The Warm Intro by Oba #6

Summer 2026 Apps + Networking conversation hack

Author

oba ajayi
August 20, 2025 • Estimated Reading Time: 10 minutes

Intro

I'm Oba. I post resources on LinkedIn & Instagram and now, I'm putting everything here in your inbox every week. In college i had 7 internships and was admitted to Stanford GSB, founded HeadStart Fellowship and now i am here to help you.

What I Wish Someone Told Me

This week's insight: Ask first-order questions to unlock second-order conversations.

I was talking to my friend about why some coffee chats feel amazing while others feel like job interviews. He shared this concept that changed how I think about networking conversations.

Most people show up with the same 5-10 scripted questions every time. "What's your role like?" "How did you get started?" "Any advice for someone like me?" These work, but they keep conversations surface-level.

The secret is asking first-order questions that unlock deeper follow-ups.

Ask “How was moving to NYC” and they might mention their dog. Now you can dive into questions about their pet without it feeling random. Maybe they mention their kid - suddenly you can ask about schools, parenting, family life. Or they just got married and you can explore that journey.

You can ask about a recent investment they made. When they mention they're worried about AI risk, you can dig deeper: "How do you guys think about AI risk? Do you see it affecting other parts of your portfolio?"

The difference is night and day. Instead of bouncing between unrelated questions, you're building conversation trees. Each answer gives you multiple branches to explore.

The takeaway: Come prepared with 3-4 first-order questions that naturally open doors. Then listen for the details in their responses - those details are your entry points to the conversations that actually matter.

Don't Miss These

Career Strategy Call with Oba 10-60 minute strategy call with someone who landed 7 internships and got into Stanford GSB. Get the exact framework I used plus see if ongoing coaching fits your goals.

Paid Part Time Remote Jobs Platform Paid part-time remote roles paying $40 to $270 per hour across different fields. SWE to finance to teaching. 20-40 hours per week on your schedule.

HeadStart Fellowship Info Session + Applications 

Mentorship program for Undergrad first/second year students interested in tech, finance, consulting. 350+ members across 60+ universities.

Resources This Week

List and Links for Resources can be found HERE

The Free Newsletter Fintech and Finance Execs Actually Read

Most coverage tells you what happened. Fintech Takes is the free newsletter that tells you why it matters. Each week, I break down the trends, deals, and regulatory shifts shaping the industry — minus the spin. Clear analysis, smart context, and a little humor so you actually enjoy reading it.

Jobs I'd Actually Apply to This Week

Investment Banking & Finance

Private Equity & Asset Management

Trading & Quant

Consulting

Tech & Product

Other Opportunities

Special Programs & Events

oba