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.
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
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
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.
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 refer a lot of people and I would be more likely to respond to the first one. Provided they supply a job link, their resume, and they were well qualified and polite.
In the second one it’s really obvious to me that they just want a referral. It would annoy me that they are making me read extraneous information.
I think that if you make your request too specific, like in the second example, you might seem less approachable, and you'll cutting yourself off from a lot of potential serendipity. The first question could result in "No, but I know someone else you could talk to." The second question requires the person you're messaging to be willing and able to go down a very specific path.
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 think the most important thing to be aware of is that your own personal estimation in how willing some group of people is to help is regularly off by several orders of magnitude.
I've had people assume that person X must be asked several times a day for help when they're really asked once every few years. Alternatively, I know people who assume they are sending some totally unique request to someone who gets a dozen of the same inquiry every single day.
Until you get a good baseline figure of how competitive your request for help is, everything else is pre-mature optimization. The best thing is to just be lightweight about it and dash something off as soon as you think of it and to not be too emotionally invested in whether you get a response or not. Only when you gather evidence that the response rate is below what you expected should you try to optimize how you ask.
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
This is what Jason Cohen did when he was getting WPEngine off the ground. He messaged 40 WordPress consultants on LinkedIn and offered to pay them higher than their hourly rate since it was a one-off task.[0]
Out of 40 messages, 38 replied and agreed to a phone call, and none of them actually asked for the money.
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.
First question that I will have would be - why do you need the what are you asking for. Because you are relying on my expertise and I do expect myself to deliver the best possible answer. And then we go into 10h+ land.
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.
One thing that always bugs me at work is when I get a slack message from someone I don't know along the lines of:
"Hello John, are you available to chat later today about Foo Product?"
Or sometimes just:
"Hello John"
I know they want something from me, but I have no idea what, how much effort it will require, how urgent it is, or whether I am even capable of helping.
A much better approach is more like this article outlines:
"Hello John. I'm looking into in a client-reported issue with Foo Product. The customer states they are unable to do X. The support ticket is <link to ticket>. I've done some investigation and think I have identified the root cause with <possible root cause>. Are you available for a brief 30 minute call this afternoon to discuss the issue as well as some potential fixes?"
That way I have some idea of context, priority, and what they are looking for from me. I can also review the details of the ticket prior to the call, which makes for a more productive conversation. Or if there is someone else who is more knowledgeable than me, I can request that we add that person as well.
If you're in the habit of starting work conversations on slack with just "Hello" - I would highly recommend that you start including additional context when initially reaching out.
Here's a tip for doing this while traveling: If you need quick help on the street from a stranger in a country where you don't speak the language, don't open by asking if they speak your language. People will almost invariably say no even if they do to avoid the imposition.
Just say "hello/excuse me" in their language and then ask the question in your language. If they speak it, they will often answer you quickly. Sometimes you can even see a look dawn on their face after the fact as they realize you skipped the first step.
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!"
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.
What always worked for me is something like, "Hey, I read your book!" or "I just heard your interview on the radio!"
It's especially effective if it's a timely event. People do talks and interviews to meet people and get some attention, so you're basically shaking hands with someone who's ready to shake yours.
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.
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.
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:
I did have in mind something more like the Socratic method, asking pointed questions of your mentee, guiding them but not pushing them. I suppose that in a weird way that essay is the Hunter S Thompson idea of the socratic method.
I really do think it's important to give thought to HOW to give help.
Especially in the technical communities, there's such an over-emphasis in "asking correctly". It perhaps started with usenet (think Eric S Raymond's INSUFFERABLE FAQ on "How To Ask Questions The Smart Way"), and ended with the persnickety and now thankfully moribund stackoverflow gameified and toxic question-and-answer forum.
From what I have seen online like for Reddit discord and online forums is that the questions with the most responses tend to be almost the exact opposite of what this post says. What you got to do is bait the audience into responding. It usually follows the following formula:
Title: “woe is me this problem with well documented answers is troubling me!”
Body: a vague description of what the problem is and what they’ve tried. Leaving out key details that would drastically change the answer.
Response to answers: now that you have them hooked most answers will be actual questions about what your original post lacked to clarify. Be sure to respond to these as the more engagement on your post makes the algorithm show it to more people. And the second round of answers has a higher chance of answering your question.
Wait until a critical mass of people have seen and attempted answering your question to exhaustion. Hopefully you will be able to piece together a solution.
It's incredibly difficult for me to ask for help because I was raised to always pull myself up by the bootstraps. This attitude has seeped into my moral framework. If I get help, it's special treatment; it's an unfair advantage that I'm getting which will harm other people who have to compete against me.
