What is the most reliable interview signal of a candidate's grit and drive?

Brad Gerstner · Oct 10, 2022

Being unable to answer 'tell me how you've made money' is a disqualifier for hiring — what matters is that the candidate has an answer at all, not what the answer is.

Many people from elite schools and banks have never actually had to make money themselves; someone who has spent their life finding hacks demonstrates the grit and resourcefulness the job requires.

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Harry Stebbings · Nov 9, 2022

The commonality among great hires is that they can answer 'tell me about the first time you made money', which reveals hustle and grit

Early money-making stories — selling sweets, redoing cars — demonstrate hustle and grit

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Harry Stebbings · Nov 21, 2022

Brad Gersor screens founders by asking every one of them how they made money the first time

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Harry Stebbings · Mar 10, 2023

Asking a founder how they first made money is a highly revealing evaluation question

Early money-making stories reveal a lot about the person's character and drive

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Harry Stebbings · Jun 26, 2023

Asking a candidate about the first time they made money is one of the best ways to detect genuine hunger

Great people, rich or poor background, have an early money-making story; nobody with real hunger answers that their first money was a salary after Stanford and a seed round

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Stevie Case · Jan 25, 2023

You test for grit by digging into accomplishments a candidate is proud of, including non-work ones, and listening for passion and stories of overcoming

People who have stuck with something hard and overcome adversity will be resilient in a dynamic workplace and figure out how to win as things change

Scope: accomplishments need not be work-related; applies to early-career candidates too

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Jean-Michel Lemieux · Mar 20, 2024

'What's the hardest thing you've built?' is the single most revealing interview question because it exposes a candidate's internal quality bar and lets you calibrate whether they can stretch to the difficulty of the role

It shows what they'd put on their life's trophy and gives you a difficulty rating to compare against the job — if the job is a 9.5 and their hardest thing was a 7.2, you can judge the stretch

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David Schneider · Sep 11, 2024

The most predictive hiring question is asking a candidate to describe something they are proud of that they had to work really hard for, because what someone had to overcome reveals what makes them tick.

You find a pattern with people who have had to dig down and overcome something; everyone is a survivor of something.

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Elias Torres · Mar 21, 2025

Interviewing with extreme intensity is itself the test — candidates who can handle it and still want to join are the right hires

That filter is what has made the teams he attracts work

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Alan Chang · Jan 5, 2026

Whether a young hire will truly commit is not a matter of luck — you can detect it by pitching the difficulty of the job and pressing on why they are sure they want it

Candidates who cite pay or say they're unsure reveal they aren't up for it, while genuinely hungry ones lean in; in his experience they rarely lie even though they could

Scope: acknowledges candidates can lie; based on his own experience

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Annie Pearl · Feb 3, 2023

Soliciting anecdotes about a candidate's own hardest experiences is far more useful than cookie-cutter interview questions

Candidates have good prepared answers for standard questions, whereas their recollection of a real challenge and how they navigated it reveals both what they've experienced and how they think

Scope: still imperfect — you won't really know until you work with someone

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Raman Malik · Nov 15, 2024

The most useful interview questions for experienced candidates are war stories about what didn't work and their biggest flops

Scope: especially for more experienced candidates

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Harry Stebbings · Jan 25, 2023

The signal worth looking for in candidates is discipline that required real sacrifice and pain, such as grueling exams or ultra marathons at the cost of social life

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Chad Peets · Jan 9, 2026

You should screen for grit by asking what hardship a candidate has been through in their life

If they've faced real challenges, then a tough sales cycle, weak pipeline, or a leader hammering them won't be the hardest thing they've ever done

Scope: credits John McMahon for the technique

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Stevie Case · Jan 25, 2023

Long-term determination on a hard personal goal is the key trait she hires for

Her own success traces back to that kind of persistence, e.g. finishing a degree one class at a time over 25 years while working and being a single mom

25:45 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Geoff Charles · Dec 6, 2023

You can hire for velocity by screening on three things: motivation to move faster, a track record of pushing something through obstacles, and a chip on the shoulder

Candidates who say the old company moved too slowly and who confronted and influenced what got in their way — ex-founders who didn't succeed, long-time engineers who just want to build — have the DNA that produces speed

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Semil Shah · Nov 21, 2022

Investors should interview founders for evidence of grit, hustle and handling adversity — not necessarily in business — because you are trading off talent and sophistication against grit, and need a blend rather than 100 on one end and zero on the other

Talent alone or grit alone is insufficient; you need to feel some of both as an investor

11:24 Blend of talent and grit not necessarily business related is needed since neither alone suffices

Anton Osika · Aug 18, 2025

The best non-obvious hiring signal is 'slope': whether a conversation with the candidate is dynamic and teaches you a lot predicts they will adapt to the organization and improve fast

A dynamic, learning-rich conversation indicates high adaptability; otherwise the best signal would be observing how they actually performed in past work

6:33 Slope dynamic conversation predicts adaptability

Sri Batchu · Jul 26, 2023

The best interview question for testing growth mindset is 'what's something you're bad at that you enjoy doing?', because it reveals appetite for learning versus only doing what you're good at, and fear of failure

Struggling to answer, or being unable to name anything, is itself a data point

22:23 Asking whats something youre bad at but enjoy reveals growth mindset

Stevie Case · Jan 25, 2023

Grit means sticking with something hard through adversity over the long term, not being a hustler who pushes hard

She screens for it by looking for someone who picked something hard to accomplish and saw it through adversity

24:23 Grit is sustained adversity not hustle

Cliff Weitzman · May 9, 2026

Shipped side projects are the best evidence of adversity quotient in a candidate

Publishing to production forces you through annoying friction like Apple developer accounts and Cloudflare setup; not having done it shows unwillingness to bear small pain

36:44 Shipped side projects prove willingness to bear friction

Cliff Weitzman · May 9, 2026

The best interview question for detecting grit is YC's 'what is a non-computer-science system you've hacked to your advantage?'

It surfaces ability to build a system, learn something, and demonstrate an inhuman amount of desire and will

38:45 Non technical system hacked to advantage is the tell

Aman Narang · Aug 21, 2024

Interviewers must ask hard, deep questions even when uncomfortable, probing where the candidate faced real challenges and was the driver rather than a passenger

You only have so much time with someone you don't know, and resilience and genuine ownership are what matter most

46:00 Probe for real ownership driver vs passenger role in past challenges