Scaling Teams and Yourself, with Cate Huston

Ep 29

Jun 12, 2024 • 62 min
Cate Huston joins to talk about her new book, The Engineering Leader. She shares why she wrote a book, leadership problems endemic to fast-growing organizations, why career growth is more than promotions, coachability, levelling up your hiring pipeline, how hiring “bars” can go wrong, and why energy management matters more than time management.

Allen: Welcome to It Shipped That Way, where we talk to product leaders about the lessons they’ve learned, helping build great products and teams. I’m Allen Pike, and today’s interview is with Cate Huston. Cate is an engineering director at DuckDuckGo and previously worked at organizations like Automatic and Google and is the author of the new book, The Engineering Leader. Welcome back, Cate.

Cate: Hi Allen. Thanks for having me.

Allen: Yeah, it’s awesome to have you back. You’re the show’s first repeat guest. You joined us all the way back in episode four, and what a great occasion to have you back.

Cate: Oh, amazing. I remember we talked about some stuff last time that is in the book somewhere.

Allen: Excellent. So typically I start the show by asking folks about their background and what brought you to where you are, which I’m sure is in the book anyways. Instead, what I’ll do is I’ll put a link in the show notes for this episode to that episode number four so people can go back and hear some of those stories. Today, the topic is your new book. The title is The Engineering Leader: Strategies for Scaling Teams and Yourself, and it ranges all the way from creative strategy, self-development through to hiring, scaling engineering orgs. You’ve been writing online about engineering leadership for some time now. You’ve developed quite a set of blog posts and reflections on topics. What led to the call that’s like, it’s time to write a whole book?

Cate: Madness. It can only have been absolute madness. Yeah, I think I finally realized that I had a book-sized message and then tested pieces of it, but once I kind of realized who it was for and why I was writing it, the whole structure of it started to fall into place.

Allen: It seems like a good metric for a book-sized message. And it seems, well, I don’t know, I found it interesting the structure of the book because in some ways, it a little bit feels like you almost have two book-sized messages. You have this piece of growing yourself and then you have this piece of growing teams. And obviously there’s this continuum both in the fact that you need to grow yourself in order to lead a team, and then also you’re going to be leading a team of people who that you want to help them grow. So the two sides of it really kind of build on each other, but it’s a big undertaking.

Cate: Yeah, I did have that thought at some point. It’s like, is this actually two books? And then it’s like, but I don’t want somebody to only read the second one and be like, “Now I know how to grow a team,” but they didn’t figure out how to grow themselves. And also I think there’s a lot of books on how to grow a team. It is kind of about that, but I think it’s also about the deeper questions that you need to start asking in order to build a team. Your team is an ecosystem. How do the things you’re doing fit together? Your team needs to deliver something. How do you make that happen? How do you make the team get better over time? And if you don’t also have a commitment to getting better over time, if you haven’t also thought through how am I scaling, how can you get a group of people to scale?

Allen: It’s an problem where, as people move up in leadership, they have less and less folks helping them consider their own development because you’re more and more not solo, but sort of operating with less and less oversight, I guess.

Cate: Yeah, I mean I think what you are saying brings me to who I wrote the book for because I have been this person, I have managed these people, I have coached these people. So many people in tech just don’t really feel like they have a manager. They have somebody on the org chart probably, but they don’t really have anybody who is showing up for them in a consistent way, giving them feedback and helping them grow. And so that’s who I wrote the book for because those people need something. And then I think this also comes to the point of these things being tied together because in scale ups, one of the things you see is that people get left behind. So somebody gets hired who knows how to run a six person team and they start as an IC and they get to six people and maybe they try really hard and they get to 10 people, but if they are not growing themselves with the team, at some point they have a team that they’re responsible for that is bigger than they actually can be responsible for. And that’s when startups come in and they hire different people and they hire people above those people to manage them. And then often those people are pissed. And understandably say that, “I was here first, I built this team.” And often they’ve worked really hard and there’s many things that they’ve done well, but if they have not also worked on themselves, then they don’t know how to get the team to the next step. They don’t know what they don’t know. And then they get stuck, they get left behind, all the rest of it. And probably nobody was helping them with that because their manager was also just in a startup trying to figure out how to found a company for the first time or whatever. Nobody there is in a great situation. And when that happens, if you are not trying to look after yourself and your own growth, you’ll definitely get stuck. You’ll probably get stuck regardless because people can only grow so fast and sometimes organizations grow faster, but at least if you are kind of mindful about it, you can probably keep pace for longer and you can probably make a more conscious decision of like, “Oh, okay, I knew how to get from here to there and this is what I don’t know and this is what I’m going to learn.”

Allen: Yeah, it makes a lot of sense. It’s one of the things that I find splits the mindset and the culture of people who came up in fast-growing organizations versus people who came up in sort of large, already pre-existing organizations that have really well set, like Google having this Byzantine promotions process, and so they build a mental model about what their career looks like based in that framework versus folks that come up in fast-growing organizations. If they’re successful almost always they come out with the mindset of, as you describe it in the book, being responsible for their own career or using the DRI language, which is an Apple-ism. I’m actually curious, this totally sidebar, you talk about being the DRI of your own career. In the orgs that you work in, is DRI a common phrase? Because I know that from Apple. Is that now spread more broadly?

Cate: Constant. Constant at DuckDuckGo, everything is DRI.

Allen: So the DRI being the directly responsible individual, or at least that’s the abbreviation I know it as.

Cate: Yeah, no, exactly. But DRI of projects, like DRI of teams, DRI of objectives, DRI everywhere.

Allen: Which is super useful and a lot of organizations have this idea, which is is helpful if you have a person who is, the buck stops with that person for this issue and so you’re applying this to your career. You’re the DRI of your career, nobody’s going to care about it more than you. So tell me a little bit about what flows out of that or maybe a way to attack it is what happens when people don’t think of themselves as the DRI of their career or they’re not self-aware of this?

