Informational Interviews: How to Actually Enjoy Them

Informational interviews feel uncomfortable for many introverts because the format seems designed for extroverts: cold outreach to strangers, small talk before substance, performing enthusiasm on demand. Yet introverts often excel at these conversations once they understand that depth, preparation, and genuine curiosity are exactly what the other person is hoping for.

Somewhere around year twelve of running my agency, a junior account manager named Priya came to me after a new business meeting. She’d sat through an hour of client conversation, said almost nothing, and was convinced she’d failed. What she didn’t know was that the client had pulled me aside afterward and said she was the sharpest person in the room. She’d asked one question, listened carefully, and asked a follow-up that nobody else thought of. That’s not a weakness. That’s a skill.

Informational interviews work the same way. The format sounds extroverted on the surface. You reach out to someone you don’t know, ask for thirty minutes of their time, and then have a conversation that’s supposed to feel natural and productive. Every part of that description can make an introvert’s stomach tighten. Yet the actual substance of what makes these conversations valuable, the preparation, the listening, the thoughtful questions, those are things introverts do naturally.

What most people get wrong about informational interviews is the assumption that they need to be performance. They don’t. They need to be genuine. And genuine is something introverts understand deeply.

Why Do Informational Interviews Feel So Hard for Introverts?

The discomfort isn’t random. It’s specific, and according to research from PubMed Central, understanding exactly where it comes from makes it much easier to handle. Studies from PubMed Central further confirm that targeted approaches based on this understanding yield better results.

Cold outreach is the first friction point. Sending a message to someone you’ve never met, asking for their time, with no guarantee of a response, feels presumptuous to many introverts. We tend to be acutely aware of other people’s energy and attention, as Psychology Today notes about introvert psychology. Asking for both, from a stranger, without obvious reciprocal value, can feel like an imposition, particularly since research from Harvard suggests introverts may face additional challenges in these initial outreach scenarios.

Then there’s the unstructured conversation format. Informational interviews don’t have a clear agenda. They’re open-ended by design, which means you can’t fully prepare for every direction the conversation might go. For someone whose mind works best when it has time to process and respond thoughtfully, according to Psychology Today, the pressure of real-time improvisation is genuinely exhausting.

A 2023 report from the American Psychological Association found that introverts consistently report higher levels of social fatigue after unscripted social interactions compared to structured ones. That’s not anxiety. That’s a neurological reality about how introvert brains process stimulation. Knowing that distinction matters, because it means the discomfort isn’t a character flaw to overcome. It’s information about how to design the experience differently.

There’s also the performance anxiety that comes from not knowing the “rules.” Networking culture is often coded in extroverted norms: be enthusiastic, be memorable, fill silences, project confidence through volume and energy. Introverts who’ve absorbed those norms often spend informational interviews trying to perform a version of themselves that doesn’t fit, which is exhausting and usually counterproductive.

The good news, and I mean this from direct experience, is that none of those norms are actually required for a successful informational interview. They’re just the dominant cultural script. You can write a different one.

What Actually Makes an Informational Interview Successful?

Over two decades of hiring, being hired, and helping people build careers through my agencies, I watched hundreds of professional conversations. The ones that led somewhere almost always had the same qualities: genuine curiosity, specific preparation, and the ability to actually listen rather than just waiting to speak.

Those are introvert strengths. Not coincidentally.

According to Harvard Business Review, the most effective professional conversations are built on what they call “listening to understand” rather than “listening to respond.” Introverts tend to do this naturally. We’re processing what the other person is saying, connecting it to what we already know, and formulating responses that actually engage with the content of what was said. That’s not a social limitation. That’s sophisticated communication.

Preparation is the other major factor. Successful informational interviews aren’t improvised. They’re shaped by research, specific questions, and a clear sense of what you’re hoping to learn. Introverts often invest more time in this preparation than extroverts do, and it shows. When you ask someone a question that demonstrates you’ve actually read their work, followed their career trajectory, or thought carefully about their industry, they notice. It signals respect for their time and intellectual seriousness. Both of those things create connection faster than small talk ever does.

Early in my career, before I had any real agency experience, I got a meeting with a creative director at one of the larger firms in the city. I’d spent a week reading everything I could find that he’d written or been quoted in. I came with five specific questions, each one tied to something he’d said publicly. He spent forty minutes with me when he’d planned for fifteen. At the end, he said something I’ve never forgotten: “You’re the first person who’s asked me something I actually had to think about.” That meeting changed my career path. And it happened because I prepared, not because I performed.

