Interviewing the Interviewer

Here's something job seekers forget: the interview is a two-way evaluation.

Yes, they're deciding whether to hire you. But you're also deciding whether to work for them. And yet most candidates spend the entire interview performing—trying to give the right answers, trying to impress—without gathering the information they need to make a good decision.

This post is about flipping that script. Not with arrogance, but with the clear understanding that you're evaluating them as much as they're evaluating you.

Why This Matters

Think about what an interview actually is from the employer's perspective. They have a list of questions designed to get you off your rehearsed answers and reveal who you really are. Open-ended questions. Behavioral questions. "Tell me about a time when..." questions.

They're trying to get past your surface presentation to understand how you actually think, work, and behave.

You should be doing the exact same thing to them.

The interview is your only window into what this job will actually be like. The job posting was marketing. The recruiter call was marketing. The interview is your chance to see behind the curtain—if you ask the right questions.

The Killer Question

There's one question I think every candidate should ask at the end of an interview:

This question works because it does several things at once:

1. It gets them off their script. They've been asking you open-ended questions all interview. Now you're asking them one. They have to actually think.
2. It reveals what they really want. The job posting says one thing. Their actual priorities might be different. This question surfaces the gap.
3. It shows you how they think. Do they have a clear vision? Are they making it up as they go? Can they articulate what success means?
4. It gives you information to close. If they describe the ideal candidate and it sounds like you, you can connect those dots explicitly. "That's interesting—that aligns well with my experience doing X."
5. It helps you assess fit. Their description of the ideal candidate might not sound like you at all. That's valuable information. Better to know now than after you're hired.

I've used this question in interviews, and the answers are often surprising. Sometimes the interviewer describes someone completely different from what the job posting suggested. Sometimes they haven't really thought it through. Sometimes they light up and give you exactly the insight you need.

Before You Deploy These Questions

A word of caution before I give you more questions: don't turn this into an interrogation.

These are examples. Don't ask all of them. Pick two or three that matter most to you, read the room, and deploy them strategically. The goal is a conversation, not a checklist.

Most importantly: pay attention. Really listen to what they're saying.

It's so easy in the pressure of an interview—whether it's a phone call, a Zoom, or in person—to be so wrapped up in your own performance that you're not actually listening. You're rehearsing your next answer while they're talking. You're worrying about how you came across on the last question.

But if you actually listen, the conversation itself will guide you. You'll notice gaps. You'll hear things that raise questions. You'll understand what matters to them. And that's when you deploy your questions strategically—not from a script, but from genuine curiosity about something they said.

Listening also makes you a better candidate. When you take time to consider your answer instead of rushing to fill silence, you give more thoughtful responses. When you take the whole conversation into context, you don't over-explain or repeat yourself. You're present, engaged, and human.

Watch Who's Doing the Talking

Here's a meta-observation that's been really helpful for me: pay attention to how much of the interview they're talking versus you're talking.

If they spend the whole time talking and you're barely getting a word in, that's telling. It often means they're trying to sell you on this job—or on themselves—rather than having a real conversation.

I see this happen a lot when you're being interviewed by the leader of a business, especially at small companies. It becomes obvious that what they're really trying to hire is a mini-me, a clone of themselves. They spend the interview over-explaining and pitching you on their perspective, because they're looking for someone who already matches how they think.

The problem? If they do all the talking, they're not actually getting a sense of you. They're talking themselves into approving what they've already decided. And they may leave the interview with an inflated sense of who you are—because they weren't really listening to you.

In a healthy hiring process, the employer should have worked out ahead of time: what is the profile of our ideal candidate? That's part of why the killer question ("what does your ideal candidate look like?") is so powerful. If they can't answer it, this process is going to be harder to navigate than it should be.

The best interviews have balance. Both sides talking, both sides listening, both sides learning.

More Questions That Reveal Reality

With that context, here are other questions designed to get past the surface. Pick the ones that matter to you based on what you're hearing:

About the role:

• "What does a typical day or week look like in this role?" (Forces specifics beyond the job description)
• "What are the biggest challenges the person in this role will face in the first six months?" (Reveals problems they know exist)
• "How will success be measured? What does exceeding expectations look like?" (Clarifies actual priorities)
• "Why is this role open? Is it new, or did someone leave?" (Context on the situation—and if someone left, why?)

