I don't remember how the topic came up when my wife and I were visiting with my parents last year, but for some reason, I asked if either of them liked the liver that my mom prepared every so often when I was growing up. As it turns out, neither of them did! I always thought that my dad liked it, and that was why we had it. If I had only asked a simple question back then…

As a developer, I'm sure I've managed to burn many hours over the years trying to figure out any number of sticky technical problems which, if I had just asked, someone could have helped me with. Perhaps I waited too long before I finally asked for help - or maybe I soldiered on until I found the answer all by myself.  The trouble is, between Impostor Syndrome and an apparent social taboo against asking questions (not to mention ego), the pressure against asking questions can be enormous.  One can easily drop into one or more of the following mindsets: “if I ask that question, I’ll look stupid,” or “they will find out that I really don’t know XYZ that well if I ask that question,” or “I figured this out once before - I can figure it out again!”

So how does a company - or an individual - foster an environment which promotes asking questions?
 

Make a Statement

For a company as a whole, I believe that management should state that "asking questions is a good thing" - be on the record with that message and state it often.  During new hire orientation at Mediacurrent, this point is made both in the context of working through technical challenges during development, as well as when interacting with clients.  (Concerning the latter, see Jeff’s excellent post, One Word to Save Your Project.)
 

Model a Culture of Asking Questions

Beyond stating that asking questions is not only OK but desirable, asking questions needs to be modeled by both management as well as the technical leadership - this reinforces that statement through leading by example. Here at Mediacurrent, the culture is very "pro" asking questions. I've seen everyone from the founding partners through every level of personnel ask questions.  The most likely way to see this cultural emphasis play out at Mediacurrent is in our help channel in Slack.  Of course, we also have specific client channels, as well as front-and back-end developer channels, and so on, where you’ll see questions specific to a particular project or domain. But on any given day, one might see questions in the help channel about hardware problems, Mediacurrent processes or procedures, apps or tools, etc.  Having such a channel is a great way for our mostly distributed team to both get the help they need when they need it and for this important concept to be modeled.
 

Repeat, Repeat, Repeat

For everyone to be very comfortable asking questions, it really helps to see the behavior frequently modeled at all levels of the company. Many times!
 

The Result

For us, this has resulted in a stronger culture within Mediacurrent, a culture where collaboration and helpfulness are the rule, rather than internal competition.

If you also find yourself lucky enough to be part of a team where asking questions is encouraged and frequently modeled, then don't hesitate: just ask!
 

Every so often, asking a question can lead to an unexpected insight or benefit for the larger group.  For example, as a young recruit at the Los Alamos Laboratory in 1943 (just one year after he had earned his Ph.D.), Richard Feynman found himself tasked with traveling to the Oak Ridge, Tennessee, uranium enrichment facility so he could go over the design of the plant.  Why did he need to review the design?  To make sure the facility was not going to blow up due to processing the uranium in an unsafe manner.  During his second trip to Oak Ridge, Feynman was presented with a refined design based on the information he gave them during his first trip.  His hosts laid out the blueprints for the facility for him to review - but he didn’t know what all the symbols on the blueprints meant!  After internally debating what to do for a few minutes, he decided to take a stab in the dark and ask a question:

I take my finger and I put it down on one of the mysterious little crosses in the middle of one of the blueprints on page three, and I say "What happens if this valve gets stuck?" -- figuring they're going to say "That's not a valve, sir, that's a window."

- Richard Feynman, Surely You’re Joking, Mr. Feynman

Even though he had guessed at the meaning of the blueprint symbol, it turns out that Feynman had indeed identified a valve - a valve which, if it had gotten stuck, would have caused significant problems! It was back to the drawing board for the design, and a great example for the rest of us on the value of asking questions. 
 

Additional Resources 
Cheers to 10 Years! Mediacurrent’s 2016 Retrospective | Blog
The Best (and Worst) Question in a Drupal Sales Presentation | Blog
Establishing a Remote Workflow | Blog