Informational Interviews: How to Actually Enjoy Them

I used to think informational interviews were just networking with a fancier name. Twenty years of running an agency taught me that assumption was completely wrong.

During my years building client relationships in advertising, I avoided the whole “can we grab coffee to pick your brain” thing like it was a particularly draining office party. Too transactional. Too performative. The idea of reaching out cold to industry contacts made me want to reschedule my entire day.

But here’s what shifted my perspective: Informational interviews aren’t about networking at all. They’re about learning. Once I understood that distinction, the entire practice went from energy drain to something closer to focused research, which actually plays to the strengths we already have.

Professional preparing for informational interview with notebook and research materials on desk

Why Standard Networking Advice Misses the Mark

Most career guidance treats informational interviews as mini job interviews where you’re supposed to impress someone enough that they remember you for future opportunities. That framing creates exactly the kind of pressure that makes introverts want to bail before the conversation even starts.

The advice typically sounds like this: work the room, collect contacts, follow up aggressively, keep yourself top of mind. This approach assumes energy comes from social interaction rather than gets depleted by it. When you’re someone who needs substantial recovery time after professional socializing, this model fundamentally doesn’t work.

A 2023 study published in The Career Development Quarterly examined how university students developed networking self-efficacy through informational interviews. The research found that structured, one-on-one conversations with professionals increased participants’ confidence in networking activities far more effectively than traditional networking events. The controlled, focused nature of these interactions particularly benefited those with lower initial social confidence.

I spent years trying to force myself into the extroverted networking mold. Managing Fortune 500 accounts meant attending industry events, conference receptions, and client dinners that left me completely drained. My calendar looked successful but my energy levels told a different story. I’d schedule nothing for the day after major networking events just to function.

What finally worked was reframing these conversations around genuine curiosity rather than strategic positioning. Instead of asking “how can this person help my career,” I started asking “what can I learn from this person’s experience?” That subtle shift changed everything about how I approached professional conversations.

The Preparation Advantage

Here’s where introverts actually excel at informational interviews: preparation plays to our strengths. While spontaneous networkers might wing it at industry mixers, we do better with structure and research.

Before any conversation, I spend time understanding the person’s background, their company’s recent initiatives, and the broader industry context. This isn’t busywork or anxious overpreparation. It’s recognizing that depth of understanding matters more than breadth of connections. Research from Northwestern’s Kellogg School of Management confirms that introverts can leverage their natural preference for meaningful, one-on-one conversations as a significant networking advantage.

Introvert writing thoughtful questions and notes in journal for upcoming career conversation

The preparation I do before informational interviews typically includes checking recent company announcements, reading the person’s LinkedIn profile thoroughly, finding any articles they’ve written or interviews they’ve given, and noting specific questions their background raises. This level of research transforms what could feel like small talk into substantive conversation.

When I sit down with someone, I’m not scrambling for generic questions. I’m asking about specific decisions they made in their career that relate directly to challenges I’m working through. The conversation becomes genuine exchange of insights rather than networking theater. This authenticity registers with people, particularly those who also value depth over surface-level interaction.

My question list typically includes three categories: career trajectory questions that explore how someone made specific transitions, day-to-day reality questions that cut through job title glamour, and industry insight questions that tap into their insider perspective. The goal isn’t to use every question but to have enough prepared that the conversation can go wherever proves most valuable.

Reframing the Ask

Most advice suggests phrases like “I’d love to pick your brain” or “can we grab coffee to chat about your career?” These requests feel uncomfortably vague. What exactly am I asking for? How much time? What specific value will they get from this exchange?

I frame requests more specifically: “I’m working on transitioning from agency work to in-house marketing roles. Would you have 20 minutes to discuss how you made that shift three years ago? I’d particularly like to understand how you approached salary negotiations and team structure expectations.”

This approach respects everyone’s time while making the conversation’s purpose clear. According to research on effective informational interviewing practices, clearly defining the conversation’s scope and duration significantly increases acceptance rates and conversation quality. People appreciate knowing exactly what you’re asking before they commit.

The specificity also helps me feel less awkward about reaching out. I’m not asking someone to be my mentor or solve my career problems. I’m requesting focused input on specific questions where their experience directly applies. That’s a reasonable ask that most professionals are willing to accommodate.

