The Most Important Technical Interview Questions You Need to Prepare For

By: Scott Morris

Category: Blog

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While some people might not find job interviews nerve-wracking, for most of us, it’s the stuff anxiety dreams are made of. And while you’ll certainly come across standard questions about your technical skills and knowledge of project management systems, tech interviews are notoriously unpredictable (hello, curveball, nonsensical questions), leaving you feeling lost when it comes to preparing. The list below includes eight of the top technical interview questions that CEOs ask.

But there’s no reason to panic. Ultimately, tech employers are interested in how you approach problems, and their questions are designed to suss out your thought process. To help demystify tech interviews, these hiring professionals supplied their key questions and some pointers for formulating answers—even to the questions nobody sees coming.

1. “What do you know about our company?”

Sound obvious? Sometimes the best technical interview questions are—and they’re more revealing that you might expect.

Alan Hattman, Manager of Talent Acquisition at Peloton Technology, has a yikes-worthy story that proves that the importance of research can’t be stressed enough: While he was looking to hire a Director of Marketing, not one but two candidates thought they were interviewing for a different company with a similar name.

“They thought we were a bike company,” Hattman says. (Peloton Technology is a vehicle technology company. The interviewees had confused it with Peloton Cycle.) “They even talked about how they used our product and everything. So those were automatic fails. Do your homework. Research the job and the company you’re applying for.”

When it comes to reading up on a prospective employer, Jenna Kass, Recruiting Manager at Tableau Software, says she always appreciates when “candidates take the time to research our company from a business standpoint.” Before you walk into the interview, find out who the company’s competitors are and gather information about their audience or customers.

The last step is to build on your research with your own expertise. ShipMonk CEO Jan Bednar asks candidates for feedback about his company’s product—specifically for changes they’d make. His ideal response “would not only explain what they would like changed but also how they would change it.”

2. “What’s the most challenging/exciting project you have done in the past two years?”

Your work should lead the way in any technical interview and Lauren Thompson, Zillow’s Communications Coordinator, says that in addition to technical specifications, Zillow’s interviewers want to see “the innovation [an interviewee] comes out with from the project.” The goal of this technical interview question? To figure out what you’re passionate about, she says.

You should start preparing for this question long before you send out resumes, and a safe bet is to dig into each of your projects as you go to focus on what parts you’re passionate about, what motivates you, and what types of work you want to do in the future. Then, practice articulating that list, so if an interviewer asks you to explain a project from your portfolio, you’ll have more to say than a simple list of specs. Your answer might sound like: “I love 8-bit gaming, so I developed a C++ emulator for Chip-8. It combined my interest in digital preservation with getting to dust off my Tetris and Pac-Man skills. I’m looking forward to applying some of the C++ tricks I used to more projects in the future.”

3. “What kind of tech projects do you work on in your spare time?”

If you haven’t already picked up on it, passion goes a long way in tech—almost everyone I spoke to for this article mentioned it at some point.

Kevin Hayen, CTO of Let’s Be Chefs, considers self-directed creative work a critical piece of assessing entry-level applicants and veteran candidates alike. The way an interviewee answers this question shows Hayen “what in tech they are really passionate about or if they even are passionate about tech” in the first place. It doesn’t matter what your hobby is: Talk it up with all the genuine enthusiasm you have. Like many of these questions, it’s not the actual answer that interests Kevin—he says he doesn’t care it the answer is open source, DIY, or even just playing around.

Hayen says that this question also helps him figure out “how the candidate might fit into a particular team and what ‘bonus’ skills they might bring to the company”—things you didn’t even think to add to your resume but will make you a more well-rounded applicant.

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4. “Tell me about the most difficult technical challenge you’ve encountered and how you resolved it.”

Bryan Petro, COO of GetMyBoat, asks this technical interview question to make sure prospective employees can do more than check off a box when a problem is fixed. “We’re not looking for people who can just churn through bugs,” Bryan says, “but people who can understand the big picture as part of a larger product team.”

So that you’re not up all night before an interview, wracking your brain for every challenge you’ve ever faced, try keeping a log of the times your skills were pushed to their limits and how you rose to the occasion as you work on projects. You don’t need to write essays here—a few bullet points to jog your memory will suffice.

5. “What technologies could you not live without?”

