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431: Developers Are Professional Question Askers

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Stephanie shares her newfound interest in naming conventions, highlighting a resource called "Classnames" that provides valuable names for programming and design. Joël, in turn, talks about using AI to generate names for D&D characters, emphasizing how AI can help provide inspiration and reasoning behind name suggestions. Then, they shift to Joël's interest in Roman history, where he discusses a blog by a Roman historian that explores distinctions between state and non-state peoples in the ancient Mediterranean.

Together, the hosts delve into the importance of asking questions as consultants and developers to understand workflows, question assumptions, and build trust for better onboarding. Stephanie categorizes questions by engagement stages and their social and technical aspects, while Joël highlights how questioning reveals implicit assumptions and speeds up learning. They stress maintaining a curious mindset, using questions during PR reviews, and working with junior developers to foster collaboration. They conclude with advice on documenting answers and using questions for continuous improvement and effective decision-making in development teams.

Transcript:

 JOËL: Hello and welcome to another episode of the Bike Shed, a weekly podcast from your friends at thoughtbot about developing great software. I'm Joël Quenneville.

STEPHANIE: And I'm Stephanie Minn. And together, we're here to share a bit of what we've learned along the way.

JOËL: So, Stephanie, what's new in your world?

STEPHANIE: So, if it has not been clear about just kind of the things I'm mentioning on the podcast the past few weeks, I've been obsessed with naming things lately [chuckles] and just thinking about how to name things, and, yeah, just really excited about...or even just having fun with that more than I used to be as a dev. And I found a really cool resource called "Classnames." Well, it's like just a little website that a designer and developer shared from kind of as an offshoot from his personal website. I'll link it in the show notes.

But it's basically just a list of common names that are very useful for programming or even design. It's just to help you find some inspiration when you're stuck trying to find a name for something. And they're general or abstract enough that, you know, it's almost like kind of like a design pattern but a naming pattern [laughs], I suppose.

JOËL: Ooh.

STEPHANIE: Yeah, right? And so, there's different categories. Like, here's a bunch of words that kind of describe collections. So, if you need to find the name for a containment or a group of things, here's a bunch of kind of words in the English language that might be inspiring. And then, there's also other categories like music for describing kind of the pace or arrangement of things. Fashion, words from fashion can describe, like, the size of things. You know, we talk about T-shirt sizes when we are estimating work.

And yeah, I thought it was really cool that there's both things that draw on, you know, domains that most people know in real life, and then also things that are a little more abstract. But yeah, "Classnames" by Paul Robert Lloyd — that's been a fun little resource for me lately.

JOËL: Very cool. Have you ever played around at all with using AI to help you come up with the naming?

STEPHANIE: I have not. But I know that you and other people in my world have been enjoying using AI for inspiration when they feel a little bit stuck on something and kind of asking like, "Oh, like, how could I name something that is, like, a group of things?" or, you know, a prompt like that. I suspect that that would also be very helpful.

JOËL: I've been having fun using that to help me come up with good names for D&D characters, and sometimes they're a little bit on the nose. But if I sort of describe my character, and what's their vibe, and a little bit of, like, what they do and their background, and, like, I've built this whole, like, persona, and then, I just ask the AI, "Hey, what might be some good names for this?" And the AI will give me a bunch of names along with some reasoning for why they think that would be a good match.

So, it might be like, oh, you know, the person's name is, I don't know, Starfighter because it evokes their connection to the night sky or whatever because that was a thing that I put in the background. And so, it's really interesting. And sometimes they're, like, just a little too obvious. Like, you don't want, you know, Joe Fighter because he's a fighter.

STEPHANIE: And his name is Joe [laughs].

JOËL: Yeah, but some of them are pretty good.

STEPHANIE: Cool. Joël, what's new in your world?

JOËL: I guess in this episode of how often does Joël think about the Roman Empire...

STEPHANIE: Oh my gosh [laughs].

JOËL: Yes [laughs].

STEPHANIE: Spoiler: it's every day [laughs].

JOËL: Whaaat? There's a blog that I enjoy reading from a Roman historian. It's called "A Collection of Unmitigated Pedantry", acoup.blog. He's recently been doing an article series on not the Romans, but rather some of these different societies that are around them, and talking a little bit about a distinction that he calls sort of non-state peoples versus states in the ancient Mediterranean. And what exactly is that distinction? Why does it matter? And those are terms I've heard thrown around, but I've never really, like, understood them. And so, he's, like, digging into a thing that I've had a question about for a while that I've been really appreciating.

STEPHANIE: Can you give, like, the reader's digest for me?

JOËL: For him, it's about who has the ability to wield violence legitimately. In a state, sort of the state has a monopoly on violence. Whereas in non-state organizations, oftentimes, it's much more personal, so you might have very different sort of nobles or big men who are able to raise, let's say, private armies and wage private war on each other, and that's not seen as, like, some, like, big breakdown of society. It's a legitimate use of force. It's just accepted that that's how society runs.

As opposed to in a state, if a, you know, wealthy person decided to raise a private army, that would be seen as a big problem, and the state would either try to put you down or, like, more generally, society would, like, see you as having sort of crossed a line you shouldn't have crossed.

STEPHANIE: Hmm, cool. I've been reading a lot of medieval fantasy lately, so this is kind of tickling my brain in that way when I think about, like, what drives different characters to do things, and kind of what the consequences of those things are.

JOËL: Right. I think it would be really fascinating to sort of project this framework forwards and look at the European medieval period through that lens. It seems to me that, at least from a basic understanding, that the sort of feudal system seems to be very much in that sort of non-state category. So, I'd be really interested to see sort of a deeper analysis of that. And, you know, maybe he'll do an addendum to this series. Right now, he's mostly looking at the Gauls, the Celtiberians, and the Germanic tribes during the period of the Roman Republic.

STEPHANIE: Cool. Okay. Well, I also await the day when you somehow figure how this relates to software [laughter] and inevitably make some mind-blowing connection and do a talk about it [laughs].

JOËL: I mean, theming is always fun. There's a talk that I saw years ago at Strange Loop that was looking at the defense policy of the Roman Emperor Diocletian and the Roman Emperor Constantine, and the ways that they sort of defended the borders of the empire and how they're very different, and then related it to how you might handle network security.

STEPHANIE: Whaat?

JOËL: And sort of like a, hey, are we using more of a Diocletian approach here, or are we using more of a Constantine approach here? And all of a sudden, just, like, having those labels to put on there and those stories that went with it made, like, what could be a really, like, dry security talk into something that I still remember 10 years later.

STEPHANIE: Yeah. Yeah. We love stories. They're memorable.

JOËL: So, I'll make sure to link that in the show notes.

STEPHANIE: Very cool.

JOËL: We've been talking a lot recently about my personal note system, where I keep a bunch of, like, small atomic notes that are all usually based around a single thesis statement. And I was going through that recently, and I found one that was kind of a little bit juicy. So, the thesis is that consultants are professional question-askers. And I'm curious, as a consultant yourself, how do you feel about that idea?

STEPHANIE: Well, my first thought would be, how do I get paid to only ask in questions [laughs] or how to communicate in questions and not do anything else [laughs]? It's almost like I'm sure that there is some, like, fantasy character, you know, where it's like, there's some villain or just obstacle where you have this monster character who only talks in questions. And it's like a riddle that you have to solve [laughs] in order to get past.

JOËL: I think it's called a three-year-old.

STEPHANIE: Wow. Okay. Maybe a three-year-old can do my job then [laughter]. But I do think it's a juicy one, and it's very...I can't wait to hear how you got there, but I think my reaction is yes, like, I do be asking questions [laughs] when I join a project on a client team. And I was trying to separate, like, what kinds of questions I ask. And I kind of came away with a few different categories depending on, like, the stage of the engagement I'm in.

