Discussion summary

The discussion covers strategies for asking for help from strangers, emphasizing credibility, presentation, and persistence. Some suggest creating attractive profiles or demonstrating seriousness to gain trust.

What the discussion says

  • Show commitment and credibility to increase chances of help.
  • Use attractive profiles or secondary accounts to attract attention.
  • Be genuine and demonstrate seriousness when asking for help.
  • Online responses vary; some suggest being direct and persistent.
“Demonstrate that you are a serious person.”
— sherlock-holmes
“Connect, show your commitment, and leave an out.”
— CGMthrowaway

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  • Hacker News
  • 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.

  • 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.

  • 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.

  • 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...

  • 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
    by mrtb
  • 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.

  • > 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.

  • 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

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