How to get strangers to help you.

Here’s how to write great cold messages asking for advice.

Annie Chen
Nov 9, 2018 · Unlisted

Four years ago, Professor Philip Guo gave a talk at my school about learning programming at scale. I wanted to learn more, so I googled him. His Email Writing Tips article, explained the importance of deciding whether you should be emailing a person in the first place and having a specific ask.

Inspired by his tips, I sent him the following:

He responded within a day with a list of active researchers and companies in education technology.

Armed with Professor Guo’s advice, I’ve since reached out to a variety of strangers. Many of them have been kind enough to respond. The information and advice I’ve received significantly influenced the decisions I’ve made throughout college.

For instance, I knew early on in college that I wanted to someday work in education technology. From LinkedIn stalking, it seemed like a lot of people did internships at big companies before working at somewhere like Khan Academy. So, I emailed a stranger who’d done a Google internship before her KA one, asking what skills and experiences she’d needed to succeed at KA. She said smaller companies typically had less onboarding infrastructure built up to help first time interns. She was glad she’d interned at KA after a summer at Google, and specifically recommended the Engineering Practicum program. Upon her suggestion, I applied and participated in the Practicum program, where I learned general workplace processes like 1:1s and performance reviews. My time at Google allowed me to confidently jump into work at the Chan Zuckerberg Initiative (CZI), where I interned this summer. Without her help, I would have been less prepared to succeed going into my dream job.

Somewhere along the way, strangers started cold contacting me asking for help. Recently, people want to know about interning at CZI (Which was an awesome experience! You should apply!). In my brief experience answering these types of messages, I’ve thought a lot more about what makes a good ask, especially from a student.

Here are my strategies for asking for help and info. If you disagree, I’d love to know what works for you.

My philosophy when asking questions is to do as much of the work as possible to figure out what you want from the person, and show in your message that you’ve done the work. In practice, this means a couple different things:

  1. Make it clear why you’re asking this specific person for help.
  2. Don’t ask about information that you can find elsewhere. If you’ve already looked for it elsewhere, say so.
  3. Then, give the context someone would need to give useful advice.
  4. Ask specific questions.
  5. Follow up at least once, but not too many times.
  6. Build a deeper relationship by letting them know how things went

Want the details? Keep reading!

“Should you even be emailing this person?” Think about why they’re the right person to answer your questions, and make that clear to them.

Here’s an email I got last week:

This is a great example of explaining why you’re reaching out to someone. I also had a CZI offer and a returning Google internship offer, so I’m a good person to compare the two experiences.

It‘s useful to say how you found the person, and a brief reference to why their experience is relevant to you and your question.

Asking a question obviously answered by the internet is a really fast way to lose your credibility. But, showing that you’ve done your research starts you off on a good note.

This doesn’t need to take hours. Just make sure that you‘re not missing something obvious, like an article they’ve published on the subject. I go a little overboard, and will usually check out their LinkedIn, look at their personal website, and try to find something they’ve written. I’ll craft a response only after I’ve processed all the information I can find.

It’s totally reasonable that your question isn’t answered anywhere, or that you still want to know more. In that case, say what information you’ve already looked at. For example, instead of “How does the interview process work?”, something like “I read the job description and the slides the recruiter gave me, but I wanted to hear about timeline for the interview process. How long did it take the recruiter to get back to you after your first interview?”

Traditional emailing advice says you should make your messages short and sweet, as few words as possible. Mattan Griffel says an ideal email is 2–3 sentences, and “people tend to think that they need to provide way more info than the reader actually need.” I prefer Professor Guo’s advice: If you must write a longer email, separate the gory details from the summary.

I think ‘gory details’ are context details that will help someone better tailor their response to what you’re looking for. Here’s a LinkedIn message I got from a stranger recently:

I responded to it by asking for the information I felt I needed to give meaningful advice: Is this for a full time or intern position? (I have no experience with the full time interview process, but could connect you to someone who does.) Have you had interview experience before? (Are you looking for generic interview advice, or whether CZI interviews are different than your average onsite?) What information has your recruiter already given you? (If you’re asking about structure or number of interviews, the recruiter would be a much better source than I would.)