I wish people would just stop 'helping' each other (as it is currently). Help should only be given to people who are in dire need and it should only be enough to allow them to stay afloat. Helping someone to become a multi-millionaire is not 'help', it's injustice; it only exacerbates the problem. It creates a system where success is impossible without receiving help. This, in turn, creates a totalitarian system where people are just trading favors with each other since everyone who succeeded helped each other to various extents and everything they're doing is balancing favors.
'Paying forward' really means; giving favors to someone new in order to obtain favors from them in the future. It's not good for anyone.
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
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
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 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
i'd rephrase as "visible lack of effort is problematic" - anything above that passes the bar for me, and other factors become critical
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.
In the second one it’s really obvious to me that they just want a referral. It would annoy me that they are making me read extraneous information.
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.
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 had people assume that person X must be asked several times a day for help when they're really asked once every few years. Alternatively, I know people who assume they are sending some totally unique request to someone who gets a dozen of the same inquiry every single day.
Until you get a good baseline figure of how competitive your request for help is, everything else is pre-mature optimization. The best thing is to just be lightweight about it and dash something off as soon as you think of it and to not be too emotionally invested in whether you get a response or not. Only when you gather evidence that the response rate is below what you expected should you try to optimize how you ask.
Out of 40 messages, 38 replied and agreed to a phone call, and none of them actually asked for the money.
[0] https://mtlynch.io/notes/designing-the-ideal-bootstrapped-bu...
First question that I will have would be - why do you need the what are you asking for. Because you are relying on my expertise and I do expect myself to deliver the best possible answer. And then we go into 10h+ land.
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...
"Hello John, are you available to chat later today about Foo Product?"
Or sometimes just:
"Hello John"
I know they want something from me, but I have no idea what, how much effort it will require, how urgent it is, or whether I am even capable of helping.
A much better approach is more like this article outlines:
"Hello John. I'm looking into in a client-reported issue with Foo Product. The customer states they are unable to do X. The support ticket is <link to ticket>. I've done some investigation and think I have identified the root cause with <possible root cause>. Are you available for a brief 30 minute call this afternoon to discuss the issue as well as some potential fixes?"
That way I have some idea of context, priority, and what they are looking for from me. I can also review the details of the ticket prior to the call, which makes for a more productive conversation. Or if there is someone else who is more knowledgeable than me, I can request that we add that person as well.
If you're in the habit of starting work conversations on slack with just "Hello" - I would highly recommend that you start including additional context when initially reaching out.
[1] https://nohello.net/en/
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.
Just say "hello/excuse me" in their language and then ask the question in your language. If they speak it, they will often answer you quickly. Sometimes you can even see a look dawn on their face after the fact as they realize you skipped the first step.
It's especially effective if it's a timely event. People do talks and interviews to meet people and get some attention, so you're basically shaking hands with someone who's ready to shake yours.
[1] I'm trying to establish this as the accepted idiom for having low quality AI output forced upon you without consent.
1. Be Rich
2. Be Attractive if you didn't complete step 1.
3. If you failed to complete steps 1. and 2., don't bother.
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.
OTOH,
> make it easy to say no
is the best piece of advice amongst many other pieces of good advice
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.
https://fs.blog/hunter-s-thompson-to-hume-logan/
I’m definitely borrowing the phrase “galloping neurosis” the next chance I get.
I did have in mind something more like the Socratic method, asking pointed questions of your mentee, guiding them but not pushing them. I suppose that in a weird way that essay is the Hunter S Thompson idea of the socratic method.
I really do think it's important to give thought to HOW to give help.
Especially in the technical communities, there's such an over-emphasis in "asking correctly". It perhaps started with usenet (think Eric S Raymond's INSUFFERABLE FAQ on "How To Ask Questions The Smart Way"), and ended with the persnickety and now thankfully moribund stackoverflow gameified and toxic question-and-answer forum.
Body: a vague description of what the problem is and what they’ve tried. Leaving out key details that would drastically change the answer.
Response to answers: now that you have them hooked most answers will be actual questions about what your original post lacked to clarify. Be sure to respond to these as the more engagement on your post makes the algorithm show it to more people. And the second round of answers has a higher chance of answering your question.
Wait until a critical mass of people have seen and attempted answering your question to exhaustion. Hopefully you will be able to piece together a solution.
Gotta get them points?
* No abbreviations like "plz"
* No wall of text (and no AI walls of text)
I wish people would just stop 'helping' each other (as it is currently). Help should only be given to people who are in dire need and it should only be enough to allow them to stay afloat. Helping someone to become a multi-millionaire is not 'help', it's injustice; it only exacerbates the problem. It creates a system where success is impossible without receiving help. This, in turn, creates a totalitarian system where people are just trading favors with each other since everyone who succeeded helped each other to various extents and everything they're doing is balancing favors.
'Paying forward' really means; giving favors to someone new in order to obtain favors from them in the future. It's not good for anyone.
a LOT of people miss this
Starting yet another project on my primary GitHub profile has zero return. My secondary profile with trivial code is getting job offers...