But, you know, when I first join a team and when I'm first starting out consulting for a team, I feel like I just ask a lot of basic questions. Like, "Where's the Jira board [laughs]?" Like, "How do you do deployments here?" Like, "What kind of Git process do you use?" So, I don't know if those are necessarily the interesting ones. But I think one thing that has been nice is being a consultant has kind of stripped the fear of asking those questions because, I don't know, these are just things I need to know to do my work. And, like, I'm not as worried about, like, looking dumb or anything like that [laughs].

JOËL: Yeah. I think there's often a fear that asking questions might make you look incompetent or maybe will sort of undermine your appearance of knowing what you're talking about, and I think I've found that to be sort of the opposite. Asking a lot of questions can build more trust, both because it forces people to think about things that maybe they didn't think about, bring to light sort of implicit assumptions that everyone has, and also because it helps you to ramp up much more quickly and to be productive in a way that people really appreciate.

STEPHANIE: Yeah. And I also think that putting those things in, like, a public and, like, documented space helps people in the future too, right? At least I am a power Slack searcher [laughs]. And whenever I am onboarding somewhere, one of the first places I go is just to search in Slack and see if someone has asked this question before.

I think the next kind of category of question that I discerned was just, like, questions to understand how the team understands things. So, it's purely just to, like, absorb kind of like perspective or, like, a worldview this team has about their codebase, or their work, or whatever. So, I think those questions manifest as just like, "Oh, like, you know, I am curious, like, what do you think about how healthy your codebase is? Or what kinds of bugs is your team, like, dealing with?"

Just trying to get a better understanding of like, what are the challenges that this team is facing in their own words, especially before I even start to form my own opinions. Well, okay, to be honest, I probably am forming my own opinions, like, on the side [laughs], but I really try hard to not let that be the driver of how I'm showing up and especially in the first month I'm starting on a new team.

JOËL: Would you say these sorts of questions are more around sort of social organization or, like, how a team approaches work, that sort of thing? Or do you classify more technical questions in this category? So, like, "Hey, tell me a little bit about your philosophy around testing." Or we talked in a recent episode "What value do you feel you get out of testing?" as a question to ask before even, like, digging into the implementation.

STEPHANIE: Yeah, I think these questions, for me, sit at, like, the intersection of both social organization and technical questions because, you know, asking something like, "What's the value of testing for your team?" That will probably give me information about how their test suite is like, right? Like, what kinds of tests they are writing and kind of the quality of them maybe. And it also tells me about, yeah, like, maybe the reasons why, like, they only have just unit tests or maybe, like, just [inaudible 12:31] test, or whatever. And I think all of that is helpful information.

And then, that's actually a really...I like the distinction you made because I feel like then the last category of questions that I'll mention, for now, feels like more geared towards technical, especially the questions I ask to debunk assumptions that might be held by the team. And I feel like that's like kind of the last...the evolution of my question-asking. Because I have, hopefully, like, really absorbed, like, why, you know, people think the way they do about some of these, you know, about their code and start to poke a little bit on being like, "Why do you think, you know, like, this problem space has to be modeled this way?"

And that has served me well as a consultant because, you know, once you've been at an organization for a while, like, you start to take a lot of things for granted about just having to always be this way, you know, it's like, things just are the way they are. And part of the power of, you know, being this kind of, like, external observer is starting to kind of just like, yeah, be able to question that. And, you know, at the end of day, like, we choose not to change something, but I think it's very powerful to be able to at least, like, open up that conversation.

JOËL: Right. And sometimes you open up that conversation, and what you get is a link to a big PR discussion or a Wiki or something where that discussion has already been had. And then, that's good for you and probably good for anybody else who has that question as well.

STEPHANIE: I'm curious, for you, though, like, this thesis statement, atomic note, did you have notes around it, or was it just, like, you dropped it in there [laughs]?

JOËL: So, I have a few things, one is that when you come in as a consultant, and, you know, we're talking here about consultants because that's what we do. I think this is probably true for most people onboarding, especially for non-junior roles where you're coming in, and there's an assumption of expertise, but you need to onboard onto a project. This is just particularly relevant for us as consultants because we do this every six months instead of, you know, a senior developer who's doing this maybe every two to three years.

So, the note that I have here is that when you're brought on, clients they expect expertise in a technology, something like Ruby on Rails or, you know, just the web environment in general. They don't expect you as a consultant to be an expert in their domain or their practices. And so, when you really engage with this sort of areas that are new by asking a lot of questions, that's the thing that's really valuable, especially if those questions are coming from a place of experience in other similar things. So, maybe asking some questions around testing strategies because you've seen three or four other ways that work or don't work or that have different trade-offs.

Even asking about, "Hey, I see we went down a particular path, technically. Can you walk me through what were the trade-offs that we evaluated and why we decided this was the path that was valuable for us?" That's something that people really appreciate from outside experts. Because it shows that you've got experience in those trade-offs, that you've thought the deeper thoughts beyond just shipping the next ticket. And sometimes they've made the decisions without actually thinking through the trade-offs. And so, that can be an opening for a conversation of like, "Hey, well, we just went down this path because we saw a blog article that recommended this, or we just did this because it felt right. Talk us through the trade-offs."

And now maybe you have a conversation on, "Hey, here are the trade-offs that you're doing. Let me know if this sounds right for your organization. If not, maybe you want to consider changing some things or tweaking your approach." And I think that is valuable sort of at the big level where you're thinking about how the team is structured, how different parts of work is done, the technical architecture, but it also is valuable at the small level as well.

STEPHANIE: Yeah, 100%. There is a blog post I really like by Hazel Weakly, and it's called "The Power of Being New: A Proven Recipe for High Impact." And one thing that she says at the beginning that I really enjoy is that even though, like, whenever you start on a new team there's always that little bit of pressure of starting to deliver immediate value, right? But there's something really special about that period where no one expects you to do anything, like, super useful immediately [laughs]. And I feel like it is both a fleeting time and, you know, I'm excited to continue this conversation of, like, how to keep integrating that even after you're no longer new.

But I like to use that time to just identify, while I have nothing really on my plate, like, things that might have just been overlooked or just people have gotten used to that sometimes is, honestly, like, can be a quick fix, right? Like, just, I don't know, deleting a piece of dead code that you're seeing is no longer used but just gets fallen off other people's plates. I really enjoy those first few weeks, and people are almost, like, always so appreciative, right? They're like, "Oh my gosh, I have been meaning to do that." Or like, "Great find." And these are things that, like I said, just get overlooked when you are, yeah, kind of busy with other things that now are your responsibility.

JOËL: You're talking about, like, that feeling of can you add value in the, like, initial time that you join. And I think that sometimes it can be easy to think that, oh, the only value you can add is by, like, shipping code. I think that being sort of noisy and asking a lot of questions in Slack is often a great way to add value, especially at first.

STEPHANIE: Yeah, agreed.

JOËL: Ideally, I think you come in, and you don't sort of slide in under the radar as, like, a new person on the team. Like, you come in, and everybody knows you're there because you are, like, spamming the channel with questions on all sorts of things and getting people to either link you to resources they have or explaining different topics, especially anything domain-related. You know, you're coming in with an outside expertise in a technology. You are a complete new person at the business and the problem domain. And so, that's an area where you need to ask a lot of questions and ramp up quickly.

STEPHANIE: Yes. I have a kind of side topic. I guess it's not a side topic. It's about asking questions, so it's relevant [laughs]. But one thing that I'm curious about is how do you approach kind of doing this in a place where question asking is not normalized and maybe other people are less comfortable with kind of people asking questions openly and in public? Like, how do you set yourself up to be able to ask questions in a way that doesn't lead to just, like, some just, like, suspicion or discomfort about, like, why you're asking those questions?

