Questions to Ask for an Informational Interview: 50+ That Actually Work

An informational interview is a conversation you request with a working professional — through LinkedIn, an alumni network, or a warm introduction — specifically to learn. You are not asking for a job. You are asking for unfiltered insight: what the work actually feels like day to day, how someone built their career, whether a company's culture matches what you've read from the outside.

The format is typically 20-30 minutes, over a video call or coffee. The person doing it well is asking questions, listening carefully, and taking notes. The person doing it wrong is treating it as a covert job interview, angling for a referral within five minutes.

A 2022 LinkedIn analysis found that 70% of jobs are filled through networking before or alongside any formal posting. Informational interviews are one of the most direct ways to build those relationships before an opening exists — not after everyone else is already applying.

Here is why the questions you bring matter more than almost anything else: unlike a job interview, you control the agenda. The professional across from you is giving you 30 minutes they could spend on anything. How you use that time — the specificity of your questions, the curiosity you signal, the research you clearly did in advance — is what they walk away remembering. A sharp, specific question is a stronger first impression than any cover letter.

The most common mistake in informational interviews is asking questions that job descriptions already answer. If you ask “What does a product manager do at your company?” you will get a version of the job listing. That tells you nothing a five-minute Google search couldn’t.

The questions worth asking are the ones only a practitioner can answer honestly.

**Questions about the work itself:**

“On a random Tuesday afternoon — not a launch week, not a crisis — what does your work actually look like?”

“What takes up more of your time than it should? And what do you wish took more?”

“What’s the hardest part of this role that never shows up in the job description?”

“How does your team decide what to prioritize when multiple things feel urgent at the same time?”

“What’s a decision you made in the past few months that you’re still not sure was the right call?”

“What do people get wrong about this field when they’re coming in from the outside?”

“What skills have mattered most in practice — not what the job listing asks for, but what you actually use every week?”

“If you could change one thing about how this role is structured, what would it be?”

**What to listen for:** The most valuable answers are the ones that don’t match what you expected. If someone describes their work as 80% stakeholder management when you assumed it was 80% hands-on building, that’s essential information. Write down the specifics. They will shape every follow-up question and tell you more about job fit than any description ever will.

Informational interviews are one of the few places where you can hear what a career actually looked like from the inside, not just how it reads on a public profile. The same job title can represent radically different trajectories depending on the path someone took.

**Questions about how they got here:**

“How did you land in this work? Was it intentional or did you kind of fall into it?”

“What did your first year in this field teach you that you didn’t expect going in?”

“Looking back, what would you have done differently when you were at the point I’m at now?”

“What’s the most useful skill you’ve built in this role that you didn’t have when you started?”

**Questions about where things go from here:**

“Where do people in this role typically go next? What does a strong next step look like from here?”

“Are there things people do early in this career that set them back without realizing it?”

“How has the field shifted since you started, and what are you watching to understand where it’s heading?”

“If you were advising someone coming from my background — [briefly describe yours] — what would you tell them to prioritize?”

A note on the retrospective questions: people genuinely enjoy being asked what they know now that they wish they’d known earlier. It’s an invitation to be generous with experience. Most professionals who agree to an informational interview want to help. Retrospective questions give them a clear and comfortable way to do exactly that.

The structure of your informational interview matters as much as the questions themselves. Thirty minutes that jumps between unrelated topics leaves both people unsure of what they actually covered. One that flows logically — from broad context to specific insight — feels like a real, productive conversation.

Just as important as what you ask is what you don’t. Several question types consistently undermine informational interviews.

**Questions that read as “give me a job”:** Asking “Is your company hiring right now?” in the first 15 minutes converts a professional development conversation into an awkward pitch. If there’s a genuine moment to mention it, that happens at the end — and only if the other person raises it first or the conversation makes it genuinely natural.

**Questions answerable in five minutes of research:** “What does your company do?” or “How long have you worked there?” tells the person you didn’t prepare. You’ve already wasted a portion of the time they agreed to give you. Read their LinkedIn profile, their company’s about page, and anything they’ve written or published before you get on the call.

**Questions that put someone in an uncomfortable position:** Compensation questions belong in a job conversation after an offer, not in an informational interview. Similarly, asking someone to evaluate current colleagues or criticize leadership directly puts them in a spot they can’t answer honestly even if they wanted to.

**Questions too broad to be useful:** “What advice do you have for someone like me?” sounds generous but gives the professional nothing to work with. They have to guess what you need. More specific: “Given that I’m coming from [background] and trying to move toward [area], what’s one thing you’d prioritize if you were starting where I am now?”

**Questions about things they’ve already answered publicly:** If you requested this informational interview after reading someone’s writing, watching a talk, or following their work, referencing those specifically shows you engaged with their actual thinking. Asking questions they’ve publicly answered at length is a missed opportunity.

The gap between knowing good questions and using them well in a live conversation is larger than most people expect. Reading a list of questions to ask for an informational interview is not the same as deploying them in a 30-minute call where you also have to listen, adapt, and follow up spontaneously when the answer takes you somewhere unexpected.

Effective preparation has three components.