Cate: I mean, they abdicate their responsibility for growth to their manager, so may or may not get it depending on how good the manager is. They externalize their value as their level on the org chart rather than their capabilities.

Allen: Yeah. You mentioned something about in the book or talk about the difference between career growth versus promotions and how those are two different things, which is another one of those. Sometimes in a large organization, people slowly to more and more just think about those two things as being the same, but especially in a fast-growing organization, they’re really not.

Cate: Super not. Also, I’ve been thinking about this time in terms of staff engineers, like staff engineer is a great title. Who doesn’t want to be a staff engineer? But then it’s like to ask people if I’m interviewing staff engineers, I’m like, “What is your definition of a staff engineer?” And the definition that I have in my teams, which is not universal, but it’s like a staff engineer is somebody who can take a horrendous technical problem and they can fix it whilst also shipping something. It turns out not everybody wants to do that. The job title is nice, but it’s like two words and that is I told somebody this definition of a staff engineer and he was like, “Maybe I’m glad that I got hired senior instead.” That’s fully fair enough.

Allen: Yeah, I think that’s really useful. And sometimes you get career ladders that clarify this stuff, but often the career ladders in smaller or fast-growing organizations get vaguer or vaguer or less and less useful as you get up to those more senior, less common levels and they sometimes elicit the things that make higher role responsibilities a mixed bag in terms of yeah, okay, obviously you’re going to have more compensation, you’re going to have more authority if that’s something that appeals to you, but you’re going to have more expectations. And some of those expectations, like one of the ones that I see increasingly on ladders explicitly, it’s like as you get higher up in levels in a lot of orgs, they explicitly expect you to take on work that other people don’t want, which is one of those it’s like of course that’s true, and if you think about some of the best people you’ve worked with, really senior people, they tackle that gnarly, totally broken login system that it is always sort of annoying to everyone and holds people back, but it works and it’s really high risk and you may have to make sure you don’t break it. And they’re like, “No, you know what? I’m going to help re-architect this login system.” And it’s not glorious, right? No one wants to do it and they’re like, “I’m going to go in a battle on this.” And that’s not everyone’s idea of fun, but it is high-impact work.

Cate: Yeah, I think it was at CLIMAS, they call it type two fun.

Allen: Yes. It’s fun once you’ve done it and you’re like, “Hey, I’m glad that I did it.”

Cate: Exactly, exactly. No, I mean you’re totally right. I mean, I think all of us have some kind of time where we’re like, oh, we did something we thought was an opportunity and we hated it. Or maybe we got more money but we didn’t feel that we were actually growing. And obviously, we live in the capitalism. Money is how we communicate value under capitalism. Totally people need money to live, but at the same time, often the amount of money we are talking about relative to the cost of being so miserable is just not worth it. If you start thinking about it in these terms, it’s like, “Okay, well I could make an extra 10 grand a year and the government would take five grand of that in tax and I would need to go to therapy twice a month. And then what’s left?”

Allen: And I think that’s something that most people in their career, by the time they’re mid-career, they understand the things that they’re not doing in terms of what role that they’re… Like a role that they would be paid more to do because there’s economic demand for someone like them to do that kind of thing, but that it just would hurt their soul or that it doesn’t motivate them or it saps their energy instead of builds it or all these sorts of things. So that’s the thing that I see most people eventually come to. Something that you talk about a fair amount in the book that I think is an interesting model that maybe fewer people think through really consciously or frequently is how there’s the economic consideration, of course, of what you’re compensated right now. There’s also economic consideration of what you will be compensated at your next role or in future roles based on what is happening to your career and what skills you’re building. They’re both about how it appears on a resume, but probably more importantly, what actually are the reps that you’re putting in right now? What kind of flows out of that mindset when you’re sort of thinking, “Okay, I’m doing multivariate optimization for all these various things, but one of them is kind of my future earning potential.”

Cate: I think for me it’s about not staying too insular. I think every organization is kind of skewed to make people insular, to believe that it’s important that the value is in the job ladder that is there. I’ve never worked in an organization that wasn’t somewhat insular. Maybe not all of them are like that, but that’s been my experience. And inside insular organizations, people don’t look externally very much and they don’t really have a sense of what their value is on the open market, so that means if there’s a re-org, if their job is bad or whatever, their value is kind of, they feel like their value is gone. They feel like their value is dictated by that. And then that can mean making decisions that are detrimental to their long-term value, but it can also mean not making decisions that are good for long-term value. I mean, Google has laid so many people off lately, so many people. And I was reading a post from somebody the other day that the way that people at Google think about scale. They’ve kind of gone to an interview with a company that was working at a different scale and they hadn’t known how to answer the questions and they’re like, “It doesn’t matter that I can solve objectively hard of problems because those are not the problems this organization has.”

Allen: And also, Google and the other companies at the extreme scale often have idiosyncratic ways of addressing the problems that they have. “Oh, well of course I would use this tool that no one else in the world has even heard of,” which just solves that problem or whatever.

Cate: Or not use a tool. We’re both in the mobile space a lot, right? And Google is still writing Objective-C.

Allen: Right.

Cate: Now, if you’ve been at Google working on an iOS app writing Objective-C and you apply, I don’t know anywhere else where people are writing Objective-C anymore, and so you’ve now got this brutal learning curve to switch to Swift, I don’t know, five years later than everybody else. And maybe that was worth it to you. That’s totally fine, but I’m not judging the decisions that anybody makes, but it’s really like are you making those decisions mindfully?