JOËL: I think that's the beauty of the consultant title. When an organization brings in outside experts, they kind of expect you to ask questions. Or maybe it's not an explicit expectation, but when they see you asking a lot of questions, it sort of, I think, validates a lot of things that they expect about what an outside expert should be. So, asking a lot of questions of trying to understand your business, asking a lot of questions to try to understand the technical architecture, asking questions around, like, some subtle edge cases or trade-offs that were made in the technical architecture.

These are all things that help clients feel like they're getting value for the money from an outside expert because that's what you want an outside expert to do is to help you question some of your assumptions, to be able to leverage their, like, general expertise in a technology by applying it to your specific situation.

I've had situations where I'll ask, like, a very nuanced, deep technical question about, like, "Hey, so there's, like, this one weird edge case that I think could potentially happen. How do we, like, think through about this?" And one of the, like, more senior people on the team who built the initial codebase responded, like, almost, like, proud that I've discovered this, like, weird edge case, and being like, "Oh yeah, that was a thing that we did think about, and here's why. And it's really cool that, like, day one you're, like, just while reading through the code and were like, 'Oh, this thing,' because it took us, like, a month of thinking about it before we stumbled across that."

So, it was a weird kind of fun interaction where as a new person rolling on, one of the more experienced devs in the codebase almost felt, like, proud of me for having found that.

STEPHANIE: I like that, yeah. I feel like a lot of the time...it's like, it's so easy to ask questions to help people feel seen, to be like, "Oh yeah, like, I noticed this." And, you know, if you withhold any kind of, like, judgment about it when you ask the question, people are so willing to be like, yeah, like you said, like, "Oh, I'm glad you saw that." Or like, "Isn't that weird? Like, I was feeling, you know, I saw that, too." Or, like, it opens it up, I think, for building trust, which, again, like, I don't even think this is something that you necessarily need to be new to even do. But if at any point you feel like, you know, maybe your working relationship with someone could be better, right? To the point where you feel like you're, like, really on the same page, yeah, ask questions [laughs]. It can be that easy.

JOËL: And I think what can be really nice is, in an environment where question asking is not normalized, coming in and doing that can help sort of provide a little bit of cover to other people who are feeling less comfortable or less safe doing that. So, maybe there's a lot of junior members on the team who are feeling not super confident in themselves and are afraid that asking questions might undermine their position in the company. But me coming in as a sort of senior consultant and asking a lot of those questions can then help normalize that as a thing because then they can look and say, "Oh, well he's asking all these questions. Maybe I can ask my question, and it'll be okay."

STEPHANIE: I also wanted to talk about setting yourself up and asking questions to get a good answer, asking good questions to get useful answers. One thing that has worked really well for me in the past few months has been sharing why I'm asking the question. And I think this goes back to a little bit of what I was hinting at earlier. If the culture is not really used to people asking questions and that just being a thing that is normal, sharing a bit of intention can help, like, ease maybe some nervousness that people might feel. Especially as consultants, we also are in a bit of a, I don't know, like, there is some power dynamics occasionally where it's like, oh, like, the consultants are here. Like, what are they going to come in and change or, like, start, you know, doing to, quote, unquote, "improve", whatever, I don't know [laughs].

JOËL: Right, right.

STEPHANIE: Yeah, that's the consultant archetype, I think. Anyway.

JOËL: Just coming in and being like, "Oh, this is bad, and this is bad, and you're doing it wrong."

STEPHANIE: [laughs]

JOËL: Ooh, I would be ashamed if I was the author of this code.

STEPHANIE: Yeah, my hot take is that that is a bad consultant [laughs]. But maybe I'll say, like, "I am looking for some examples of this pattern. Where can I find them [laughs]?" Or "I've noticed that the team is struggling with, like, this particular part of the codebase, and I am thinking about improving it. What are some of your biggest challenges, like, working with this, like, model?" something like that.

And I think this also goes back to, like, proving value, right? Even if it's like, sometimes I know kind of what I want to do, and I'll try to be explicit about that. But even before I have, like, a clear action item, I might just say like, "I'm thinking about this," you know, to convey that, you know, I'm still in that information gathering stage, but the result of that will be useful to help me with whatever kind of comes out of it.

JOËL: A lot of it is about, like, genuine curiosity and an amount of empathetic listening. Existing team knows a lot about both the code and the business. And as a consultant coming on or maybe even a more senior person onboarding onto a team, the existing team has so much that they can give you to help you be better at your job.

STEPHANIE: I was also revisiting a really great blog post from Julia Evans about "How to Ask Good Questions." And this one is more geared towards asking technical questions that have, like, kind of a maybe more straightforward answer. But she included a few other strategies that I liked a lot. And, frankly, I feel like I want to be even better at finding the right time to ask questions [laughs] and finding the right person to ask those questions to.

I definitely get in the habit of just kind of like, I don't know, I'll just put it out there and [laughs], hopefully, get some answers. But there are definitely ways, I think, that you can be more strategic, right? About identifying who might be the best person to provide the answers you're looking for. And I think another thing that I often have to balance in the consulting position is when to know when to, like, stop kind of asking the really big questions because we just don't have time [laughs].

JOËL: Right. You don't want to be asking questions in a way that's sort of undermining the product, or the decisions that are being made, or the work that has to get done. Ideally, the questions that you're asking are helping move the project forward in a positive way. Nobody likes the, you know, just asking kind of person. That person's annoying.

STEPHANIE: Do you have an approach or any thoughts about like, once you get an answer, like, what do you do with that? Yeah, what happens then for you?

JOËL: I guess there's a lot of different ways it can go. A potential way if it's just, like, an answer explained in Slack, is maybe saying, "We should document this." Or maybe even like, "Is this documented anywhere? If not, can I add that documentation somewhere?" And maybe that's, you know, a code comment that we want to add. Maybe that's an entry to the Wiki. Maybe that's updating the README. Maybe that's adding a test case. But converting that into something actionable can often be a really good follow-up.

STEPHANIE: Yeah, I think that mitigates the just asking [laughs] thing that you were saying earlier, where it's like, you know, the goal isn't to ask questions to then make more work for other people, right? It's to ask questions so, hopefully, you're able to take that information and do something valuable with it.

JOËL: Right. Sometimes it can be a sort of setup for follow-up questions. You get some information and you're like, okay, so, it looks like we do have a pattern for interacting with third-party APIs, but we're not using it consistently. Tell me a little bit about why that is. Is that a new pattern that we've introduced and we're trying to, like, get more buy-in from the team? Is this a pattern that we used to have, and we found out we didn't like it? So, we stopped using it, but we haven't found a replacement pattern that we like. And so, now we're just kind of...it's a free-for-all, and we're trying to figure it out.

Maybe there's two competing patterns, and there is this, like, weird politics within the tech team where they're sort of using one or the other, and that's something I'm going to have to be careful to navigate. So, asking some of those follow-up questions and once you have a technical answer can yield a lot of really interesting information and then help you think about how you can be impactful on the organization.

STEPHANIE: And that sounds like advice that's just true, you know, regardless of your role or how long you've been in it, don't you think?

JOËL: I would say yes. If you've been in the role a long time, though, you're the person who has that sort of institutional history in your mind. You know that in 2022, we switched over from one framework to another. You know that we used to have this, like, very opinionated architect who mandated a particular pattern, and then we moved away from it. You know that we were all in on this big feature last summer that we released and then nobody used it, and then the business pivoted, but there's still aspects of it that are left around. Those are things that someone knew onboarding doesn't know and that, hopefully, they're asking questions that you can then answer.

