Here's Why I Fearlessly Ask Stupid Questions As An Engineering Manager

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Hey folks, I'm just headed to the office. I got uh my almost third on call shift back to back to back. Had a few days off in between, but I had to take another on call shift. But I'm driving in, so it's halfway through the day. Uh I just wanted to make sure I had some office time, so I'm doing that. Um, I have a topic that was from an interesting experience yesterday that I wanted to share and I'll generalize it. Um, but it's it's like it's based on like a real thing and I it felt very relevant to kind of walk through. So, um, I wanted to talk about like I wanted to come up with a like a catchy way to say this, but like I wanted to talk about being the person that asked the stupid questions.

And uh I thought that this was just like such a such a good like example that came up and I want to like I said I'm going to generalize it but I had this assumption about how something works on our team and uh it just has to do with the technology so it doesn't really matter for the details here but I had this assumption about how it works and um it's not that it's like uh like spoiler alert, the assumption is wrong. And it's not that this was like a an assumption that was going to be catastrophic to get wrong, but it's kind of just been something I've assumed and have operated with that in the back of my mind. And I had an email that came in where someone was asking a question and the fact that they were asking their particular question made me go, "Wait a second." like either either this person's completely missing it or maybe my assumption that I've had for a while is actually just wrong.

And uh so that was reason enough for me to go, hey, you know what? Like maybe I don't know the way that this works because if this person's asking and I guess I'm not giving you the details. So like the way that they were asking implied that something was completely optional and I thought that it was there was no option. Um and clearly they had evidence that it was it was not optional or sorry that it was optional cuz they were already operating without the thing. So I was like oh crap like I must be wrong like there's there's just a gap in my understanding. So, I had messaged one of the the product managers and I said, "Hey, like you're on this email thread. I'm trying to respond to this person, but um I'm pretty sure that like this has been my assumption." And uh I uh I don't think so anymore.

And he responded to me and he said, "Uh, good question, but like I'm pretty sure I had the same assumption as you." So, I'm going, okay, like, you know, it's rebuilding my confidence a little bit, but I'm going I still something's up now, right? Like, there's seemingly some evidence here that my view is not right, but there's at least one other person that is kind of on the same page as me, but they're willing to accept that they don't know. Okay. So I was at the office. So I asked one of the engineers on my team who doesn't work in that particular space, but I said, "Hey, like do you know the answer to this?" And they, you know, totally fair. They're like, "Actually, I don't." And so I was like, "Okay, like, you know, there's there's at least now some evidence growing that maybe this isn't obvious information." So even if I'm wrong, maybe I shouldn't feel so bad about it, right?

Um, the reality is if you're wrong, you shouldn't feel bad about being wrong, just like you learn from it. But, okay, let's go to the next group of people. I had two other people walk in the office and I said, "Hey, I got a question for you." And then I explained my assumption and then they had said I actually don't know if we have the same assumption about that but here is like one variation of that but they were also unable to say with confidence sort of the counterpoint like we don't know if your assumption is right but we don't know if the sort of the other side is 100% true either. So, so far I've now talked to four different people who can't say and five including me who now can't say with confidence. And so we were kind of joking about this, right? Like it's kind of funny like hey we don't know we got we should go figure this out.

And as we were joking about that we had another product manager walk in and uh we have a pretty good working relationship I feel with. So I made a joke and I said hey I said I got a question for you in front of this group. And so I asked him the question and uh and then I immediately followed up with not to put you on the spot. And he's like, "Well, come on, man. You are putting me on the spot literally." And um so he actually said, "I I don't think that assumption is true." So now we're getting this different perspective coming in. And I said, "Okay, totally fair." And then I said, "If it's not this, then what is the other thing?" and he had a partial answer but he was like but I actually cannot say that with confidence right so how

many people is that now that's two four five people I can't remember counting's bad but that's that's a decent chunk of people I think it's five six including me where we're going you know what we actually don't know so what I was trying to demonstrate and we we talked about it yesterday was like, I'm going to be the person that's going to ask that, you know, air quotes like stupid question. I'm going to do it because if I don't know and now some assumption I have is being tested and is very likely wrong, which is it's fine. I can't run from that. I can't just go like, hm, guess I'm going to, you know, try and hide from this going forward. like I really need to know the answer to that because if I going forward have to keep trying to dodge it, that's going to be a weird avoidance in my career.

Like it's it's going to be more uncomfortable to try and you know run away from that assumption. And so um the first person that I said I messaged um while this is all happening in parallel I had reached out to two other people that uh I know I like knew with a high degree of confidence they would be able to give us a very concrete answer and you know put that put that to rest but they weren't responding while all of this was happening. So, um, you know, that person, that first product manager I reached out to, he said like, "Hey, thanks for, you know, thanks for being the person who's going to go ask." I said, "No problem." And then the people that I was talking to in the office.

I was we literally talked about this idea like hey look like I'm I'm going to be the one here that I will show you it's okay to ask questions and like even if it makes you feel a little awkward or a little embarrassed that you don't know um like I I need to demonstrate that we have to create an environment where that's okay and the sort of conclusion to this example is that uh uh my manager had come into the office for a meeting that was right at the end of the day. Actually, two meetings that were at the end of the day. And so in between those two meetings when we were all kind of sitting in this conference room, I said, "Hey, now that you're here," I said, "I got a dumb question for you." So he laughed and he said, "Okay, what's up?" And this is again in front of all the other people that were having this conversation with me.