Allen: Yeah, there’s a trade off. There’s the sort of bad way in the good way I think of thinking about this, like the sort of simple way would just to be resume driven development. Just like, “Okay, well the cool new thing is Rust and I think that will be highly employable, so I’m going to advocate in my company, we need to write everything in rust now or whatever and maybe only accept jobs that are doing that thing,” or whatever. But then the way that you sort of describe it in the book, which is the more kind of pragmatic, thoughtful way is to think of, “Okay, well how much compensation am I getting for this role and what is the impacts on the fact that I’m still writing Objective-C instead of Swift or whatever it is, or maybe working in an organization where I’m not necessarily learning the certain skills that I think would be really applicable elsewhere in future roles that I want to have?” And thinking, “Okay, well am I getting compensated for that sort of opportunity cost? If I’m making double, if Google is paying me double what I would writing Swift somewhere else to write Objective-C, then maybe at my current stage in my career, that’s a good trade-off for a while,” and then you can use that to save up and then start a startup writing Swift or whatever. You could imagine that working.

Cate: Yeah, exactly. But I mean, I also think sometimes you just need to go and get data from the market. If you are like, “Oh, I’m not sure how employable my job makes me,” rather than doing a theoretical exercise where you evangelize Rust, maybe just go and interview. You don’t have to take another job, but you can learn something about it. I remember going through this phase and being like, “All right, I’m going to go an interview.” And then what I learned in the market was, and this was right before everything crashed, that there was a huge anchoring on number of people.

Allen: Interesting.

Cate: So I remember interviewing with this person’s like, “Oh, you only have 30 something people. How can you be a director?” I’m like, “I don’t know. Really complicated stuff for building and only senior engineers.” I was like, wow, this is good information for me about how my job does not meet the market. Now I can decide what to do with that. I can wait it out until it does match the market. I can make number of people a metric if I also want to care about it or I can just take it under advisement, which is like, okay, this is something people really care about and it’s something I’m going to be judged on, and so I need to make sure that my counter narrative is much more compelling than being put on the spot, being like, “Whoa, this is a very important metric for you that I hadn’t fully thought about.”

Allen: And that number of people thing, I’ve only in the last few years started to realize just how dramatic. I think director is an extreme, maybe I don’t want to say the worst, the most extreme case of different orgs at different sizes have different ideas of what makes for a director. And so in 1,000 person org or 10,000 person org, like at Apple or whatever you end up with or Amazon or Microsoft fan type companies, you have 10 layers from the bottom to the top. And so you can’t just say, “Oh, okay, well the third layer is a director.” You have to have two or three or four layers before there’s directors and at that point any reasonable fan out and you have 100 people or something like that, right? Or more.

Cate: Totally. But where did this line of thinking of you need so many people to justify your job takers? That company did two layoffs after that call and I was not surprised.

Allen: Yeah, well, I mean there’s a reason why we end up in the pendulum in our industry, or at least individual companies do, of going back and forth in between thinking, “Okay, well the more people someone manages in an org, that means they have more span of responsibility and therefore maybe more compensation and then maybe more impact,” or whatever. And then a whole bunch of bad incentives happen when you incentivize the whole org to just hoard reports.

Cate: Right, totally. It’s like lines of code. It starts in a kind of reasonable place where it’s telling you something but then at some point it’s telling you everything, and then you’ve just lost everything that goes.

Allen: Working through some of the things found interesting in the book on the self-development and thinking about careers, before we switch over to the scaling orgs piece. You talk about hybrid roles in one of the passages, which I find interesting because especially working in startups and small companies and scaling companies and an extreme case like being a founder, I see this a lot or this is a lot of my reality. You talk about these or they call them “and” roles. Maybe you’re the head of product and engineering or maybe you’re a designer and developer or whatever, and that appeals to a generalist like myself and I think a lot of people who fit well in a startup like the idea of wearing multiple hats, but you write a bit about how it can cause challenges for people’s employability or how they might then fit into another organization or even just grow in their own organization as it sort of matures, I guess. Can you talk a little bit what causes that and what you’ve seen with that?

Cate: Yeah, I think it’s a little bit related to the, are you developing yourself thing, like that small company to medium-sized company to large company. There’s huge value in small companies of people who do an okay job at five different things because you probably don’t have enough work for five different specialists, but when you get to this specialist place and then you’ve got the person who’s not as good at development as the developers you hire, is not as good as design as the designers you’ve hired, is not as good as leadership as the engineering manager you hired. And that can put somebody in not the best place. And so it depends on what they want to do. If they like doing this, you see people who’d like go to start, they go to startup after startup and there was a phase of company they like, and when the company leaves that phase, they know what they like, they go to the next thing, power to them. And then you also see people who just kind of get stuck or get left behind because the team grows and the value of the kind of and skills is less valuable once there’s five specialists. So I use somebody who’s actually close to the level on one thing and does some extra things because then maybe it can be like, “Okay, I’m going to close this 20% gap. This is my opportunity to learn.” Or you kind of half a developer and half a designer and then it’s just going to be a much harder time and depending on where the market is and the kind of place you’re looking for, it’s just going to be more difficult. If you apply for a developer job and they have a robust mature design team, they’re not going to necessarily value your design skills as much.

Allen: Or my experience going into a developer job when I was fresh out of university, I was half design, half development kind of, but my degree was in comp-sci and that was my more employable skill. And so I drove my manager crazy, like going to try to talk to the designers and we had a good relationship, but she was always joking saying like, “Oh, don’t talk to the designers. Go fix some bugs. Don’t give them any ideas.” I was like, “I want to talk to the designers. I have great ideas. Why don’t you listen to me?” Of course, I knew perfectly well why they didn’t listen to me because I was just some kid out of university hired as a programmer to fix bugs.

Cate: Amazing. I mean, I think that’s a good example. You have that core skill and you have that extra skill and I’m sure it doesn’t sound at that time you’re like, “Okay, in retrospect I was not channeling that productively,” but I’m sure now you’ve learned how to channel it more productively.

