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This was an excellently written, salient post with some good tidbits.

I've learned some of these lessons the hard way. I'll add a few. Proof of work is important, but it's not about the magnitude of energy you spend. I went through two iterations of reaching out to my college network. The first time I put so much time into handwriting notes and trying to provide my relatable background. 100 notes, not a single response.

The second time I sent emails that were a few sentences. I had a much clearer ask and devoted the effort into fitting my questions into the email. I wanted a conversation really, but I also tried to communicate what I planned to ask.

15% response rate and invaluable conversations. Less overall "work".

Secondly, and relatedly, don't ever waste someone's time. Don't ask for / accept a meeting if you don't have some semblance of a clear ask. It's hard, especially in early stage business where you're trying to discover what you don't know. But you can try to lay out your tier 1 "here's what I think", "here are the follow ups".

I sensed once that I had irritated someone by lacking the agenda. Another time I took a mutual connection up on an intro where I didn't know what I really needed. I regret both of these.

Thirdly try to pay it forward. It won't always come back around, but you can feel more comfortable asking for help and more cognizant of what a helper (so to speak) is thinking



> I went through two iterations of reaching out to my college network. The first time I put so much time into handwriting notes and trying to provide my relatable background. 100 notes, not a single response.

This is a thoughtful gesture, but there are at least two problems with it

First, a handwritten note isn't easy to respond to. With an e-mail, you can leave the message in your inbox until you have time to respond and then it's one click to start responding. With a hand-written letter the recipient would have to context-switch from reading mail to using a digital device and they'd have to transcribe your e-mail address. It's not much work, but it's still work that someone has to make time for.

Second, it's an unusual thing to do. It's important to communicate with people through normal, comfortable communication channels where the etiquette is known. Having someone handwrite a letter and look up your mailing address is unusual. Unusual behavior triggers people's suspicions. You weren't trying to scam anyone, but you should be aware that one of the tricks used in scams is to invest unusual amounts of attention and energy into someone. It can trigger a suspicion that you're really after something else.

Your second round of sending short e-mails had neither of these problems. Easy to reply to, nothing unusual about it. It's the way to go.


When I was younger, I was always paranoid when I reached out to somebody and didn't hear back. Now that I'm older and busier, I totally get it. Clearly state who you are, what you want, and what your timeline is. It's far easier to reply to a message like that, than to parse paragraphs of fluffery looking for an ask.


> I sensed once that I had irritated someone

Solid advice, (but to others reading) don’t optimize for not irritating people.

Especially your professional network. You built those relationships because you wanted to use them in the future, and the future is now… so, tap them! If they don’t like that, no big deal, no sweat, move on.

If you’re irritating multiple people constantly, then yea you’re probably doing something wrong. But if it’s one person once in a blue moon, that happens, don’t over optimize for avoiding that. You can’t make everyone happy


+1 that there are few things more exhausting than listening to someone's "proof of work"

i'd rephrase as "visible lack of effort is problematic" - anything above that passes the bar for me, and other factors become critical


  > Thirdly try to pay it forward.
An important step. If you don't it's not dissimilar from pulling up the ladder behind you.

The thing I've found is that often what's simple and easy for me (the person being asked) is difficult or overly cumbersome for the person asking (or even not asking). Often it's due to simply being in the right position or knowing the right people. We're all in this together and there's so much to success that's beyond talent and skill. All the small little actions add up even if you don't get to see how


This is good advice. I run the mediatec workshop at a art university, meaning my daily job involves many student requests. A good request is one where the student thought about what I need to know and which question they need answered. A bad request is a wall of prose that leaves you wondering about what, precisely it is they now want from you, potentially also leaving out key information like duration, place, etc.

My number one tip therefore is to try to put yourself into the perspective of the other side. Did you give them all the information they need to know? Of course you will know a lot of things about your project that are really obvious to you, but that you would need to mention to others so they understand what you are talking about. On the other hand if you want to hire a plumber, you don't need to tell them a long story about the roof of the house. Conceptually the plumbing and the roof may both be house-related issues in your mind, but you're wasting the plumbers time. So that means the time/patience of the person on the other side is a valuable resource.


> 100 notes, not a single response.

Similar story. Sent out 900+ emails to scientific illustrators; about 25 accepted. Here's the result:

* https://impacts.to/downloads/lowres/impacts.pdf

* https://impacts.to/bibliography.pdf


How to ask for help is an under-discussed important topic.

Women are way better at asking for help and getting it as compared to men.

there's some very well-known psychology tricks that you can use to get better outcomes. Cialdini's book and Munger's speech on psychological bias are first class.

you want to be opportunistic but not too attached to your ask.

ask for a lot and then back off works tremendously better even with kids

perception (looks, reputation, stereotypes) have an outsized impact on outcomes. look at any successful sales department for proof of this. perception can be faked unfortunately.

put hard limits (of time) on your ask. make it clear that its a one time ask.

The most counterintuitive aspect (covered in the article) is that you'll get a yes more often if it's easy for them to say no.


I disagree with everything you said. It's basically just pure luck in terms of something like repairing a flat tire, etc., and then in a professional setting none of this applies at all.




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