STEPHANIE: Have you been in the position where you have all that, like, institutional knowledge? And then, like, how do you maintain that sense of curiosity or just that sense of kind of, like, what you're talking about, that superpower that you get when you're new of being able to just, you know, kind of question why things are the way they are?

JOËL: It's hard, right? We're talking about how do you keep that sort of almost like a beginner's mindset, in this case, maybe less of a, like, new coder mindset and more of a new hire mindset. It's something that I think is much more front of mind for me because I rotate onto new clients every, like, 6 to 12 months. And so, I don't have very long to get comfortable before I'm immediately thrown into, like, a new situation.

But something that I like to do is to never sort of solely be in one role or the other, a sort of, like, experienced person helping others or the new person asking for help. Likely, you are not going to be the newest person on the team for long. Maybe you came on as a cohort and you've got a group of new people, all of whom are asking different questions. And maybe somebody is asking a question that you've asked before, that you've asked in a different channel or on a call with someone. Or maybe someone joins two weeks after you; you don't have deep institutional knowledge.

But if you've been asking a lot of questions, you've been building a lot of that for yourself, and you have a little bit that you can share to the next person who knows even less than you do. And that's an approach that I took even as an apprentice developer. When I was, like, brand new to Rails and I was doing an internship, and another intern joined me a couple of weeks after, and I was like, "You know what? I barely know anything. But I know what an instance variable is. And I can help you write a controller action. Let's pair on that. We'll figure it out. And, you know, ask me another question next week. I might have more answers for you." So, I guess a little bit of paying it forward.

STEPHANIE: Yeah, I really like that advice, though, of, like, switching up the role or, like, kind of what you're working on, just finding opportunities to practice that, you know, even if you have been somewhere for a long time. I think that is really interesting advice. And it's hard, too, right? Because that requires, like, doing something new, and doing something new can be hard [laughs]. But if you're, you know, aren't in a consultant role, where you're not rotating onto new projects every 6 to 12 months, that, I feel like, would be a good strategy to grow in that particular way.

JOËL: And even if you're not switching companies or in a consulting situation, it's not uncommon to have people switch from one team to another within an organization. And new team might mean new dynamics. That team might be doing a slightly different approach to project management. Their part of the code might be structured slightly differently. They might be dealing with a part of the business domain that you're less familiar with. While that might not be entirely new to you because, you know, you know a little bit of the organization's DNA and you understand the organization's mission and their core product, there are definitely a lot of things that will be new to you, and asking those questions becomes important.

STEPHANIE: I also have another kind of, I don't know, it's not even a strategy. It's just a funny thing that I do where, like, my memory is so poor that, like, even code I wrote, you know, a month ago, I'm like, oh, what was past Stephanie thinking here [laughs]? You know, questioning myself a little bit, right? And being willing to do that and recognizing that, like, I have information now that I didn't have in the past. And, like, can that be useful somehow?

You know, it's like, the code I wrote a month ago is not set in stone. And I think that's one way I almost, like, practice that skill with myself [laughs]. And yeah, it has helped me combat that, like, things are the way they are mentality, which, generally, I think is a very big blocker [laughs] when it comes to software development, but that's a topic for another day [laughs].

JOËL: I like the idea of questioning yourself, and I think that's something that is a really valuable skill for all developers. I think it can come up in things like documentation. Let's say you're leaving a comment on a method, especially one that's a bit weird, being able to answer that "Why was this weird technical decision made?" Or maybe you do this in your PR description, or your commit message, or in any of the other places where you do this, not just sort of shipping the code as is, but trying to look at it from an outsider's eyes.

And being like, what are the areas where they're going to, like, get a quizzical look and be like, "Why is this happening? Why did you make this choice?" Bonus points if you talked a little bit about the trade-offs that were decided on to say, "Hey, there were two different implementations available for this. I chose to take implementation A because I like this set of trade-offs better." That's gold. And, I guess, as a reviewer, if I'm seeing that in a PR, that's going to make my job a lot easier.

STEPHANIE: Yes. Yeah, I never thought about it that way, but yeah, I guess I do kind of apply, you know, the things that I would kind of ask to other team members to myself sometimes. And that is...it's cool to hear that you really appreciate that because I always kind of just did it for myself [laughs], but yeah, I'm sure that it, like, is helpful for other people as well.

JOËL: I guess you were asking what are ways that you can ask questions even when you are more established. And talking about these sorts of self-reflective questions in the context of review got me thinking that PRs are a great place to ask questions. They're great when you're a newcomer. One of the things I like to do when I'm new on a project is do a lot of PR reviews so I can just see the weird things that people are working on and ask a lot of questions about the patterns.

STEPHANIE: Yep. Same here.

JOËL: Do a lot of code reading. But that's a thing that you can keep doing and asking a lot of questions on PRs and not in a, like, trying to undermine what the person is doing, but, like, genuine questions, I think, is a great way to maintain that mindset.

STEPHANIE: Yeah, yeah, agreed. And I think when I've seen it done well, it's like, you get to be engaged and involved with the rest of your team, right? And you kind of have a bit of an idea about what people are working on. But you're also kind of entrusting them with ownership of that work. Like, you don't need to be totally in the weeds and know exactly how every method works. But, you know, you can be curious about like, "Oh, like, what were you thinking about this?" Or like, "What about this pattern appeals to you?" And all of that information, I think, helps you become a better, like, especially a senior developer, but also just, like, a leader on the team, I think.

JOËL: Yeah, especially the questions around like, "Oh, walk me through some of the trade-offs that you chose for this method." And, you know, for maybe a person who's more senior, that's great. They have an opportunity to, like, talk about the decisions they made and why. That's really useful information. For a more junior person, maybe they've never thought about it. They're like, "Oh, wait, there are trade-offs here?" and now that's a great learning opportunity for them.

And you don't want to come at it from a place of judgment of like, oh, well, clearly, you know, you're a terrible developer because you didn't think about the performance implications of this method. But if you come at it from a place of, like, genuine curiosity and sort of assuming the best of people on the team and being willing to work alongside them, help them discover some new concepts...maybe they've never, like, interacted so much with performance trade-offs, and now you get to have a conversation. And they've learned a thing, and everybody wins.

STEPHANIE: Yeah. And also, I think seeing people ask questions that way helps more junior folks also learn when to ask those kinds of questions, even if they don't know the answer, right? But maybe they start kind of pattern matching. Like, oh, like, there might be some other trade-offs to consider with this kind of code, but I don't know what they are yet. But now I know to at least start asking and find someone who can help me determine that. And when I've seen that, that has been always, like, just so cool because it's upskilling happening [laughs] in practice.

JOËL: Exactly. I love that phrase that you said: "Asking questions where you don't know the answers," which I think is the opposite of what lawyers are taught to do. I think lawyers the mantra they have is you never ask a witness a question that you don't know the answer to. But I like to flip that for developers. Ask a lot of questions on PRs where you don't know the answer, and you'll grow, and the author will grow. And this is true across experience levels.

STEPHANIE: That's one of my favorite parts about being a developer, and maybe that's why I will never be a lawyer [laughter].

JOËL: On that note, I have a question maybe I do know the answer to. Shall we wrap up?

STEPHANIE: Let's wrap up. Show notes for this episode can be found at bikeshed.fm.

JOËL: This show has been produced and edited by Mandy Moore.

STEPHANIE: If you enjoyed listening, one really easy way to support the show is to leave us a quick rating or even a review in iTunes. It really helps other folks find the show.

JOËL: If you have any feedback for this or any of our other episodes, you can reach us @_bikeshed, or you can reach me @joelquen on Twitter.

STEPHANIE: Or reach both of us at hosts@bikeshed.fm via email.

JOËL: Thanks so much for listening to The Bike Shed, and we'll see you next week.

ALL: Byeeeeeeee!!!!!!!

