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Guide to Asking Good Questions

A Guide to Asking Good Questions

It’s very hard to maximize interest and information per unit conversation while constrained by professional etiquette and verbosity. I think this optimization task is the basis of good communication. I have by no means found a global optima for this problem (as I’m sure you’ll see), but I do have a sense of some local optima with respect to improving my own bad habits and I provide that as an example of how you could learn to improve your own conversations.

In my case, this chapter is for the people asking the questions I have already answered on a different search engine-indexed platforms. This is about those individuals who asked me to show them my resume, even after I took the pains to carefully delineate every project I have ever worked on in the internship description field on LinkedIn, where they originally connected with me (not to mention posting it on my website) This is about the students whom I want to help, but feel exhausted trying to direct towards publicly accessible information on very well-constructed websites. Finally, and most importantly, this is to 18-year old Swapneel who asked a lot of busy, kind, and intelligent people some really stupid questions that they spent time answering anyway. I owe it to them to return the favor.

This guide does not cover cold emails because that’s a whole different ball game, but I can say that there are similar principles involved that require you to write shorter, memorable emails that make the other person want to write back.

The Back-story

You do not need to read this section to understand the rest of the article. No, really. It’s arguably straight-up narcissism, but I’m leaving it in because it is an accurate depiction of my state of mind.

In June 2017, I posted an update to my LinkedIn profile, adding a position with the title “Openlab Intern” at the European Organisation for Nuclear Research (CERN) in Geneva, Switzerland. As an undergraduate student of Computer Science studying at a Tier-2 institution in India, it was a rather amazing opportunity to get an international internship at CERN. To top it off, my project was focused on anomaly detection, a topic of much interest across various disciplines, and funded by an industry sponsor.

While I had been active on LinkedIn since years, I hadn’t really been inundated with requests like I did immediately after this update. My inbox had practically ten new requests each day for a short period of time (it doesn’t sound like a lot but for me that was huge). To be fair, it was quite the ego-boost for a while but I realised soon enough things are not that simple. I started noticing some details about the people sending me connection requests. A lot of the accounts didn’t have profile pictures, education, experience, or even capitalized names (I’m rather finicky about this stuff so I tend to notice). About 1% of them were people I knew while most of them were students from random (and remote) institutes that wanted to add me as a connection for some reason. Some were people with thousands of followers but very little information listed on their profile, no posts, and sparse, generic activity. Given that I used the LinkedIn app, it became painful dealing with ‘manually vetting’ requests after a point and I started ignoring requests from people I didn’t know and those with incomplete (or ‘barely complete’) profiles. I was afraid most of these would turn out to be fake accounts and embroil me—as part of the legitimate nodes in their network.

The problem with ignoring all the requests was that there were a lot of students who simply wanted some advice regarding some projects, fellowships, and internships—most notably the CERN Openlab Program. If I filtered out their requests, that meant their questions would remain unanswered. Now, being an avid Quora user, I’ve always tried to use my knowledge and experience with the application process at CERN to guide students by writing answers on Quora. I tried to cover as much as I knew about the process for different programs since I had applied and received three separate offers from CERN between 2017 and 2018. I had assumed this would reduce the number of people who used to send me messages since they now had access to the information already. Well, as it turns out, many of the people who wrote to me did actually end up reading my website beforehand and the overall quality of questions I got did improve. But in recent times, it came up in a discussion with a friend, that some people who try to reach out just ask questions that can be answered with a Google search for the same question typed out. Case in point, if you’re looking for graduate school advice there are so many websites, blog posts, podcasts, and tweet threads out there that you’re doing yourself a disservice if you ignore these and come in with zero understanding of how to make a decision while reaching out to some specific person. On the other hand, I’ve come across the same question many times–should I take up graduate school or pursue a job. This is a very personal question and unless you provide me with a lot of context on yourself (which takes a longer conversation, and thus time), I cannot give you an answer. However, if you ask me why I pursued either of them, then we have an excellent starting point for a conversation. Why do I say this? Because I was in the exact same boat a few years ago and asked a few folks about their own MBA journeys before explaining my backstory and that worked out much better than making it all about me.

