404: Estimation

Joël was selected to speak at RubyConf in San Diego! After spending a month testing out living in Upstate New York, Stephanie is back in Chicago.

Stephanie reflects on a recent experience where she had to provide an estimate for a project, even though she didn't have enough information to do so accurately. In this episode, Stephanie and Joël explore the challenges of providing estimates, the importance of acknowledging uncertainty, and the need for clear communication and transparency when dealing with project timelines and scope.

• RubyConf 2023
• How to estimate well
• XKCD hard problems

Transcript:

STEPHANIE: Hello and welcome to another episode of The Bike Shed, a weekly podcast from your friends at thoughtbot about developing great software. I'm Stephanie Minn.

JOËL: And I'm Joël Quenneville. And together, we're here to share a bit of what we've learned along the way.

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

JOËL: Big piece of news in my world: I recently got accepted to speak at RubyConf in San Diego next month in November. I'm really excited. I'm going to be talking about the concept of time and how that's actually multiple different things and the types of interactions that do and do not make sense when working with time.

STEPHANIE: Yay. That's so exciting. Congratulations. I am very excited about this topic. I'm wondering, is this something that you've been thinking about doing for a while now, or was it just an idea that was sparked recently?

JOËL: It's definitely a topic I've been thinking about for a long time.

STEPHANIE: Time? [laughs]

JOËL: Haha.

STEPHANIE: Sorry, that was an easy one [laughs].

JOËL: The idea that we often use the English word time to refer to a bunch of, like, fundamentally different quantities and that, oftentimes, that can sort of blur into one another. So, the idea that a particular point in time might be different from a duration, might be different from a time of day, might be different to various other quantities that we refer to generically as time is something that's been in the back of my mind for quite a while. But I think turning that into a conference talk was a more recent idea.

STEPHANIE: Yeah, I'm curious, I guess, like, what was it that made you feel like, oh, like, this would be beneficial for other people? Did everything just come together, and you're like, oh, I finally have figured out time [laughs]; now I have this very clear mental model of it that I want to share with the world?

JOËL: I think it was sparked by a conversation I had with another member of the thoughtbot team. And it was just one of those where it's like, hey, I just had this really interesting conversation pulling on this idea that's been in the back of my mind for years. You know, it's conference season, and why not make that into a talk proposal?

As often, you know, the best talk proposals are, at least for me, I don't always think ahead of time, oh, this would be a great topic. But then, all of a sudden, it comes up in a conversation with a colleague or a client, or it becomes really relevant in some work that I'm doing. It happens to be conference season, and like, oh, that's something I want to talk about now.

STEPHANIE: Yeah, I like that a lot. I was just thinking about something I read recently. It was about creativity and art and how long a piece of work takes. And someone basically said it really just takes your whole life sometimes, right? It's like all of your experiences accumulated together that becomes whatever the body of work is. Like, all of that time spent maybe turning the idea in your head or just kind of, like, sitting with it or having those conversations, all the bugs you've probably encountered [laughs] involving date times, and all of that coalescing into something you want to create.

JOËL: And you build this sort of big web of ideas, not all that makes sense to talk about in a conference talk. So, one of the classic sources of bugs when dealing with time are time zone and daylight savings. I've chosen not to include those as part of this talk. I think other people have talked about them. I think it's less interesting or less connected to the core idea that I have that, like, there are different types of time. Let's dig into what that means for us. So, I purposefully left that out. But there's definitely a lot that could be said for those.

STEPHANIE: Awesome. Well, I really look forward to watching your talk when it is released to the public.

JOËL: So, our listeners won't be able to tell, but we're on a video call right now. And I can see from your background that you are back at home in Chicago. It's been a few weeks since we've recorded together. And, in the last episode we did, you were trying out living somewhere in Upstate New York. How was that experience? And what has the transition back to Chicago been for you?

STEPHANIE: Yeah, thanks for asking. I was in Upstate New York for the whole month of September. And then I took the last two weeks off of work to, you know, just really enjoy being there and make sure I got to do everything that I wanted to do out there before I came home to, you know, figure out, like, is this a place where I want to move? And yeah, this is my first, like, real full week back at work, back at home.

And I have to say it's kind of bittersweet. I think we really enjoyed our time out there, my partner and I. And coming back home, especially, you know, when you're in a stage of life where you're wanting to make a change, it can be a little tough to be like, uh, okay, like, now I have to go back [laughs] to what my life was like before.