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Stephanie shares her newfound interest in naming conventions, highlighting a resource called "Classnames" that provides valuable names for programming and design. Joël, in turn, talks about using AI to generate names for D&D characters, emphasizing how AI can help provide inspiration and reasoning behind name suggestions. Then, they shift to Joël's interest in Roman history, where he discusses a blog by a Roman historian that explores distinctions between state and non-state peoples in the ancient Mediterranean.

Together, the hosts delve into the importance of asking questions as consultants and developers to understand workflows, question assumptions, and build trust for better onboarding. Stephanie categorizes questions by engagement stages and their social and technical aspects, while Joël highlights how questioning reveals implicit assumptions and speeds up learning. They stress maintaining a curious mindset, using questions during PR reviews, and working with junior developers to foster collaboration. They conclude with advice on documenting answers and using questions for continuous improvement and effective decision-making in development teams.

Transcript:

 JOËL: Hello and welcome to another episode of the Bike Shed, a weekly podcast from your friends at thoughtbot about developing great software. I'm Joël Quenneville.

STEPHANIE: And I'm Stephanie Minn. And together, we're here to share a bit of what we've learned along the way.

JOËL: So, Stephanie, what's new in your world?

STEPHANIE: So, if it has not been clear about just kind of the things I'm mentioning on the podcast the past few weeks, I've been obsessed with naming things lately [chuckles] and just thinking about how to name things, and, yeah, just really excited about...or even just having fun with that more than I used to be as a dev. And I found a really cool resource called "Classnames." Well, it's like just a little website that a designer and developer shared from kind of as an offshoot from his personal website. I'll link it in the show notes.

But it's basically just a list of common names that are very useful for programming or even design. It's just to help you find some inspiration when you're stuck trying to find a name for something. And they're general or abstract enough that, you know, it's almost like kind of like a design pattern but a naming pattern [laughs], I suppose.

JOËL: Ooh.

STEPHANIE: Yeah, right? And so, there's different categories. Like, here's a bunch of words that kind of describe collections. So, if you need to find the name for a containment or a group of things, here's a bunch of kind of words in the English language that might be inspiring. And then, there's also other categories like music for describing kind of the pace or arrangement of things. Fashion, words from fashion can describe, like, the size of things. You know, we talk about T-shirt sizes when we are estimating work.

And yeah, I thought it was really cool that there's both things that draw on, you know, domains that most people know in real life, and then also things that are a little more abstract. But yeah, "Classnames" by Paul Robert Lloyd — that's been a fun little resource for me lately.

JOËL: Very cool. Have you ever played around at all with using AI to help you come up with the naming?

STEPHANIE: I have not. But I know that you and other people in my world have been enjoying using AI for inspiration when they feel a little bit stuck on something and kind of asking like, "Oh, like, how could I name something that is, like, a group of things?" or, you know, a prompt like that. I suspect that that would also be very helpful.

JOËL: I've been having fun using that to help me come up with good names for D&D characters, and sometimes they're a little bit on the nose. But if I sort of describe my character, and what's their vibe, and a little bit of, like, what they do and their background, and, like, I've built this whole, like, persona, and then, I just ask the AI, "Hey, what might be some good names for this?" And the AI will give me a bunch of names along with some reasoning for why they think that would be a good match.

So, it might be like, oh, you know, the person's name is, I don't know, Starfighter because it evokes their connection to the night sky or whatever because that was a thing that I put in the background. And so, it's really interesting. And sometimes they're, like, just a little too obvious. Like, you don't want, you know, Joe Fighter because he's a fighter.

STEPHANIE: And his name is Joe [laughs].

JOËL: Yeah, but some of them are pretty good.

STEPHANIE: Cool. Joël, what's new in your world?

JOËL: I guess in this episode of how often does Joël think about the Roman Empire...

STEPHANIE: Oh my gosh [laughs].

JOËL: Yes [laughs].

STEPHANIE: Spoiler: it's every day [laughs].

JOËL: Whaaat? There's a blog that I enjoy reading from a Roman historian. It's called "A Collection of Unmitigated Pedantry", acoup.blog. He's recently been doing an article series on not the Romans, but rather some of these different societies that are around them, and talking a little bit about a distinction that he calls sort of non-state peoples versus states in the ancient Mediterranean. And what exactly is that distinction? Why does it matter? And those are terms I've heard thrown around, but I've never really, like, understood them. And so, he's, like, digging into a thing that I've had a question about for a while that I've been really appreciating.

STEPHANIE: Can you give, like, the reader's digest for me?

JOËL: For him, it's about who has the ability to wield violence legitimately. In a state, sort of the state has a monopoly on violence. Whereas in non-state organizations, oftentimes, it's much more personal, so you might have very different sort of nobles or big men who are able to raise, let's say, private armies and wage private war on each other, and that's not seen as, like, some, like, big breakdown of society. It's a legitimate use of force. It's just accepted that that's how society runs.

As opposed to in a state, if a, you know, wealthy person decided to raise a private army, that would be seen as a big problem, and the state would either try to put you down or, like, more generally, society would, like, see you as having sort of crossed a line you shouldn't have crossed.

STEPHANIE: Hmm, cool. I've been reading a lot of medieval fantasy lately, so this is kind of tickling my brain in that way when I think about, like, what drives different characters to do things, and kind of what the consequences of those things are.

JOËL: Right. I think it would be really fascinating to sort of project this framework forwards and look at the European medieval period through that lens. It seems to me that, at least from a basic understanding, that the sort of feudal system seems to be very much in that sort of non-state category. So, I'd be really interested to see sort of a deeper analysis of that. And, you know, maybe he'll do an addendum to this series. Right now, he's mostly looking at the Gauls, the Celtiberians, and the Germanic tribes during the period of the Roman Republic.

STEPHANIE: Cool. Okay. Well, I also await the day when you somehow figure how this relates to software [laughter] and inevitably make some mind-blowing connection and do a talk about it [laughs].

JOËL: I mean, theming is always fun. There's a talk that I saw years ago at Strange Loop that was looking at the defense policy of the Roman Emperor Diocletian and the Roman Emperor Constantine, and the ways that they sort of defended the borders of the empire and how they're very different, and then related it to how you might handle network security.

STEPHANIE: Whaat?

JOËL: And sort of like a, hey, are we using more of a Diocletian approach here, or are we using more of a Constantine approach here? And all of a sudden, just, like, having those labels to put on there and those stories that went with it made, like, what could be a really, like, dry security talk into something that I still remember 10 years later.

STEPHANIE: Yeah. Yeah. We love stories. They're memorable.

JOËL: So, I'll make sure to link that in the show notes.

STEPHANIE: Very cool.

JOËL: We've been talking a lot recently about my personal note system, where I keep a bunch of, like, small atomic notes that are all usually based around a single thesis statement. And I was going through that recently, and I found one that was kind of a little bit juicy. So, the thesis is that consultants are professional question-askers. And I'm curious, as a consultant yourself, how do you feel about that idea?

STEPHANIE: Well, my first thought would be, how do I get paid to only ask in questions [laughs] or how to communicate in questions and not do anything else [laughs]? It's almost like I'm sure that there is some, like, fantasy character, you know, where it's like, there's some villain or just obstacle where you have this monster character who only talks in questions. And it's like a riddle that you have to solve [laughs] in order to get past.

JOËL: I think it's called a three-year-old.

STEPHANIE: Wow. Okay. Maybe a three-year-old can do my job then [laughter]. But I do think it's a juicy one, and it's very...I can't wait to hear how you got there, but I think my reaction is yes, like, I do be asking questions [laughs] when I join a project on a client team. And I was trying to separate, like, what kinds of questions I ask. And I kind of came away with a few different categories depending on, like, the stage of the engagement I'm in.

