Flipping questions on its head

🌿 Sprout
#interviewing 4 minutes read 02 May, 2025

A cardinal sin when it comes to design research is when some one asks a leading question. If you’re interviewing a consumer of Pepsodent toothpaste, you should almost never, ever, ever, ask “How much do you enjoy using Pepsodent toothpaste?”. That’s a leading question, and the answers you might get from this question are usually loaded with confirmation bias. It would be more along the lines of ‘what they think you might want to hear’, rather than ‘what they actually think/feel/do’.

This guiding principle of interviewing without asking leading questions applies to various facets: market research for F&B brands, company interviews, philosophy debates, and even some negotiations. The thumb rule here is to start initiation and ask more generic open-ended questions such as “How does your day in your life look?”, and then gradually narrow down some topics based on what the end-user wants to say/express.

More recently, I’ve created a variation of the the ‘leading question’, and flipped it on it’s head. I call it as the ‘non leading leading question’. I can’t think of a better term without convoluting the crux of what this does: Let me illustrate this 4D chess move with an example.

Let’s say I want that there is a restructuring in your company, and you are being moved to a new team and a new project. Your expectation is that the new team/project is much more ambitious/chaotic, highly charged and even (stressful) at times. (This is counter-intuitive and not what everyone would want). But you are hell-bent on wanting to work in such an environment, and the mythical “work-life” balance is not something you are considering it as much. How do you then gauge if this new team/project is ambitious/chaotic through a series of questions?

What I would do in such situations is to pull up the “non leading leading question” card.

I would ask — “Would there be good work life balance in the new team?”. The natural expectation for the manager here would be to say that there is good work-life balance. It’s not against the grain, and it’s not counter-intuitive. But by doing so, you reveal the true nature of the new team. The inverse of the inverse question has helped you reveal how this team works, in other words, the question has achieved it’s purpose.

The manager thinks this is a leading question (as they think you’re inclined towards changing your role into a new team where there is better work-life balance, but you’re not revealing your cards entirely and playing a bluff here)

If for the same question, “Would there be good work life balance in the new team?”, the manager says, “Actually, Shreyas, you know what, this is a mission-critical project, and a lot of dependencies to get the right outcome.” Even in this case, this question has achieved it’s purpose. You are now being posted into a more ambitious, growth-oriented team hungry for shipping fast, and moving at break-neck speed. This is what you want!

On the contrary, if I had asked — “Would there be too much stress in the new team?”, there might be a risk of getting a lot more smoke signals which make the response unclear.

This was one specific example, but there could be more situations where such non-leading leading questions can be leveraged.

I’d used this in a more recent interview I’d taken. To one of the candidates, I’d asked — ‘How do you ensure that you do ethnographic studies for all your projects?’ (what I expect here is them calling out the bluff, that it’s impossible to do extensive user research for all projects as in reality you’re dealing with tradeoffs of time/effort/complexity etc). Again, the non-leading leading question acts as an inverse-of-an-inverse.

Found a typo or want to suggest changes? Send a PR on GitHub

Liked this post? Get email for new ones:

Here are some popular posts you might like

In-person vision transmission

I recently transitioned from leading a product team in a region to a more centralised role overseeing products across multiple geographies. As part of that transition, I needed to onboard the new product lead of that region, ensuring they were fully briefed While a virtual onboarding could have covered the basic documents and data points, I knew an in-person handoff was crucial. Slide decks can lay out objectives, milestones, and KPIs all day long, but it would definitely lack that oomph factor of an in-person transmission. This was one of the rituals which warrant an in-person interaction even while almost 90% of our interactions are virtual....

rough-notes
Better way to think about conflicts

What's the hardest conflict you've ever encountered at your work? It's hard to avoid conflicts, but there are various ways in which we could mitigate conflict as much as possible. As a product person, apart from keeping the team running, working with stakeholders, shipping successful products, you're also tasked with resolving conflicts. As Feynman once said, '**Imagine how much harder physics would be if electrons had feelings**'. While dealing with people and emotions, It takes time and effort to identify conflicting situations in advance, and to nip them in the bud if possible. And this requires expertise maneouvring the field space of 'feelings'....

conflict-management
It's computational everything

I was listening to a talk by [Debbie Mcmahon from Financial Times recently at Productcon](Notes%20from%20ProductCon%202025.md) recently and I was surprised by the fact that even in journalism we're seeing tailwind trends more and more computational skills required — genAI is now used to spot stories, and to spin up newsworthy headlines and narratives around these stories. They are now, '**computational journalists**'...who are equipped with AI, data and trendspotting skills. ...

rough-notes
Git way of learning to code

My last year's resolution was to learn how to build on Rails. I taught myself the basics by following some courses, but nothing really stuck with me. I wasn’t building apps; I was getting into a tutorial rut. I needed a better way to learn, akin to being pushed into the river with a swimming instructor. So, I discovered the Founder/Hacker course, which provided more tactical insights into the actual process of building Rails apps. Most online courses polish the loose ends and make it look spotless, but Ryan Kulp didn’t want to do that. He wanted us to see through the mistakes he made as he built the app in a spontaneous manner. I enjoyed this approach so much and have been practicing Rails fundamentals ever since....

rough-notes
Design that's so bad it's actually good

Recently, a relative sought my help to tweak a badly designed poster on Microsoft Paint. This was meant to be circulated on Whatsapp as an advertisement for the handyman services his friend was offering in his locale....

design