During my agency years, I received dozens of these requests myself. The ones I said yes to were always the specific, time-bounded asks that demonstrated someone had already done their homework. Generic “pick your brain” requests usually got ignored, not because I didn’t want to help but because I couldn’t figure out what specific value I could provide.

The Small Talk Problem

Extended small talk before getting to substantive topics drains my energy faster than almost anything else in professional settings. The weather, traffic, weekend plans, these conversational warm-ups feel like wasted time when I’m genuinely interested in someone’s professional expertise.

Quiet workspace with typewriter representing focused preparation for meaningful professional dialogue

After initial greetings, I transition quickly: “Thanks so much for making time. I know you’re busy, so I’d like to jump right into what I’m curious about if that works for you?” Most people seem relieved to skip the performative chitchat and get to substance.

This direct approach works because the other person already knows why we’re meeting. They’ve agreed to discuss their career experience, so moving into those questions feels natural rather than abrupt. The key is framing it as respecting their time rather than being socially awkward.

Studies examining introversion and social engagement patterns found that introverts demonstrate strong collaborative skills in focused, purpose-driven interactions. When conversations have clear objectives, introverts often outperform extroverts at maintaining depth and extracting valuable insights. The challenge isn’t the conversation itself but the unfocused social warm-up that precedes it.

Some conversations naturally include personal elements that emerge organically from the discussion. If someone mentions their kids or a recent vacation in the context of explaining a career decision, that connection feels authentic. But forcing those personal touches before establishing professional rapport just creates more social friction for everyone involved.

Virtual Versus In-Person

The shift to remote work created something of an advantage for introvert-friendly informational interviews. Video calls eliminate travel time, reduce energy expenditure, and create built-in time boundaries that feel less awkward to enforce than in-person meetings.

When someone suggests meeting for coffee, I often propose a Zoom call instead. I frame this as respecting their schedule: “Would a 30-minute video call work better than meeting in person? I know how valuable your time is, and this way we can both avoid commute time.”

Most professionals actually prefer this format. The time boundaries are clearer, the conversation stays focused, and there’s no pressure to extend the meeting into lunch or additional topics. Career development research from MIT shows that virtual informational interviews often produce higher-quality exchanges because both parties can reference notes, resources, and relevant materials more easily than during in-person meetings.

Video calls also allow me to have my prepared questions visible without seeming overly scripted. In coffee shop meetings, pulling out detailed notes can feel awkward. On Zoom, having a second monitor with research and questions feels professional rather than anxious.

The energy management aspect matters too. After a 30-minute video call, I can close my laptop and move directly into focused work. After an in-person meeting, I need recovery time to process the social interaction before returning to productivity. For someone managing limited social energy, that difference compounds significantly across multiple conversations.

The Follow-Up Framework

Standard networking advice emphasizes aggressive follow-up: send thank-you notes immediately, reach out monthly to stay top of mind, look for excuses to reconnect. This approach assumes more contact always equals better relationships, which isn’t necessarily true.

I follow up with purpose rather than frequency. After an informational interview, I send a brief thank-you email that references specific insights from our conversation and how I’m applying them. Then I reconnect only when I have something genuinely relevant to share: an article related to our discussion, an update on implementing their advice, or a specific new question their guidance raised.

This measured approach respects boundaries while maintaining authentic connection. People remember quality interactions more than frequent check-ins. When I do reach out again, they remember our substantive conversation rather than feeling like I’m just maintaining a contact for career leverage.

Person crafting personalized follow-up message after informational interview conversation

One executive I interviewed about transitioning from agency to in-house roles gave me advice about negotiating autonomy in corporate structures. Six months later, when I’d successfully implemented that approach in a new position, I sent him a brief update explaining what worked. That single follow-up maintained the relationship far more effectively than monthly generic check-ins would have.

The key is making each contact purposeful. I keep notes after informational interviews that include specific advice given, topics we discussed, and potential future points of connection. When something relevant emerges, I have context to reach out authentically rather than forcing connection.

Managing the Emotional Labor

Even well-structured informational interviews require emotional energy. Preparing questions, maintaining engaged conversation, processing insights, and following up all draw from limited social reserves. Pretending otherwise leads to burnout.

I limit informational interviews to two per month maximum. This pace allows me to prepare properly, engage fully during conversations, and implement insights before seeking new input. When I tried scheduling more frequently, the quality dropped noticeably. I started asking generic questions, not listening as carefully, and treating conversations as boxes to check rather than learning opportunities.

