Inspired by one of Philip Guo’s vlogs, I spent a good chunk of August arranging chats with people whose work paths intrigued me. Here are a few thoughts on reaching out. 

Overarching Themes

In every chat there were two conflicts at play: 

1. A clash between [1] a desire to get to know the individual better as a person, and [2] a desire to be considerate of their time. 

When I set these meetings up, my primary goal was to gain insight to guide my own path. This goal resulted in many logistical questions for practical advice.
  • “CHI, SIGRAPH, etc: what are some great conferences to attend?”
  • “What did you wish was taught in the curriculum, that you had to compensate in your own time?”
  • “Do you wish you were more technical? Or that you had dedicated code-learning time to accumulating other skills?”
  • “What criteria do you use to decide on projects? Pure excitement, the learning potential, the novelty, the feasibility?The question boils down to: What are the ingredients for a self-directed side project that is worthwhile yet realistic?”
  • “Do you first learn tools, then come up with ideas to apply it to, or do you first come up with ideas, then collect tools to acheive them?”
  • “You've published papers! With your own ideas and creative input as an undergrad, from start to finish — how could you predict the idea would be well received, what was the submission process like?” 

However, there were always questions that arose from pure curiosity in the person’s story, outside of their accomplishments. These questions don’t necessarily grant me any practical lessons, and may be perceived as vague, open-ended, and even cliche.
  • “What inspired you to go down this path? Why did you choose academia over industry despite its brutality?”
  • “What are you motivated by? Social impact, the prospect of stability for your family, the sheer intellectual challenge?”
  • “Which part of the process do you most enjoy? The broad, overarching questions, or the feeling of little steps of progress each day?”

I did not ask questions in the latter category, in the interest of conserving the other person’s time. However, I did wonder if doing so would make the chat more interesting and personal for the other individual, or if I’d just be an annoying teenager wasting their time with vague questions.

There is always a little part of me that wants to get to know the individual on a more personal level. After all, my good friends from school and I are buddies despite lack of common interests. That is due to chance pushing us into regular proximity and the accumulation of time. In contrast, these people I reach out to, I reach out to with intention, because we do have some overlaps in thinking and interests. Potential for connection knocks at the back of my mind.

But, I do understand that the both of us are limited on time, and it is not wrong to focus on the more practical advice.

2. The difference between an interview, and a conversation

An interview: I purely question and listen.
A conversation: I offer my own perspectives in return. There is more give and take.

An interview would be less time-consuming and allow the other person talk at length about themselves. A conversation could potentially feel more personal and less one-way. Which option would be most considerate and interesting for the other person? I want to cultivate chats that are mutually beneficial, rather a one-way stream that is only interesting or useful to me, the advice-seeker*.

*(For this reason, I drew small blind contours for the people I met in person. What are other ways advice-seekers can pay advice-givers back?)

Preferences likely vary according to the individual. There are other factors, like age and seniority gap, which could determine whether or not the advice-giver would be interested in a more conversation-leaning meeting.

If you are someone senior to me (even just by a year) and reading this, I am curious — what is your personal preference for chats with juniors? What is the perfect ratio of interview to conversation; logistical to personal?

Reaching out also took longer than I expected. Crafting the email, articulating questions: all of that took TIME. I had to sharpen a vague sense of lostness and confusion into actual, targeted questions, and discovering those knowledge gaps followed by describing those gaps took some effort on my part.

After all, it’s hard enough to describe what you know, how do you describe what you don’t know? Trying feels a bit like grasping in the dark.

But at the same time, while I strive to be thoughtful with my questions, this aspiration is a double-edged sword, because it means that I do not jump in unless I feel prepared, and my window of opportunity can blur past.

Tiny, logistical details

The first in-person meeting I arranged, I focused more on what questions I would ask: the contents of the conversation. On the train ride there, however, it struck me — commute distance, locating the meeting point, walking home after dark— so many logistics could have gone wrong and inconvenienced my advice-giver, especially because they were not local to city. 

So, here are some logistical considerations at every stage, outside of the usual “keep the email short” advice. This list is a compilation of my own observations and advice I received from others.

I. Reaching out and sending the initial email
  • Give the person a sense of what you want to talk about — I linked a Google doc with specific questions, so they would not be put on the spot and could ponder it beforehand if they wanted.
    • Questions do not have to be super specific and targeted. Often the advice-giver possess information you are unaware of. If you are unaware, how can you know to ask about that information?
    • Google doc also enables you to take notes if it is not an in-person meeting
  • Set an expectation of the amount of time it will take. My convos have taken 1.5-3 hours (longest thus far was 5).
  • Give 3 options for location if you're going to meet in person. Propose a time range upfront.
  • Give them the option or a phone call or email meeting, because some people are busy, but they feel bad for downgrading, so it's better for you to provide the option.
  • Provide your phone number in case you or they get lost on the way there.

II. Selecting places to meet
  • Commute — bus price; distance; parking price (especially if you're meeting in a city where parking is pricey)
  • Is the store easy to find?
  • Price level of the location.
  • Noise level — can you talk comfortably there?
  • Does the place have weird hours? The place I selected closed at 8PM and was completely closed on Tuesdays and Wednesdays. Thankfully, our meeting went smoothly, but what if not?
  • Don't go to places with wait times + reservations

III. Timing/General Safety
  • Store hours
  • If you’re out late, after work or school, when is sunset?
  • If you're a minor, ask your parents beforehand if you can be out when it’s dark.

IV. Follow-up email
  • What do I send in a follow-up email? This I am still unclear about.
  • I just sent some overall impressions and notes from the meeting along with the usual thanks.

III. Questions! (This is an Open Solicitation for Advice.)

If any of you reading this post have any thoughts, please DM, email, or leave a comment! 

Some questions:
  • If you are someone senior to me (even just by a year) and reading this, what is your personal preference? What is the perfect ratio of interview to conversation, logistical questions to personal?
  • What kind of questions do you most enjoy answering? Specific, targeted questions, or broad, general questions? What kind of questions do you feel you are best equipped to answer?
  • What do I send in a follow-up email? This I am still unclear about.
  • Most of the people I talked to were fresh college graduates working in industry. Would any of these tips change if you were talking to, say, a grad student in academia, or a professor (who likely has piles of tasks stuffed in their schedule)?
  • General tips on making the chat more mutually-beneficial and less one-sided?
  • Office hours: what should the first meeting with a professor look like?
    • What would the dialogue sound like?
    • “Hi, I’m Mengming, I scanned your paper, and I jotted down some questions because I find the work interesting.”

ALSO, to advice-givers: feel free to ramble and give us advice-seekers more information than we ask for. We cannot ask about what we are unaware of, so by providing that information, you expand our circle of awareness. This has been especially true for me when it comes to school programs, fellowships, and conferences that were previously outside the perimeters of my exposure.

10/11/2019 Edit

I’ve received some great tips since writing this. In particular, I wanted to share this Twitter thread (thank you Wesley!).