15 Must Ask Interview Questions for Your First Few Startup Hires

by / ⠀Startup Advice / June 15, 2012

Q. What’s one must-ask interview question for your first few startup hires?

The following answers are provided by the Young Entrepreneur Council (YEC), an invite-only nonprofit organization comprised of the world’s most promising young entrepreneurs. The YEC promotes entrepreneurship as a solution to unemployment and underemployment and provides entrepreneurs with access to tools, mentorship, and resources that support each stage of their business’s development and growth.

A. Will You Make Copies?

At startups, everyone needs to pitch in, including doing the occasional administrative task. By asking prospective hires if they will make copies, you can identify those who have the “do whatever it takes” attitude that will help your startup succeed.

Bhavin Parikh, Magoosh Test Prep

A. Past Experience Takes Precedence

I would want to know, first and foremost, that the hire has had success in the startup environment before. It’s a unique culture that requires a certain mindset and approach.

Alexandra Levit, Inspiration at Work

A. Where’s Your Initiative?

“Can you give me an example of when you demonstrated high initiative?” As a startup, you need people that will go above and beyond their role and produce amazing value for the company.

Jun Loayza, RewardMe

A. Completion Is Key

How have you worked around resourcing and staffing limitations to accomplish a project? Startups are always trying to juggle multiple priorities and there’s never enough manpower to get stuff done. Asking about times where someone was able to come up with a project, idea, or initiative, and then oversee it to completion — despite obstacles — allows you to discover a lot.

See also  4 Ways to Protect Your Online Business in 2022

Matt Mickiewicz, Flippa

A. Find Out About the Formative Years

vanessa-nornbergI always ask candidates to tell me about a difficult or challenging event from their childhood that they feel has shaped them into who they are today. It gives me insight into who they think they are as a person, what motivates them, and how they deal with unexpected issues that may arise.

Vanessa Nornberg, Metal Mafia

A. One Word: Why?

Why do you want to join a startup? Understanding one’s motivation for pursuing a job, particularly an entrepreneurial one, is critical. Make sure your first few hires are risk-tolerant entrepreneurs like yourself, and that your objectives are aligned. You want people who aren’t going to bail at the first bump in the road.

Michael Tolkin, Merchant Exchange

A. Stump Them With the Obvious

Ask them if this a job or is it a career. The two are very different from each other, and can sum up the persons work mentality.

Jerry Piscitelli, Portopong LLC

A. Do You Get Seasick?

kenthealyI would ask the following: “If we had news that the company may go belly up in two weeks, what would you do?” This question will test the person’s stomach for the swaying seas of a startup. If they respond by indicating an “increased” level commitment, then you have a winner. If they allude to retreating and “playing it safe” they may not have the necessary fervor.

Kent Healy, The Uncommon Life

A. What’s Your Favorite Movie?

Startup hires need to be almost as passionate as you are about your vision. By asking, “What is your favorite movie?” you can see how they can passionately express themselves. Don’t hire those who are as dead a a door knob when they answer this question.

See also  Born Global: 5 Great Cities for Young Professionals

Nancy T. Nguyen, Sweet T

A. Identify Their Personality

Ask simple questions to determine the character of the potential hire. Some startup hires cannot handle the startup mode, not because of education and past experience, but simply because their character does not fit the type of environment one would find in startups. One question to ask is, “Do you want to be in a startup, or do you want to appear to be a in a startup?” It’s an honest question.

George Mavromaras, Mavro Inc. | Praetor Global LLC.

A. Make It an RPG

Ask plenty of role-playing questions — the interviewee will project their motivation for applying to the startup. You’ll also get a deeper understanding of them as an individual and what they can bring to the table.

Justin Beck, PerBlue

A. What Happens When You’re Wrong?

Ask for an instance of when they were dead wrong about something. How they respond is telling — do they have the ability to admit it, ask for help and move on, or do they try to fix it themselves? Are they willing to admit it happens often? That’s a sign of not being afraid to fail.

Susan Strayer, Exaqueo

A. All Roads Lead to Success

The first few hires in a startup are crucial, so make sure they’re on-board with your company’s vision, first and foremost. Ask where they see themselves in relation to the company five years down the road. Make sure they envision the company’s destination the same way you do, even if they see the path a little differently.

See also  11 Leadership Lessons Men Can Learn From Women

Nick Friedman, College Hunks Hauling Junk

A. Let’s Talk Numbers

Ask them how much they want to earn. First, this question usually catches people off-guard, which helps you evaluate how quickly they can adapt. Second, it allows you to see how flexible they are, as well as how committed they are to the company’s growth.

Nicolas Gremion, Paradise Publishers

A. Change Is Constant

How comfortable are you with change, and how do you handle it? If you run a startup, you need people who are flexible enough to grow with you. If someone doesn’t handle transitions and change well, you need to know that before you invest in them.

Brent Beshore, AdVentures

Course Recommendation: Startup Hiring – How to Hire and Retain the Best People. Get it Now

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


Get Funded Faster!

Proven Pitch Deck

Signup for our newsletter to get access to our proven pitch deck template.