But, you know, when I first join a team and when I'm first starting out consulting for a team, I feel like I just ask a lot of basic questions. Like, "Where's the Jira board [laughs]?" Like, "How do you do deployments here?" Like, "What kind of Git process do you use?" So, I don't know if those are necessarily the interesting ones. But I think one thing that has been nice is being a consultant has kind of stripped the fear of asking those questions because, I don't know, these are just things I need to know to do my work. And, like, I'm not as worried about, like, looking dumb or anything like that [laughs].

JOËL: Yeah. I think there's often a fear that asking questions might make you look incompetent or maybe will sort of undermine your appearance of knowing what you're talking about, and I think I've found that to be sort of the opposite. Asking a lot of questions can build more trust, both because it forces people to think about things that maybe they didn't think about, bring to light sort of implicit assumptions that everyone has, and also because it helps you to ramp up much more quickly and to be productive in a way that people really appreciate.

STEPHANIE: Yeah. And I also think that putting those things in, like, a public and, like, documented space helps people in the future too, right? At least I am a power Slack searcher [laughs]. And whenever I am onboarding somewhere, one of the first places I go is just to search in Slack and see if someone has asked this question before.

I think the next kind of category of question that I discerned was just, like, questions to understand how the team understands things. So, it's purely just to, like, absorb kind of like perspective or, like, a worldview this team has about their codebase, or their work, or whatever. So, I think those questions manifest as just like, "Oh, like, you know, I am curious, like, what do you think about how healthy your codebase is? Or what kinds of bugs is your team, like, dealing with?"

Just trying to get a better understanding of like, what are the challenges that this team is facing in their own words, especially before I even start to form my own opinions. Well, okay, to be honest, I probably am forming my own opinions, like, on the side [laughs], but I really try hard to not let that be the driver of how I'm showing up and especially in the first month I'm starting on a new team.

JOËL: Would you say these sorts of questions are more around sort of social organization or, like, how a team approaches work, that sort of thing? Or do you classify more technical questions in this category? So, like, "Hey, tell me a little bit about your philosophy around testing." Or we talked in a recent episode "What value do you feel you get out of testing?" as a question to ask before even, like, digging into the implementation.

STEPHANIE: Yeah, I think these questions, for me, sit at, like, the intersection of both social organization and technical questions because, you know, asking something like, "What's the value of testing for your team?" That will probably give me information about how their test suite is like, right? Like, what kinds of tests they are writing and kind of the quality of them maybe. And it also tells me about, yeah, like, maybe the reasons why, like, they only have just unit tests or maybe, like, just [inaudible 12:31] test, or whatever. And I think all of that is helpful information.

And then, that's actually a really...I like the distinction you made because I feel like then the last category of questions that I'll mention, for now, feels like more geared towards technical, especially the questions I ask to debunk assumptions that might be held by the team. And I feel like that's like kind of the last...the evolution of my question-asking. Because I have, hopefully, like, really absorbed, like, why, you know, people think the way they do about some of these, you know, about their code and start to poke a little bit on being like, "Why do you think, you know, like, this problem space has to be modeled this way?"

And that has served me well as a consultant because, you know, once you've been at an organization for a while, like, you start to take a lot of things for granted about just having to always be this way, you know, it's like, things just are the way they are. And part of the power of, you know, being this kind of, like, external observer is starting to kind of just like, yeah, be able to question that. And, you know, at the end of day, like, we choose not to change something, but I think it's very powerful to be able to at least, like, open up that conversation.

JOËL: Right. And sometimes you open up that conversation, and what you get is a link to a big PR discussion or a Wiki or something where that discussion has already been had. And then, that's good for you and probably good for anybody else who has that question as well.

STEPHANIE: I'm curious, for you, though, like, this thesis statement, atomic note, did you have notes around it, or was it just, like, you dropped it in there [laughs]?

JOËL: So, I have a few things, one is that when you come in as a consultant, and, you know, we're talking here about consultants because that's what we do. I think this is probably true for most people onboarding, especially for non-junior roles where you're coming in, and there's an assumption of expertise, but you need to onboard onto a project. This is just particularly relevant for us as consultants because we do this every six months instead of, you know, a senior developer who's doing this maybe every two to three years.

So, the note that I have here is that when you're brought on, clients they expect expertise in a technology, something like Ruby on Rails or, you know, just the web environment in general. They don't expect you as a consultant to be an expert in their domain or their practices. And so, when you really engage with this sort of areas that are new by asking a lot of questions, that's the thing that's really valuable, especially if those questions are coming from a place of experience in other similar things. So, maybe asking some questions around testing strategies because you've seen three or four other ways that work or don't work or that have different trade-offs.

Even asking about, "Hey, I see we went down a particular path, technically. Can you walk me through what were the trade-offs that we evaluated and why we decided this was the path that was valuable for us?" That's something that people really appreciate from outside experts. Because it shows that you've got experience in those trade-offs, that you've thought the deeper thoughts beyond just shipping the next ticket. And sometimes they've made the decisions without actually thinking through the trade-offs. And so, that can be an opening for a conversation of like, "Hey, well, we just went down this path because we saw a blog article that recommended this, or we just did this because it felt right. Talk us through the trade-offs."

And now maybe you have a conversation on, "Hey, here are the trade-offs that you're doing. Let me know if this sounds right for your organization. If not, maybe you want to consider changing some things or tweaking your approach." And I think that is valuable sort of at the big level where you're thinking about how the team is structured, how different parts of work is done, the technical architecture, but it also is valuable at the small level as well.

STEPHANIE: Yeah, 100%. There is a blog post I really like by Hazel Weakly, and it's called "The Power of Being New: A Proven Recipe for High Impact." And one thing that she says at the beginning that I really enjoy is that even though, like, whenever you start on a new team there's always that little bit of pressure of starting to deliver immediate value, right? But there's something really special about that period where no one expects you to do anything, like, super useful immediately [laughs]. And I feel like it is both a fleeting time and, you know, I'm excited to continue this conversation of, like, how to keep integrating that even after you're no longer new.

But I like to use that time to just identify, while I have nothing really on my plate, like, things that might have just been overlooked or just people have gotten used to that sometimes is, honestly, like, can be a quick fix, right? Like, just, I don't know, deleting a piece of dead code that you're seeing is no longer used but just gets fallen off other people's plates. I really enjoy those first few weeks, and people are almost, like, always so appreciative, right? They're like, "Oh my gosh, I have been meaning to do that." Or like, "Great find." And these are things that, like I said, just get overlooked when you are, yeah, kind of busy with other things that now are your responsibility.

JOËL: You're talking about, like, that feeling of can you add value in the, like, initial time that you join. And I think that sometimes it can be easy to think that, oh, the only value you can add is by, like, shipping code. I think that being sort of noisy and asking a lot of questions in Slack is often a great way to add value, especially at first.

STEPHANIE: Yeah, agreed.

JOËL: Ideally, I think you come in, and you don't sort of slide in under the radar as, like, a new person on the team. Like, you come in, and everybody knows you're there because you are, like, spamming the channel with questions on all sorts of things and getting people to either link you to resources they have or explaining different topics, especially anything domain-related. You know, you're coming in with an outside expertise in a technology. You are a complete new person at the business and the problem domain. And so, that's an area where you need to ask a lot of questions and ramp up quickly.

STEPHANIE: Yes. I have a kind of side topic. I guess it's not a side topic. It's about asking questions, so it's relevant [laughs]. But one thing that I'm curious about is how do you approach kind of doing this in a place where question asking is not normalized and maybe other people are less comfortable with kind of people asking questions openly and in public? Like, how do you set yourself up to be able to ask questions in a way that doesn't lead to just, like, some just, like, suspicion or discomfort about, like, why you're asking those questions?