Noone truly enjoys ‘vanilla’ questions just as noone likes a plain pizza base. You need to add layers to make it worth the time spent answering them.

Let people talk about their own stories, most of us love to do that. And if they have already spoken about their back-stories, for instance in a podcast (wink, wink), then please listen to these beforehand to ask them better questions so as to not make them repeat the same things again!

I realize that a nonzero number of people are reading my blog, after having received a few messages about it. So I decided to write an article that I can point to when I deal with questions that I have answered before–and hopefully this helps students create lasting engagement with the folks they try to reach out to for advice.

Are there ever Bad Questions?

Yes. Controversial opinion. But there almost always are bad questions in every conversation.

To me, ‘bad’ indicates sub-optimality. It means that you are not exploiting the full potential of a conversation by keeping it limited to surface-level discussion. Imagine having Walt Disney sitting next to you on a flight and asking him if free coffee is served to Disney Imagineers. Sure, there are worse questions, but is free coffee really what you want to talk about? And I should clarify this is an example that you might call a hyperbole because by no means is every conversation supposed to be optimized. But when people talk about first impressions mattering, I believe that is strongly correlated with asking great questions and making your conversational partner participate in a two-way information exchange as opposed to being a standalone contributor. Here are some things I have learnt by asking my own set of bad questions over the years:

  1. The most common reason for ignoring your message has nothing to do with you. It’s simply that most folks don’t have the time to monitor social media and LinkedIn tends to have a lot of noise ever since it turned into a self-promotion network that now has everyone and their mother posting their ‘Today I Learned’, and other humblebrags (I’m equally culpable). My own Ph.D. advisor didn’t respond to my LinkedIn message until a year after taking me on as a student. Don’t take it personally!

  2. Aside from a lack of time, the most common reason that I think conversations fail is because your question is asking them to save you the hardwork you should be putting in to get your answers. Most of them don’t want to discourage you by shooting down your question, but they want to help you out in a more impactful manner that doesn’t involve them spoonfeeding you the information you seek; a ‘teaching man to fish’ moment if you will.

  3. Sometimes it is the case that your messages lack basic courtesy. I cannot emphasise how important professional etiquette is to establish the comfort level especially given that tech is an industry that treats men and women very differently. This doesn’t necessarily mean calling someone “Dear Honorable Sir” or “Respected Ma’am” but conveying a certain tone of respect and gratitude for their time that is hard to frame as a set of to-do’s.

  4. The next most-likely reason is you causing someone ‘explanation-fatigue’ by asking them a question whose answer is already available on public platforms. They might point you somewhere or they might answer you anyway, but if you could ask ‘newer’ questions, at least for my part I’d appreciate the challenge of thinking through an answer.

  5. Your questions were too personal or probing. Questions about salary details are a no-go (unless that is the pre-determined topic of the conversation)! It is also awkward to ask someone about their personal life when you are discussing professional career choices especially in a setting where they are taking time out with no fiscal or other incentive to do so. It is not nice to put someone who is trying to help you in such a position, and while many people I spoke with were very willing to discuss the personal factors affecting their lives, I always did my background reading about their work and prefaced my questions with ‘no obligation to answer’.

How Can I Improve My Questions

Good questions require a lot of thought to be put into them and a lot of reading to be done beforehand. If you take away one piece of advice, it would be to consume heterogenous information. Do not ever read things with a goal. Relax, do what you enjoy, and let the information come to you–if you’re like me, you’ll have fun as it does!

Concretely, I think there’s a set of levels at which our questions operate and I can probably only speak to the levels I have explored personally.

