Hiring hustlers is not easy.

There really isn’t a simple way of identifying whether or not someone is a hustler at heart, neither is there a specific question you can ask a job candidate that will easily get them to admit all prior examples of hustle.

Why is it so hard to find hustlers?

I ask myself this question a lot, and it has lead to another question, which is “Can someone be trained to become a hustler?”

Personally, I think the answer to that question is no. Simply being that not everyone is particularly interested in doing what it takes to be successful, and not everyone comes away from failure a stronger person.

You also can’t ask someone if they are a hustler, because they will just tell you what they know you want to hear.

So how do you figure out if someone is a hustler while interviewing them for a job?

Here are a few methods that I’ve found have been pretty good identifiers:


Does the Candidate Accept Defeat?

When speaking to a potential “hiree”, ask them questions about their failures, their mistakes and their regrets.

Although this may seem counter-intuitive, if someone has previously failed and is still determined to succeed, it shows perseverance; a very important quality among hustlers.

Bill Walsh, previously the Head Coach of the San Francisco 49ers, and the one who lead them to multiple Super Bowl victories says that you can’t truly know success until you have known failure. And he’s not the only one who believes in this statement.

What does he mean by this?

Well, for one have you ever heard of a CEO, Entrepreneur, Musician, Actor, Director or anyone successful for that matter who got it right on the first try? Of course not! Most of the stories we hear about the world’s best leaders is how they overcame obstacles and learned from their mistakes. You need to fail in order to know what not to do the next time around.

By learning about the obstacles that job candidates have faced in the past, and what they have done despite those struggles, you will be able to identify just how determined and how much of a go-getter a certain person is.

Possible questions you can ask are:

  • Give me an example of a time where a decision you made turned out to be a horrible idea. What happened, or what did you do about it?
  • When is the last time something didn’t go as planned? How did you react?

questions for hustlers

Image made with infographic generator Venngage

Notice that these questions don’t directly require the candidate to tell you how they “turned the failure around”, but rather they prompt the candidate for their reactions to those failures. It frames the question as having no right or wrong answers, but will provide you with more of an opportunity to figure out whether the person is the right fit for your team.

Has the Candidate Been Successful With a Personal Project?

Every single one of the best hustlers I know has an origin story. I love hearing these origin stories because they always make it easier to identify whether the person is a risk-taker. For instance, a friend of mine, Ross Simmonds talks about how his first business venture was selling do-rags from his locker in high school.

My story origin story began in 3rd grade, when I took over the swingsets with my friends and charged the younger students a nickel for a ride on the swings. Another time I sold T-shirts that I had made myself and then donated all the profits to the Heart and Stroke foundation. I also made Christmas ornaments out of clay and sold them for a dollar each. I even started a secret underground restaurant in my own apartment that got national coverage. Did they all succeed? In their own ways, absolutely!

The point is that every hustler has an origin story of their own, and all hustlers will know exactly what that story is when prompted. Why? Because they are truly proud of their innovation and their success.

Possible questions you can ask are:

  • Tell me about a personal project that you are truly proud of.
  • What is one of the most inventive things you did as a child (or an adult) that you still talk about today?

questions for hustlers

Image made with infographic generator Venngage

If the candidate hesitates to talk about something truly inventive, or if you can see that they are talking out of their ass, it’s probably because they never discovered their origin story. Once again, these questions don’t have a right or wrong answer that can be identified by the candidate, but they will help you better identify what kind of person the interviewee is.

Has the Candidate Demonstrated Fast, Upward Motion?

There is a reason companies ask to see an interviewee’s college grades. If you have good grades, it means you are a hard worker and you’re smart.

Naturally, not all hustlers perform well in structured academia, but there are other ways to figure out whether a person is intelligent and hardworking.

One of the reasons hustlers are so hard to find is because they know how to climb the ladder of success. They don’t often remain in the same position with the same responsibilities for long. Every job they get is better in some way than the last position they had. For hustlers, there is no backwards, only forwards. More importantly, there is a constant thirst- a hunger for growth.

