Learn what you need to learn with better interview questions

There are lots of ways to ask a question. You can make the most of your interview time by guiding the conversation with effective question design. Don’t hesitate to do this—HR folks and hiring managers use these techniques all the time.

Job interviews can feel like an awkward, off-balance dance. As an applicant, you’re often told there will be time at the end to ask your questions—but, after two hours of fielding theirs, you’re left with five rushed minutes to learn about the company in ways that are important to you. It’s frustrating, especially when interviews are supposed to be a two-way street—a mutual evaluation to see if you’re a good fit for each other. The process rarely feels symmetrical.

Having worked in tech for over 25 years, I’ve been on both sides of the table. As an interviewer, I’ve evaluated candidates 20–30 times more often than I’ve been the one applying. And here’s the truth: I’ve never felt anxious as the interviewer. Why? Because the stakes are far higher for the candidate. If the company doesn’t think you’re a fit, they move to the next name on the list. But if you don’t land the job, maybe you can’t pay your rent. That inherent power imbalance fuels anxiety and makes it hard to focus on what really matters: learning whether this role is right for you.

Companies have more tools at their disposal than you do when setting the stage for interviews. They may have a professional HR team. They likely have a pool of questions that have been refined over the years. And they design the interview process.

Asking better questions

In my world (I work as a researcher and designer for a deep tech startup), one of the books I keep within arm’s reach is Steve Portigal’s “Interviewing Users”. [The second edition was recently published by Rosenfeld Media.]

The book describes how to improve research by asking different or better questions during interviews. It’s aimed at those doing user experience research, but the techniques it describes are almost always applicable to any sort of interview—including a job interview.

Much of the advice I share below I learned from Portigal’s book (I’ve explicitly called out which bits), while adding my spin on how that advice might help when writing questions you can ask as a candidate.

Ask open-ended questions

Unless you’re asking simple, factual questions (“Is there an on-site gym?”), yes-or-no questions are underperformers.

Questions should tease as much information out of someone as they can. Asking ‘how’- and ‘why’-type questions is a better option than yes-or-no questions which seem to end the conversation as quickly as they started.

Probe for meaning

If an interviewer mentions the company is “dynamic,” follow up with “Can you tell me more about what makes the company dynamic? How does that show up in day-to-day work or team culture?” This cuts through buzzwords and gives you a clearer picture of the work environment.

I usually have two categories of probing questions. Topic-agnostic probing questions are ones like “Can you tell me more about <some topic> and how that shows up in day-to-day work?”. They often follow a pattern and you can use them everywhere.

Topic-specific probing questions are used to dig deeper after asking an important question or to avoid chaining questions (see below). For example, you may ask “Can you provide recent examples of how your team members give back to their respective professions?” Probing questions might include “What is the team budget for professional development?”

Embrace silence

After asking a question, give your interviewer a few seconds to think before jumping in (often just to avoid that awkward silence). Waiting can often prompt them to share additional, possibly revealing details about the role or company.

I sometimes struggle with embracing silence during job interviews, especially if I have a few probing questions on deck, ready to use; most of us aren’t wired to watch someone flounder. But you can often learn as much from how someone wrestles with a question as you can from the answer itself. Besides, if they need something clarified, they’ll ask.

Encourage storytelling

Try phrasing questions in a way that invites the interviewer to tell a story. For example, “Could you share a time when the company faced a challenge and how the team came together to address it?” This can reveal insights into company resilience, teamwork, and values.

And don’t forget to ask for stories that are personal and specific. This will increase the chance of getting an authentic answer while still being able to ask for more detail through probing questions.

Pay attention to non-verbal cues

During interviews, my team often finds itself looking at each other, smiling, and seeing who wants to field a question from a candidate. We do this because we all have something we want to share—this is a good thing! The body language (smiles, looking at each other, laughing) are signs to a candidate that we’re happy to hear the question and excited to share our experience.

In general, notice if an interviewer lights up or becomes guarded when discussing specific topics such as company culture or work-life balance. You can use this as a cue to either explore those areas further or to tread carefully if they seem reluctant.

This is a bit harder when interviews are virtual, but certainly not impossible. Tone and pacing/pauses are more important in such situations (vs. just body language).

Ask the ‘why’ behind the ‘what’

If the interviewer describes a recent change in the company, you might ask, “Why was this change important to the team or company’s goals?” This shows your curiosity about the company’s mission and reveals the decision-making culture.

The ‘why’ is often more interesting and involves different people, processes, and situations. The answer you get to a ‘why’ question will help you more—including seeing how that answer is considered and laid out.

You can tailor a ‘why’ question to things that you care about: “Why was that decision critical to sales performance?” is different than “Why was that decision critical to product nimbleness in the market?” Use every opportunity to extract information that you value.

Be prepared, but flexible

Come prepared with questions. However, don’t be afraid to pivot based on the interviewer’s responses. For example, if they mention a big new project, follow up with a question like, “How might that project impact this role?”

Sometimes you can react to an answer with follow-up questions that you might have from your list of probing questions. But often you’re best served by curiosity: Did the answer to your question given you the information you need? Did the answer surprise you and you need to make sure you understand what they mean?

In the research world, the ‘semi-structured’ interview uses a set of core questions to guide the thread and respect the goals of an interview. It also recognizes that rigid scripts can stifle curiosity and often beneficial ‘riffing’ within a conversational interview. So use your question list as a guide, not a rigid script.

Make it specific

When you ask a question, it is a good idea to ask for evidence to support the answer. But without qualification, you don’t have much control over what, if any, evidence is provided. Using qualifiers is a great way to define the scope of the question.

Consider asking how the company supports the professional development of its employees; this is a reasonable thing to want to know. Consider the differences (shown in bold) between these two questions:

• “How does the company support the professional growth of its employees?”
• “Can you provide a recent, high-impact example of how you supported the professional growth of someone on your team?”

Both questions ask about support for an employee’s professional development. The first question may trigger a stock answer while the second question tightens the scope considerably and makes it personal.

Make it personal

Consider “How does the company help employees?” versus “How do you, the hiring manager, help your team members?” The first question is begging to be answered using an HR or company talking point. The second forces someone to consider their personal experience and role; it becomes more authentic.

Making questions specific and personal improves your odds of getting an answer that is less abstract and more practical. If you see someone pause before answering, you’re onto something. When this tactic works, it can feel like you’ve gotten a peek behind the curtain.

Don’t chain questions

Humans have limited working memory (see Miller’s Law) and being stressed doesn’t help the situation.

Asking someone “How do you support new employees during on-boarding, learning new skills, growing professionally, and taking medical leave?” is a lot to remember and answer. Instead, cluster similar topics and try to coalesce things into several, focused questions that you can ask one at a time.