JOËL: I think that's the beauty of the consultant title. When an organization brings in outside experts, they kind of expect you to ask questions. Or maybe it's not an explicit expectation, but when they see you asking a lot of questions, it sort of, I think, validates a lot of things that they expect about what an outside expert should be. So, asking a lot of questions of trying to understand your business, asking a lot of questions to try to understand the technical architecture, asking questions around, like, some subtle edge cases or trade-offs that were made in the technical architecture.

These are all things that help clients feel like they're getting value for the money from an outside expert because that's what you want an outside expert to do is to help you question some of your assumptions, to be able to leverage their, like, general expertise in a technology by applying it to your specific situation.

I've had situations where I'll ask, like, a very nuanced, deep technical question about, like, "Hey, so there's, like, this one weird edge case that I think could potentially happen. How do we, like, think through about this?" And one of the, like, more senior people on the team who built the initial codebase responded, like, almost, like, proud that I've discovered this, like, weird edge case, and being like, "Oh yeah, that was a thing that we did think about, and here's why. And it's really cool that, like, day one you're, like, just while reading through the code and were like, 'Oh, this thing,' because it took us, like, a month of thinking about it before we stumbled across that."

So, it was a weird kind of fun interaction where as a new person rolling on, one of the more experienced devs in the codebase almost felt, like, proud of me for having found that.

STEPHANIE: I like that, yeah. I feel like a lot of the time...it's like, it's so easy to ask questions to help people feel seen, to be like, "Oh yeah, like, I noticed this." And, you know, if you withhold any kind of, like, judgment about it when you ask the question, people are so willing to be like, yeah, like you said, like, "Oh, I'm glad you saw that." Or like, "Isn't that weird? Like, I was feeling, you know, I saw that, too." Or, like, it opens it up, I think, for building trust, which, again, like, I don't even think this is something that you necessarily need to be new to even do. But if at any point you feel like, you know, maybe your working relationship with someone could be better, right? To the point where you feel like you're, like, really on the same page, yeah, ask questions [laughs]. It can be that easy.

JOËL: And I think what can be really nice is, in an environment where question asking is not normalized, coming in and doing that can help sort of provide a little bit of cover to other people who are feeling less comfortable or less safe doing that. So, maybe there's a lot of junior members on the team who are feeling not super confident in themselves and are afraid that asking questions might undermine their position in the company. But me coming in as a sort of senior consultant and asking a lot of those questions can then help normalize that as a thing because then they can look and say, "Oh, well he's asking all these questions. Maybe I can ask my question, and it'll be okay."

STEPHANIE: I also wanted to talk about setting yourself up and asking questions to get a good answer, asking good questions to get useful answers. One thing that has worked really well for me in the past few months has been sharing why I'm asking the question. And I think this goes back to a little bit of what I was hinting at earlier. If the culture is not really used to people asking questions and that just being a thing that is normal, sharing a bit of intention can help, like, ease maybe some nervousness that people might feel. Especially as consultants, we also are in a bit of a, I don't know, like, there is some power dynamics occasionally where it's like, oh, like, the consultants are here. Like, what are they going to come in and change or, like, start, you know, doing to, quote, unquote, "improve", whatever, I don't know [laughs].

JOËL: Right, right.

STEPHANIE: Yeah, that's the consultant archetype, I think. Anyway.

JOËL: Just coming in and being like, "Oh, this is bad, and this is bad, and you're doing it wrong."

STEPHANIE: [laughs]

JOËL: Ooh, I would be ashamed if I was the author of this code.

STEPHANIE: Yeah, my hot take is that that is a bad consultant [laughs]. But maybe I'll say, like, "I am looking for some examples of this pattern. Where can I find them [laughs]?" Or "I've noticed that the team is struggling with, like, this particular part of the codebase, and I am thinking about improving it. What are some of your biggest challenges, like, working with this, like, model?" something like that.

And I think this also goes back to, like, proving value, right? Even if it's like, sometimes I know kind of what I want to do, and I'll try to be explicit about that. But even before I have, like, a clear action item, I might just say like, "I'm thinking about this," you know, to convey that, you know, I'm still in that information gathering stage, but the result of that will be useful to help me with whatever kind of comes out of it.

JOËL: A lot of it is about, like, genuine curiosity and an amount of empathetic listening. Existing team knows a lot about both the code and the business. And as a consultant coming on or maybe even a more senior person onboarding onto a team, the existing team has so much that they can give you to help you be better at your job.

STEPHANIE: I was also revisiting a really great blog post from Julia Evans about "How to Ask Good Questions." And this one is more geared towards asking technical questions that have, like, kind of a maybe more straightforward answer. But she included a few other strategies that I liked a lot. And, frankly, I feel like I want to be even better at finding the right time to ask questions [laughs] and finding the right person to ask those questions to.

I definitely get in the habit of just kind of like, I don't know, I'll just put it out there and [laughs], hopefully, get some answers. But there are definitely ways, I think, that you can be more strategic, right? About identifying who might be the best person to provide the answers you're looking for. And I think another thing that I often have to balance in the consulting position is when to know when to, like, stop kind of asking the really big questions because we just don't have time [laughs].

JOËL: Right. You don't want to be asking questions in a way that's sort of undermining the product, or the decisions that are being made, or the work that has to get done. Ideally, the questions that you're asking are helping move the project forward in a positive way. Nobody likes the, you know, just asking kind of person. That person's annoying.

STEPHANIE: Do you have an approach or any thoughts about like, once you get an answer, like, what do you do with that? Yeah, what happens then for you?

JOËL: I guess there's a lot of different ways it can go. A potential way if it's just, like, an answer explained in Slack, is maybe saying, "We should document this." Or maybe even like, "Is this documented anywhere? If not, can I add that documentation somewhere?" And maybe that's, you know, a code comment that we want to add. Maybe that's an entry to the Wiki. Maybe that's updating the README. Maybe that's adding a test case. But converting that into something actionable can often be a really good follow-up.

STEPHANIE: Yeah, I think that mitigates the just asking [laughs] thing that you were saying earlier, where it's like, you know, the goal isn't to ask questions to then make more work for other people, right? It's to ask questions so, hopefully, you're able to take that information and do something valuable with it.

JOËL: Right. Sometimes it can be a sort of setup for follow-up questions. You get some information and you're like, okay, so, it looks like we do have a pattern for interacting with third-party APIs, but we're not using it consistently. Tell me a little bit about why that is. Is that a new pattern that we've introduced and we're trying to, like, get more buy-in from the team? Is this a pattern that we used to have, and we found out we didn't like it? So, we stopped using it, but we haven't found a replacement pattern that we like. And so, now we're just kind of...it's a free-for-all, and we're trying to figure it out.

Maybe there's two competing patterns, and there is this, like, weird politics within the tech team where they're sort of using one or the other, and that's something I'm going to have to be careful to navigate. So, asking some of those follow-up questions and once you have a technical answer can yield a lot of really interesting information and then help you think about how you can be impactful on the organization.

STEPHANIE: And that sounds like advice that's just true, you know, regardless of your role or how long you've been in it, don't you think?

JOËL: I would say yes. If you've been in the role a long time, though, you're the person who has that sort of institutional history in your mind. You know that in 2022, we switched over from one framework to another. You know that we used to have this, like, very opinionated architect who mandated a particular pattern, and then we moved away from it. You know that we were all in on this big feature last summer that we released and then nobody used it, and then the business pivoted, but there's still aspects of it that are left around. Those are things that someone knew onboarding doesn't know and that, hopefully, they're asking questions that you can then answer.

