High School Cafeteria Part 2: Turn Every Job Hunt Conversation Into Multiple Opportunities
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High Level Concept:
You can transform every job-related conversation from a single shot at one specific role into a gateway that opens multiple doors. Building relationships that lead to referrals, contract work, future roles, and connections throughout the company.
Some Context: The High School Cafeteria Analogy for Job Hunting
Picture a big cafeteria full of round tables, each with a group of people building something different — one’s working on a puzzle, another’s building a Lego tower, another’s sewing, etc.
Your goal in job hunting is to find a table where you (1) are excited about what they’re building, (2) enjoy working with the other people around the table, (3) have unique value they need that you actually want to bring everyday, and (4) are set up for success and can work in a way that matches your lifestyle needs.
You could walk up to every table and say “hire me! I’m great!” - but in this market, you’ll likely be drowned out by the noise. Instead, start with these two steps.
Part 1 - Get clear on what you want and what you have to offer before walking in.
Part 2 - Have conversations and explore a mutual fit.
If you follow this, you’ll soon tell if what they’re building excites you, if you like the people enough, and if you could see if they’re working style could align with your lifestyle needs. If yes, keep exploring. If not, thank them, reflect on what you learned (maybe back in your study room), and move on to other tables a little bit more clear on what’s important to you. You're searching for a mutual fit.
In this blog post, we’ll talk about Part 2.
How to get the most out of your conversations once you’re in the cafeteria. Just having one conversation is fine. But what if you could turn every conversation into a node that connects you to other potential conversations that are a true fit? Or what if you each conversation built a stronger network of people working behind the scenes to send jobs your way, especially when they’re not even posted yet?
If you haven’t already, check out “Job Hunting is like a High School Analogy” first.
Level 1: The Traditional Approach
Cold applying + asking connections to push your resume up the pile.
What happens if you stay at Level 1:
You pitch yourself for the one open job in the conversation. If it's not a fit, you say thanks and walk away. Move on to the next job and repeat.
High School Cafeteria Analogy: That’s the equivalent of walking up to a table, asking "Do you have space for me here?" If they say no, you say thanks and leave.
Result: They likely forget you within minutes. You’ve limited yourself on how else they could help you.
This isn't wrong, but it's limiting. You're capping your opportunities at the exact number of 1:1 conversations you can have, and the timing has to be perfect.
Level 2: Uncover Needs & Genuinely Offer to Help
Goal: The goal of this is to genuinely offer value and build a relationship with this specific person. This is not transactional. This person you’ll talk to is doing a job that matters to them. Be yourself and build a relationship with them as you would with anyone else new. Discover what they're struggling with and offer to help in a shorter-term capacity while you continue your search.
How to do it:
Express genuine interest in helping them:
"I'd love to learn more about what you're building—maybe I know someone in my network who could help, or there's another way I could be useful."
Ask discovery questions to understand their hopes and dreams:
"What are you trying to build?"
"What would success look like if you knocked this out of the park?"
"If you got the perfect hire, what would you want them to accomplish?"
Identify what's missing:
"Where do you think you're short on resources or know-how?"
"What would be most helpful to you right now?"
Offer help - a connection, a resource, an idea, or even some contract/fractional support if you see a fit:
I might have someone in my network who could help - can you tell me more about specifically what that issue is? Or who would be a most helpful?
"While I'm job searching, I'm taking on some contract work. If you're interested, I'd be happy to talk about helping you with [the specific need they mentioned] on a short-term basis. Would that be useful?"
Maybe this conversation will turn into nothing. Or maybe it’ll end up being the most valuable conversation you’ve ever had. You can’t know. But assume you’ll talk to 10 people and you only need 1-2 people to make connections or share a new job rec to make all the difference.
Level 3: Build Your Brand & Get Connected
Goal: Make it really easy for this person to know how you could help them, and how they could help you. They’re much more likely to open doors for you and see opportunities for you within their team or elsewhere if you’re clear and speak to your audience.
How to do it:
Clearly communicate who you are, what value you offer, and why you're excited about the company/team—confidently but with flexibility
Explore any potential roles that could be a fit
If there’s an existing rec, explore if the role could be reshaped (more senior, different location, expanded scope)
If not an open rec, see if they’re considering expanding their team to tackle that particular thing - explore that with them as far as you can go.
If it can't be reshaped, ask them to connect you elsewhere in the company:
"Who else is working on [X type of work you want]?"
"Is there a team focused on [new products/launches/whatever excites you]?"
"Do you know anyone who might need someone with my skillset?"
You can always leave with a clear ask that would help you:
Connect them with people who could help
Share relevant resources
Provide value to what they're working on
Make a specific request:
"I think I could help you with X on a contract basis. If that sounds useful, we could talk through what you really need. Are you open to that?"
"Is there someone within this company working on [launching new products/starting something new]? I'd love an intro if it's not too much trouble—I'm really excited about what you're building."
What you're hoping for:
They reshape the current headcount to fit you better, OR
They remember you when a senior role opens up, OR
They connect you to a colleague in another department, OR
They tell you about other teams/projects that might need you
Level 3 should be your goal for every conversation. Aim to leave every conversation with a connection to another person or information about other opportunities within the company. It may or may not happen, but make the ask clearly and they can say yes or no.
Why this works:
You're playing in the sandbox with them—getting to know their work, their challenges, their world
You're being genuinely helpful without expecting anything back
You might earn income while job searching (reducing any thoughts of desperation and building credibility)
You're building your network with external-facing work
You might convert it to full-time down the line, or they might refer you elsewhere
Core Guiding Principles
Be human - Build relationships. Don't view this as transactional. People want to help people they've connected with.
Learn their hopes and dreams - Understand what they're trying to accomplish and why it matters to them.
Explore what's missing - What do they already have vs. what's standing in their way?
Be genuinely helpful without expecting anything back - Share articles, contacts, resources. Be useful in the moment and after.
Be crystal clear on what YOU want - What you're great at, what you're looking for next, what excites you.
Offer clear next steps and specific asks - a connection, information on the company, etc.
The Bottom Line
The more helpful and compelling you are, the more popular you become in that high school cafeteria. People will advocate for you behind your back. Jobs you didn't know existed will surface. You transform from a forgettable resume into someone people want to help, connect with, and pitch for opportunities—even ones that haven't been posted yet.