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

There's a big difference between:

"Hey, I saw this job at [company you work at], could you refer me please? I'm [lists skills and experience]"

and

"Hey I'm thinking of applying to [company you work at] for the product designer position and I want to make an impression, so I'm putting together a demo Figma with a couple of things I'd fix and how. I spotted those when I did the onboarding for your free trial. I'm curious if you could tell me whether [design flaw] is intentional to deter abuse or if that's something I could fix? Totally get if that's confidential"

The part where you're solving the problem instead of hoping someone else will solve it for you, that's much more important then how you word it.

When I’ve been in positions where a lot of people ask for help, this is the #1 place I saw people drop the ball.

The advice to show proof of work up front is important. What isn’t so obvious is that the proof of work needs to go deeper than surface level. Putting up a single blog post or having Claude write some code that you upload to GitHub doesn’t cut it. You have to show that you’ve been putting effort into this for all the right reasons, not just as a ploy to appear like a serious person. When you get 10 requests for help every week you get very good at being able to tell who has been putting in the work and who thought they could appear like a serious person by putting on a little show.

This doesn’t end after you get the meeting. Following up is just as important. When someone makes time to hear you out and offer advice, you need to demonstrate that you tried what they suggested. You can choose not to follow their advice, but that’s probably the end of the help you receive. It’s a choice.

The easiest way to blow it is to ask for someone’s help, then ignore it or fail to follow through. If someone helps you, follow up with some contact to explain how it helped, or at least how you tried it. Nothing is more frustrating than setting aside time to help someone and then a month later you run into them and learn that they haven’t gotten around to doing the thing they wanted help with.

I wrote about this from the perspective of someone with no connections [0] but I think even if you're well connected, reaching out to people from other networks is a useful way to gain access to great thinking, information, and opportunity.

[0] https://www.nair.sh/guides-and-opinions/marketing-under-pres...

But what about advice for giving help to someone?

There's plenty of ways that giving someone help can go horribly wrong, and I think that it's not uncommon for people to be blindsided by such a request.