  1. The most shallow level has to do with credentials–for me this had to do with discussions of an event, internship, or educational program that the other person participated in. It is a low-stimulation discussion because it is mainly one-sided–they are laying out a rather mechanistic picture of their background on a platter for your benefit.
  2. The next level of questions have to do with experience and takeaways and while slightly deeper and more stimulating than credential-based questioning, this isn’t too stimulating for someone who has likely been asked about these many times already.
  3. The third level for me would be to discuss their advice to reduce the uncertainty in your life decisions–I have mixed feelings about this, having done this in the past. I think the best mentors will not give you an answer but rather provide evidence for more than one side of the argument and let you evaluate which is the optimal choice.
  4. The fourth level is questions about their take on the world–discussing society at present and how we are affected by the powers that be, that make the world go round. In this, I include stimulating conversations about current issues pertaining to politics, economics, tech, healthcare etc. This is nice because it is not just one-sided, it involves information that might not be public; it can help mould opinions, and forces people to think as they speak.
  5. I think the final level–one that I aspire to reach–is to discuss the nuances of the future of industry, society, in a manner that draws on inferences from history and their present state. This is an insightful conversation that draws on the the sum total of both parties’ experiences and worldview in order to build up new knowledge about the evolution of the world, or a particular field, at any rate.

Now we get to that part about actionable advice on where to get this ‘information’ that I speak of other than to read newspapers and magazines. In case it slipped through, I should mention that this is also an opinion, and I’m probably being one of those people who talk too much without saying a lot (cf. Mokokoma Mokhonoana). For starters, I would recommend listening to some podcasts–I am biased by the content that I’ve recently consumed and will recommend corresponding videos because I remember them the best. Here is one of the podcasts that I enjoyed, as an Indian-origin engineering student, about a similar person who writes well and whose life I generally appreciate knowing more about:

The Early Twenties Podcast: Guest Episode with Debarghya (Deedy) Das!

I also enjoy the structure of Andrew McAfee’s podcasts particularly the points where he is alert enough to actively ingest what the interviewee is saying and churn out thoughtful comments and questions in real-time, even on topics where he is clearly a layperson.

The point I’m trying to drive home is not that that you’ll have to step into an interviewer’s shoes and match the amount of preparation that has been invested into a single conversation. But rather my point is IF you do invest that much effort into a conversation, I can almost guarantee you will end up winning their respect and establishing some really meaningful connections for life. I know that there have been some mentees that I have gone above and beyond for, in terms of time, effort, and sheer life-force expended to discuss their career outcomes, purely because they forced me to think, avoided all manner of generic questions, ‘knew their shit’, and just were nice people! In general, at least spend an hour or two looking into someone’s personal websites, their social media (Twitter, maybe LinkedIn), their research, their interests, and any articles they have written that are publicly available. For my part, this helped me place folks on a grid that allows me to define the parts of my life and career that they are best qualified to advise me on. Not everyone is able to speak knowledgeably about all topics and particularly when you want good advice, it isn’t helpful to try and push your mentors to step outside their area of expertise (although there are some merits to that, I would suggest you save it for a second conversation).

I have said this before but it is important enough to repeat. Genuine curiosity is impossible to feign. You can only pretend to be interested in someone for about ten minutes/five messages before it becomes evident that you don’t have any real questions that you want their help with. You probably just want to try and network or maybe use them as a stepping stone to some other goals. While this isn’t wrong, it’s not a nice feeling and definitely not interesting enough for the other party to continue the conversation. I strongly believe everyone has non-zero good advice to offer, and the onus is on you to direct the conversation in a manner that allows them to share it with you. If you feel a conversation was unhelpful, most likely you were underprepared for it. So before you go off finding random folks online to seek advice from, try to find your friends and get their perspective on things you want to discuss. Try to talk to seniors at your institute, professors that might just know a bit more than you do about career goals through sheer volumes of students that they have seen pass through the same corridors year after year.

From Bad Questions to Good Ones: A Case Study

Like I mentioned earlier, I’ve asked my fair share of bad questions (and been ignored) and my main challenge was verbosity or wordiness. I simply did not understand when to stop typing a message, because I just assumed everyone would be interested in reading through paragraphs of information. Well, surprise surprise! They’re NOT.