About the team and management:

• "How would you describe your management style?" (For your potential boss)
• "How does the team handle disagreement? Can you give me an example?" (Reveals conflict culture)
• "What's the team's biggest strength? What's an area where you're trying to improve?" (Balanced question that invites honesty)
• "How long have people on the team been here? What's kept them?" (Tenure and retention signals)

About the company:

• "What's changed most about this company in the last year or two?" (Reveals trajectory and stability)
• "What's the hardest part about working here?" (Invites honest criticism—watch for deflection)
• "If you could change one thing about the company, what would it be?" (Similar—reveals real concerns)
• "Why do you work here? What keeps you?" (Personal and revealing—authentic enthusiasm vs. rote answers)

About growth and future:

• "Where have people in this role gone next?" (Career path visibility)
• "What would I need to demonstrate to be considered for advancement?" (Clarity on expectations)
• "How does the company invest in professional development?" (Actions, not just policy)

How to Read the Answers

The content of their answers matters, but so does how they answer.

Good signs:

• They think before answering (genuine engagement)
• They give specific examples, not just generalities
• They acknowledge challenges honestly
• They seem to enjoy talking about their work and team
• Their answers are consistent with each other and with what you've heard from others

Warning signs:

• They deflect or give non-answers ("Oh, there's no typical day here!")
• They seem uncomfortable with honest questions
• They oversell relentlessly without acknowledging any downsides
• Different interviewers give you contradictory information
• They can't articulate what success looks like

The Mindset Shift

Most candidates approach interviews trying to get an offer. That's understandable—you need a job.

But there's a difference between wanting an offer and wanting this specific offer. If you're desperate for any offer, you won't ask the hard questions. You'll accept vague answers. You'll ignore warning signs.

This mindset shift is powerful. It makes you more confident in the interview (because you're a peer evaluating fit, not a supplicant begging for a job). It helps you gather better information. And paradoxically, it often makes you more attractive as a candidate—because genuine engagement and thoughtful questions signal competence.

Signs of Dysfunction You Can Spot in an Interview

Sometimes the interview itself reveals problems. Watch for:

• Process chaos: Interviews that start late, go over time, or involve people who seem confused about why they're there suggest organizational dysfunction.
• Inconsistent stories: If different interviewers give you different descriptions of the role, team, or company direction, there's misalignment.
• Inability to answer basic questions: If they can't tell you what success looks like, or how performance is measured, or why the last person left, those are gaps that will affect you.
• All selling, no substance: If every answer is about how great everything is, they're either not being honest or not self-aware. Neither is good.
• Bad-mouthing: If they speak negatively about former employees, competitors, or other teams, that says something about the culture.
• Pressure tactics: "We need to move fast on this" or "other candidates are in process" might be true, but they might also be manipulation.

What You're Really Trying to Learn

Underneath all these specific questions, you're trying to answer a few fundamental things:

1. Is this role what they say it is? Does the reality match the job posting and the description?
2. Will I succeed here? Not just "can I do the work," but does this environment set me up for success?
3. Will I be happy here? Does the culture, management style, and day-to-day reality fit how I work best?
4. Is this organization healthy? Not perfect—nowhere is perfect—but functional, stable, well-managed?
5. What am I not being told? What are they avoiding, deflecting, or glossing over?

Putting It Into Practice

At the end of every interview, you should have time to ask questions. Use it. Don't ask questions you could Google. Don't ask questions designed to impress. Ask questions designed to inform your decision.

Take notes during the interview, including on their answers to your questions. Debrief yourself afterward: What did I learn? What's still unclear? What concerns emerged?

If you're going through multiple rounds, your questions should evolve. Early rounds: understand the role and team. Later rounds: dig into specifics, address concerns that emerged, meet more people.

The goal is to leave the process knowing whether this is the right opportunity for you—not just whether they'll make you an offer.

Coming Up: Negotiation

In Part 3, we'll talk about what happens if they do make an offer: how to negotiate without playing games, when to push and when to accept, and how to get what you actually need.

But negotiation only matters if you've done the work of evaluation first. If you don't know whether this is the right opportunity, you can't negotiate from a position of clarity.

Know what you're getting into. Then negotiate for what you need.

New to this series? Start with Part 1: Know What You're Getting Into.

Need help with interview prep? Check out You Got the Interview: How to Actually Prepare.