How Asking Stupid Questions Transformed My Learning

In law school, not being afraid to “look stupid” was my superpower. After my first year, when I barely said a word, I started to ask my professors a lot of questions. I asked what I thought were pretty dumb questions, but questions I was genuinely unsure of (if I felt the question was on the dumber side, I would usually send an email after class or ask the question in private).

I was not afraid to raise my hand and give my best effort at an answer if no one else wanted to participate. It would usually come after looking around the room and seeing that no one else wanted to participate, usually after 10 seconds of an awkward silence.

Since I was going to law school at night and working as a special education teacher during the day, I was very familiar with that type of awkward silence as a classroom teacher myself and knew how agonizing it felt. Every teacher has experienced it, but that silence makes you feel like a bad teacher who isn’t able to engage your students well.

If I looked stupid in front of my peers and my professor, then so be it. I was very afraid of the perception of looking stupid during my first year of law school. But as every class had an incentive for participation in a participation grade, and as I knew that by participating once or twice, I would keep myself more engaged and focused in the lesson. I regretted staying quiet as a mouse after my first year and sitting on the sidelines for most of my first year, and so I resolved to do better.

I started to participate more and often became a professor’s “go to” student if no one else wanted to volunteer to answer a question. I was not always right — in fact, I would say my answers were wrong a good 30–40% of the time, but I always tried to get thoughtful, nuanced, and well-reasoned answers that at least came close to the target. During my second and third years, all my professors greatly appreciated this tendency, and I appreciated this in myself since I started to get much better grades and got the most out of my learning.

Now, in my first few months as a lawyer at a law firm, I feel like I don’t have as much of that energy and risk taking spirit— I am sometimes afraid to make mistakes and look stupid. I am in a new environment with people I did not know before. I am trying to read the room and not be overly brash as the new guy as I get integrated both professionally and socially. Since I am so new and junior, the stakes of looking stupid and seeming annoying to peers and bosses seem higher, and I am a bit worried about sacrificing the good or neutral impression I’ve made so far.

This is slowly going away because I am getting more comfortable on the job and am communicating with my team more, even if I still stay silent during meetings. I will ask team members in private many questions I feel like are too dumb to ask in front of an audience, but that is sometimes a great thing because I am learning a lot of new concepts for the first time. I am starting to be not afraid to put myself out there, put in a lot of effort, and allow myself to make mistakes instead of being scared and reticent.

In the past, like in college, I would have just sat in the back of the classroom and been clueless, waiting for the class to end. I would have been too embarrassed to raise my hand when I did not know the answer or ask a question if I was confused. I think there is certainly a place for holding back when you don’t know the answer and to think about it, but as a teacher, I learned that any teacher would much rather have someone give a guess and an effort than have most of the class not participate at all.

It took a long time in law school and other spaces to simply get comfortable to where I cared less about what others thought and was more willing to take risks. Of course, my law school education was more of an individual endeavor, whereas on most assignments I’m on now, I’m working on teams. But I have realized I am a much more contributing member to the team when I allow myself to dig deep into details, don’t give up when confused, and seek the advice of other attorneys rather than struggling in silence.

. . .

As learners, some of us don’t always learn through asking a lot of questions and many of us prefer figuring things out ourselves. I know a lot of people have anxiety speaking in public and would rather ask questions in private. A lot of my classmates studied better in groups where they could get feedback from others and work through problems collaboratively, while others preferred studying alone.

I was more of the former — I needed to ask questions instead of hiding my lack of knowledge. There are, of course, other considerations — if I can wait until a meeting is over or there isn’t an audience to just ask a question to someone 1-on-1 and in private, I would prefer doing that instead of holding everyone else up. I can usually see if everyone is inching to be able to leave the meeting or the room, and the end of a presentation where someone asks “does anyone have any questions?” can actually not be the most ideal time to ask a question. And there are also times when I know I have to dive into the deep end, wander into the wilderness, and try to figure things out before asking a question, to show I really tried and thought deeply about the topic.

For me, there are no stupid questions, but there are sometimes unprepared questions (that I can ask). At some point, I was about to go up to a more senior member of my team and just say “I have no clue what’s going on” about a complex matter I was working on. While this may have been cathartic to say, and while this is very common for new attorneys getting assigned to complex cases, I realized that it might not be the best use of my or the more senior member’s time if I could compose some more specific questions about what was particularly confusing to me.

I have also learned there are people whom I can ask more stupid and honest questions to than others — the people who are closest to me and juniors know the “I have no clue what’s going on” feeling much more intimately than others and are often the most helpful. I learned “I have no clue what’s going on” is a very common feeling among new attorneys, particularly when they are staffed on new cases. However, I also know not to overburden one individual person and to also get a read of the other person’s bandwidth and availability.

. . .

There is a deeper significance to asking dumb questions— being honest and being myself rather than trying to play it safe and be more careful. Even in a new and high stakes work environment, being myself is a lot more important than how I’m perceived on first impression. It’s who I am and it’s how I learn.

As a teacher, I had a lot of smart students who tested well but did not work as hard, and a lot of really hard working students who did not test as well. Of course, there were students who tested well and worked hard, but the students who worked hard but didn’t have the most advanced academic abilities at the beginning of the year often had the most improvements in their scores and were often leaders within the classroom by the end of the year. I would love it when students were willing to take risks than when students didn’t engage at all.

I hate to go with the cliche that hard work beats talent when talent doesn’t work hard, but it’s a cliche I believe and have lived by my whole life. I think it was only in recent years that I truly embraced that mantra in academic and professional settings, however. It was gaining perspective as a teacher that improved my disposition, mindset, and attitude as a student and professional.

I wanted to protect my image as someone who was competent and smart, and giving the hint or confessing when I had no clue what was going on would damage that perception.

I didn’t realize that by worrying too much about image and perception, I was not only playing it too safe and not taking risks — I was keeping myself out of the arena. At least the person who was deemed annoying by colleagues for asking a lot of questions and answering too many questions was in the arena.

I wasn’t letting myself be in the ring, but was just a spectator from the outside looking in. The goal of my education throughout high school, college, and law school was to learn and get the most out of my education. Instead, I was too scared to do that for fear of what my professors, bosses, and colleagues thought about me.

So now, I do resolve to be honest and tell people, “I have no clue what’s going on” when I don’t. I will, of course, be a bit more discerning about who I tell that to, but I know that showing that I’m trying as hard as I can and willing to do whatever it takes to learn is incredibly important.

As a teacher, I wish more of my students told me “I have no clue what’s going on” when they didn’t, so I could have the feedback to improve as a teacher. I could usually tell what the student’s understanding was when it came time for a test, anyway, but I do wish for more honest academic and professional environments where we aren’t afraid of judgment and are more willing to swing hard and strike out than the other way around, but I know to some extent, that’s how the world is.

Regardless, if I want the world to change, I know I should try to be the change I want to see. And even if the world won’t change, I want to be the change that I want to see in myself — and if that means being seen as the buffoon who asks really dumb questions, then that’s a lot better than the alternative.