Ask HN: How do you ask users about their pain point?

You might have incorrect expectations - if you are scraping contact info from LinkedIn and getting any responses at all, you are doing well. 25% connections and 1% interview rates sounds like you are doing great.

If you follow Steve Blank's approach, the ideal thing to do is start with "friendly first contacts" - that is, people you actually know personally and/or people who you are referred to by people you know personally. Then, once you get even a few "friendly first contact" meetings, you ask those people to refer you to their contacts, and so on in turn.

Note that this stuff is never as easy as it sounds on paper, but if you put enough effort in, it eventually works (in my experience anyway).

Also note that even if you're not pitching a product for sale (yet) asking people for their time for an interview is still an ask. Ideally you'd like to be able to offer to compensate people for their time somehow. I don't mean paying them cash or anything, but think about how to structure your invitations in such a way as to communicate that you're offering them something in return for their time. That "something" might be "an early peek at a revolutionary new technology for ABC" or whatever you can think of that is a way of giving some value to them. Be creative.

Also, it's not always the easiest thing to go in asking people "what are your pain points" in an extremely open-ended way. You might find that it's easier to start with a hypothesis about a possible pain point, and pitch things in terms of "We've noticed that firms like yours often have to deal with problem $FOOBAR. To that end, we're developing a novel solution for $FOOBAR, and we'd love a few minutes of your time (no sales pitch!) to talk about how $FOOBAR and related problems affect you. In return for a 30 minute interview, we'll offer you $SOMETHING".

Consider the situation from your prospects' perspective: most likely your outreach is being lost in a sea of SPAM.

I am not a doctor, but my university email was somehow put on a list of medical professionals.

So now my university email is barraged with all sorts of SPAM targeting medical professionals. It's impossible to unsubscribe/opt out. (I've tried, but I keep getting added to new lists. It's like the original list keeps reselling my email address.) I'm sure it's much worse for an actual medical professional.

I'm assuming you're not calling (Even with calls, I personally don't answer calls from unknown numbers due to the SPAM calls. You need to be leave a text if it is important, or be very persistent.)

I'll check Steve Blank out (didn't know him), but I've been trying to follow this technique ad-hoc. Like you said, easier said than done. Even friendly people aren't very responsive to requests for intros. In the few interviews I did I made a point to ask for intros at the end and although they say "sure", it's crickets afterwards.

This is a humbling realization of what salespeople are up against. We all love to hate on these guys but man... What a hustle and you need armor-like skin and insane optimism and persistence.

Thanks for the PDF. Generally, I try to set up Zooms because it's a great back-and-forth. In-person meetings would be insanely good just for the human factor, but docs aren't into that it seems.