STEPHANIE: Have you been in the position where you have all that, like, institutional knowledge? And then, like, how do you maintain that sense of curiosity or just that sense of kind of, like, what you're talking about, that superpower that you get when you're new of being able to just, you know, kind of question why things are the way they are?

JOËL: It's hard, right? We're talking about how do you keep that sort of almost like a beginner's mindset, in this case, maybe less of a, like, new coder mindset and more of a new hire mindset. It's something that I think is much more front of mind for me because I rotate onto new clients every, like, 6 to 12 months. And so, I don't have very long to get comfortable before I'm immediately thrown into, like, a new situation.

But something that I like to do is to never sort of solely be in one role or the other, a sort of, like, experienced person helping others or the new person asking for help. Likely, you are not going to be the newest person on the team for long. Maybe you came on as a cohort and you've got a group of new people, all of whom are asking different questions. And maybe somebody is asking a question that you've asked before, that you've asked in a different channel or on a call with someone. Or maybe someone joins two weeks after you; you don't have deep institutional knowledge.

But if you've been asking a lot of questions, you've been building a lot of that for yourself, and you have a little bit that you can share to the next person who knows even less than you do. And that's an approach that I took even as an apprentice developer. When I was, like, brand new to Rails and I was doing an internship, and another intern joined me a couple of weeks after, and I was like, "You know what? I barely know anything. But I know what an instance variable is. And I can help you write a controller action. Let's pair on that. We'll figure it out. And, you know, ask me another question next week. I might have more answers for you." So, I guess a little bit of paying it forward.

STEPHANIE: Yeah, I really like that advice, though, of, like, switching up the role or, like, kind of what you're working on, just finding opportunities to practice that, you know, even if you have been somewhere for a long time. I think that is really interesting advice. And it's hard, too, right? Because that requires, like, doing something new, and doing something new can be hard [laughs]. But if you're, you know, aren't in a consultant role, where you're not rotating onto new projects every 6 to 12 months, that, I feel like, would be a good strategy to grow in that particular way.

JOËL: And even if you're not switching companies or in a consulting situation, it's not uncommon to have people switch from one team to another within an organization. And new team might mean new dynamics. That team might be doing a slightly different approach to project management. Their part of the code might be structured slightly differently. They might be dealing with a part of the business domain that you're less familiar with. While that might not be entirely new to you because, you know, you know a little bit of the organization's DNA and you understand the organization's mission and their core product, there are definitely a lot of things that will be new to you, and asking those questions becomes important.

STEPHANIE: I also have another kind of, I don't know, it's not even a strategy. It's just a funny thing that I do where, like, my memory is so poor that, like, even code I wrote, you know, a month ago, I'm like, oh, what was past Stephanie thinking here [laughs]? You know, questioning myself a little bit, right? And being willing to do that and recognizing that, like, I have information now that I didn't have in the past. And, like, can that be useful somehow?

You know, it's like, the code I wrote a month ago is not set in stone. And I think that's one way I almost, like, practice that skill with myself [laughs]. And yeah, it has helped me combat that, like, things are the way they are mentality, which, generally, I think is a very big blocker [laughs] when it comes to software development, but that's a topic for another day [laughs].

JOËL: I like the idea of questioning yourself, and I think that's something that is a really valuable skill for all developers. I think it can come up in things like documentation. Let's say you're leaving a comment on a method, especially one that's a bit weird, being able to answer that "Why was this weird technical decision made?" Or maybe you do this in your PR description, or your commit message, or in any of the other places where you do this, not just sort of shipping the code as is, but trying to look at it from an outsider's eyes.

And being like, what are the areas where they're going to, like, get a quizzical look and be like, "Why is this happening? Why did you make this choice?" Bonus points if you talked a little bit about the trade-offs that were decided on to say, "Hey, there were two different implementations available for this. I chose to take implementation A because I like this set of trade-offs better." That's gold. And, I guess, as a reviewer, if I'm seeing that in a PR, that's going to make my job a lot easier.

STEPHANIE: Yes. Yeah, I never thought about it that way, but yeah, I guess I do kind of apply, you know, the things that I would kind of ask to other team members to myself sometimes. And that is...it's cool to hear that you really appreciate that because I always kind of just did it for myself [laughs], but yeah, I'm sure that it, like, is helpful for other people as well.

JOËL: I guess you were asking what are ways that you can ask questions even when you are more established. And talking about these sorts of self-reflective questions in the context of review got me thinking that PRs are a great place to ask questions. They're great when you're a newcomer. One of the things I like to do when I'm new on a project is do a lot of PR reviews so I can just see the weird things that people are working on and ask a lot of questions about the patterns.

STEPHANIE: Yep. Same here.

JOËL: Do a lot of code reading. But that's a thing that you can keep doing and asking a lot of questions on PRs and not in a, like, trying to undermine what the person is doing, but, like, genuine questions, I think, is a great way to maintain that mindset.

STEPHANIE: Yeah, yeah, agreed. And I think when I've seen it done well, it's like, you get to be engaged and involved with the rest of your team, right? And you kind of have a bit of an idea about what people are working on. But you're also kind of entrusting them with ownership of that work. Like, you don't need to be totally in the weeds and know exactly how every method works. But, you know, you can be curious about like, "Oh, like, what were you thinking about this?" Or like, "What about this pattern appeals to you?" And all of that information, I think, helps you become a better, like, especially a senior developer, but also just, like, a leader on the team, I think.

JOËL: Yeah, especially the questions around like, "Oh, walk me through some of the trade-offs that you chose for this method." And, you know, for maybe a person who's more senior, that's great. They have an opportunity to, like, talk about the decisions they made and why. That's really useful information. For a more junior person, maybe they've never thought about it. They're like, "Oh, wait, there are trade-offs here?" and now that's a great learning opportunity for them.

And you don't want to come at it from a place of judgment of like, oh, well, clearly, you know, you're a terrible developer because you didn't think about the performance implications of this method. But if you come at it from a place of, like, genuine curiosity and sort of assuming the best of people on the team and being willing to work alongside them, help them discover some new concepts...maybe they've never, like, interacted so much with performance trade-offs, and now you get to have a conversation. And they've learned a thing, and everybody wins.

STEPHANIE: Yeah. And also, I think seeing people ask questions that way helps more junior folks also learn when to ask those kinds of questions, even if they don't know the answer, right? But maybe they start kind of pattern matching. Like, oh, like, there might be some other trade-offs to consider with this kind of code, but I don't know what they are yet. But now I know to at least start asking and find someone who can help me determine that. And when I've seen that, that has been always, like, just so cool because it's upskilling happening [laughs] in practice.

JOËL: Exactly. I love that phrase that you said: "Asking questions where you don't know the answers," which I think is the opposite of what lawyers are taught to do. I think lawyers the mantra they have is you never ask a witness a question that you don't know the answer to. But I like to flip that for developers. Ask a lot of questions on PRs where you don't know the answer, and you'll grow, and the author will grow. And this is true across experience levels.

STEPHANIE: That's one of my favorite parts about being a developer, and maybe that's why I will never be a lawyer [laughter].

JOËL: On that note, I have a question maybe I do know the answer to. Shall we wrap up?

STEPHANIE: Let's wrap up. Show notes for this episode can be found at bikeshed.fm.

JOËL: This show has been produced and edited by Mandy Moore.

STEPHANIE: If you enjoyed listening, one really easy way to support the show is to leave us a quick rating or even a review in iTunes. It really helps other folks find the show.

JOËL: If you have any feedback for this or any of our other episodes, you can reach us @_bikeshed, or you can reach me @joelquen on Twitter.

STEPHANIE: Or reach both of us at hosts@bikeshed.fm via email.

JOËL: Thanks so much for listening to The Bike Shed, and we'll see you next week.

ALL: Byeeeeeeee!!!!!!!

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