Allen: Yes. And find roles where it’s useful. You have a section about coaching, which makes a kind of sense. That’s a key part of how a lot of managers operate these days. Something that stuck out to me is you talked about coachability, which is something that I think maybe gets under talked about or maybe people don’t think about a lot. How do you think about what makes someone coachable, whether you’re thinking about yourself? Obviously we want to be coachable so that we can get benefit from all the smart knowledgeable people that we talk to, but then also maybe helping the people that we’re coaching be coachable as well.

Cate: I think we talk about potential a lot more that we talk about coachability, but actually maybe coachability is almost like my definition of potential. So it’s like you have where somebody is today and you have where you think they can get to. And that’s almost the potential. And then coachability is how much work is it going to be to get them up that curve?

Allen: Yeah, I like that framing for it. So one of the things that you talk a little bit about is some of the aspects that lead to someone being coachable that they think that they can learn from, that they have this mental model, they can learn from anyone and that they’re keen to receive feedback and stuff like that. And you talk about trying to help people be more coachable, but do you think of that as a pretty trainable, teachable skill or is it a little bit more kind of a thing you hire for?

Cate: I prefer to hire for it because it’s a lot of work, but I would say in terms of trainable, I can make somebody more coachable if they meet me halfway. If they don’t, they’re probably going to hate me.

Allen: Well, if they’re not willing to be coachable, then yeah, don’t want to be mean, but…

Cate: It depends on what, right. There are things that sometimes not everybody is in the same way on everything. There are people who, I don’t know, maybe they’re really coachable on some aspect. They’re like, “No, okay, I’m not the best people manager, team leader, and I want to get better at it.” And they’re really coachable on that aspect. But then if you came to them and said, “I have some feedback on your architecture.”

Allen: And you’re challenging their self-worth.

Cate: Yeah, and then it could be a totally different conversation. We’re not everywhere and everything.

Allen: Of course.

Cate: There are and people with topics and people with whom I am highly coachable and there are topics and people where it’s like, no, this is not a place that we are going to be because I don’t know. If somebody who I thought was bad at people management tried to coach me on people management, I’d be like, “I wrote a fucking book now.” I don’t know, that person would probably hate me too. But it’s almost kind of having judgment in terms of who you listen to I think is part of being coachable and this is the 50% of work that’s for me is helping convincing somebody that it’s worth listening to me. It’s not like I expect somebody to come in off the bat and listen to everything I say. That person is maybe like, maybe I don’t know what I’m talking about. They have to have a point of view on where the reality of the advice and suggestions meets their actual work.

Allen: Kind of obvious, but maybe I hadn’t really thought about, I don’t think I had at all thought about that aspect of how coachability is on different axes and I think that probably says something for how I should be assessing it in the hiring loop, because you try to gauge for it and you poke at it a little bit, but you may accidentally find the one thing that they’re coachable on.

Cate: I mean, I do just have a policy of if I run a hiring process, we’re going to try and give everybody feedback and see what happens.

Allen: Yeah, it’s interesting. And you have some great, which we’ll get into, you have some great tactical stuff in the book about not just being a hiring manager but scaling a hiring process. If you’re growing an org, like scaling and iterating and improving a hiring process and making it more effective, which is awesome. How do you think about the feedback piece, which is just one of the very little sub tactics a lot of orgs will have, especially the larger ones, will have a policy against like, “Oh, be careful. You don’t necessarily want to give feedback to interviewees because you might expose us to liability because they might not like why you imply why you didn’t hire them.” Obviously you’re going to be thoughtful about your feedback isn’t going to be, “Oh, I noticed this. You’re in some underrepresented group and I don’t like that,” or something. But still, you could imagine how illegal or wouldn’t trust every single person in the org to be 100% thoughtful about how they phrase whatever their reasons for hiring someone. How do you think about what is good kinds of feedback or the most useful kinds of feedback may be to give people in the hiring loop?

Cate: I think it really has to be about the work and not the person. So my current job, we use a lot of within documents and so there’s just a conversation about a document they’ve written that’s like, “Oh, what about this? Can you explain this to me?” And then it is feedback, but it’s not, I think often when you use the word feedback, people think it’s like they sit down, I’m like, “Allen, I would like to give you some feedback.” And I say, “Well, your podcast hosting was very good,” and then I complain about something and I’m like, “But overall, I’m sure.” People have this model of this is what feedback is. It’s not. It’s too simplistic. Feedback is just your work reflected back to you or how you’re showing up in the world reflected back to you. So if you sit down with somebody and say, “Hey, I have these questions about this,” or, “Can you explain this to me better?” Or, “I thought this could be more clear,” then normally there’ll be really happy that you took the time. I’ve given some surprisingly harsh feedback in terms of… Let’s hope legal don’t listen to this. But I’ve given some surprisingly harsh feedback in terms of the hiring process, especially when people have asked for it directly. I’ve got two examples of people who asked me directly for feedback and I was like, “Look, I’ll be candid with you.” And I gave them some feedback and both of them came back with something amazing and I hired both of them.

Allen: Nice.

Cate: And I was really like, honestly, this is the kind of hiring decision where I’m just very confident. I’m like, this person knew to ask and when I told them, they actioned it. Didn’t tell me I was wrong. They didn’t kind of argue with me. They were like, “Okay, I see what you’re saying.” Those normally are the people where they have high resilience, they are the easiest people to get up the curve from wherever they’re at to wherever the people are going.

Allen: And that’s that coachability piece. I always wonder, I see it’s a common trope on Twitter or Mastodon or whatever your social network is of choice that you’ll see a post that someone will make about, “Here’s this company. I interviewed at this company and they had this horrible misunderstanding of how great I am and their process was flawed and they lost me, an amazing hire.” And this has been retweeted and has a thousand retweets. And I’m sure sometimes that really is the person, the interviewee has the right perspective, but it can be really difficult as someone scrolling past this context list to be like, is there a useful lesson in here that in fact the interviewer, that we need to make sure that our interviewers understand this dynamic well? Or is this a case of somebody who wasn’t a good fit for the org, who maybe got actually reasonable feedback, that is not coachable and would be… And of course they’re going to be a little bit annoyed when somebody who is correctly screened out for being difficult to coach is almost certainly by definition going to bristle at it.

