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Don't ask me, I'm a guesser

Rach Smith
Technical knowledge is just one part of being a great Engineer. I like to think and write about everything else.
Originally published at rachsmith.com ・3 min read

Back in the days when I was making CodePens rather than making CodePen, speaking at conferences and building a Twitter following, I would get many emails from strangers asking me for things. The requests ranged from asking me to adapt my Pen code in some way or helping them to build their website, to full-on mentoring. These emails used to bother me. In my mind, cold emailing someone you don’t know personally to ask if they would do things for you (for free) was presumptuous, entitled and borderline rude. I certainly had never made such requests of people I didn’t work with or was friends with.

Then I read about Ask Culture vs. Guess culture.

In Ask culture, people grow up believing they can ask for anything – a favour, a pay rise– fully realising the answer may be no. In Guess culture, by contrast, you avoid “putting a request into words unless you’re pretty sure the answer will be yes…

When I realised that the people sending me requests were likely Askers, I felt much differently about the emails hitting my inbox. As a Guesser, I assumed that people were expecting a “yes” from me and would be very upset if I said no, therefore putting me in an uncomfortable position where I am forced to disappoint people right and left. Learning about the Asker world view empowered me to TextExpand a polite response to such requests, without the guilt.

Some people have an opinion on whether it is better to be an Asker or Guesser. Despite being a steadfast Guesser, I think it isn’t any better to be one or the other, and the world definitely needs both. Sites like Stack Overflow wouldn’t work without Askers. If everyone was like me, just lurking and reading other people’s questions, there would be nothing to read!

If you are an Asker, I have some Guesser tips that might make your asks-via-email more likely to get a positive response.

  • If you are emailing someone an ask, you are infinitely more likely to get a yes if you have some sort of pre-established relationship with the person. This doesn’t have to be an in-person friendship. It could be an online relationship that has been built over trading a few pleasant Twitter replies back and forth. You just need the person to know your name and have positive associations with it. This is why it pays to spend time and energy on building a network early in your career.
  • Make your requests very specific, and provide as much info as possible while being concise. “Can you solve a code problem for me?” may be ignored, while a reduced test case in an online demo with the exact issue you’re trying to debug may just get a response. Similarly, I doubt “can you mentor me” has ever worked for anyone, but a request of “I would like to spend a 40 minute call with you, once a month, where you can give me feedback on X, Y and Z things I am trying to improve on” may just get you there (with someone who knows who you are! see above).
  • When emailing people with larger followings online, try and come up with a request that requires minimal effort on their end, and maximum impact towards what you are trying to achieve.
    • “Can you debug this for me?” - too much time/effort required, will likely get a no.
    • “Can you RT my Tweet asking for help with debugging my reduced test case demo?” - minimal effort on their end, and their audience may include people willing to help you solve your problem.

Discussion (3)

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kspeakman profile image
Kasey Speakman

Thanks for posting this. I had never run across it before and it makes a ton of sense.

I tend to be a guesser around people in real life. But in the digital world I occasionally venture into the world of asking. It's actually quite stressful because I fear the other person will feel offended if they have to say no. Or they might think I will react negatively to their no. I almost always give them the out of "no is really quite okay."

Usually I am asking on the premise that if the universe aligns, they will be more than happy. (Example: They were just thinking about that very issue.) But if it doesn't, that is fine too.

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phantas0s profile image
Matthieu Cneude

Interesting thoughts.

I'm more of a guesser, but I realize more and more than asking doesn't cost anything. Even better: when you get a no, you have an upper limit; you can then lower your expectations to see if the other can help you solve part of your problem.

It's easier to ask when you have some kind of relationship, that's true. But how do you build it? There are many ways, but one of the most powerful is to help people, and helping somebody who's in need is always good for everybody. Of course coding a whole project for two full days for free is not sustainable. But how can you help this same person in an easier way? Maybe giving him (or her) some links to interesting article? Maybe providing one or two advice?

Of course, if 1000 people ask me something everyday, it's not sustainable. But even so, I think I would try to help some of them depending on my time. Either way directly, or by writing something as you just did.

People are not bad per se; they're just sometimes awkward or incompetent. That's fine, we're all like that, depending on the context. I think it's better not to take it personally and try to help anyway. IMHO.

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greenroommate profile image
Haris Secic

Very well put. But I just gotta say StackOverflow is not to much Ask culture and it's well known for toxicity even it's team decided to do something about it. One of the resons I like Dev.to is because of policy to be nice even if someone is asking questions or writing posts about things given on search result of the first page on Google/DuckDuckGo/StartPage/Whatever. But also if I had this kind of post maybe some of my anger would be avoided and I would still work for same clients. Anyway, I learned it the hard way that just because they ask doesn't mean they demand. It's applicable quite well in comercial area.