But we've been very intentional about trying to bring back some of the things that we enjoyed being out there, like, back into just our regular day-to-day lives. So, over the weekend, we were making sure that we wanted to spend some time in nature because that's something that we were able to do a lot of during our time in New York. And, yeah, I think just bringing a bit of that, like, vacation energy into day-to-day life so the grind of kind of work doesn't become too much.

JOËL: Anything in particular that you've tried to bring back from that experience to your daily life in Chicago?

STEPHANIE: Yeah. I think, you know, when you're in a new place, everything is very exciting and, like, novel. Before work or, like, during my breaks, I would go out into the world and take a little walk and, like, look at the houses on the street that I was staying at. Or there's just a sense of wonder, I suppose, where everywhere you look, you're like, oh, like, this is all new. And I felt very, like, present when I was doing that.

And over time, when you've been somewhere for a long time, you lose a little bit of that sense of, like, willingness to be open to new things, or just, like, yeah, that sense of like, oh, like, curiosity, because you feel like you know somewhere and, like, you kind of start to expect oh, like, this street will be exactly like how I've walked a million times [laughs].

But trying to look around a little more, right? Like, be a little aware and be like, oh, like, Halloween is coming around the corner. And so, enjoying that as, like, the thing that I notice around me, even if I am still on the same block, you know, in my same neighborhood, and, yeah, wanting to really appreciate, like, my time here before we leave. Like, I don't want to just spend it kind of waiting for the next thing to happen. Because I'm sure there will also be a time where I miss [laughs] Chicago here once we do decide to move.

JOËL: I don't know about you, but I feel like a sense of change, even if it is cyclical, is really helpful for me to kind of maintain a little bit of that wonder, even though I've lived in one place for a decade. So, I live in New England in the Northeast U.S. We have pretty marked seasons that change. And so, seeing that happen, you know, kind of a warm summer, and now we're transitioning into fall, and the weather is getting colder. The trees are turning all these colors.

So, there's always kind of within, like, a few weeks or a few months something to look forward to, something that's changing. Life never feels stagnant, even though it is cyclical. And I don't know if that's been a similar experience for you.

STEPHANIE: Yeah, I like that a lot because I think one of the issues around feeling kind of stuck here in Chicago was that things were starting to feel stagnant, right? Like, we're wanting to make a big change in our life. That's still on the table, and that's still our plan. But noticing change, even when you think like, ugh, like, this again? [laughs] I think that could really shift your perspective a little bit or at least change how you feel about being somewhere. And that's definitely what I'm trying to do, kind of even when I am in a place of, like, waiting to figure out what the next step is.

Speaking of change, I had a recent lesson learned or, I suppose, a story to share with you about a new insight or perspective I had about how I show up at work that I'd like to share.

JOËL: What is this new perspective?

STEPHANIE: Well, I guess, [chuckles], first of all, I'm curious to get your reaction on this. Have you ever heard anyone tell you estimates are lies?

JOËL: Yes, a lot. It's maybe cynical, but there are a lot of cynics in our industry.

STEPHANIE: That's true. Part of this story is me giving an estimate that was a lie. So, in some ways, there is a grain of truth to it [laughs]. But I wanted to share with you this experience I had a few weeks ago where I was in kind of a like, project status update meeting. And I was coming to this meeting for the first time actually. And so, it was with a group of people who I hadn't really met before. It was kind of a large meeting. So, there were a handful of people that I wasn't super familiar with. And I was coming in to share with this bigger group, like, how the work I had been doing was going.

And during that time, we had gotten some new information that was kind of making us reassess a few things about the work, trying to figure out, like, where to go next and how to meet our ultimate goal for delivering this feature. With that new information in mind, one of the project managers was asking me how long I thought it might take. And I did not have enough information to feel particularly confident about an answer, you know, I just didn't know.

And I mentioned that this was kind of my first time in this meeting. There were a lot of people I didn't know, including the person who was asking the question. And they were saying, "Oh, well, you can just guess or, like, you know, it doesn't have to be perfect. But could you give us a date?" And I felt really hard-pressed to give them an answer in that moment because, you know, I kind of was stalling a little bit. And there was still this, like, air of expectancy.

I eventually, I have to say, I made something up [laughs]. I was like, "Well, I don't know, like, three weeks," you know, just really pulling it out of thin air. And, you know, that's what they put down on the spreadsheet, and then they moved on [laughs] to the next item. And then, I sat there in the rest of the meeting.

