dorsey has lived his life learning bit by bit, and so what he – and any serious, demanding interviewer – wants to hear is that you’re constantly learning, constantly optimizing, constantly getting better.


“My whole life has been pretty much like that,” he said. He says he learned how to be a CEO, hiring, team building, and fundraising all at once.


It’s like Vin Diesel saying, “I live my life a quarter-mile at a time.” Jack might say he lives his life one lesson at a time.


Even when he started Square, Jack and his team knew zilch about banking, credit cards, and finances. But he built a successful business on it.


So if you ever find yourself in a job interview with someone like Jack Dorsey, and he asks this question, don’t even think twice before saying yes, and follow it up with a personal example of how you find ways to learn in real life.

4. Why do you think you’re the right fit for sales?

If you go all technical about your sales expertise and fail to mention company culture… that’s it, you’re done. Out.


If he worried about the technicalities, he wouldn’t have hired more than 50 employees for Square and not one with any financial experience.


Here’s the kicker – he gave those first 50 employees a catch. He said, “This company will either be a massive success or I’m going to jail. There’s no in-between.”


That’s a real risk taker, right there. And the way to make an impression on someone like that is to understand how they think.


If he ever asks this during a sales job interview, just know that he expects you to answer this with keywords such as “team player,” “delegate,” and “empower.”


Real-life examples are a must. Dorsey wants everyone in his company to be on the same wavelength as him.   You may think he’s crazy, or that he’s a genius. He is definitely unconventional. (That’s probably why he let Lil Nas X come to his office and fire him.) But whatever your opinion of Jack Dorsey, it’s good to practice the skills that would get you through an interview with him. Once you do, your interview skills will be unstoppable – no matter who’s sitting across the table from you.