Asking for help when you don’t know all the answers (which is pretty much always)

There’s a great meme that circulates frequently in the circles I run in:

i have no idea what I'm doing

I’ve used this meme to describe myself many times. I came to fully embrace it at Automattic when I was a support person embedded on a development team who were building an internal live chat tool. Talk about imposter syndrome. When the developers started talking code in our Slack channel, I’d frequently ask, “Do I need to understand what y’all are talking about? Because I don’t, so if you need my input on this particular issue, please let me know.”

At first I was scared to ask questions. Questions would reveal my ignorance. They’d expose me as the fraud I surely was. If I asked questions, which would inevitably be dumb, the developers would think, “Jeez, who hired this clown? And then put her on our team?”

But the thing was, it was through questions — mine and the developers — that we explored, that we discovered, that we built a tool that benefitted from all of our strengths. It was through questions that we had conversations: conversations that ultimately led to a product that suits the unique needs of Automattic’s support teams (and also led to friendships 🙂 ).

This is one of the great lessons of my life: ask questions. Show your vulnerability, and ask for help filling in the gaps in your knowledge.

And then listen to the answers.

A similar phenomenon is happening right now in my work with Support Driven. For weeks I’ve been trying to figure out how to organize a support conference in Europe while being based in the US. In my near 44 years of life, I have spent about 2 weeks in Europe, and none of that time was in the cities or even countries we are looking at for the European conference.

I mentioned my worries to Scott, the organizer of Support Driven, and he said, “Let’s ask for help, then.”


He recommended I write a draft describing what we’re hoping to do, and how we need help, then send it to folks from the European communities to get their thoughts before publishing it.

So I wrote a draft. And then I dropped it in the European channels in the Support Driven Slack and asked their advice:

  • Does the post make sense?
  • Is there something obvious I’m missing?
  • What questions do you have after reading it?

And the feedback was amazing! The first thing that became clear was that the community really appreciated the transparency of the post, and of our reaching out for help. Based on that feedback alone, I knew we’d done the right thing to ask.

And there were so many things people brought up that I hadn’t thought of!  Things that seem obvious now after someone pointed them out, like the fact that I used EU as a synonym for Europe. As in, Europe and the EU are not synonymous.

In my original draft, I also neglected to mention when we hope to hold the conference, where in Europe we’re considering holding it, and specifics of what kind of help the conference will need in order to happen. All of those particulars were things I was taking for granted because I’ve been thinking about them so much, but I didn’t make the leap of communicating them. Nobody else is inside my head to see those details, and if I hadn’t asked for help, the post probably would have resulted in more questions than answers, which would have been great for conversations, but would have distracted from the post’s ultimate purpose.

I was able to make adjustments based on the generous feedback of the people I asked for help. The post is stronger and tailored to the community we’re hoping to serve, and it provides more of the details folks wanted to know before making a decision about how they might be able to contribute.

The best part of asking questions, though, even better than improving the finished product, and even better than the learning, is the great people you meet through your inquiry. Questions allow people to share their knowledge and to ask questions of their own.

Questions start conversations, and from conversations, relationships bloom.

Here’s the finished product from my request for help on the Europe post: Building an event that works for the European Support Driven community.

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