Ask HN: How can I “learn” to talk to people?

Stop caring about what others think of you.

Back in the day, I was pretty shy and probably still am to a certain point. I was always self conscious; was I dressed properly, did my hair look ok, etc...

I made it a point to stop being like this. To just be me. It's not to say, don't care what you look like or how you carry yourself or etc... But stop worrying about what others think. You can't please everyone; not everyone will like how you dress, talk, etc... That's ok. Your not out to please everyone.

Own the room / conversation / email.

Over the last 5 years of doing my startup, we started going to events where we were exhibitors. I go to help out - pass out free t-shirts, tell the students what we do; how we help them, etc... So a shy person having to talk to 600 strangers inside of 3 hours? Yeah, no. So I decided to own the room. I walked into that room prepared; I knew what I'd say; I knew what I'd have to offer and if I couldn't answer; I'd defer to my partner. At first, I wore a suite / tie. This last year; I wore our t-shirt and a sports jacket / jeans. We own the room at these events.

Know what your talking about.

At first, I was just the developer. I knew very little about our target industry. I built the site for sure, but anything past that - "I'd like to introduce you to my partner..." It wasn't until I took an interest in our industry could I speak confidently to our users. Being confident in what I was talking about took time for sure; but where I was nervous about going to this event in years past; now I walk in like it's a party. We're there to see our users face to face, give out some cool free stuff and make new connections. It's become my favorite thing of the year to do. Smile from ear to ear, baby.

So - confidence, knowledge and level of comfort with a given subject. Nail those, and you'll have an easier time.

You start reaching out and talking to people.

Expect some initial trepidation and the occasional epic failure. Learn from it all.

You could also try something like Toastmasters (https://www.toastmasters.org/) which some folks I know have said helped them quite a bit.

It's a skill to develop and practice, like any other, except that humans are awful.

The answer to this question depends upon what specific issues you have talking to people. If you merely have unfounded anxiety, confidence-increasing tactics like joining toastmasters will help (although that will give you experience in public speaking, which is very different from private speaking). If your fear of talking to people stems from poor social skills, I recommend reading the first half of the book Games People Play, because it explains in pretty concrete and procedural terms a model of communication that addresses some common mistakes people with poor social skills make (particularly, talking significantly more or significantly less than justified by the situation). (I don't really recommend the second half of the book, because those ideas are less useful for the purpose of keeping good relationships & have also spread much more widely.)

Very very few people enjoy cold call sales pitches...or you're not alone in how you feel. Cold calls are hard because the odds are you, or anyone else, will be rejected.

One technique I heard about some where is to measure and track the number of rejections. Partially because this is a big number and easy to increase, partially because it aligns with the hard part of making calls...calling and risking rejection.

Another technique is to team up with someone who likes talking to people.

Good luck.