And I said, "I have made an assumption and I'm pretty sure that it's invalid." So I wanted to to kind of walk through it. So I said, "This is what my assumption has been." And he said, "Okay." And I said, "But I'm pretty sure that's wrong." And he's like, "It is wrong." And I said, "But when I started thinking through the options for this, I thought it was either 100% this." When I thought that it was being disproven, I said, "The only other thing I could think of, and again, I'm not going to explain the technology." I said, "But the only other thing I can think of is that it's like this other thing." And he's like, "It can be that other thing, but there's even one more option." So point is, he then took the time to explain to the whole room of us like, "Here's how this stuff works.

you know, there's one option, there's a second option that we talked about and there's actually a third option that kind of surfaced in our conversations and they were all technically, you know, part of it. So, it was very interesting because in our conversation together as a group before my manager came in, we were actually arriving at the right conclusion, but none of us could say with full confidence. And sure enough, when I had gone back to my desk and I did have a response from the people that I reached out to, it was very much in line with what my manager said. So, all of this to say that I took I think three opportunities there to basically try to demonstrate to a group of people like it's okay to go ask a question where you're like feeling a little bit embarrassed about not knowing. And in fact, like we need to continue to demonstrate that kind of behavior so that as a team we can be more comfortable doing that.

So I thought this was an important topic because I think that a lot of the time, especially for more junior developers and depending on the team culture that you have, this is something that people try to hide from, right? Like I don't want to ask questions cuz I don't want to look stupid. Um, or you know it might be and I I think I made I made a LinkedIn post about this one time and someone was like very offended by it because I said in the same like sentence I had said like I don't want to look stupid or I don't want to look more junior and they were like oh so you're calling juniors stupid. I was like, "That's Yeah, you can try to take my words and twist them however you want to tell the kind of narrative you want to tell, but

like the only stupid person here is you for doing that." Um, but like if you're you don't want to ask a question cuz you don't want to be perceived in a different way. There we go. Right. I don't know. I'm not trying to call junior engineers stupid. That's the last last thing on my mind or else I wouldn't be making the majority of the content I make to try and encourage junior engineers. But anyway, um it's the internet, right? So, I think it's really important to talk about this stuff or else you get stuck in a culture where, you know, you feel like that's the normal thing that you're not allowed to ask questions or that you're going to be, you know, ridiculed for it or that you're going to be thought of like, you know, people aren't going to come to you with tasks now or like you're going to not grow in your career because you're the the guy or the gal with dumb questions.

like you know it's it's just not true and in fact the other way is more problematic because as I kind of hinted earlier if your next opportunity is then to be like I need this avoidance pattern how do you think that you're going to be successful in the work that you're doing if you're constantly trying to like run from a scenario that comes up right so in this Like I was saying, for me, I had made this assumption and like it's not like it wasn't coming up all of the time, but when it did and my assumption was wrong, it wasn't detrimental. It's just like it was almost like peripheral to the stuff I'm doing. So, okay, I keep going. But it's not like it's going to get less or lessened, right? It's not that it's not the frequency of that's going to go down. It's going to keep showing up.

And in fact, now that I understand that better, I was able to fully respond to, you know, the the partner that had reached out for some information and I could give them better information now that I had that background. The next person cuz there there will be more. The next person that asks about that, I will be better equipped. And you know what? I'm still not an expert on that, right? But now I know and I can defer to other people, right? I will keep learning and growing from it and I need to be able to demonstrate that. Right? So in this example, I was able to say, "Hey, here's the part that I can explain, you know, pretty confidently." I said, "Here's how this other part works." And if you have more questions about that for now, this other part, I said, "Here's another person that that you can talk to." And then I also encouraged them.

And I said, you know, because you're reaching out over email, if you need more help like getting this pulled together, like schedule a call with us. Like we'll all jump on a call then talk about it together because it's a little bit ambiguous, right? If you're not familiar with it. So just trying to remind people that like just because now I have this extra piece of information, I'm not trying to pretend like I'm an expert on it now because I'm not. There's like there's no benefit to just like trying to lie about that. I would much rather get someone the help they need because I can use the resources I have to do that and then it's not I guess the last part to mention there is like I don't just let it end there because it's a reminder to me I need to learn more about that and I will learn more about that.

Right? That's it's an identified area where I'm like, "Oh crap." Like I I should pay more attention to this, but we like we shouldn't punish ourselves for doing that, right? And that I think that takes a little bit of mental training to like to keep that in mind. So, you know, if you're thinking about a scenario like this for yourself, whether that's happened to you already or you're kind of anticipating now that we've talked through it, what that might look like for you, it's like don't don't beat yourself up for not knowing something, right? Don't um when you get the answer, don't go, "Okay, great. Like, I did it." Like, like get that out of the way and let's never talk about it again. Like, no. It's you you identified something that you don't know that you can improve on. Great. Like go spend more time on that.

Like do the opposite. Do the opposite of running away from it or trying to minimize it. It's like that's clearly something that you could do better at if you knew more about it. So spend the time, invest in it, understand it more. Right? there's in when we're working in these big complex areas and I mean for for any of us I'm not just saying like specifically what I do at Microsoft this is like this could be on your team working on a you know single mobile app or something and there's still going to be a lot of complexity in the domain the code base that you're working in. It's it's not realistic for everyone to know everything, right? You need to make assumptions about things, but if those assumptions are wrong or you just haven't known something and it's finally come up, don't run from it.

Like, run into it. Go learn about the thing. It's only going to make you better. And it doesn't make you look like a dumbass for asking questions. You might feel like it does. But you're just going to learn like oh no I learn new things right it's uh we got to we got to train ourselves to get like out of that uh or else you kind of you'll stay stuck there. So anyway I just wanted to share that I feel like I'm going to be on repeat if I keep talking about it. So thanks very much for listening. I hope that was helpful. I thought it was very relevant. And uh if you have questions leave them below in the comments. And of course, if you want to be kept anonymous, go to codeccommute.com. Submit your question there. Check the box for being anonymous, I got you.

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