When I was an undergrad, I had this fantastic opportunity to choose between summer school + research with a professor at Stanford vs. a summer internship at CERN which was unheard of at least at my institute in the past. There were awesome folks to work with on both sides and I was extremely torn because the offer from CERN came through after I got the Visa for Stanford’s summer school and was mentally prepared to go through with it. And to top it off, I actually got two offers from CERN–one as a summer internship and the other for a year. It was a dream come true! Naturally, I wanted to make the most of what I had but I couldn’t decide and as with all my blog posts, I was too verbose in writing to folks that I sought advice from. Ultimately, my CERN guide said he’d help me do both (if it was feasible) and the Stanford professor said I should take CERN which I agreed with in large part because all else being equal, CERN was paying me a neat stipend whereas I would have to pay Stanford for the summer school, and I wasn’t a fan of making my folks pay through their noses just to see me take a few classes abroad. In hindsight, it was a no-brainer but hindsight is usually 20/20 and the excited schoolkid that I was would not have been able to reason that out in time.

A bit later I was selected for a Reliance Fellowship that would fund me if I got into Stanford for an MBA (I was super interested in capitalizing on my people skills–still do think about it) and I reached out to a bunch of Stanford GSB folks who were very kind and immediately set up calls to discuss my goals. They did ultimately dissuade me from going into business school too early and without strong direction so it was quite helpful to hear from the people in the best position before making a career-defining decision.

On the other hand, it might just be the platform because most of the time I got ignored was on Quora whereas LinkedIn had a much better response rate. I would guess LinkedIn restricting me to a 300 character message made the difference! I did improve my follow-ups and some of them are highlighted here.

This section had screenshots but I’ve been lazy whilst switching over machines and those are now lost in an abyss of bits.

Unrelated: An Opinion about Role Models

Replicating the careers of your role models is nearly impossible simply because even the exact same combination of factors will not provide the same results at such different points in time. You’re not going to be Zuckerberg because he will either offer you a billion dollars for it, or copy your features, or both. You cannot have another Steve Jobs because Apple’s supply chain efficiency beats the crap out of your mobile device startup’s business model since they are already manufacturing at scale. You cannot be Elon Musk because Tesla will buy out your battery company for its patents. You cannot be Yahoo because, well, do you really want to be them? (maybe Yahoo in the 2000’s, yeah). The point is we are told all these great stories that are 50% exaggeration, 25% PR-cleansed stories, 25% fact. For instance, how many of us were told that Bill Gates’ mom was a friend of IBM’s CEO (they sat on a board together) and it is plausible that he may have gotten the defining contract for the company through this connection (not going to share links because they’re also just opinions). Very few people talk about this and heck, it might be misinformation for me to say this given that there is little to zero evidence of this, but there is enough evidence of his mother playing a strong and supportive role in his life at every point, and that of her being a reasonably well-connected woman. This doesn’t mean Zuckerberg, Jobs, Musk, and Gates are not visionaries or ruthless business moguls, it simply means that they are outdated role models to try to emulate! With full credit to their accomplishments, I am saying that luck and external factors may have played a far more important role in most of their lives than we tend to picture in our heads. So fangirling/fanboying is perfectly fine, but remember that all your role models are human and thus flawed. They became who they are through the combination of a rigorous work ethic, opportunism, knowledge, and determination, along with a fair bit of luck. Respect them for what they achieved, by all means. But don’t put them on a pedestal claiming they’re perfect because no good ever comes of it.

I guess the point I was trying to get to was I’ve had moments where I thought some people did some incredibly awesome stuff listed on their CVs, and wrote to them all googly-eyed. But that is not a measure of who they are. Eventually I learned to just lead with the direct acknowledgment of their achievement(s), express my interest in their advice on a specific topic related to achievement, and started the conversation there. This led me to learn a lot more from them by treating them as people first and awesome later. And a crucial experience is that most secure, successful people will have disarmingly honest, often serendipitous stories about how that little glowing embellishment on their resume came to be. So my advice to you advice-seekers is to try to connect with people, talk about both of you, learn from their mistakes, but do not try to emulate their success. You define what success means to you, and fight to achieve it on your own timeline. Let noone tell you otherwise.