Person targeted questions for roadmapping

Before jumping into the exact questions — a few notes on the general philosophy on questions. I believe that while Thoughts should be written, Questions should be verbal for the express purpose of clarification and tangents. Given that philosophy, it’s important to not be too prescriptive about the wording of a question or getting to all of them. Similarly, questions should enable situations where you want to dig into something unexpected. To that end they should be short and open-ended.

Another thing is to go in always having done some pre-work. <The law about being wrong on the internet> also works in conversations as well, so it’s much more productive to throw out a wrong hypothesis and be corrected than to ask the other person to come up with a hypothesis on the spot. Of course, this runs the danger of anchoring them too hard.

People are very bad at answering questions like What are the most important problems in your field?. Most people outside of fields think about fields but not how (most) people inside of them think.
I suspect that Hamming didn’t randomly walk up to people he had never met before and ask them — he was asking people in the Bell Labs cafeterias who he probably had preexisting relationships with or didn’t ask in exactly that way.

The goal of roadmapping questions is to figure out:

  • In a given area, what are the compelling goals (in as much detail as possible)
  • (As MECE as possible) what are the paths to get to that goal.
  • What (roughly indivisible) projects/intermediate goals need to be done along each of those paths
  • What does the dependencies between each of those projects look like?
  • Which people/organizations are best suited to do each of those projects
    • Note here that “best suited” is not just about skill, but about alignment about the end goal, willing to do it, etc.

The trick is that in almost every situation, you cannot ask those questions. People do not think in this way, especially practitioners in a field.

  • Questions after doing this for almost two (!? Oh Lord) years

    • I was very impressed by <thing in paper that shows you read it> where did the idea for that come from?
      • Notes: this only works if you are actually impressed. People can smell fake interest a mile away.
      • This question is much less about the answer than signaling that you actually did your homework, making them feel special, and helping them understand which aspect of their work you’re most interested in.
    • It seems to me based on your work that <X> might be promising but I haven’t found anybody working on it. Have you thought about that?
    • Why isn’t anybody doing that work?
    • What would enable them to do it?
    • Have you considered working with <other discipline informed>? why not?
      • Note that this question can make you sound extremely dumb in the bad way if you don’t have a strong hypothesis for why they would want to work with that sort of person.
    • So it sounds like <X> is particularly <hard/expensive> is that right? Why do you think that is?
    • Do you have a sense of the big audacious goal for your work?
      • This question is less meant to answer the question but to see how people react to it.
    • Other people have told me <devil’s advocate position> what do you think about that?
    • <at the end of a conversation> Who else do you think I should talk to about this?
  • Original questions from 22 May 2020


A bit of an ask if I may be so bold. I’m working on a hypothesis (inspired in part by Adam Marblestone’s lecture on roadmapping biology that you can map research paths that can then enable coordinated work that wouldn’t happen otherwise.

If you (or someone you know) is down to do a sort of “user interview” about the frontier of your discipline, please do let me know.


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