I consider myself an expert in asking Stupid Questions.  It’s my Super Power.

I learned the value of the Stupid Question early in my career, and have since carefully cultivated its use to an art form. The trick is to develop a greater tolerance for appearing stupid than for remaining ignorant.

Two formative events cemented my choice for apparent stupidity over real ignorance.

The Big “Oh!”

In the mid-1990’s telecommunications companies began experimenting with VoIP offerings in my market. As an alternative to traditional landline phones, VoIP promised to usher in new cost savings by avoiding increasingly painful long-distance charges.

At the time, email systems were still extremely complicated to set up, and the Internet was only a dial-up glimmer in the eyes of SMB’s. Cell phones were gaining traction, but per-minute roaming and call charges were even more expensive than long distance. In this pre-dawn darkness before the broadband dawn, landline phone calls were still the undisputed heavyweight champion of communications. The environment was ripe for disruptive technologies, and half-baked VoIP offerings sprouted up like so many trial balloons.

It was around this time that the company I worked for heard about a new VoIP offering from AT&T. Before long I, the mid-20’s office nerd, was sitting in a conference room with my company’s owner and senior management, being briefed on the bountiful harvest we were about to reap as first-movers.

The system seemed simple enough: AT&T would directly network our offices together via Ethernet, and all our calls would route through AT&T as if we were part of their LAN. The catch: each location had to be within roughly 500 feet of the “home office.”

The distance limit was a real problem for us and frankly seemed to make the whole thing worthless. What kind of company would have all their satellite locations so close to their home office? My superiors drilled the sales rep on that limit, but he did not budge – nor did he seem to think it was particularly important.

Something did not seem right to me, so I asked the Stupid Question: “What do you mean by ‘home office?'” The sales rep replied, “The home office is your local AT&T location.” He was answered by a comically long and synchronized “Ohhhhhhh!” as everyone else in the room experienced a paradigm shift. We had all assumed that “home office” referred to our corporate headquarters, which was at least 250 miles from the nearest branch office.

The Inexperienced Experience

At one of my first meetings as the newest, youngest, least experienced member of a management team, we were working with a consultant in the form of Scott Rosenthal. (I would link him here, but I have not seen him in 20 years, and I have just now proven that I could not pick him out of a lineup of LinkedIn profiles. Any help?)

Scott was walking us through a group exercise about questioning our paradigms. His lesson was that we needed to challenge the status quo and our long-held beliefs to improve our current processes. At some point, he looked at me, observed aloud that I had been quiet, and asked what I thought.

I replied to Scott (and the room) that I felt unqualified to question the often complex current methods because, unlike everyone else in the room, I did not know all the history that led to the way things were. I did not want to waste everyone’s time getting a history lesson and revisiting discussions they had probably had many times before.

Scott seized on my answer and replied “That is exactly why you should be here and why you should question how things are done! Your thinking is not limited by all the things you already know.” Wow. What an eye-opener! I now had an excuse to question everything…and over the next 25 years, I did exactly that. It worked out pretty well for me, and for my company as well.

Lessons Learned

This is just a small sampling of the coursework for my advanced degree in Stupidology, but enough to demonstrate the key takeaways:

• You are rarely alone. If you are feeling totally lost in a group discussion, there is an excellent chance others are as well. The others often secretly fear that they alone are the only stupid person in the room. Do not wait. Ask questions. Ask for clarifications. Ask what that word or acronym means. You will gain respect from at least some people in the room, and often your question will be met with sympathetic (and relieved) echoes.
• Inexperience can be an asset. As Scott Rosenthal taught me: Youth, newness, and inexperience all bring the benefit of fresh perspectives. The “newbie” is unconstrained by past debates, preconceived notions, conventional wisdom, and taboos. If you want a striking example, just look at the story of Cliff Young that Scott shared with our company in a group meeting. Those who dare to ask the Stupid Questions (maybe only of themselves) are capable of huge leaps forward.
• One possible reason to keep quiet (sometimes.) I am likely to keep quiet and hold my questions only when I have completely failed to do any required “homework” before a meeting or class. In the few cases when I have not prepared at all, I will go ahead and pose a Stupid Question if I notice a lot of other confused looks in the room. Pro tip: At a minimum, skim any provided materials and links for bold type, bullet points, and opening and closing paragraphs. You will get a general idea.

Have courage! When you ask Stupid Questions, some people of low character may mock or ridicule you. If such rude people run the company, politely smile and thank them for their correction, then go find a new company to work for. True leaders recognize and value the unique Super Powers of each person on their team.

Photo credit: Tom Bullock / Creative Commons