Stephen Negron of LegalTech Consulting, Inc. wants to know what tech skills candidates bring to the table, of course. But after that’s out of the way, he has a different line of questioning—a list of “revealing questions” that tell him about the interviewee’s life as a techie.

He asks:

  • Tell me about your computers at home. What’s your internet speed?
  • What are your favorite gadgets? Apps?
  • What kind of phone do you have?
  • What are your tech pet peeves?

“I really want to know if they practice what they preach, if they live the tech life, and if they have an understanding of the everyday tech frustrations,” he says.

This is a point that’s easy to overlook amidst loftier talk of expertise, but if you’re not consciously engaging with devices, apps, and websites, all the technical skills in the world won’t bridge that gap toward empathizing with the end user when it comes to designing your own products.

6. “What would you bring to our monthly bakeoff?”

“It may sound like a silly question,” says Max Schleicher, Digital Marketing Manager at Insureon, but this job interview question gives him insight into candidates that a resume simply can’t. It’s a twist on the curveball question—which usually shows an interviewee’s logic skills. While he appreciates those questions, Schleicher wants to see creativity, social skills, and communication style. “Trust me,” he says. “You can learn a lot about someone from their baking preferences.”

There’s no wrong answer, whether it be a standard “brownies” or “double butterscotch blondies with almonds,” he says. The critical tell is whether interviewees “buy in, whether they’re excited, and how well they’re going to fit into the culture we’re working to create.”

This question has another purpose: Schleicher says that a question like this humanizes him and the company because he wants to win over the applicant, too. “We want to sell our culture and our sense of teamwork to new candidates. We want to attract candidates that buy into that,” he says.

7. “Tell me about a time you were asked to do something you had never done before. How did you react, and what did you learn?”

The key to working in tech isn’t knowing everything–that’s not even possible for multi-decade vets of the industry. For Brendan Browne, VP of Talent Acquisition at LinkedIn, this question boils down to the number one soft skill needed at LinkedIn: adaptability.

“Soft skills like adaptability are a hard thing to suss out but they’re critical for someone to be successful here,” Browne says. Projects change direction all the time, while departmental reorganizations and management shifts lead to priorities being rearranged. “Your ability to deal with these scenarios will impact where you’re best able to contribute at a company.”

As far as the best way to show your adaptability in an interview setting, Browne says he’s “looking for real answers, not the canned, stereotypical responses.” Go with an experience from your career (a department re-org, a client changing their mind last minute) or personal life (becoming a parent, a cross-country move) that shows how you’ve been able to “adapt, persevere, and manage change.”

Not a particularly adaptable person? Don’t panic. Self-awareness is also a key trait Browne looks for. “You don’t need to pretend certain skills are your strong point if they aren’t. If adapting quickly is hard for you, that’s okay. You likely have other soft skills an employer wants (collaboration, culture fit, etc.), so play those up during your interview,” he says.

8. “How much does a first class one-way ticket from New York to Abu Dhabi cost on Etihad?”

ShipMonk CEO Jan Bednar doesn’t really expect anyone to know the answer—it’s the infamous curveball question. “Frankly,” he says, “we’d be a bit surprised if they did.” Then why ask it?

“Whether they guess $3,000 or $80,000 is functionally immaterial,” Bednar says. Instead, it’s all about the process. “What steps do they take to solve the question? Do they draw upon past experiences? Projections? General knowledge? These are the skills we want to see,” Bednar says.

Having a set of tech skills is one thing, but communicating your ability to use them practically, creatively, and efficiently is what will help you land the job. As I interviewed hiring professionals for this article, multiple people told me that surprise brain teaser questions are all about your thought process, not your answer. So if you find yourself face-to-face with one of these seemingly ludicrous technical interview questions, take a breath, don’t get flummoxed, and talk the interviewer through your thinking. That’s all they want to hear.

Scott Morris

Scott Morris is Skillcrush's staff writer and content producer. Like all the members of Skillcrush's team, he works remotely (in his case from Napa, CA). He believes that content that's worth reading (and that your audience can find!) creates brands that people follow. He's experienced writing on topics including jobs and technology, digital marketing, career pivots, gender equity, parenting, and popular culture. Before starting his career as a writer and content marketer, he spent 10 years as a full-time parent to his daughters Veronica and Athena.