They tell us this when we’re young: There’s no such thing as a dumb question.

But the older I get, for some reason, the harder it is to remember this. Maybe there’s something about ego that gets in the way — a sense that I either should know or I ought to know, ergo it would be dumb to ask. There’s also a case where I think asked that question already and either forgot the answer or didn’t understand the first response so feel silly repeating myself. Or maybe I feel like, rather than ask questions, I should be sharing my own knowledge instead to demonstrate my equal status in a peer group. Or, worst of all, I actually don’t understand the basic premise of the topic at all, and therefore I can’t even think of a single good question to ask. So I stay silent.

All of these lead to the dumb question danger zone. I think it’s really important to break free.

I’ve noticed this paranoia (“I should know this already”), is what often prevents me from asking super basic questions to people I’ve known for a very long time. Things like:

“What are your kids names? And how old are they?”

“Wait, what exactly is your job?”

“Um… I kind of forget how we are related?”

This is too bad because the more I fail to ask and remember core pieces of information about people close to me, the more disconnected I feel. Sometimes, you just have to rip off the band-aid.

It comes out at work, too. After the “sweet spot” 6–12 month onboarding period in a new job, where I feel like it’s critical to ask all the best questions, it feels silly to interject and ask things like:

“Wait, how did you come to work here? What were you doing before?”

“What does that acronym mean? When is it used?”

“How do we make money, for real?”

Of course this is a slippery slope. Because a failure to ask these questions (and truly understand the answers) might trickle down the line to a lack of willingness to interject on other, more important topics or projects down the road. Things like:

“Wait, what exactly is that other product that we sell? How does it work? How do we know it’s working?”

“Why are we doing things this way? Is there another option?”

“Did anyone else notice that in our latest user feedback survey, our numbers are way down? What happened there?”

And this lack of asking is the dumb question danger zone.

If everyone in the room feels some weirdness about asking “dumb questions,” then none of these may get answered. And if none of them are answered or addressed, then you may continue to operate in a direction that either hasn’t been properly challenged or vetted, or just no longer works for the current time.

A few weeks ago at work, in our big Monday Meeting at USV, I was sending an email on an unrelated topic during the meeting and thought I overheard someone use the phrase, “Well, but they only have comet shares.” I perked up. Wait, was “comet” a new type of equity model with super-speedy vesting schedule or liquidation preferences?

I asked the question: “Wait, what kind of shares?”

The room looked at me like I was an idiot. “Common?”

“OH. COMMON shares. Got it. Carry on.”

At the end of the meeting, one of the partners came up to me and asked, “Hey, Bethany, that question you asked there… do you want to sit down for a few minutes and talk about common vs. preferred shares together? This is important stuff.”

I immediately blanched. “No no no…” I said a bit too quickly. “I thought I heard you say comet shares. I thought it was some new thing. All good.”

I’ll be honest — I was pretty mortified by this. If one person thought in a room of 12 people thought I didn’t understand this basic VC cap table term, odds are pretty good that other people did, too. And at three years into a job, that felt to me like a pretty bad perception to broadcast.

This is just the sort of thing that will happen sometimes, I guess. Or your relative might ask, “Wait, how do you not know Aunt Mary?” (IDK — I just don’t. Or maybe I was too young to remember.) Or your friend might wonder, “How is it that you’ve known me for five years and don’t know what my job is?” (Well, I guess we’ve been able to have fun together in other ways.) Or your colleague might think, “How is it that you’ve worked here for three years and don’t know that comet shares is not a thing?”

To be clear, those ten seconds suck. But people forget things faster than you’d think. And in the end, I’d rather have someone be temporarily surprised than stay ignorant about a thing. So that’s why I’m trying to push myself to ask “the dumb questions.” Because guess what? In the end, there are no dumb questions. Just things you don’t know.

Originally published at Dry Erase, my personal blog and digital whiteboard.