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.
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
The problem here is that most points are about how to formulate your ask. I think the biggest thing is that you're much more likely to get help if you show you're doing the best to solve it yourself.
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.
I agree with this and think the most important part here is less about you actually solving any specific problem and more about your prospect as a possible value add instead of just another task on your TODO list
> One of the strongest ways to show that you’re worth helping is to demonstrate that you are a serious person
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 literally wrote a similar comment to this. I think the core differentiator is whether they want to solve the problem or whether they want the problem to be solved.
Is this person actively solving the problem, tried a bunch of approaches and ran into a road block where they're asking for help?
Or are they wishing the problem didn't exist, so they do as little as possible, hoping somebody else will solve the problem for them?
I've been DM'ing randos on LinkedIn for lightweight consults and found that offering to pay up front and asking strangers to price their own time can help to show seriousness and often results in free interactions or buy-me-a-coffee pricing. e.g. "Hey I love your work on X, I've been thinking about / working on related thing Y and would love your feedback on aspect Z. How much $$ to rent your brain for 20 minutes? I'm mainly wondering what you think/know about specific questions A, B, and C." They can either reply with a price, suggest a time for a short call, or just answer directly
Maybe that's linkedin people. There are others like me: there is no such thing as 20 minutes. If I take on something, it's at least 10 hours effective. So we would just flat out refuse any such offer while on the other hand you can get those hours free if the question is sufficiently interesting.
The strongest signal you can give people now is offering personal interaction. It's expensive to go meet someone or ask someone if you can call them.
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.
Also remember that most people want to be helpful. You can play into that by starting with something like, "I was hoping you could help me get myself out of a little pickle." A little self deprecation combined with a compliment goes a long way, so if you're truly asking them to help you get out of a jam and they're one of the few people that can truly help you, say something like, "boy I really screwed this up and I'm not sure what the best approach would be, but I figured that someone with your expertise could get me reoriented quickly!"
Especially when starting something yourself. It sounds obvious but it took me far too long to long to go to people actively talking about their problems and help them vs asking them for problems they are facing.
Making that switch was a big difference in terms of outreach.
For technical requests, one of the most effective ways to demonstrate that you are serious is to cite something about the person's published work that is relevant to the request. There is no more effective way to get someone's attention than showing that you have read and appreciated something they've written.
unfortunately everyone is now doing this with LLMs, it actually feels like it might be on its way to being a negative signal, as strange as that sounds.
I've found that making the request easy to decline is surprisingly effective. People are much more willing to help when they don't feel trapped into saying yes.
There is plenty advice around for "how to ask" (really, it's the same if you know the person or not). It all boils down to a Calvinistic "show you're worthy" kind of exercise.
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.
A pretty incredible answer to your question comes from a perhaps wholly unexpected source: Hunter S. Thompson, in a letter responding to a friend's request for life advice:
Alright, after reading this, I'll put it into practice right away. First, I'll make a list of people I want to get close to, and then I'll shoot them an email to see if they'd like to stay in touch with me
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.
> 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
Identify yourself clearly.
Explain your rationale for picking that person you are trying to reach.
Put yourself at mercy of the helper.
Last but not least.
End the recording and turn of the camera on your R2D2 droid.
But how will I know which droids I'm looking for? Are these the droids?
The problem here is that most points are about how to formulate your ask. I think the biggest thing is that you're much more likely to get help if you show you're doing the best to solve it yourself.
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.
I agree with this and think the most important part here is less about you actually solving any specific problem and more about your prospect as a possible value add instead of just another task on your TODO list
I think that was the gist of the first point: “show you’re a serious person”
"Help me help you" stands.
I don't think it's just that, I also think it's "be someone I want to help"
> One of the strongest ways to show that you’re worth helping is to demonstrate that you are a serious person
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 literally wrote a similar comment to this. I think the core differentiator is whether they want to solve the problem or whether they want the problem to be solved.
Is this person actively solving the problem, tried a bunch of approaches and ran into a road block where they're asking for help?
Or are they wishing the problem didn't exist, so they do as little as possible, hoping somebody else will solve the problem for them?
I've been DM'ing randos on LinkedIn for lightweight consults and found that offering to pay up front and asking strangers to price their own time can help to show seriousness and often results in free interactions or buy-me-a-coffee pricing. e.g. "Hey I love your work on X, I've been thinking about / working on related thing Y and would love your feedback on aspect Z. How much $$ to rent your brain for 20 minutes? I'm mainly wondering what you think/know about specific questions A, B, and C." They can either reply with a price, suggest a time for a short call, or just answer directly
Maybe that's linkedin people. There are others like me: there is no such thing as 20 minutes. If I take on something, it's at least 10 hours effective. So we would just flat out refuse any such offer while on the other hand you can get those hours free if the question is sufficiently interesting.
In that case, I appreciate your comment here! Not sure it was worth 10 hours, but it was good of you to share.
The strongest signal you can give people now is offering personal interaction. It's expensive to go meet someone or ask someone if you can call them.
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...
Also remember that most people want to be helpful. You can play into that by starting with something like, "I was hoping you could help me get myself out of a little pickle." A little self deprecation combined with a compliment goes a long way, so if you're truly asking them to help you get out of a jam and they're one of the few people that can truly help you, say something like, "boy I really screwed this up and I'm not sure what the best approach would be, but I figured that someone with your expertise could get me reoriented quickly!"
100% in terms of people before project.
Especially when starting something yourself. It sounds obvious but it took me far too long to long to go to people actively talking about their problems and help them vs asking them for problems they are facing.
Making that switch was a big difference in terms of outreach.
For technical requests, one of the most effective ways to demonstrate that you are serious is to cite something about the person's published work that is relevant to the request. There is no more effective way to get someone's attention than showing that you have read and appreciated something they've written.
unfortunately everyone is now doing this with LLMs, it actually feels like it might be on its way to being a negative signal, as strange as that sounds.
Hm, hadn't thought of that.
I've found that making the request easy to decline is surprisingly effective. People are much more willing to help when they don't feel trapped into saying yes.
Don't say, I've been working on your neighbors house and figured you might want to hire my crew to work on yours. We all know it's a lie.
There is plenty advice around for "how to ask" (really, it's the same if you know the person or not). It all boils down to a Calvinistic "show you're worthy" kind of exercise.
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.
A pretty incredible answer to your question comes from a perhaps wholly unexpected source: Hunter S. Thompson, in a letter responding to a friend's request for life advice:
https://fs.blog/hunter-s-thompson-to-hume-logan/
Alright, after reading this, I'll put it into practice right away. First, I'll make a list of people I want to get close to, and then I'll shoot them an email to see if they'd like to stay in touch with me
Connect, show your own commitment, size for success their requested commitment, leave them an out.
The complete article hinges on the fact that, it's not X; but Y.