The Boss's Boss's Boss Test
Use internships to eliminate careers by asking whether you want the job three levels above you, not the one you are doing.
- Difficulty
- Starter
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 82%
Ahmed assumed he would go into finance after Harvard, partly because that is what a lot of people seemed to do and partly because his father had worked in finance. Instead of deciding in the abstract, he used internships as elimination tools, working at a hedge fund after his freshman year, an investment bank after his sophomore year, and a private equity firm after his junior year. At each one he asked himself not whether he liked the work but whether he wanted to be his boss's boss, and that person's boss's boss, one day. His framing is that internships are a great thing to figure out what you don't want to do. He never felt the gravitational pull toward those senior roles, and in parallel became obsessed with the continuous-monitoring idea, so he says he became an entrepreneur before he really knew what an entrepreneur was, never choosing between three or four ideas but following the single one he could not shake.
Origin
Ahmed developed it across three summer internships at Harvard while on the default Long Island to finance track his background pointed him toward.
Core principles
- 01Internships are elimination tools, not audition tapes.
- 02Judge the path by its destination, not its entry point.
- 03Look for a gravitational pull, not a rational justification.
- 04A default path inherited from family or peers is a hypothesis, not a decision.
- 05Obsession with one idea beats choosing between several.
How to run it
- 1
Name the default you are drifting toward
Ahmed thought in the back of his mind he would go work in finance because that is what a lot of people seemed to do and his dad had worked in finance. Making the inherited assumption explicit is what allows it to be tested at all.
Pro tip If you cannot articulate why the path is yours rather than your environment's, it is a default.
- 2
Get inside it cheaply and repeatedly
He took three separate placements across three summers, a hedge fund, an investment bank, and a private equity firm, rather than sampling the sector once. Multiple variants stop you from mistaking one bad team for a whole industry.
Watch out One internship can be dismissed as an outlier, which is how people talk themselves back onto a path they disliked.
- 3
Look three levels up, not at your own desk
The operative question at each placement is whether you want to be your boss's boss, or their boss's boss. The entry-level job is temporary and unrepresentative; those senior roles are the actual product of the path.
Pro tip Find the person three levels up and observe their week, their hours, and how they talk about their work.
- 4
Test for pull rather than justification
Ahmed's answer was not an argument against finance, it was an absence: he just didn't feel this gravitational pull towards it. The test is emotional rather than analytical, because you can always construct a rational case for a prestigious path.
Watch out If your only reasons to continue are salary and prestige, you have failed the test and are rationalising.
- 5
Follow the obsession you already have
While eliminating finance, Ahmed was becoming obsessed with the idea of continuously measuring the human body, having read roughly 500 medical papers. He never chose between three or four ideas; he followed the one that had already taken hold.
Pro tip Ahmed says he became an entrepreneur before he really knew what one was, so do not wait to feel qualified for the label.
In the wild
Ahmed worked at a hedge fund after his freshman year, an investment bank after his sophomore year, and a private equity firm after his junior year, running the boss's boss question at each. All three returned the same answer: no gravitational pull toward the senior roles those paths led to.
→ He walked away from the default Long Island to Wall Street track and instead founded WHOOP at 21 or 22 as a Harvard senior, building it into a company later valued at $3.6 billion.
Common mistakes
Judging the path by the entry-level job
Analyst work bears little resemblance to what a partner or managing director actually does day to day. Deciding on the basis of whether you enjoyed the internship itself evaluates a role you will hold for two years instead of the life you are signing up for.
Treating an internship as something to succeed at rather than learn from
Ahmed's framing is that internships are a great thing to figure out what you don't want to do. If you go in optimising for the return offer, you will suppress exactly the discomfort the test is meant to detect.
Waiting for a better alternative before rejecting the default
Ahmed was not choosing between three or four ideas; he had one obsession and an absence of pull toward finance. Insisting on a fully formed alternative before saying no keeps people on default paths for years after they know the answer.
Is it for you?
Best for
Students and early-career people on a default prestige track who are unsure whether they actually want the destination.
Not ideal for
People already committed to a path who would only use the test to manufacture doubt.
From the transcript
“internships are a great thing to figure out what you don't want to do”
“the question I asked myself at each of those places is you know did I want to be my boss's boss her boss's boss's boss”
“I just didn't feel that pull I didn't feel this like gravitational pull towards it and at the same time I was becoming sort of…”
From the episode
WHOOP Founder Will Ahmed: How I Built A $3.6 BILLION Company
WHOOP Founder Will Ahmed