How Do You Write an Outreach Message That Doesn’t Feel Awkward?

The outreach message is where most introverts get stuck. They either overthink it into paralysis or send something so brief it reads as cold. There’s a middle path that works well, and it plays to introvert strengths.

Specificity is what separates a message that gets a response from one that gets deleted. Generic outreach (“I’d love to pick your brain”) signals that you haven’t done any work. Specific outreach (“I read your piece on agency culture and had a question about how you handled the transition to remote teams”) signals that you’re worth someone’s time.

A strong outreach message has four components. First, a specific connection point that shows you know who this person is. Second, a clear and honest reason for reaching out. Third, a specific ask with a defined time commitment. Fourth, an easy way to say yes or no without awkwardness.

consider this that looks like in practice. “I came across your work on [specific project or article] and found your perspective on [specific point] genuinely useful. I’m exploring a transition into [field] and would value twenty minutes of your time to ask a few questions about your experience. I’m happy to work around your schedule and keep it brief. No pressure if your calendar is packed.” That’s it. No elaborate flattery. No lengthy explanation of your entire career. Just specificity, honesty, and respect for their time.

Introverts write excellent messages like this because we tend to be precise with language and genuinely thoughtful about other people’s experience. The discomfort comes from the vulnerability of sending it, not from the quality of the message itself. Send it anyway. The worst outcome is silence, and silence is survivable.

What Questions Should You Bring to an Informational Interview?

Your questions are the architecture of the conversation. They determine whether the thirty minutes feels like a genuine exchange or an awkward audition. Preparing them carefully is one of the most important things you can do, and it’s something introverts are naturally positioned to do well.

For more on this topic, see one-sided-friendships-why-introverts-attract-them.

Avoid questions with obvious answers. “What does your company do?” signals you didn’t prepare. “What do you enjoy most about your work?” is fine but generic. The questions that create real conversation are the ones that invite reflection, that ask about experience rather than information, and that show you’ve thought about the complexity of what they do.

Some examples that tend to open up genuine conversation: “What surprised you most about this field once you were actually in it?” “What do you wish someone had told you before you made the transition you made?” “What does a good day look like in your role, and how often do you actually have one?” “What’s something about your industry that most outsiders misunderstand?”

Those questions work because they invite the other person to share real experience, not a rehearsed answer. People remember conversations where they felt genuinely heard and where they said something true. Introverts are good at creating those conditions because we’re genuinely interested in depth, not surface-level exchange.

Prepare eight to ten questions and expect to use four or five. The rest are backup in case the conversation moves in an unexpected direction. Having more than you need reduces the anxiety of running out of things to say, which is a common fear that preparation almost entirely eliminates.

How Do You Handle the Small Talk at the Beginning?

Small talk is the part that most introverts dread most, and it’s worth addressing directly rather than pretending it doesn’t exist.

The opening minutes of an informational interview are often the most uncomfortable because they’re genuinely unstructured. There’s no agenda, no clear purpose, just two people warming up to each other before the real conversation starts. For introverts who find small talk draining and slightly pointless, this can feel like an obstacle to get through before you reach the part that actually matters.

A few things help. First, you can transition into substance faster than you think. After a minute or two of pleasantries, it’s entirely appropriate to say something like “I really appreciate you making time. Can I jump into a question that’s been on my mind?” Most people are relieved to skip the extended warmup. They agreed to the meeting because they wanted to have a real conversation too.

Second, you can prepare a small number of bridge questions that feel more natural to you than generic small talk. Something like “How has your week been?” feels hollow. Something like “I saw you just launched [project], how’s that going?” feels specific and real. It’s still light conversation, but it’s grounded in something actual, which makes it easier to sustain.

Third, accept that some discomfort in the opening minutes is normal and doesn’t mean anything is going wrong. Introverts often interpret early awkwardness as evidence that the whole conversation is failing. It almost never is. Most informational interviews find their rhythm after the first few minutes, and the person across from you is often just as uncertain about how to start as you are.

You might also find journalism-for-introverts-who-hate-interviews helpful here.

Psychology Today has written extensively about how introverts often have richer one-on-one conversations than extroverts do, precisely because they’re more comfortable with the kind of focused, substantive exchange that informational interviews are designed to be. The small talk is the price of admission. Once you’re past it, you’re in territory where you naturally excel.