Cate: I mean possibly, but I don’t know. I got an email to that effect once that our hiring process was wrong and I went and looked at it and I was like, “You know what? You’re right.” And we opened it and again, I hired this person. And he’s killed it.

Allen: Nice.

Cate: But this is just the right feedback. There’s another piece of it about implicit feedback and how rarely people give you feedback directly, but I think watching who leaves your process is a form of feedback. If they tell you, “Hey, I think you made a mistake here, why?” I will always entertain that they could be right, that they have a valid position. If they open that on Twitter, I might not see it because Twitter is dead to me, but if they open it on Mastodon, I will still entertain that. If they send me an email that it’s much more likely I can do something about it.

Allen: You talk in the book about metrics and thinking about you’re scaling up a hiring process. Obviously you’re a startup and you just hire at one to two a season. It’s difficult to really be systematic about it, but if you’re scaling up, then in order to actually do that effectively, you have to start actually measuring things. You have to be reflecting. You start to get to run an experimental process, which is great. One of the things you talk a bit about is these withdrawal reasons. You have someone, they’re in the pipeline and they were passing through levels, but then they decided I’m not going to continue and then collecting why that might be. Tell me a little bit about how you think about that, what you’ve learned, some of the things that you’ve seen around what data you can gather from that.

Cate: It’s a form of implicit feedback. Normally you’ll hear some varying of the same three things. One is the process was too long and I got a job elsewhere. Totally fair. The second one is comp, and I write about comp in the book. I think it’s kind of a bit of a loaded topic sometimes, but it’s worth knowing. And then the third one I think which is most interesting, which is normally the value proposition of the job was not clear to me.

Allen: Do people say that explicitly?

Cate: No, they don’t say it explicitly, but that is fundamentally there’s a genre of feedback and that’s what they’re saying. They say, “I wasn’t clear about what my growth would be. I wasn’t sure about who my manager would be. It wasn’t clear to me what the scope of this role is compared to my current role.” And I think this feedback is most likely to come from people who already have a job. And so if they have a job somewhere and when people are looking, it’s different. They’re like they don’t have a job, they’re looking for a job and they’re trying to find the thing that fits best for them. They have more time, but they’re more likely to be on a deadline. But you are essentially competing with other unknown entities to close them. And when somebody has a job, maybe it’s a job that they kind of mostly like, but coming back to the earlier topic, they’re not sure about the value proposition on the open market. So they went and did a bit of due diligence and then you trying to sell them an unknown compared to their known entity. And that is a very different decision making process and there’s a lot more risk aversion there. And so let’s say somebody in their current role has a certain job title, they have a certain comp, they know what their career progression is going to be. They’re not super happy about it, but it’s not bad. Or maybe they’re like, “Okay, I’m here, I made it to staff, but I can never make it be on staff at this company or something like that.” And then you are offering them something and it’s like maybe the comp is the same, maybe the job title is lower, and then you’re giving them this uncertain story about career progression. And then they have to decide whether they want to take the known thing or if they want to gamble on you.

Allen: The devil you know versus the devil you don’t.

Cate: Yeah, totally. And there’s two bad ways to make the decision. One is risk aversion. Not obviously better than what I have, stay put. And then there’s another bad way to make the decision of just like, “I’m angry, I’m going for something else.” And then six months later they’re also angry because it is also every job is kind of good and bad in different ways.

Allen: Yes. So let’s dig in. So the second half of the book is on scaling teams, and I’m particularly interested in the hiring process. That’s something I’m probably going to be doing. And coming up soon and starting to think through some of the things, mindsets for it. One of the things that you said, which I found entertaining because of course it’s true, but you said it in a succinct way that I enjoyed, which is talking about, okay, people are now going to be designing a hiring process. And you say that when given the opportunity to establish a hiring process, we’re all biased to advocate for a process in which we would be successful ourselves. Tell me a little bit what you’ve seen as fallout from that.

Cate: Yeah, I mean I think A players set a kind of narrow modern culture standard, and B players hire C players.

Allen: Famous mindset. So if I’m an A player, I’m going to want other people who challenge me to do better and push the envelope and all these sort of things. And if I’m a B player, I’m worried about, “Oh these…” Well see, it’s interesting. I think you phrased a little in the book about maybe B players are afraid of other B players and A players and so they hire C players, but I’ve seen other people sort of advocate that it’s less that B players hire C players because they’re afraid of A players and more that they just can’t tell the difference.

Cate: Yeah, I think there’s a little bit of that. I mean this is something that sometimes if I’m not sure if somebody is doing a good job on or if they’re good, I look at who they hire. And if they hire badly, I’m way more cynical how good they are at their job. I think that A players just tend to take a very narrow view of high performance that is normally their high performance. Very few people are very good at everything. So you might have a player who’s like, they’re fantastic technically, they do very good code reviews, they’re really strong in systems architecture, but they’re bad at process. And this is fine for a three person team. But then you’re like, okay, well we have seven people. There’s some value to somebody who’s like, “Oh, hey, code review’s taking a while. Can we make them better?” And that a player will not want to hire that type of person like, “Oh, do we need that kind of work? Let’s just hire another killer person.”

Allen: A process. And they might have a bias like, “Oh, well process people slow things down. We move fast here.” I mean, while there’s flames going on in the background.

Cate: Exactly. Or just some people are more team-minded than other people. They write good code, but they also think about helping something, writing code in a way that makes it easier for other people to contribute to it. And then you have the person who writes good code and they write really performing code and they think that performing code is a moral good and they kind of miss some of the onboarding stuff. So I think that’s kind of the failure mode A players and you have to kind of round them out by being like, “Look, I think you’re overvaluing this thing and undervaluing this thing. Wouldn’t it be useful if we had somebody on the team who was really good in this kind of way?”

