Lately I’ve been working with a few founders who are navigating early, high-stakes hiring decisions. The roles were fuzzy, and they needed an extra layer of calibration to figure out who they were actually looking for. I have a process that works well with the founders I partner with, but there’s always a layer of ambiguity that takes a little longer to polish.
Around the same time, Roger (my husband and unofficial Fulltilt research department) introduced me to The Five Types of Wealth by Sahil Bloom. If you haven’t read it, the book offers a set of clear, actionable frameworks for thinking through life’s bigger decisions. It focuses on creating clarity through structure, and progress through prioritization and iteration. It’s the kind of book that doesn’t just give advice. It gives you the mental scaffolding to act on it. (And yes, there’s a digital PDF workbook you can download and print out.)
After reading the Time Wealth chapter — which had some of the most powerful takeaways for me personally — I started to see a few parallels. Some of these frameworks felt surprisingly relevant to hiring, especially when it comes to helping founders get clearer on who to hire next. Not hypothetically, but practically. The kind of clarity that cuts through noise and helps them answer their own questions with more confidence.
I know many founders have read Sahil’s book or already operate with mental models, so this is my attempt to step slightly outside of my usual lane. This isn’t tactical advice on recruiting or sourcing. It’s not about writing the perfect job description. It’s about decision clarity.
These aren’t recruiting frameworks. They’re just useful ones. And if you apply them to early-stage hiring, they might help you find the right answers faster — without too many outside opinions muddying what you’re facing day to day, and where a strong founding hire can actually make the difference.
1. Reframe the Role: What’s the Job to Be Done?
Let’s say you’re thinking, “We need a Head of Marketing.” Maybe. But maybe what you really need is someone to spin up outbound for the first time. Or plan your first founder-led event. Or figure out why your paid channels aren’t converting.
Don’t start with a title. Start with the outcome.
Ask: What progress are we trying to make in the business right now?
That’s your real “job to be done.”
It could be:
Unlocking qualified pipeline for your sales team
Getting a handle on burn and forecasting before your next fundraise
Hiring ten people in the next 90 days without setting your interview process on fire
Once you’re clear on the business outcome, you can reverse engineer the kind of hire that moves the needle. And more often than not, it’s not the role you thought you were hiring for.
2. Strip It Down with First Principles Thinking (Minus the Musk)
You don’t need to be an Elon fan to appreciate the core idea here. First principles thinking is about breaking things down to their essentials, then rebuilding based on what actually matters right now.
Instead of asking, “What’s the standard title for this?” ask: “What absolutely needs to happen in the next 90 days to move the business forward?”
Maybe your board thinks you need a VP of Sales. But your product’s still evolving. You’re the one still closing most of the deals. What you probably need is a hands-on seller who can run experiments, chase down cold leads, and help you test what a real sales motion looks like.
Hiring for scale too soon is a common trap. If you bring in someone who’s used to optimizing a machine that doesn’t exist yet, you’re both going to be frustrated.
3. Use Inversion to Avoid a Six-Month Setback
When the role still feels blurry, flip the question.
Instead of asking, “What makes a great hire?”, ask: “What kind of person would completely tank this role?”
This is a concept called inversion, made popular by Charlie Munger, Warren Buffett’s longtime partner. The idea is simple: define what failure looks like, then make sure you avoid it.
Bad Hire Scenario #1: Founding Account Executive
You’re hiring your first AE. Sales is still founder-led, the ICP is fuzzy, and there’s no RevOps in sight. You don’t need someone polished. You need someone hungry.
A bad hire here might be:
Someone who’s never prospected cold and waits for leads to show up magically in HubSpot
A big-logo seller who’s used to an army of SDRs and a mature playbook
Someone who asks, “Do we have a case study for this?” five times a day (spoiler: no, we don’t)
You’re not looking for someone to run a process. You need someone who can build one and stay scrappy while doing it.
Bad Hire Scenario #2: Head of Marketing
Now imagine you’re hiring your first marketing lead. You need someone who can generate pipeline, write solid positioning, and execute fast.
The wrong person might be:
A brand marketer from a late-stage company who hasn’t touched an ad platform in years
A “team leader” who gets lost without reports but can’t write a landing page or test headlines
A strategist who’s great in a Notion doc but panics when asked to launch a $500 paid test or write launch copy solo
Six months later, you’re rewriting their campaigns and wondering if you should have just done it yourself from the beginning.
Write these anti-profiles down. Design your interviews to pressure-test for them. Ask what they’ve built from scratch. Give hands-on tasks.
Knowing who not to hire is just as powerful as knowing who to go after.
4. Calibrate Fast with the OODA Loop
Early-stage hiring is rarely clean. You post the JD, meet a few candidates, realize your role is off, adjust the spec, and start over. It’s normal. But it doesn’t have to be as time consuming..
That’s where the OODA Loop comes in. Originally created by U.S. Air Force Colonel John Boyd for combat strategy, it stands for: Observe, Orient, Decide, Act.
It’s used in everything from military operations to startup product teams. Why? Because it works under pressure.
Here’s how to run your hiring loop:
Observe: How do candidates respond to the pitch? What backgrounds seem promising?
Orient: React to real people, not idealized role descriptions.
Decide: Pick the direction that best serves your near-term business needs.
Act: Move quickly. Don’t let great candidates get scooped by someone else.
Every loop sharpens your thinking. And instead of “guessing and waiting,” you’re learning and adjusting in real time.
5. Ask “Who,” Not “How”
Here’s a simple shift that unlocks real leverage.
Instead of asking, “How am I going to get this done?” Ask: “Who can own this, so I don’t have to?”
This idea comes from coach and author Dan Sullivan, who reframed delegation as a leadership skill, not just a time-saver. You’re not hiring people to follow instructions. You’re hiring them to take whole problems off your plate.
Think about it:
You don’t want to build the hiring playbook. You want someone who’s already built one.
You don’t want to be chasing leads. You want someone who lives for that first call.
The right “who” removes entire layers of context-switching from your week. You stop being the glue and start being the multiplier.
Final Thought: Clarity Comes Through Motion
You don’t need the perfect job description to start hiring. You just need a way to trust your gut to make better decisions, faster.
Start with business outcomes. Question your assumptions. Get clear on what failure looks like. And if you’re unsure, don’t stall, calibrate in motion.
The right hire won’t just help you grow. They’ll change how you operate.
If you're in the middle of hiring, sit down and go through each of these frameworks against the role you want to hire for. If you've created a JD already, do a quick A/B review and see if anything changed materially. If this exercise provides at least a speckle of additional clarity towards who you need to hire, then you can now call me the framework queen. You're welcome.