And afterwards, I felt really bad. I, like, really regretted it, I think, because I knew that the answer I gave was mostly BS, right? Like, I can't even say how I came up with that. Just that I, like, wanted to maybe give us some extra time, in case the task ends up being complicated, or, you know, there are all these unknowns. But yeah, it really didn't feel good.

JOËL: I'm curious why that felt bad. Was it the uncertainty around that number or the fact that the number maybe you felt like you'd given, like, a ridiculously large number? Typically, I feel like when estimates are for a story, it's, like, in the order of a few days, not a few weeks. Or is it something else, the fact that you felt like you made it up?

STEPHANIE: I think both, where it was such a big task. The larger and higher level the task is, the harder it is to come up with an answer, let alone an accurate one. But it was knowing that, like, I didn't have the information. And even though I was doing as they asked of me [chuckles], it was almost like I lost a little bit of my own integrity, right? In terms of kind of based on my experience doing software development, like, I know when I don't know, and I wasn't able to say it. At least in that moment, didn't feel comfortable saying it.

JOËL: Because they're not taking no for an answer.

STEPHANIE: Yeah, yeah, or at least that was my interpretation of the conversation. But the insight or the learning that I took away from it was that I actually don't want to feel that way again [laughs], that I don't want to give a lie as an estimate because it didn't feel good for me. And the experience that I have knowing that I don't have an answer now, but there are, like, ways to get the answer, right?

What I wish I had said in that meeting was that I didn't know, but I could find out, or, like, I would let them know as soon as I did have more information. Or, like, here is the information that I do need to come up with something that is more useful to them, honestly, and could make it, like, a win for all of us. But yeah, I've been reflecting on [chuckles] that a lot. Because, in a sense, like, I really needed to trust myself and, like, trust my gut to have been able to do my best work.

JOËL: I wonder if there's maybe also a sense in which, you know, generally, you're a very kind of earnest person. And maybe by giving a ridiculous number there just to, like, check a box, maybe felt like you gave way to a certain level of cynicism that wasn't, like, true to who you are as a person.

STEPHANIE: Yeah, yeah, that feels real [laughs].

JOËL: Have you ever done estimation sessions where you put error bars on your number? So, you say, hey, this is my estimate, but plus or minus. And, like, the more uncertainty there is around a number, the larger those plus or minus values are to the point where I could imagine something as ridiculous as like, oh, this is going to take three weeks, plus or minus three weeks.

STEPHANIE: I like that. That's funny. No, I have not ever done that before or even heard of that. That is a really interesting technique because that seems just more real to me, where, again, people have different opinions about estimation and how effective or useful it is. But for organizations where, like, it is somewhat valuable, or it is just part of the process, I like the idea of at least acknowledging the uncertainty or the ambiguity or, like, the level of confidence, right? That seems like an important piece of context to that information.

JOËL: And that can probably lead to some really interesting conversations as well because just getting a big number by itself, you might have a pretty high certainty. I mean, three weeks is big enough that you might say, okay, there's definitely going to be some fuzziness around that. But getting a sense of the certainty can, in certain contexts, I find, drive really interesting conversations about why things are uncertain.

And then, that can lead to some really good conversations around scoping about, okay, so we have this larger story. What are the elements of it that are uncertain that you might even talk in terms of risk? What are the risky elements of this story or maybe even a project? And how do we de-risk those? Is there a way that we could remove maybe a small part of the story and then, all of a sudden, those error bars of plus or minus three weeks drop down to plus or minus three days? Because that might be possible by having that conversation.

STEPHANIE: Yeah, I like what you said about scope because the way that it was presented as this really big chunk of work that was very critical to this deadline, there was no room to do scope, right? Because we weren't even talking about what makes up this feature task. We hadn't really broken it down.

In some ways, I think it was very, like, wishful, right? To be like, oh yeah, we want this feature. We're not going to talk too much about, like, the specific details [laughs], as opposed to the idea of it, right? And that, I think, is, you know, was part of what led to that ambiguity of, like, I can't even begin to estimate this because, like, it could mean so many different things.

JOËL: Right. And software problems, often, a slight change in the scope can make a massive change in complexity. I always think of a classic xkcd comic where two people are talking about a task, and somebody starts by describing something that kind of sounds complex. But the person implementing it is like, "Oh yeah, no, that's, you know, it's super easy. I can do that in half a day." And then, like, the person making the ask is like, "Oh, and, by the way, one small detail," and they add, like, one small thing that seems inconsequential, and the person is just like, "Okay, sorry, I'm going to need a research team and a couple of PhDs. And it's going to take us five years."