Allen: Yeah, that approach, I’m curious what tactics you have for scaling that mindset, but that’s something I’ve always found a lot of help with when you’re thinking about hiring process about not just how do we try to hire another of the person that we already think is great, but what are the adds? What are the culture adds? What are the level ups? Where are our gaps that we can try to fill? Obviously we want to hire someone great, but also what are their weaknesses? So often people at a more senior level and the higher levels looking down on the team can have a view of that, but sometimes the ICs that are going to be peers to this person that are participating in an interview process don’t have as much clarity about where those gaps are or maybe not even fully agree on them. Do you have any approaches that you like for trying to sort of culture or just educate or give clarity or context for folks that are participating in the hiring process? Do you make that explicit, like attached to wherever they write their notes for the round of interviews? Like, oh, a reminder, these are the things that we’re looking for in general and for this particular role, here are some of the things we want to see more of?

Cate: Yeah, complete clarity about that. Hiring, we evaluate everything very consistently and we have specific things, and if it’s not in there, it’s not relevant.

Allen: Interesting.

Cate: And I think the more kind of the things are standardized and clear, not everybody’s going to agree as you standardize it. You also have to be right, and if you are wrong, you have to be willing to correct it too.

Allen: For sure.

Cate: So let’s say invert my example. You have somebody who really cares about writing very readable code, and you have somebody who submits their code test and they’ve heavily optimized for performing code. And the person who really likes readable code is like, “Oh, I don’t know. Are they going to be difficult to work with?” And you’re like, “Well, maybe, but it’s really, performance is a really useful skill. We have these problems. We saw these other good signs, we validated this person’s coachable. I’m going to make this decision anyway and I’m going to take what you said and to advise them.” So okay, you bring them in, you onboard them. A month later you get a complaint. This PR isn’t readable, it’s completely optimized for performance. Performance doesn’t matter in this case. Well then you have to go back around to the person you hired and be like, “Hey, I really value how much you care about performance. It did not matter here. And do you realize that when you write code in this way, it has this impact on your teammates?” And you have to give that coaching to them until they change. And if you validated they’re coachable, then you can reasonably expect them to change, but you’re also going to have to do that work.

Allen: That coachability thing I think is a great power up in terms of the mental model. If you can build faith in your team that you are effectively assessing coachability and that you have the leadership and management layers that can actually coach people, then it’s less scary to hire someone that is currently a little bit off on one of these areas if they’re coachable in that area rather than what I think the bad experience a lot of people have had, which is being in an interview process, flag an issue and be like, “I don’t know, this Steve guy seems like he’s going to write only just Optimized-C and JavaScript.” And then in fact, they do do that. And then everyone’s like, “Well, I guess yeah, it’s not great, but we’re not going to let them go over it.” And they’re stuck in their ways. And so then they just present Steve for five years.

Cate: I mean that totally happens, but again, it’s like why is it important? Why is it not important? What’s the mindset you want to be in to give to people? And then how can they instill that mindset in other people over time? Because often I find when I’m disagreeing with somebody on a hiring, we’re disagreeing on one of two things. One is what matters versus what doesn’t? What’s trainable versus what’s not? And the second is what timeframe matters to us? We hire Windows developers. It is very hard to hire Windows developers. And so I would happily hire somebody who I was confident would ramp up on WPF and I wouldn’t care if it takes them an extra month or two, it’s like I know how long it takes to hire Windows developers. That’s a perfectly reasonable trade off to me. But somebody who’s looking at it in a different perspective might be like, “Oh wow, it’s going to take them a couple of months to ramp up on WPF.” And it’s like, well, that or it takes us a couple of months to hire somebody else. Which one is better actually if we know they’re coachable?

Allen: Especially to hire a Windows developer that cares a lot about quality and user experience and his values aligned with the rest of your product team. Something that kind of related to some of the things that we’re talking about I thought was interesting you said in the book is you push back on the idea of raising the bar. This is something a lot of people love talking about in interview processes. Like oh, Amazon famously had a bar raiser role where this person tries to raise the bar on hiring, and you sort of posit in the book that the idea of having a bar at all is pernicious, which I love, of course, because it’s contrary and it’s not what everyone else says. So I want to dig into it. Tell me more about that terminology, what you don’t like about it and how you think about that.

Cate: I think the first thing that I… Okay, so firstly, I don’t think we should talk about Amazon bar raises without also talking about their diversity stats. Because who do they reject when they do this? I don’t really want to know. If you want to tell me, you’re going to brag about your hiring process. I would like to know your diversity metrics. But setting that aside, well, I think that’s related to what I really hate about it, is the easiest bar to raise is the effort bar.

Allen: Sure. But make them jump through more hoops and some more people bail on the process basically?

Cate: Yeah, exactly. And then you’re selecting for people who have more time, who have more free time, who are more willing to spend the time on interviews, who have more time to spend on interviews. And then having raised the effort bar, we go in with this completely false confidence of like, “Look, we evaluate this person more and therefore they must be better.”

Allen: Yeah, I don’t think anybody… Well, I don’t know, maybe they do. But I think that might be, or see, it strikes me as maybe a little bit of a strawman argument in that I don’t know if anyone is advocating, “Let’s raise the bar. And by raise the bar, I mean burn out almost everyone so they bail on the interview process.” I think most people, at least academically know that they don’t want to do that, even if their revealed preferences is that they do build processes that are like that.

Cate: Yeah, I mean, I get your point, but also when we talk about raising the bar, what happens in practice? We had another interview, we had another evaluation, we make the evaluation harder, so it’s like, yes, it is kind of like you are right. On some level it’s a strawman argument, but on the other side of it it’s like what do people do when they want to raise the bar?

