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...
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.
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 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
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.
i'd rephrase as "visible lack of effort is problematic" - anything above that passes the bar for me, and other factors become critical
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
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.
30 June 2026
No matter what you’re doing, from building a civilization on Mars to getting a summer internship, you will have to ask people for help. Yet, most people get this crucial skill wrong. They put themselves at the front of their request, when they should be putting the other person there. But isn’t getting help just charisma and luck? No, asking for help is a skill, not an attribute you are assigned at birth like green eyes.
How do you ask for help from people? There is only one principle. Put yourself in their mind. All good communication is grounded in an understanding of the reader’s mind. And so, I have some heuristics I would recommend when you ask for help from people you don’t know.
One heuristic to remember is that help is about people before it is about projects. When you ask for help from someone, their helping your project is predicated on them wanting to help you. So, you should make it clear that you are someone worth helping. One of the strongest ways to show that you’re worth helping is to demonstrate that you are a serious person. You might claim that you want to enter machine learning or learn to lift weights. Lots of people say that though, and the way you show that you’re serious is by showing proof of work. A trained model, a blog post that shows depth and thought and a vlog of your training are all ways to show that you are serious.
Another way is personal connection: you could say “Steve suggested I reach out” which situates you more warmly in their mind. But be careful here, because you’re borrowing against someone else’s credibility. If this person doesn’t like Steve, then this might hurt your credibility. Or, if you aren’t as good as Steve says, his credibility is hurt.
And finally, we get to institutional credibility. You could mention that you’re a student at some famous university, or work at a large corporation. This is the weakest because at best it proves you cleared a filter once, and nothing more. It also doesn’t situate you to them specifically and can feel like you’re signalling status. So use it sparingly and avoid making it your only source of credibility.
Once you have situated yourself (or not), the next step is to explain context. Before you ask them for help, you have to answer the question: what is going on here? If you have done the previous step well, you have borrowed their attention and you must spend it judiciously. Here, your description must be so short as to be unsummarizable. You are spending lent attention which is the most precious currency. To do this, think of what makes your context connect to things that they would already know. Do not explain to your elected representative the factionalism of your university club, but do explain how the club connects to their legislative priorities. Or when asking a scientist for an internship, don’t talk about how you’ve loved science since you were a child, but do talk about how you’ve implemented and extended their paper from 2023.
The next heuristic is to make your request easy to accept. Making something easy to accept largely is about reducing the cost of acceptance. One clear kind of cost is the magnitude. Do ask someone for twenty minutes of their time, but don’t ask them to read your five-hundred-page manuscript in a week. Another is to make it specific: asking for a resource to start with is better than “can I pick your brain?”. When you’ve made your request, make it low friction for them. If you’re asking for an introduction, write a blurb about yourself which they can forward. If you have a question, ask it in writing rather than over a call. And last on cost, make your ask bounded. Don’t ask for recurring obligations like being your mentor for your whole life, but do keep it limited to asking them to read a blog post. If that instance goes well, they’ll gladly read more.
My last heuristic is stranger: make it easy to say no. You might think that the worst outcome is a no, but the worst outcome is a pressured, begrudging yes. If you get a no, a good response is for you to thank them for their time and move on. Making your message carry emotional guilt or pestering them over time will not have the effect you intend. Your coercion will have poisoned your relationship with this person while you feel the false glow of a hard-won victory. A person who helps you with gritted teeth is one who will never help you again. And even then, the help will be a half-hearted effort to get rid of the obligation you manufactured. By contrast, help freely given is effortless, the way you’d hold the door open for someone. Help willingly given keeps your conscience clear, free from the burden of having pressured someone. And help, when given from the heart, is the foundation of a relationship where both of you contribute to what you’re building.
These are only heuristics. You can, when following the principle, reorder or drop them altogether. What matters is whether you’re thinking from the perspective of your reader. Except. Never lie. All your asks for help come from the person attached to them – you. And if your reader gets even a whiff of something off, then no request, no matter how small, specific, low-friction, and bounded, can get a yes.
Edit: added a line on how to respond when you get a no.