Preparing for your 1st Interview … as the Interviewer

S Shekhar
7 min readOct 8, 2020
Photo by Christina @ wocintechchat.com on Unsplash

In professional life, new experiences and opportunities creep up on you unannounced.

In one of my previous roles, I was once asked to come to office on a Saturday as the CEO wanted to talk to me. I was in a junior individual contributor role and my team was in turbulence at that point with the recent exit of the team leader. I guessed that it was either to show me the door or, at the very least, ask me some tough questions. I prepared well for such a conversation and made a list of all that I had done in the past few months.

I was, understandably, taken aback when it turned out that I was being offered the role of interim leader. Unprepared, I bumbled through the conversation giving the impression (as I was told later by another person in the room) that I was not excited about the opportunity. In any case, the decision had already been made and I started the role next week while the hunt for a permanent leader continued.

I did reasonably well in the new role as the team exceeded its targets in the next quarter and I got the role permanently a few months later. At the same time, I let the team down as I was thoroughly unprepared for the role of managing people. I had taken on the new role as an inflated version of my previous role, but I was wrong: it was an altogether different role.

I hope I am not presumptuous when I say that this story might resonate with people who are a few years into their career: You start as an individual contributor, you do that well, and suddenly it’s decided that you are qualified to lead people. It’s like you were riding the bike very well so they let you drive a car now. To point out the obvious: it’s a similar but different set of skills. The similarity makes it even worse as it fools you into not noticing the difference.

There are a few companies that formally train, or at least try to train, first-time managers. Most companies don’t. And, surprise, people who can crib an essay about how clueless their managers and leaders are, one day suddenly in that job, find that it was not that intuitive after all.

Being an effective manager is a big topic and perhaps not suitable to be covered in its entirety in an article (High Output Management is a great manual for managers and also removes stigma from the word — I preferred being called a manager than a leader after reading this book). I used that incident merely to illustrate the opening line: In professional life, new experiences and opportunities creep up on you unannounced. Being a first-time manager is just one of them. Getting to present a report to the team for the first time; getting to lead a project for the first time; getting to represent your company in a negotiation for the first time: the list of things that happen for the first time without you realizing how it is a different skill-set, and therefore you might be under-prepared for it, is endless.

One such thing which happens very frequently but people are under-prepared for it over and over is interviewing other people. To hammer on the point I made in the previous section: Being a good analyst, for example, doesn’t automatically make you a good interviewer for that role.

I have been a terrible interviewer (and interviewee, come to think of it) though out my career but in the pursuit of getting better at it, I have learnt a few things now. Here is the mental model I now try to follow as an interviewer.

There are, broadly, two things you are trying to check as an interviewer: Aptitude and Attitude. The dichotomy can be thought of more clearly as: Ability (whether you can do the role) and Willingness (whether you are willing to do the role). Even if your company has a checklist of things to rate against in the interview, every item will probably fall in one of the two buckets.

Aptitude can again be broken down into two parts: general aptitude and domain-specific knowledge. Interviewers generally ask domain-specific questions well, but trip up while trying to check general aptitude. But before I go into how to check general aptitude, the often debated point: should you even check it? If you are hiring someone as, say, merchandiser and they know that job well, why bother with them ‘being smart’ (I was in this camp once)? Also, isn’t ‘general smartness’ subjective?

To answer the first question: if you hire a smart person, you can teach them the job. If you hire someone who knows the job but doesn’t have the required aptitude, they won’t learn the next job as the function or role evolves, as it so often does in modern workplace.

To answer the second question: all interviews are subjective but you can strive to remove the subjectivity by having a framework. So, what’s the framework to check general aptitude or smarts?

Guesstimate questions like ‘estimate the number of red cars in Mumbai’ were devised to check general smarts — not to actually get the answer but to see how a candidate approaches the problem — but interviewers ask that same question so many times across interviews that they know the right approach to that problem, thus defeating the purpose. (I don’t ask them anymore.)

One hack I learnt from a senior was to have a new problem every time chosen by the candidate, e.g. a product or service of their choice that they are discussing from the perspective of their function: product, growth, analytics, marketing, etc. For example, if they pick Swiggy for the discussion and they are applying for customer relationship management (CRM) function, you can start with what will their framework of managing the CRM in Swiggy be, and dive into specific aspects they bring up. If they pick WhatsApp and they are applying for analytics function, you can ask about the analytics framework for WhatsApp: top business metrics its CEO would be tracking, and so on.

You, as an interviewer, will also be thinking about the problem at the same time, thereby reducing the chances of you having preconceived notions about the ‘correct approach’, or worse, the ‘correct answer’. Of course, don’t discuss your company or their current/last company, as both of you will have very hard opinions on the right way for them. You can invent a similar open-ended problem that suits your domain.

This bring me to the second half of the skill set being checked in the interview: Attitude or Willingness.

Attitude is an even more amorphous, and loaded, term than Aptitude. How do you check for attitude? Isn’t everyone at their best behavior anyway during an interview?

Common ways to check for attitude is to look for ‘culture fit’ (I often find myself wondering if I fit into a culture, let alone test others), conducting a separate ‘stress round’ (I once was subjected to a stress interview which was a borderline Roadies episode), or leave it for the ‘HR round’ to ask for their ‘favourite book’ and ‘biggest weakness’. All of them are flawed, in my humble opinion, but instead of nitpicking about them, let me instead take a step back and ask: why is measuring Attitude important and can you even measure it?

The purpose of an interview is to predict if the candidate can function in the role in consideration or not. Measuring aptitude is a ‘selection’ game where the default answer is no and during the interview, you move to yes, if the aptitude is good enough (raises the bar, etc.) On the other hand, measuring attitude is a ‘rejection’ game where, once satisfied with the aptitude, the default answer is ‘yes’ and you are ensuring that they don’t turn to be a ‘brilliant jerk’ and make the entire team suffer every time they have to work with that person.

The hack that I found was that people don’t like their ideas being challenged. I don’t like it, either. It’s the degree to which you hate your idea being challenged, and, inversely, the degree to which you are ready to consider the idea of the person who just challenged your idea, which I sought to check in the interviews.

This did not need a separate round or even a separate section in same round. In the same open-ended general aptitude section, you can put your thought process out there for the problem being discussed (it’s a new problem for you too) and see how they react to it, understand it, debate it, modify it.

This method is highly relevant to your objective as it predicts how the person will react to different situations, especially conflicting ones, in the workplace.

So, that was it: a framework I learnt from conducting hundreds of interviews, but mostly from talking to/observing people who are smarter or have done this even longer. It’s important that you throw out the parts you don’t agree to (Naval Ravikant checks for integrity too, apart from intelligence and energy), but keep the parts you agree to. You can, also, agree to the broad framework, but change the operational aspects of it i.e. which questions to ask or not ask. I have personally struggled to use this framework for hiring very senior roles, and have fallen to the usual trope of discussing the resume.

Also, the larger point: keep an eye out for need of new skill sets that are required of you in the workplace, and research and think deeply about how you can develop them.

Thank you for reading this. Please share your views too.

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S Shekhar

On building and growing internet products. And on books.