Research from Johns Hopkins examining social expectations found that introverts typically anticipate social interactions will be more draining than they actually are. However, the study also confirmed that social engagement does require genuine energy expenditure for introverts, even when the experience proves positive. Acknowledging this cost helps us plan appropriately rather than pushing through until we hit exhaustion.

I schedule informational interviews on days when I have fewer other meetings and can block recovery time afterward. This isn’t weakness or being difficult. It’s recognizing how professional growth actually works for introverted professionals. Sustainable engagement beats forced overextension.

Some months I don’t schedule any informational interviews. If I’m focused on implementing previous insights or my social battery is depleted from other professional demands, that’s fine. Career development isn’t a race. Quality of connections and depth of learning matter more than volume of contacts.

The Value Exchange Myth

One barrier that stopped me from doing informational interviews earlier was thinking I needed to offer equivalent value in return. What could I possibly give a senior executive that would justify their time? This mindset created unnecessary pressure.

Most professionals actually enjoy sharing their experience when asked thoughtful questions. According to Columbia University’s career research, people who conduct informational interviews report that both parties benefit from the exchange. The person being interviewed gets to reflect on their career decisions, crystallize their thinking, and feel helpful. Those are genuine benefits, not just polite rationalizations.

I stopped trying to manufacture reciprocal value and instead focused on asking questions that let people share expertise they’ve genuinely earned. That’s the exchange. They provide insights from experience, I provide engaged listening and appreciation for their time. Neither party needs to do more.

During my agency years, the best informational interview requests I received came from people who were clearly wrestling with substantive professional questions, not just collecting contacts. Getting to think through challenges I’d already solved felt valuable in itself. The person wasn’t taking from me; we were having a genuinely interesting conversation.

When to Skip Them Entirely

Not every career question requires an informational interview. Sometimes research, reading, or experimenting provides better answers with less energy expenditure. I do informational interviews when I need insider perspective on specific decisions, want to understand organizational culture details not visible from outside, or need guidance on approach rather than just information.

Calm reflective scene symbolizing thoughtful approach to career networking and relationship building

If my question can be answered through public resources, informational interviews waste everyone’s time. Before reaching out, I ask myself: What specific knowledge does this person have that I can’t get elsewhere? If the answer is vague, I do more research first.

I also avoid informational interviews during high-stress periods or when my social capacity is already stretched. Career development activities should support sustainable work patterns, not add pressure. If scheduling another conversation feels draining before it even happens, that’s important feedback to respect.

Some career stages don’t require informational interviews at all. Early in transitions when you’re still building foundational knowledge, reading and observation often provide more value than conversations. Later, when you’re making specific strategic decisions, targeted conversations become more useful. Timing matters as much as technique.

The Long-Term Approach

The most valuable professional relationships I’ve built didn’t come from aggressive networking or frequent check-ins. They developed from a small number of genuinely substantive conversations that created foundation for ongoing exchange.

One conversation with a marketing director about agency-to-corporate transitions led to three follow-up discussions over two years as I implemented her advice and encountered new questions. That relationship proved more valuable than dozens of surface-level networking contacts because it had real depth.

Quality connections built through thoughtful informational interviews create professional relationships that sustain over time. Research published in Harvard Business Review confirms that smaller, more intimate professional networks often prove more powerful than large, superficial ones, particularly for introverts who excel at maintaining depth in relationships.

This approach requires patience. Building a network of meaningful professional relationships takes years, not months. But those relationships provide better career guidance, more authentic support, and stronger foundations for collaboration than aggressive contact collection ever could.

I now view informational interviews as one tool among many for professional development, not a mandatory networking activity to force myself through. When used strategically and authentically, they provide genuine value. When approached as obligatory career maintenance, they drain energy without delivering proportional benefit.

Working with your natural communication style rather than against it makes career development sustainable. Informational interviews can absolutely work for introverts, but only when we stop trying to do them the extroverted way.

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About the Author

Keith Lacy is an introvert who’s learned to embrace his true self later in life. With a background in marketing and a successful career in media and advertising, Keith has worked with some of the world’s biggest brands. As a senior leader in the industry, he has built a wealth of knowledge in marketing strategy. Now, he’s on a mission to educate both introverts and extroverts about the power of introversion and how understanding this personality trait can unlock new levels of productivity, self-awareness, and success.

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