How Do You Recover When the Conversation Stalls?

Silences happen. Conversations stall. The person you’re talking to gives a short answer and then looks at you expectantly. This is the moment that can make introverts freeze, because it feels like a test you’re suddenly failing.

The most effective recovery is a follow-up question, and introverts are actually very good at these when they’re not panicking. A follow-up question takes something the other person just said and goes one level deeper. “You mentioned that the transition was harder than you expected. What made it harder?” That’s it. You don’t need to fill the silence with commentary or summary. You just need to show that you heard what they said and you want to know more.

This is where preparation pays off in a second way. When you’ve thought carefully about your questions in advance, you have a mental reservoir to draw from when the conversation loses momentum. You’re not improvising from zero. You’re selecting from options you’ve already considered.

I’ve had conversations in client meetings that went completely off the rails from what I’d planned. The clients would answer a question in two sentences and then go quiet, looking at me like I was supposed to produce something brilliant on the spot. What saved those meetings every time wasn’t spontaneous charm. It was having thought carefully enough about the topic that I could pivot to a related question without losing the thread. Preparation is a form of confidence that doesn’t require you to be naturally gregarious.

What Should You Do After the Informational Interview?

The follow-up is where introverts often outperform everyone else, because it requires exactly the kind of thoughtful, written communication that comes naturally to many of us.

Send a thank-you note within twenty-four hours. Not a generic “thanks for your time” message. A specific one that references something from the conversation. “I’ve been thinking about what you said about the difference between managing up and managing expectations. That reframe is genuinely useful and I’m going to carry it forward.” That kind of specificity tells the person that you were actually present in the conversation, that you processed what they said, and that their time had real impact.

This is something introverts do well because we tend to remember the substance of conversations, not just the social surface of them. We process what people say. We connect it to other things we know. We notice when something shifts our thinking. Writing that down and sending it back to the person creates a genuine connection that a generic thank-you never does.

Beyond the immediate follow-up, consider how to maintain the relationship over time without it feeling forced. Sharing an article that’s relevant to something they mentioned, congratulating them on a professional milestone, or sending a brief update when you’ve acted on their advice are all ways to keep a connection alive without requiring ongoing social energy. These are low-pressure, asynchronous interactions that introverts generally find much more manageable than scheduled social time.

How Do You Build a Consistent Practice Without Burning Out?

One of the biggest mistakes introverts make with informational interviews is treating them like a sprint. They schedule four in a week, exhaust themselves, and then avoid them entirely for three months. That cycle produces neither relationships nor results.

A sustainable practice looks different. One conversation every two weeks is enough to build meaningful professional connections over time without depleting your social reserves. That’s twenty-six conversations in a year, which is a substantial network built on genuine exchange rather than mass outreach.

Build recovery time into the schedule deliberately. If you have an informational interview on a Tuesday, protect Wednesday morning for quiet work. Don’t schedule back-to-back social or professional conversations without space between them. This isn’t indulgence. A 2019 study published by the National Institutes of Health found that introverts show measurably different patterns of cortisol response to sustained social interaction compared to extroverts, suggesting that recovery time is a physiological need, not a preference.

Also, be selective about who you reach out to. Not every informational interview is worth the energy it costs. Prioritize people whose work genuinely interests you, whose career path connects to something you’re actually considering, or whose perspective would add something real to how you think about your own work. Quality over volume is a principle that fits introvert energy budgets much better than the “talk to everyone” approach that networking culture often promotes.

When I was building my second agency, I made a deliberate choice to have fewer but deeper professional relationships than most agency owners I knew. I wasn’t at every industry event. I wasn’t collecting business cards. I was having one or two substantial conversations a month with people I genuinely wanted to know. That approach built the kind of trust and mutual respect that actually generates referrals and collaboration. Depth compounds in ways that breadth doesn’t.

Can Video Calls Make Informational Interviews Easier?

For many introverts, yes. Video calls remove several of the friction points that make in-person informational interviews harder: the physical navigation of a new space, the ambient noise of a coffee shop, the logistical coordination of getting somewhere on time while managing pre-conversation anxiety. A video call happens in your own environment, which gives you a meaningful degree of control over your energy state going in.

You can also have your notes visible without it being awkward. In a coffee shop, pulling out a page of prepared questions can feel formal or overly rehearsed. On a video call, having notes just off-screen is completely normal and nobody knows they’re there. That preparation safety net reduces anxiety significantly.