STEPHANIE: That's really funny. I haven't seen this comic before, but I need to [laughs] because I feel that so much where it's like, you just have different expectations about how long things will take. And I think maybe that is where, like, I felt really disappointed afterwards. Because in my inability to, like, just really speak up and say, like, "In my experience, like, this is kind of what happens when we don't have this information or when we aren't sure," yeah, I just wasn't able to bring that to the table in that, you know, meeting.

And I really am glad we're having this conversation now because I've been thinking about, like, okay, when I find myself in this position again, how would I like to respond differently? And even just that comic feels really validating [laughs] in terms of like, oh yeah, like, other people have experienced this before, where when we don't have that shared understanding or, like, if we're not being super transparent about how long does a thing really take, and why does it make it complex, or, like, what is challenging about it, it can be, like, speaking in [chuckles] two different languages sometimes.

JOËL: I think what I'm hearing almost is that in a situation like what you found yourself in, you're almost sort of wishing that you'd picked one extreme or the other, either sort of, like, standing up to—I assume this is a project manager or someone...to say, "Look, there's no number I can give you that's going to make sense. I'm not going to play this game. I have no number I can give you," and kind of ending it there.

Or, on the other hand, leaning into, say, "Okay, let's have a nuanced conversation, and we'll try to understand this. And we'll try to maybe scope it and maybe put some error bars on this or something and try to come up with a number that's a little bit more realistic." But by kind of, like, trying to maybe do a middle path where you just kind of give a ridiculously large number that's meaningless, maybe everybody feels unfulfilled, and that feels, like, maybe the worst of the paths you could have taken.

STEPHANIE: Yeah, I agree. I like that everyone [laughs] feels slightly unfulfilled point. Because, you know, my estimate is likely wrong. And, like, what impact will that have on other folks and, you know, their work?

While you were saying, like, oh yeah, here were the kind of two different options I could have chosen, I was thinking about the idea of, like, yeah, like, there are different strategies depending on the audience and depending who you're working with. And that is something I want to keep in mind, too, of, like, is this the right group to even have the, like, okay, let's figure this out conversation? Because it's not always the case, right? And sometimes you do need to just really stand firm and say, like, "I can't give you an answer. And I will go and find the people [laughs] who I can work this out with so that I can come back with what you need."

JOËL: And sometimes there may be a place for some sort of, like, placeholder data that is obviously wrong, but you need to put a value there, as long as everybody's clear on that's more or less what's happening. I had to do something kind of like that today. I'm connecting with a third-party SAML for authentication using the service Auth0. And this third party I'm talking to...so there's data that they need from me, and there's data that I need from them. They're not going to give me data until I give them our data first, so this is, like, you know, callback URLs, and entity IDs, and things like that you need to pass.

In order to have those, I need to stand up a SAML connection on the Auth0 side of things. In order to create that, Auth0 has a bunch of required fields, including some of the data that the third party would have given me. So, we've got a weird thing where, like, I need to give them data so they can stand up their end. But I can't really stand up my end until they give me some data.

STEPHANIE: Sounds like a circular dependency, if I've ever heard one [laughs].

JOËL: It kind of is, right? And so, I wanted to get this rolling. I put in a bunch of fake values for these callback URLs and things like that in the places where it would not affect the data that I'm giving to the third party. And so, it will generate as a metadata file that gets generated and stuff like that. And so, I was able to get that data and send it over. But I did have to put a callback URL whose domain may or may not be example.com.

STEPHANIE: [laughs] Right.

JOËL: So, it is a placeholder. I have to remember to go and change it later on. But that was a situation where I felt better about doing that than about asking the third party, "Hey, can I get your information first?"

STEPHANIE: Yeah, I like that as sometimes, like, you recognize that in order to move forward, you need to put something or fill in that gap. And I think that, you know, there was always an opportunity afterwards to fix it or, like, to reassess and revisit it.

JOËL: With the caveat that, in software, there's nothing quite so permanent as a temporary fix.

STEPHANIE: Oof, yeah [laughs]. That's real.

JOËL: So, you know, caution advised, but yes. Don't always feel bad about placeholders if it allows you to unblock yourself.

STEPHANIE: So, I'm really glad I got to bring up this topic and tell you this story because it really got me thinking about what estimates mean to me. I'm curious if any of our listeners if you all have any input. Do you love estimates? Do you hate them? Did our conversation make you think about them differently? Feel free to write to us at hosts@bikeshed.fm.

JOËL: On that note, 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: Byeeeeeeeeeeeee!!!!!

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