Allen: It’s interesting you made this point about diversity and obviously there’s a lot of ways to raise the bar that will create a monoculture and just hire more Steves. “All right, Steve raised the bar,” he hires more people that are just like Steve and you end up with a whole bunch of white guys named Steve. Nothing against Steve’s that are out there in the world who are wonderful people. I love you all. Well, except that one guy that was writing the code that was frustrating everyone. But you sort of mentioned this idea that teams that think about raising a bar in hiring processes can end up with less diverse results, and for that reason. But I think that, I don’t know, maybe this is just what I want to believe, but I think that it seems that you can hold a high bar and even raise the bar if you define the bar well and get a diverse team. It seems like intuitively, it seems like those two concepts are compatible.

Cate: I guess my question is, if you define the bar well, is it a bar anymore? Because a bar is like a narrow metric, it’s like a hurdle. Did people jump over this? So you make it higher, you’ve just made it narrow. But what you’re talking about is when you say define it well, I think sure, let’s define it well. Then it’s no longer a bar, right? Then it’s a set of competencies and it is a well-defined and understood idea of what does it take to be successful here.

Allen: So as you’re thinking of the idea that you think is problematic, which now I’m buying into, which is that if you start thinking of the hiring, kind of crunching it down to one single assessment by one senior person is the bar, as opposed to really trying to actually properly understand what positive impact this person could have on the team, which is like, yeah, in theory, okay, you could say the bar is how much positive impact impact they could have and how much they could add, but you can’t actually directly measure that. It’s 40 different subcomponents, in which case then it’s not a bar.

Cate: Yeah, exactly. But it’s also like there is the person and there is the role. When you take narrow definitions and you focus on the person, you are not actually thinking about the role and the definition of the role. And those things have to go together. There are people who would be a fantastic fit for either of our teams, and there are people who would work great for you and not for me and vice versa. And there are people who could be absolute stars somewhere else and would hate the way that we work. And it’s not often when we talk about hiring. The thing that I wanted to change in the conversation about hiring is that often what I see as a very narrow conversation, either the hiring manager was talking about how they do it effectively. Or people in hiring processes saying, “This is why all hiring processes are shit.” And I wanted to have a different conversation of these are actually two sides of the same thing. We are trying to find matches where somebody thrives in an organization that gets value from them, and that is a different and slightly more holistic problem. And concepts like hiring bars are just lazy.

Allen: I don’t disagree with any of that. There’s a related thing that you talk about, which I thought was interesting and it does kind of instinctually resonate with me and what I’ve seen. Talking about job postings, which we’re sort of doing our hiring process in reverse here, kind of going from the race that people are bailing on now where at the job posting. But the thing that you talk about, one of the things you write about job postings is you encourage people to think about how can your job posting encourage great applicants to apply and be excited about the process rather than just focusing on filtering out, which is an antipattern I’ve seen a lot before where it’s just like, you look at this job ad and it looks like it’s a challenge. “Beware of this job.” Someone is sick of filtering out a ridiculous amount of resumes or just getting bad resumes and they’re like, “Oh, let’s try to change this job ad so fewer bad people apply.” Of course, as you point out, a lot of people are just have a bot applying to every job anyway, so no matter what you write in there, they’re going to apply.

Cate: It’s all AI on both sides. We don’t use AI in our job postings, at least.

Allen: But it’s only getting worse. So what do you think drives this mentality about how people write job posts to be sort of prioritizing the discouragement over the encouragement, and then what do you think flows out of a process where you do it the other way, where you do it, where you’re writing a job post that’s kind of written to the best applicants, if that makes sense?

Cate: Oh, I see. I think just being a hiring manager is really hard. It’s a lot of work. It’s relatively thankless. You are hiring somebody because you need somebody, you’re strapped until they arrive. Everybody’s complaining to there aren’t enough people, or you’re seeing the problem day in, day out. And then you go to your candidate funnel, and I admit this in the book, when I was reviewing resumes myself, I had a 10.9 point scale or nine point scale and one through six was just how annoyed I was.

Allen: I am currently very annoyed.

Cate: Yeah, exactly. It was just like, come on, come on. But it’s because it’s hard and I think as a hiring manager, you have to be like, “Okay, this is a hard, thankless job.” So much of leadership is, but I actually want to be effective at it. And I will be more effective at it if I can have empathy for the people on the other side. So everybody who was unqualified, who applied when I didn’t have a recruiter and my life was hell got put in these one to six buckets, but then the people who were really qualified, who were really a good fit for the role, I try to have more empathy for their experience.

Allen: That makes a lot of sense. One of the things I think that flows out of this, and you say it kind of maybe explicitly or at least implicitly in the book, is that if you want to have a great hiring process, you need to have a pre-filter before the hiring manager. If the hiring manager is manually reviewing every single application, then they will probably be more annoyed and probably have a little bit of pressure mentally to take shortcuts or get a little bit less rigorous with some of that evaluation or be tempted to do things like make the job application filter out more people by saying you’ll have to have 20 years of Swift UI experience.

Cate: I mean, this is a very engineer thing to do. It’s like I put in a unit test for that.

Allen: Yeah, well, you told the story about making people hit a curl request in order to apply for a job.

Cate: So bad. That was such a bad idea, but it was put in in a completely rational way. The team was completely rational.

Allen: It seemed clever to me when you first described it. You describe how that came about and what happened.

Cate: Yeah, so just they were getting doxxed by applicants and they were trying to validate that people had a baseline developer proficiency more outside of the WordPress ecosystem. And so they asked people to submit this kind of Easter egg that was on a URL that could be accessed easily by using Curl. And it kind of worked because they could quickly filter out everybody who hadn’t solved the Easter egg. But this is the problem.

Allen: There’s that autobot applying people that are putting zero effort in and/or have no concept of how programming even works or this type of programming anyway, so seems to an engineering mind is like, “Oh, great, we’ve already got 80% of them filtered out. This is a big win.”

