5 Questions to Ask at Any Startup Event (That Actually Matter)
Skip the awkward small talk and ask questions that actually lead somewhere. Better questions → better conversations → real opportunities. Walk into any room with intention, not just a drink in hand.
Hey, Let’s talk about startup events.
You show up.
You grab a drink.
You say “what do you do?” about 11 times.
You leave with… maybe 2 LinkedIn connections and one “let’s catch up soon” that never happens.
Cool. Very productive. 10/10 ROI.
But here’s the thing most founders miss:
It’s not the event. It’s the questions you ask.
Because the difference between:
“just another networking night”
and“this actually changed something for me”
…usually comes down to one good conversation.
And good conversations don’t start with:
“So… what do you do?”
They start with better questions.
🧠 1. “What are you currently trying to figure out?”
This question is gold.
It cuts through:
polished pitches
rehearsed intros
“we’re doing great” energy
And gets straight to reality.
You’ll hear things like:
“Honestly, we’re struggling with distribution”
“Trying to crack retention right now”
“We have users… but not the right ones”
Now you’re not networking anymore.
You’re in a real conversation.
And that’s where value starts.
🚀 2. “What’s been working surprisingly well for you?”
Founders LOVE talking about wins they didn’t expect.
Not the obvious stuff.
Not the pitch deck highlights.
The real stuff:
“This one channel randomly took off”
“Cold emails actually started converting”
“We changed one thing and signups doubled”
This is where you get insights you won’t find on Twitter threads or LinkedIn posts.
It’s like unlocking a cheat code… except it’s legal.
😅 3. “What’s been way harder than you thought?”
Now we’re getting honest.
Because behind every “we’re scaling fast” post is:
something breaking
something not working
something stressful
And when someone answers this honestly, two things happen:
You learn faster
You connect deeper
Also, it’s oddly comforting to hear:
“Oh… it’s not just me.”
🎯 4. “Who would be a great person for you to meet tonight?”
This is how you actually network.
Not by collecting contacts.
But by creating connections.
When you ask this:
you position yourself as helpful
you become memorable
you instantly stand out from 90% of people in the room
And ironically?
This is the fastest way to build a strong network. (Yes, helping others works. Annoying but true.)
🔥 5. “What are you building towards right now?”
Not “what do you do.”
But:
where is this going?
This shifts the conversation from:
present → future
features → vision
job → mission
And you’ll feel the difference.
Energy changes.
People lean in.
The conversation becomes… interesting.
The Real Game
Here’s what most people get wrong:
They think startup events are about meeting more people.
They’re not.
They’re about:
having better conversations
going one level deeper
leaving with real connections
Because one strong conversation > 20 forgettable ones.
Every time.
Community Partnership [WAYO x Startup+]
We’ve teamed up with Wayo to bring something that genuinely fits our community, curated Community Workdays hosted at some of NYC’s best venues, from rooftops and restaurants to unique private spaces designed for daytime professionals.
Instead of working solo at home or squeezing into a crowded café, you’ll spend the day alongside 12–15 founders and professionals in a relaxed, focused environment, no forced networking, no panels, just good energy and productivity.
And yes, lunch plus coffee or tea from the host venue is included for $5.
And That’s Exactly the Energy We’re Building
Startup+ Networking Night isn’t:
awkward small talk
surface-level intros
“what do you do?” on repeat
It’s a room full of:
founders figuring things out in real-time
operators sharing what’s actually working
people open to real conversations
No fluff.
No forced vibes.
Just high-signal interactions.
📍 Event Details
Startup+ Networking Night
Date: May 7
Time: Doors Open 5PM
Venue: Sour Mouse, NYC
If You Come, Try This
Instead of asking:
“So what do you do?”
Try just one of the questions above.
That’s it.
One better question → one better conversation → one unexpected opportunity.
That’s how this works.
Final Thought
Most people will show up and network. A few will show up and connect. Save your spot
Aneesh Lal, Founder
Jaynish Shah, Community Lead
Team Startup+
🌐 www.startupplus.club
Great article layout!