What to Ask When Interviewing Your First Employees

Many employers ask the same basic interview questions:

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

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

Just one poor employee is enough to derail the company 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 go beyond salary expectations and get to the heart of the skill set, behaviors, attitudes, and perspectives you truly need your first team members to possess for experience and cultural fit.

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 instead, try these startup interview questions and these questions successful CEOs ask when exploring who has the potential to join their companies as their next new employees.

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.” 

Most early-stage 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, elbow grease, and resiliency. 

Ask this question during the hiring process 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.”

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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.

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

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.”

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.”

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.

Specific questions CEOs ask to size up candidates

Here is a collection of questions startup and top CEOs ask potential hires that you can explore to see what is the right fit for your company’s needs and also aligns with your personal interview style:

“What are your career goals?”

That was the second of two questions Ann Hiatt answered for Jeff Bezos, who hired her on the spot when she was starting out, seeking a junior assistant role more than 20 years ago. She is now a Silicon Valley veteran with 15-plus years of experience working as an executive business partner for Jeff Bezos, Marissa Mayer, and Eric Schmidt.

The first question also sussed out how she thinks: “I want you to estimate the number of panes of glass in the city of Seattle?”

In an essay she wrote for CNBC about the experience, Hiatt said: “Knowing Bezos as well as I do now, I see why those were his only two questions. He was measuring my potential by asking questions that would explore whether I had the grit, courage and motivation to run at his pace and be brave enough to consistently jump with him and level up.”

“What’s the difference between someone who’s great in your role versus someone who’s outstanding?”

That was one of a few questions from Matt Humphrey that stood out when First Round Capital, a venture capital firm, reached out to many startup leaders, including CEOs for its article, 40 Favorite Interview Questions from Some of the Sharpest Folks We Know. Humphrey—who knows how to distinguish the best from the best—is the former co-founder and CEO of LendingHome, now Kiavi.

He’s what he shared with First Round Capital:

“I always follow-up with: ‘Can you give me some specific examples of this in your career and the results you saw?’ I look for how they answer the question just as much as the content of the answer itself,” he says. “The best candidates can answer almost immediately, maybe even with a wry smile because they know exactly what I’m getting at and they’re proud of doing something that was truly above and beyond.”

“We’ll ask about this in references, but I’d love to hear it from you as well: Very specifically, what’s the most recent piece of critical feedback that you’ve gotten?”

That’s another top interview question Humphrey shared with First Round Capital:

“I’ve found that throwing in the ‘references’ comment is important because it tends to bring out more honest responses. I’m literally looking for them to get into the nitty-gritty of the when and the how, not fluffy or abstract responses. So it’s helpful to have candidates know that if they lob in a softball, I may hear something different when I’m doing reference checks.”

“Tell me about a time you really screwed something up. How did you handle it and how did you address the mistake?”

The 40 favorite interview questions in the First Round Capital article contains a lot of gems. It’s worth a close review. This is the last among them included in this roundup, and it’s from former Etsy CEO, Chad Dickerson, who said this to First Round Capital: “In one fell swoop, this question tests for humility, self-reflection, problem-solving and communication skills. The bigger one’s scope, the bigger the mistakes and the more complex the remediation of those mistakes.”

“What didn’t you get a chance to include on your résumé?”

“Obviously a good CV is important, but if you were going to hire by what they say about themselves on paper, you wouldn’t need to waste time on an interview,” Richard Branson writes in his book, The Virgin Way: Everything I Know About Leadership. “As important as it is to look at what a candidate has achieved elsewhere, I have always believed that the single most important thing to consider is ‘personality fit,’“ he says. “By that I mean, is this someone whose way of being, sense of humour, and general demeanour will dovetail easily with your company’s culture?”

“Can you tell me about a time you ran with a project from start to finish?”

When Jess Levin was the founder and chief executive of Carats & Cake, an online wedding resource, she told Business Insider why she asks every job candidate that question:

“We are in the service of small businesses and are a true startup ourselves so we look for people who get what it means to do big things without a lot of hands.” She said there is no “one size fits all” answer, but she always looks for an example that “communicates independent drive, proactive problem solving, and humility,” adding, “For small, nimble teams, like Carats & Cake, it’s so important that everyone shares a desire to be thoughtful and committed to our business and the businesses we work with. A sense of humility signals an ability to truly work together and to be open to learning from mistakes and each other.”

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To build a great startup team from scratch, don’t settle for asking the same old interview questions. These focused tell-me-about-yourself type of discussion points get to the heart of problem solving, revealing how an interviewee thinks in a startup environment or small business work environment. Leave the basic queries to those established 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 that goes beyond the startup job description—and supports the startup culture you hope to build. The last thing your business can afford is to settle for good when you should hit the ground running and need to have great.