Hiring and Growth

What to Ask When Interviewing Your First Employees

Jeff Haden Inc. columnist and small business management expert 
woman interviewing a candidate in a colorful office space

Many employers ask the same basic interview questions:

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  • What’s your work experience?
  • Achievements?
  • Biggest weakness?
  • Greatest strength?

Boilerplate stuff. And sometimes that’s OK—but not if you’re just starting a business.

Just one poor employee is enough to derail the culture—and by extension, the brand—you hope to build. Not to mention your bottom line.

Nope: When you’re building your team from scratch, every employee needs to be great.

Which means the questions you ask a potential employee need to get to the heart of the behaviors, attitudes, and perspectives you truly need your first team members to possess.

If you’re ready to start assembling your team, throw out what you might have heard about which questions to ask when interviewing someone and try these startup interview questions instead.

5 of the best interview questions to ask candidates at a startup

1. “Tell me about a time you did a lot—with very little.” 

Focus area: Resourcefulness

Why it’s a good interview question for employers: Startup employees need to be able to find creative solutions to the challenges new businesses naturally face.

Most startups are bootstrapped; very few have significant funding at their disposal. Some startup founders even swear by forced austerity. In other words, they believe that not being able to throw money at problems fosters creativity and innovative solutions to problems. 

A great startup employee embraces the idea of doing more with less. They take pride in humble beginnings. They take pride in making something out of seemingly nothing.

They don’t care about plush offices or fully stocked snack cabinets. They’re motivated to solve problems with a combination of brain power and elbow grease. 

Ask this question and a poor candidate will look puzzled. Great candidates will offer so many examples you’ll have to ask them to stop.

2. “Tell me about a time you made a decision without having much data.”

Focus area: Adaptability

Why it’s a good interview question for employers: Especially early on, great startup employees are willing to take intelligent risks—and learn from the results.

Detailed action plans are great. That’s why most entrepreneurs create comprehensive business plans. But within days, those plans change. (As the eminent philosopher Mike Tyson says, “Everyone has a plan… until they get punched in the face.”) 

That’s why many thriving startups look very different compared to their original plan. Smart entrepreneurs adapt and modify and shift to meet actual market and business realities.

So do great startup employees. The people you need on your team are willing to embrace the Jeff Bezos method of making decisions. Bezos says that if a decision is easily reversible, don’t overthink it. Otherwise you’ll be too slow, too risk averse, and too unwilling to experiment.

Great startup employees spend some of their time planning and most of their time doing. 

Because you can always learn from what you’ve done. But you can’t learn anything from what you never do.

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3. “Tell me what you do that makes the biggest impact on the organization in your current job.” 

Focus area: Key motivators

Why it’s a good interview question for employers: Startups need employees who don’t care about the job title; they want to do the work.

Every startup employee—every employee period—is an investment, an investment that should generate a return. That’s why every employee should generate, directly or indirectly, actual revenue. (Seriously: Can you afford to hire someone who will only show up as a cost on your profit and loss statement?)

But not all employees embrace that fact. Before you know it, they’ve started holding meetings just to meet. Started creating reports just so they can distribute them. Launched initiatives that fall into the “nice to have” category even though all you can afford are “absolutely need to have.” 

Candidates who don’t know how they make the biggest impact—or think that what they do makes an impact when it doesn’t—are candidates to avoid. The people you need understand what drives value and spend the majority of their time delivering that value.

If they do branch out from their core tasks, they pick areas that add additional value, like increasing sales, improving efficiency, reducing waste, or improving customer satisfaction. 

So ask what makes the biggest impact. Then ask what projects or initiatives the candidate has taken up on their own. And finally, determine whether these projects fall into the “nice to have” or “need to have” category.

Because the employees you need to have consistently focus on what your business needs: results. 

4. “Tell me about a time you feel a boss treated you unfairly.”

Focus area: Accountability

Why it’s a good interview question for employers: The best employees own their mistakes and learn from them.

While some people will claim they’ve never been treated unfairly, that’s almost impossible. Every boss makes mistakes. (I made plenty.) Every boss makes bad decisions in spite of best intentions.

Still, some candidates will demur because that makes them look more tolerant or easy to get along with. Great candidates will be honest—which is exactly what you want your employees to be. 

Beyond that, great candidates will describe a situation where a boss truly did treat them unfairly rather than unequally. There’s a huge difference: Since every employee is an individual, great bosses treat every employee fairly, but not necessarily equally. 

For example, in any business, pay should be based on performance, not tenure. Responsibility, authority, and freedom should be earned, not automatically given. 

Listen to how the candidate answers and decide whether their definition of “unfair” matches yours, and the type of business you hope to build. Neither of you is right or wrong, but there can definitely be a “right” definition for your business.

5. “Tell me about a time you went the extra mile for a customer.”

Focus area: Customer focus

Why it’s a good interview question for employers: Businesses that last are built on a foundation of genuinely loyal customers, which requires building genuine customer relationships.

A business without customers is not a business; it’s a hobby. That’s why great startups provide more than just a transaction; they constantly solve for their customers’ pain points.

That’s where true customer loyalty starts: when you provide an unmatched level of service and customer care.

Great candidates have plenty of “above and beyond” stories. They can readily share instances when their actions transcended formal processes and guidelines. When they thought about the customer, not themselves. When they did not necessarily go by what was written, but what was right.

Because great startup employees aren’t worried about being right—they’re worried about doing right.


To build a great startup team from scratch, don’t settle for asking the same old interview questions. Leave those to companies willing to settle for average employees. 

Take the time to ask questions that get to the heart of the skills, attitude, and experience you need—and the culture you hope to build. 

And don’t stop interviewing candidates until you find the perfect person. Because the last thing your business can afford is to settle for good when you can have great.

Updated: November 13, 2019

Jeff Haden
Jeff Haden Jeff Haden is a writer, speaker, small business management expert, and Inc.’s most popular columnist. He's the author of The Motivation Myth: How High Achievers Really Set Themselves Up to Win.

Comments

  • Tom Boon

    Was the “…less with more.” intended in the article? “A great startup employee embraces the idea of doing less with more.” is contained in Item 1.

    Reply
    • Mohini Kundu

      Hi Tom—thank you for catching that! We’ve updated the piece.

      Reply

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