The Culture-fit Conundrum

10 Questions to Ask Interviewers on Work Culture

The Art of Interviewing the Interviewer

Rohit Malekar
6 min readFeb 2, 2021
Photo by Olya Kobruseva from Pexels

“There are no stupid questions” is a nice sentiment that may be appropriate in some contexts, however, the art of asking questions is an underrated skill, especially when we look for our next career move.

For example, asking “How is the culture at your organization?” to an interviewer is like asking “What kind of a person are you?”. You may not hear intentional lies, but human minds are often incredibly biased against acknowledging vulnerabilities.

If you truly want to understand the culture of an organization, you need to ask questions that focus on the choices, behaviors, and actions during a crisis.

The Why

I wrote about the need to get an intimate understanding of the culture and your future leaders in the article The Three Most Unexplored Aspects of A Job Switch in Early Career Transitions.

No amount of research can replace first-hand information on this topic from an interviewer. You can read more on the importance of preparing your questions for the interviewer in the article Why Is “Do You Have Any Questions?” One of The Most Important Questions In Your Interview.

This article offers a few specific areas of inquiry that you may consider to help assess culture at your prospective workplaces.

Generally speaking, it is easier for a person in a leadership role with a title and power to say things like “we have a flat culture” and “titles don’t matter”.

However, the degree of truth in most assertions on work culture is best viewed in the rearview mirror by understanding how the organization responded to unplanned situations.

Caveat Emptor (Buyer Beware)

How to use these questions?

Context is King

Please review the rationale behind each of the questions below so you can adapt and tweak it to fit your context. Make adjustments to include what you have learnt so far about the company, the role you are seeking, the role of the interviewer, and their experience (not in years, but in terms of exposure with the organization).

Timing is Everything

There is no perfect workplace because there are no perfect people. The key is to gain awareness and then determine alignment between your aspirations and the company’s journey. Use these questions as a selection and not filtration criteria. Focus the first half of your recruiting experience to align on the role, expectations, and benefits. If everything else checks out, make inroads to find out about the culture as you get closer to the final rounds.

Tone and Trust Matters

Some of these questions are direct and can put most recruiters and interviewers on the back foot. Make sure you have gained a level of trust where your audience knows that you are genuinely interested in the role if offered. Blend these questions with your own experiences to set the context with the interviewer as to why a particular topic interests you.

Understanding Workplace Culture

Edgar Schein, the author of the book “Organization Culture and Leadership”, defines culture in these terms:

Culture is a way of working together toward common goals that have been followed so frequently and so successfully that people don’t even think about trying to do things another way. If a culture has formed, people will autonomously do what they need to do to be successful.

Communities that are focused on creating an authentic work culture recognize that this pursuit is a journey. They are not afraid to embrace the vulnerabilities of acknowledging current gaps. Companies that want to print neat looking values to post on the walls will shy away from having a direct conversation on these topics. Use these questions as a litmus test to assess your future workplace.

1. Can you share an example of how leaders in your company resolve a difference in opinion or a conflict amongst themselves?
Much like in a family where children pick cues from adults, leaders set the tone for the rest of the community at work. The clearest lens to evaluate a culture of a family or a workplace is by looking at how they resolve conflicts.

2. What are some of the ways leaders in your company keep themselves accountable in their roles?
An authentic work culture fairly evaluates the performance of its leaders with the same rigor as employees. Moreover, authentic leaders will share wins and loses openly and invite opinions. I like the last suggestion in this Tweet on transparently tracking metrics — the clarity in defining it and the eventual choice itself can tell a lot between the lines.

3. When was the last time an idea that came from a junior employee was adopted in your organization?
It is easy to say we have a flat culture. However, it takes courage to acknowledge shortfalls especially when that feedback is from someone not in a position of authority. It speaks volumes when such feedback is encouraged and acted upon.

4. Can you share an example of how your company resolves conflicts with clients (or VCs, or any vested stakeholder in a position of power)?
Would you rather work for an employer who is focused on keeping clients happy or invested in making them successful? At times, there may be a fork in the road where both may not be correlated to each other.

5. Under what circumstances would you say no to new business from a client (or pass an investment from a VC)?
What made Vijay Deenanath Chauhan roll in the 1990 movie Agneepath is also great advice for individuals and organizations attempting to stay true to their values, “Is duniya mein tarraki karne ke liye na bolna bahot jaruri hein commissioner” (It is often necessary to say “no” in order to get somewhere in life.)

6. What is one internal policy that you wish you could eliminate or change?
Use this question to gain insights into current challenges and how do they stack rank across the interviewers you get to interact with.

7. When was the last time the company changed its mind about an important topic?
No organization can make the perfect calls 100% of the time. The key is to know how nimble the setup is to adapt once new data, insights, and learning become evident.

8. What has been the toughest message you had to deliver to your employees and how did you do it?
In her book Fierce Conversations, author Susan Scott contends, “The communication is the relationship”. When we avoid tough conversations in the relationship, the possibilities for that relationship shrink. Worst, when the conversation stops, the relationship deteriorates.

9. What is the boldest decision the company has recently taken in favor of employee experience at the cost of financial growth?
The larger the company, the trickier it gets to gain consensus on balancing the competing priorities between a rewarding employee experience and attaining financial success. Responses to this question can truly attest statements like “employees are our assets”.

10. When was the last time you had to make a decision that was taken after having the most differences in opinions within your team/organization?
As an organization, you run the risk of running into a local maximum if you only hire people who you like or superficially assess for abstract ideas of “fit”. Environments that encourage healthy dissent and diverse opinions have the potential for breakthrough results.

Just like how ideal relationships are rare, so are ideal workplaces. And if there is a perfect workplace that you were to join, you won’t learn there much either if there is nothing to solve for. What you should look for through questions like these is a place where you can contribute, grow, and leave it better than you found.

(This article was attempted to be “written in public”. After a skeleton draft was posted on LinkedIn and Twitter seeking feedback, the attributed responses were used to further add to the key takeaways.)



Rohit Malekar

Building a digital studio, creating the culture and craft for digital product development, writing on decentralization. More at