Phone calls are another option worth considering for shorter conversations. Without the visual component, many introverts find they can focus more completely on what’s being said rather than managing their own facial expressions and body language simultaneously. Some of the best professional conversations I’ve ever had happened on the phone, where the only thing that mattered was what we were actually saying to each other.

The format should serve the conversation, not conform to some standard of what a “real” informational interview looks like. Choose the medium that lets you show up most fully. That’s the one that will produce the best outcome for both people.

What If You Feel Like You Have Nothing to Offer in Return?

This is one of the quieter fears that doesn’t always get named directly. Many introverts feel uncomfortable with the perceived imbalance of an informational interview: you’re asking for someone’s time and expertise, and what are you giving back?

More than you think. People who are willing to share their experience and perspective generally do so because they find it meaningful, not because they expect something transactional in return. Most professionals who agree to informational interviews do so because they remember being earlier in their career and wanting exactly this kind of conversation. The act of asking someone thoughtful questions about work they care about is itself a form of value. It’s attention, genuine interest, and the opportunity to articulate things they may not often get to say out loud.

That said, if the asymmetry bothers you, there are real ways to add value without pretending to expertise you don’t have. Share an article that’s relevant to something they mentioned. Introduce them to someone in your network who might be useful to them. Write a LinkedIn recommendation that specifically reflects something they said in your conversation. These are small, genuine gestures that introverts tend to execute well because they require thought rather than social performance.

The APA’s research on social reciprocity suggests that people evaluate relationships less on strict exchange balance and more on whether they feel genuinely seen and respected. An informational interview where someone feels heard and appreciated creates a positive relational memory regardless of any formal exchange of value. Your thoughtful questions and genuine attention are the contribution. They matter more than most introverts realize.

Informational interviews aren’t a networking performance. They’re a conversation between two people who both have something real to offer. Once you stop measuring yourself against an extroverted standard that was never designed for how you work, the whole format becomes something you can actually look forward to.

Explore more career and networking strategies built around introvert strengths in our complete Career Development hub at Ordinary Introvert.

About the Author

Keith Lacy is an introvert who’s learned to embrace his true self later in life. After 20 years in advertising and marketing leadership, including running agencies and managing Fortune 500 accounts, Keith now channels his experience into helping fellow introverts understand their strengths and build fulfilling careers. As an INTJ, he brings analytical depth and authentic perspective to every article, drawing from both professional expertise and personal growth.

Frequently Asked Questions

Are informational interviews worth it for introverts who find networking exhausting?

Yes, and often more so than for extroverts. Informational interviews are one-on-one, focused, and built around substantive conversation rather than social performance. Those conditions play directly to introvert strengths. The energy cost is real, but the return on a single well-prepared informational interview often exceeds that of an entire networking event. Scheduling them selectively and building in recovery time makes them sustainable without depleting your reserves.

How many informational interviews should an introvert aim for each month?

One or two per month is a sustainable pace for most introverts. That’s enough to build meaningful professional connections over time without creating the kind of social fatigue that leads to avoidance. Quality matters far more than volume. Two well-prepared, genuine conversations will produce better results than six rushed ones, and they’ll cost you less in recovery time and energy.

What should you do if the conversation goes quiet and you don’t know what to say?

Use a follow-up question based on something the person just said. Take one element of their last answer and ask to go one level deeper. “You mentioned that was harder than you expected. What made it harder?” That kind of question is easy to generate when you’ve been genuinely listening, and it signals that you’re engaged rather than just waiting for your turn. Preparing eight to ten questions in advance also gives you a reservoir to draw from when the conversation loses momentum.

Is it acceptable to use notes during an informational interview?

Completely. Having prepared questions in front of you signals that you took the meeting seriously and respected the other person’s time enough to prepare. In a video call, notes just off-screen are invisible. In person, a small notebook with questions is a sign of professionalism, not a weakness. Most people who agree to informational interviews are genuinely pleased when the person they’re meeting has done real preparation. It makes the conversation better for both of you.

How do you write a follow-up message that actually strengthens the relationship?

Send it within twenty-four hours and make it specific. Reference something concrete from the conversation, something they said that shifted how you think about a topic, or a question they raised that you’re still considering. Generic thank-you notes are forgotten immediately. Specific ones create a genuine relational memory. Introverts tend to excel at this because they process conversations deeply and remember the substance of what was said, not just the social surface of the exchange.