It took a lot more back and forth; definitely more time than it would have taken to read a context paragraph in the first message.

I like to add a bit at the bottom of the message that literally starts with “For context.” In this case, it might look like this:

For context, I’m a junior looking for a summer 2019 internship. My recruiter gave me information about what the day would look like. I’ve done phone interviews before, but this is my first technical interview onsite, so I’m pretty nervous.

It’s at the bottom, so it doesn’t weigh down the initial question, but the recipient also doesn’t have to go back and ask you for more information.

Getting super general questions is my own pet peeve, and I know other people that don’t feel this way at all. But in my opinion, a general question like “what was it like?” forces the answerer to figure out what you’re actually looking for, which feels lazy. Most of the time, if you don’t know what you want to know, you should do a bit more thinking.

For instance, you might think asking “What was it like?” will prompt the person to tell you what parts of the experience were most unique. In that case, you should just ask “What part of it was most unique, compared to your previous experiences?”

Or you might think you don’t want to make the question too specific, because you could miss hearing about something you didn’t know to ask about. Then, end with the question “Is there anything else I didn’t ask about that you think I should know?”

From the answerer’s perspective, it takes much less thinking to answer a specific prompt. And, it shows that the asker has really thought about what they want to know.

Another way to think about this: Much of the time, people know what they actually want to know. They just don’t ask directly because they think it’s blunt or abrupt or impolite. For instance, my friend was deciding between a few job offers. I was helping him draft a message asking someone’s opinion on a company they’d worked for and then left. He started with “What were your favorite things about <company>?”. I didn’t think that was what he was actually looking for, so I just prompted: “What do you actually want to know?” Turns out, with a little more thought, he worked out what information would actually help with the decision. These are the questions he ended up asking:

Don’t make someone answer a bunch of random filler questions if you know what information you want.

I get a relatively low volume of messages, compared to the people who I’ve gotten advice from. I still forget to respond to some on time. It’s okay to bump busy people once, about a week after the first email. I usually set myself a task due the week after, and send something along the lines of:

Hi again,

Just making sure this wasn’t stuck in your spam folder! If you have time, I’d really appreciate your thoughts on <very specific and limited question>.


It might be useful to be explicit if you‘re on a timeline. For instance, if you need to decide by X date, consider adding something like:

I need to make my decision by X, so I’d really appreciate your thoughts by Y. I know you’re incredibly busy — let me know if you have 10 minutes to talk via email/phone/chat/whatever is easiest for you.

I love knowing the impact of things I’ve done/help I’ve given, and I don’t think I’m alone in this. If someone takes the time to help you, tell them how things turned out! Did you get the job? Did you choose the company? How was your experience there?

This is critical if you’re hoping to establish a deeper relationship with the person. If you let them know how their advice helped you out this time, they’ll have context for the next time you need advice.

Most of my career experience and most of the advice I’ve asked for and given has been in computer science and tech. I think a lot about accessibility and inclusivity. I know that underrepresented minorities are less likely to have a preexisting network, and perhaps also less likely to be reach out to strangers for help. Is it elitist of me to prefer to answer queries from people who have enough previous experience to know what they’re asking for?

Ultimately, my philosophy is about helping you help yourself, and helping people best help you.

As an asker, looking for information before I ask — and taking the time to show the work I’ve done before asking the question — means that I feel totally confident asking it. It’s empowering to not feel intimidated when emailing impressive people. It’s addicting to hear someone say you have great questions. And it’s awesome to receive thoughtful responses with the information you need to succeed.

Thanks to Nick Abouzeid, Daniel Farrell, Colin Hill, Ellis Burgoon Miskell, Shivam Sarodia, Tim Deng and Ming Dai for edits and feedback!

(Selfishly, these tips directly map into the types of requests I’m most receptive to. I’m happy to talk to literally anyone about things I can help with, especially my time at the Chan Zuckerberg Initiative. I try to respond to every request I get, no matter what. You will probably get a better and more thorough response from me if you‘ve followed these tips!).

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