Why the Smartest People Ask the Simplest Questions

They’re Focused on Learning, Not Seeming Smart

Have you ever been confused by a discussion in a meeting, team chat, or something a colleague said to you in a one-on-one conversation?  Me too!  This has happened to me approximately [checks notes] a bajillion times. I’ve seen even the most brilliant of my colleagues bump into new terms and concepts they weren’t familiar with, so I know it happens to even the best of us. Since it happens so often to me, I’ve had to find ways to cope. 

If you work in Product, you’re hopefully already in the habit of asking “Why?” both early and often. While that’s a critical skill in PM — perhaps one owed its own post at some point — I’ll focus here on doubts and questions in a broader sense. 

My Observations

After nearly two decades working in Product, I’ve worked with a lot of folks. And I’ve been lucky to work with some exceptionally smart people, who are far more effective than the average colleague — and certainly more impactful than I am. While I’ve not kept a spreadsheet to track it, I do think I’ve observed an unexpected pattern among these colleagues which differentiates them from the rest. 

The smartest people I’ve worked with tend to ask the “simplest” questions. While this observation is based in my own experiences, I suspect it may be representative of a broader trend among professionals — and offer insight as to how to learn faster, become more effective at work, and grow professionally. 

The Power of Asking

If you don’t understand something that comes up in a discussion at work, you may be able to get along by just smiling and nodding. How likely it is to work out probably depends on your context. But no matter your situation, isn’t there at least some chance that it will come back to bite you?  And even worse, how much knowledge are you sacrificing to silently pretend you know something you don’t? 

If you don’t know a term or understand a concept being discussed, there are only a few possibilities: 

• You understand it in principle, but are the only one being tripped up by the terminology — and a one sentence clarification would catch you up; 

• You aren’t familiar, but you could benefit from learning about it; 

• You don’t actually need to understand it (typically because it’s a technical concept that your engineering partners have covered for your team); or

• You’re not the only one in the conversation who’s confused.

In any of those scenarios, it’s better to ask than not, in my experience. 

The smartest people I’ve worked with are the ones willing to ask the seemingly most naive questions — because they're not concerned with how they appear in the moment. Over time, they just keep getting smarter because of always asking.

And sometimes the person willing to ask the "simple" question is asking the thing that everyone wanted to ask. Even to the point of revealing that a premise of the discussion is totally invalid, though no one else was willing to question it, for fear of seeming like they didn't know what everyone else knew.

I learned this lesson as a young musician, growing up in the days before a Web search could offer a great explanation for any topic or concept. As soon as you pretend you know something you don't, you've backed yourself into a corner where you can't ever ask about it later (without looking like a liar). I once silently implied that I understood what a friend meant by “the third” and “the fifth” when describing how to play a song — and didn’t learn this valuable musical concept until years later.  In hindsight, I could have taken a multi-year shortcut by simply admitting, “Oh, I’m not familiar with that. Is it easy to explain?”  Instead, I pretended to know more than I did, to seem impressive. I prioritized seeming smart over becoming smart. Lesson learned!

When pondering the cause of this correlation, I think there’s two plausible explanations.  Either: 

1. People who already know a lot have earned a sense of confidence in their body of knowledge, which allows them to feel safe to ask a seemingly naive question; or,

2. People who have a personal policy of always asking questions when they don’t understand something (whether because of a deliberate strategy or natural curiosity) gain more knowledge than others over time.

I have no data to justify either of these, but my gut says the latter is the more likely explanation.  That’s because of my personal experience running my own N-of-1 experiment. 

Once I started to notice this pattern, I started to intentionally ask more questions when I felt like I was the only one not understanding the discussion.  When I did so, I found the following results: 

• I did indeed learn faster, by internalizing new concepts that would have otherwise flown over my head — even if some of them took some offline follow-up on my part (e.g. reading more after the meeting, watching an explainer video on YouTube, etc.).

• Sometimes I was the only person in the conversation who was willing to ask a clarifying question about some implicit premise, and it turned out to not withstand even the slightest interrogation. 

I recall one instance where the person who called a meeting had spent a few minutes introducing the topic of a discussion about “Omni-channel Commerce” — and I didn’t understand what was “Omni-channel” about the discussion, given everything else the meeting organizer had mentioned in the preamble.  I simply asked, “Sorry, I’m probably missing something, but how is this involved with the work for the Omni-channel Program?”

Much like I’d observed at times, when folks smarter than me would ask the “simple” question, the meeting organizer’s answer was, “Oh, sorry, I should have said ‘Source-aware Inventory’.  I just misspoke.  It’s got nothing to do with the Omni-channel Program.”  And the rest of the room joined me in a collective chorus of, “Aaaaaah…”. In this case, the “simple” question turned out to be quite apt.  Then we were able to have the conversation with everyone on the same page about the scope of the subject matter.

Developing a Playbook

Since then, I’ve developed the following playbook for myself, to maximize my opportunities to learn on the job: 

1. Never pretend you understand something you don’t!

2. You don’t need to stop every meeting about everything anyone says that you don’t understand, but if you’re being asked a question about something you don’t understand, you should not try to fake an answer. “I don’t know, but I’ll figure it out and report back” is always an option, and it’s radically more productive than just trying to guess or make things up. 

3. You can quickly search the Web for a term/concept you’re wondering about, to figure out whether it’s something you can read up on by yourself or you’ll need help from a team member to understand (e.g. some terms and concepts will be unique to your company, team, codebase, etc.).

4. It’s totally fine to interject with something like, “I am not familiar with X [or don’t understand X fully]. Is it easy to explain now — or should I read up on that, or connect with someone later, to learn about that?”

5. Keep a running list of things you’re not sure about, so you can do your own research when you have time and ask teammates about the things you couldn’t understand on your own. 

6. Get to know anyone who you notice asking the “simple” questions in work discussions. They may be an especially smart and effective teammate — or on their way to becoming one. It’s a big signal that someone may bring a high level of both character and competence to your team or organization. 

For me, these strategies are more critical when I’ve joined a new company or team, or have taken on new scope in my role.  Still, even after years on the same team and product, the not-knowing-things phenomenon may happen less frequently but never entirely stops.

The great news is, I’ve found that experts tend to enjoy sharing what they know. If someone is put off by you asking about a term or concept, either you are asking something that you could have gotten an answer to on the first page of Google results, or that person is somewhat of a jerk — or perhaps they’re a good teammate having a hard day, which happens to the best of us.  If someone’s frustration about being asked turns out to be a pattern, just try to find someone else who seems to know things and is happier to help.  

As a kind engineer (now a friend) once told me, when I apologized for asking a lot of questions, “No need to apologize. We all need to get up to speed!”

The next time you’re assuming you’re the only one in the conversation who’s confused or not totally following, take a moment to look up an explanation. If clarification is not readily available, asking the simple question could be your chance to learn something new, or it might just be the question everyone else was too scared to ask for themselves.