Good Morning [%first_name |Dear Reader%],

“If you were a pizza deliveryman, how would you benefit from scissors?”

If there is one thing I have realised over the last couple of weeks, speaking to founders and hiring managers, it is that interviews today often have very little to do with the role on paper.

For instance, “What do you do outside of work?” is Prateek Jogani’s go-to. He’s the former CTO of insurtech platform Qoala.

If you interviewed in tech in the early 2000s, this genre of question might feel familiar. Microsoft built an interview culture around puzzles, brainteasers, and questions with no single “correct” answer, and became famous for it. But by the mid-2000s, most major companies realised that these questions measured cleverness far better than real, long-term ability.

Now, more than a decade later, these questions are making a comeback in a different format, but with the same intent.

Jogani’s reasoning is simple. The need of the hour has completely changed. Though younger hires learn quickly and work hard, they need time and attention.  

“Today, I can spend that same amount of time explaining a task to an AI agent,” Jogani told me over a Zoom call a few weeks ago. “It will record everything, remember it forever, and there are no people problems to deal with.” 

With CVs starting to look the same and take-home assignments becoming easier to game, young applicants now need to bring something else to the table. Founders sometimes call this “fit plus”: being right on paper, but also showing the traits that matter currently, like the ability to pick up new skills quickly, think independently, and stay steady when the work is unclear. 

And these oddball interview questions are one of the few remaining ways to understand a candidate’s inner-workings. 

In this edition, I want to zoom in on these off-script questions. From the open-ended “What excites you most right now?”  to the borderline bizarre “If you were an animal, what would you be?”

If you have ever wondered what founders like Vineeta Singh of Sugar Cosmetics or Arjun Vaidya of Dr Vaidya’s actually ask in interviews, tune into the latest episode of the 90,000 Hours podcast, where I have crowdsourced close to 20 off-script questions.

In this newsletter edition, I’m sharing a selection, with the reasoning behind each of them. Here you go:

Dasarathi GV, CEO and Chief Product Officer, Leanworx Technologies

The question: “Say you have two plants: one has small leaves, the other has large leaves. Which one would you put in bright sunlight, and which one would you keep indoors? Walk me through your thinking.”

What he’s looking for: “We are not focused on whether the final answer is right. Even if it isn’t, that’s okay. What we care about is the reasoning behind it. If that holds up, we know the person can think.”

Nehaarikaa, hiring manager at a Bengaluru-based fintech firm

The question: “No one uses the paved paths in your local park. People cut across the grass instead, creating worn dirt trails. How would you fix this?”

What she’s looking for: “It’s a fairly open-ended question. The goal is twofold. To understand how the candidate frames the problem: whether they see it as a user-experience issue (the park isn’t designed the way people actually move), or as a compliance issue (people aren’t following the “rules”); and how they approach solutions: do they default to enforcement (fences, penalties), or do they adapt the system to reality by paving the organic paths and redesigning the park around actual behaviour?

Richa Verma, Head of Product, Aurasell 

The question: “If you got a billion dollars, no strings attached, what would you do with it?”

What she’s looking for: “It reveals a lot about who you are as a person and what you prioritise. I’ve heard all sorts of responses. But one that stuck with me was this: they actually broke the money down and bucketed it across different parts of their life. They thought through how to use it meaningfully… It wasn’t a throwaway answer.” 

Aruna, CEO of a sales consulting firm 

The question: “What are we getting wrong as a firm?”

What she’s looking for: “How they handle discomfort.”

Kuldeep Parashar, co-founder, Pensionbox 

The question: “Pick a superpower between flying and being invisible?”

What he’s looking for: “Candidates who pick invisibility tend to be more inward-looking. Usually, they are observers who prefer working behind the scenes. Those who choose flying often signal comfort with visibility, energy, and being out in the open. It’s a quick way to understand how someone instinctively sees their place in a group.”

There’s more where these came from. In the latest episode of 90,000 Hours, I unpack how these questions play out in real interviews and some of the best responses these interviewers have received. 

But before you go, here’s a question I was asked that has stuck with me: “Assume you get the job. One year from now, what would make you leave?” Well, safe to say, here we are two years later 🙂 

I would love to hear the interview questions that really made you think. As always, you can write to me at [email protected].

Until next week,
Rahel 

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