The Importance Of Questioning

Problem

I joined a fairly early stage analytics and monitoring startup to build out the Quality organization. Because the startup was producing a very technical product for a very technical audience, this informed the culture of our engineering team. I was the new kid on the block, and everyone else already appeared to know everything. When I gathered up the courage to ask questions, I was told to just go read the code. There was very little documentation and the assumption was that we were all smart people, so we could find the answers in the undocumented, complex codebase. I struggled with a major case of imposter syndrome, for more than one reason. I was a woman in tech, I was working on QA side rather than as a developer, and I am self-taught in computer science. In the first 100 days, I considered quitting about twice a week because of how difficult my ramp-up was. That feeling went away as I gained mastery over how everything worked technically and organizationally. However, as I was making my next hire, I reflected on my experience and questioned why it had to be so hard.

Actions taken

I realized the problem hadn't been with me, it had been with the company's culture. That culture was worth changing - we didn't want to lose people early on after working so hard to hire them onto the team, and we didn't want to lose the fresh perspective that people bring in when they question things because they aren't familiar with everything. I started out by building a new culture within the Quality team, and then expanded this out to our entire engineering culture. To make sure there were no barriers to asking questions, I made our team's Slack channel very open and welcoming. We added every new hire to the channel and vowed to never label any question as silly. Using this channel, we helped people to ask questions in a better way, publicly praised their questions, and supported people who were hesitant to ask for assistance by telling them that each question would contribute to our knowledge base. We also encouraged watercooler talk in the Slack channel, using chatter as a way to build up the sense of psychological safety. This had a cost, as we had to answer a lot of people and were having our work interrupted by these questions. However, we knew why we were doing it and, over time, it got easier as we grew the knowledge base and began to be able to point people to answers. This also helped us to realize where the weak areas in the organization were, so we could then work to fix those areas through documentation, organizational structure, or fixing bugs. Over the next year or so, doing this led to the gradual disappearance of barriers to asking questions, and the culture of not asking went away by itself. People started talking more freely, both over Slack and in-person, because there was no longer an expectation that people should figure things out by themselves. On one hand, we gained greater technical understanding across the team, and quality of decision making improved as the result. On the other hand, the organization simply became a happier place to be, with team members feeling more confident and communicating freely.

Lessons learned

This process wasn't perfect. As we became old-timers and internalized a lot of tribal knowledge, we started to appear all-knowing and less approachable. To counter this, it really helped to hang out with new people and to get their opinion on what we were doing. In addition, it helped to work with team members from outside of technology and end-users. I was able to bring this attitude into my next company and instill it from the get-go. If you come in and feel as though you can't ask questions, you need to fix that. The problem is not with you, it's with your company's culture, and your company will be much more productive if it encourages questioning. In addition, it is often the case that the questions you are scared to ask will come up as problems later anyway .