Look at the example of Richard Branson, who began his entrepreneurial endeavors by starting a student magazine. Later, he transitioned that business into a mail-order record company, despite not knowing anything about the music industry. That company eventually became Virgin Records and he continued to grow his business to what it is today. The point is, he didn’t just settle with the student magazine, or with the record business. He kept finding ways to grow and expand his projects and his ventures.

Possible questions to ask are:

  • Have you ever been promoted, why or why not?
  • Have you ever gotten a job for which you were not fully qualified?

questions for hustlers

Image made with infographic generator Venngage

I like the second question a lot because one of the greatest qualities of a hustler is that they believe they can figure out any problem. Although they may not be qualified for a specific role, they are willing to go for it and learn how to be the best at that role.

Most of the jobs I have gotten in life, I have had almost no prior experience. The same goes for most entrepreneurs and CEOs. Ben Horowitz’s beautifully articulates this in his book, The Hard thing about Hard things when he says that everybody learns to be a CEO by being a CEO. Hustlers realize that sometimes you need to throw yourself into the deep end and figure out how to swim.  


Do They Work Until The Task is Done or Until The Time is Up?

Finally you want to figure out whether the person you are interviewing works to get the job done, or just puts in their hours.

Whether you run a small business or a major enterprise, the goal is the same; you want to see positive results. You may have heard of the Vitality Curve, also known as the 80/20 rule. It means that 20% of your activities result in 80% of your outcomes. Jack Welch’s version of this same principal goes by the 20-70-10 ratio. It means that 20% of your workforce is the most productive, 70% work adequately and 10% are non-producers and should be fired.

Why is this important?

Well, it’s important because you need to identify if the person being interviewed will be part of the 20, 70 or 10 percent. Hustlers almost always makeup the 20%. The reason being, they work until a task is done, not just to log their hours. Hustlers get shit done.

Possible questions to ask:

  • Have you ever asked for an extension on an assignment or a task? Why or why not?
  • When was the last time, if ever, that you stayed late at the office or at school? What was it for?

questions for hustlers

Image made with infographic generator Venngage

What’s important to note about these questions, is that it doesn’t matter if they said yes or not. What matters is the why. If the candidate asked for an extension on an assignment because they waited until the last minute to even look at it, they may not fall into the 20% bracket. If they stayed late at the office to finish a task before a deadline, or better yet, to get a head start on another project, you know they work to complete the job and not just to log their hours. The why always outweighs the what.


Does the Candidate Truly Speak Their Mind?

There are two kinds of people who speak their minds. The first kind are speaking just for the sake of speaking. The second kind actually have something to contribute to the conversation.

Hustlers speak their mind. But only when there is something of value to add.

The other speaks because no one else is speaking. These are the douchebags of the world.

Hustlers back their suggestions with evidence, research and experiments. The douchebags make suggestions solely on speculation or to have the last word. Kind of like how Trump only spoke during the 2016 Presidential Elections to have the last word, despite saying nothing of value.

Hustlers are not afraid to tell their manager or their CEO that they don’t agree with something that has been said or with a decision that has been made.

Hustlers are not afraid to point out other people’s flaws, as well as their own flaws.

Hustlers are not afraid to be direct and are willing to tell the bad news as well as the good news. They are not overly optimistic when times are rough, and they can sometimes be pessimistic when things are going well. Meaning, they constantly believe that things can improve.

Because of their confidence and willingness to speak up, hustlers also make great networkers. They understand how to network and connect with the right influencers. They are not afraid of putting themselves out there.

Possible questions to ask are:

  • When looking at our company/product, what is something that you think should change? Why?
  • What is a question that I should have asked you during this interview but didn’t?

hiring hustlers

Image made with infographic generator Venngage


These two questions force the candidate to think critically not just about your business, but about the overall interview process. Both of these questions require the candidate to 1) do their research about company, and 2) listen carefully. The more specific the candidate’s responses and the more thought they put into their answers, the easier it will be to identify whether they speak to add value or speak empty words.


Holding onto Hustlers

Hiring hustlers, or “A-players” is not always easy because most of them either already have jobs, or run their own businesses. It’s also not easy to identify if someone is a hustler because most people will say they are if asked directly.

If you do find a strong hustler and happen to hire them, you need to make sure you are keeping them happy. The second they find a better opportunity elsewhere, they will leave you. So when you find the right hustler, never let them go.