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.