Let’s be real for a second. Most networking sucks. You sit there, clutching a lukewarm latte, desperately trying not to look like you're begging for a job while the person across from you checks their watch. You’ve probably heard the standard advice: "just be yourself" or "ask about their day." Honestly? That’s terrible advice. If you want to actually move the needle on your career, the questions to ask during a coffee chat need to be way more surgical than "So, do you like working here?"
Most people treat these meetups like a casual hang. They aren't. They are low-stakes interviews where the person across the table is subconsciously deciding if they’d ever want to vouch for you. According to LinkedIn’s long-standing data, upwards of 85% of jobs are filled via networking. You aren't there for the caffeine; you're there for the endorsement.
Why Your Questions Usually Fail
The biggest mistake is being too generic. I’ve seen it a thousand times. A student or a career-changer asks, "What's a typical day like?" That is a boring question. It’s a chore to answer because most jobs don't have a "typical" day, and you're making your contact do the heavy lifting of synthesizing their entire work-life into a soundbite. It's exhausting for them.
Instead, you need to flip the script. You want to ask questions that make them look smart and feel valued. People love talking about their hurdles and how they jumped over them. If you can tap into that, you aren't just another name in their inbox. You become a peer.
The "Pain Point" Strategy
Try asking about the stuff that keeps them up at night. Not in a weird way, obviously. But something like, "If you could hire someone tomorrow to solve just one recurring headache for your team, what would that be?"
See what happened there? You didn't ask about the job description. You asked about the gap in their team. This identifies exactly how you should pitch yourself later. It’s a trick used by high-level consultants to land seven-figure contracts, and it works just as well for a mid-level marketing role or a junior dev position.
The High-Value List: Questions to Ask During a Coffee Chat
You need a mix. Start with the "why" and move into the "how." Don't go through these like a checklist—that feels robotic and weird. Pick three or four that actually fit the vibe of the conversation.
- "What’s the one thing you wish you knew about this company before you signed the offer letter?" This usually gets a laugh, but the answer is gold. It reveals the culture quirks that aren't in the handbook.
- "I noticed [Company Name] recently pivoted toward [Trend]. How has that actually changed your daily workflow?" This shows you did your homework. You aren't just looking for a job; you’re looking at their job.
- "Who else in this space is doing things that actually impress you?" This is a sneaky way to find out who their competitors are and who else you should be chatting with.
- "What does a 'win' look like for your department six months from now?" This tells you their priorities. If they say "retention" and you’re a "growth" person, you know there’s a mismatch.
Basically, you’re looking for the narrative. Everyone has a story they tell themselves about their career. Your goal is to find your place in that story.
Avoiding the Awkward Silence
We’ve all been there. The conversation hits a lull. You’re staring at the foam in your cup. To avoid this, you need "bridge" questions. These are low-pressure but keep the momentum going.
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Think about asking about their transition. "You moved from finance to product management—what was the biggest 'culture shock' in that first month?" It’s personal but professional. It shows you’ve looked at their LinkedIn and you actually care about their trajectory, not just what they can do for you right now.
The Expert View on "The Ask"
Herminia Ibarra, a professor at London Business School and an expert on professional identity, often talks about "outsight." It’s the idea that we learn who we are by testing things out in the real world. Coffee chats are the ultimate outsight tool. But they only work if you're getting raw data. If you’re asking polite, "safe" questions, you’re getting "safe," useless data.
Ask about the failures. "What’s a project that didn't go as planned, and how did the leadership react?" That tells you more about a company’s soul than any Glassdoor review ever could. If the leadership pointed fingers, run. If they did a blameless post-mortem, you might have found a winner.
The Technical Side of the Conversation
If you’re in a specialized field like tech or data science, your questions to ask during a coffee chat need to reflect that. Don't just stay in the clouds. Get into the weeds.
- What’s the tech debt like on the current flagship product?
- How much autonomy do individual contributors actually have over their stack?
- Is the "agile" environment here actually agile, or is it just "waterfall" with more meetings?
These questions prove you know the industry's frustrations. It builds instant rapport. You’re "one of us."
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The Follow-Up is Where the Job Lives
The chat ends. You shake hands. You leave. Most people think they're done. They aren't.
The follow-up isn't just a "thank you" note. It’s a continuation of the dialogue. If they mentioned a specific book or a software tool, go look it up. Then, in your email, mention it. "Hey, I checked out that article you mentioned about LLM latency—really interesting point about the trade-offs."
This proves you weren't just nodding along. You were listening. In a world of distracted, "me-first" networking, being a good listener is a superpower. It’s rare. It’s memorable.
A Note on Power Dynamics
Don't be a sycophant. Seriously. There is nothing more uncomfortable for a senior executive than someone acting like a groveling fan. Treat them like a future colleague. You are evaluating them just as much as they are evaluating you. This shift in mindset changes your body language and the way you phrase your questions. It moves you from "applicant" to "talent."
Actionable Steps for Your Next Meetup
Before you head to the cafe, do these three things:
Research the "Third Tier." Most people look at the company website. Some look at LinkedIn. You should look at the "third tier"—recent podcasts the CEO was on, the company’s GitHub (if applicable), or recent industry whitepapers they’ve cited. Find one specific detail to ask about.
Prepare your "Short Story." You’ll be asked what you're looking for. Don't ramble. Have a 30-second "commercial" that ends with a question. "I’ve spent three years in logistics, but I’m moving toward supply chain tech because I’m fascinated by automation. Given your background, do you think that's a viable pivot right now?"
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Set a specific goal. Don't just go to "network." Go to find out three specific things: What is their biggest project? Who is the decision-maker for the role you want? And what is the one skill they think is missing in the current applicant pool?
Audit your list. Look at your list of questions. If more than half of them can be answered by a Google search, throw them away. Your questions should require a human brain and personal experience to answer.
Watch the clock. This is the most important "question" you can ask: "I want to be respectful of your time—do we have five more minutes, or should we wrap up?" It shows you’re a professional who understands that their time is literally money. Usually, they'll give you another ten minutes just because you asked.
Close with a "Who." Never leave without asking, "Is there anyone else you think I should talk to?" This is how a single coffee chat turns into a web of opportunities. If they give you a name, ask if you can use their name when you reach out. That "warm" intro is worth ten cold applications.
By focusing on high-friction, high-reward inquiries, you transform a standard networking event into a strategic career move. You aren't just asking questions; you're building a bridge between where you are and where they already sit.