Cate: Right, totally. But who else have you filtered out? If you’ve started, if you’ve put in things even in a well-intentioned way, where you start filtering out well-qualified applicants, because what you’re communicating in that, and this is something like job seekers especially right now are really attuned to, is they don’t want to apply to an AI. And if you make it look like that’s the experience you’re giving people, then the job seeker is like, “Well, this is not respectful of my time. I don’t want to work at a place that’s not respectful of my time. I don’t want to waste my time applying to a place that’s not respectful of my time.” Because again, we’re back at the problem of people who are looking for jobs, especially in this market, it’s so hard. If somebody who is hunting for a job does not want to hear from me how much I hate reviewing resumes, I totally get it. But this is why we like both sides of this conversation almost never meet each other because job hunting is really hard, really hard. And being a hiring manager, it’s also really hot. And unless we can have a little bit of empathy in both directions, but definitely hiring managers need to have more empathy for people applying to jobs. But then it’s hard if you have so much to do, you have four hours a week for hiring and you’re reading so many resumes that are just like, why did this person apply? It’s very hard to connect to that empathy and be like, “Well, this is a bad market.”

Allen: Yeah. It’s hard. I feel like that it’s easy to spend other people’s money or other department’s money, but I feel like having humane human-filtering processes in between the hiring managers and the mass volume of applicants. Rather than making the applicants jump through the hoops, have your own org jump through the hoops is maybe a helping hand there.

Cate: Well, I’d say it’s offensive, right? It is. Why a great recruiter is just amazing. I like my recruiter. There are many recruiters, but my recruiter, Diana, this is our third company we’ve worked at together.

Allen: Oh, wow.

Cate: They’re amazing. Yeah.

Allen: Is that coincidence? Did you bring them in?

Cate: We’re a package deal at this point. Yeah.

Allen: Nice. It’s great when you’re at the part of your career it’s like, “Yeah, I could work here, but also I’ve got my team. So you going to bring us all on?

Cate: Yeah. So I’m opening a new role and I’m like, oh, this role is how I’m like, “I need Diana.”

Allen: Nice. A couple last things I want to touch on. One, back from this self-growth thing, because I find it interesting, and I’ve been personally thinking through this and being more thoughtful about this recently, you talk about managing your time and how in fact actually it is maybe more important to manage your energy rather than manage your time, which is, I think I hear people talk about sometimes, but still most of the time when people are talking about how to reason about being a productive leader and scaling yourself, people talk about time. So tell me a bit about energy management and what goes into how you developed that model of thinking about it.

Cate: Yeah. I think the thing that’s made the time energy dichotomy most clear to me is periods where I was feeling very burnt out, but I didn’t feel that I was working that many hours. A decade ago, we run this schedule, which is no meetings on Wednesday, no recurring meetings on Thursday. So that means Monday and Tuesday are very hellish because everyone crams. I have eight direct reports and other things that I really, really struggled with this for a long time. I would finish my last meeting and just be like, oh, but I have other things to do. I can’t think anymore. I have an ongoing negotiation with surviving Monday and Tuesdays because it’s so difficult to do so many meetings and to do so much. It’s so difficult for me. Maybe other people are better at meetings. I don’t know.

Allen: I don’t think anyone loves an all day back-to-back meeting two days in a row.

Cate: So that for me is like, these are days where I don’t know how many hours I worked, but I know that the energy cost for me is very expensive. I used to feel like, I remember talking to my coach about it once and saying it was a seven-hour day in time and a 10-hour day in energy. And starting to think about it that way and kind of use that kind of language for it is helpful to me. And so like I said, I’m in this constant negotiation with it, and the thing that this week is Tuesday, I’m somewhat coherent on a podcast at 7:00 PM for me, so I guess we can say it’s worked this week is to exercise at lunchtime and use that or in the afternoon and use that as a time to think through some of the meetings I have in the afternoon. So to kind of disconnect, think through stuff, have some space for it, and that allows me to be more effective. But when I was viewing it as a pure time management problem, I was like, I’m not working enough.

Allen: And you end up sitting, or at least my experience with it, and that’s how I got religious about this in the last year, I would sometimes be sitting there knowing I should do a thing I didn’t want to do, but it was the right thing to do with it. It’s like, okay. And so I would just spin my wheels and be super unproductive at it. Something that I could probably at my peak get done in an hour and I spend three hours sort of doing it and getting distracted, really easily distracted because I have no energy or whatever.

Cate: Yes. Or trying to notice when it’s just time to eat lunch.

Allen: Sure.

Cate: I don’t know if you have that. It’s kind of lunchtime, but it’s not really, and it’s just like…

Allen: I’m going to get interrupted.

Cate: I feel like my brain has stopped.

Allen: And so the thing that I was encouraged to do also from my coach is I would say, “Oh, I really should,” I keep wanting to do this task, like work on some branding thing or something that I find exciting and fun is like, “Oh, but it’s a distraction.” And then she would ask, “Well, yeah, you say it’s a distraction, but does it energize you?” And I’m like, “Oh, yeah, it gives me all the energy in the world, and when I do something like that, then it’s like, great. I both felt like I accomplished something and I felt like I was good at it, and I found it interesting.” And it’s like, okay, well that seems like a thing worth doing then. It’s like, that’s what you’re actually limited by. And then sure enough, as I’ve started to more often think about things and also feel less guilty about then sort of procrastinating by doing these tasks that I find exciting, motivating and energizing, now thinking of them in terms or even just like you say, exercising, which is something I’ve gotten a lot more in the habit of and pays for itself in total productivity, even under a fixed number of hours if I spend 20 minutes exercising on a day and then it reboots my brain and body. So I like that you called that out explicitly in the book.

Cate: Oh, thank you. Yeah, I mean, I think it’s the biggest challenge that I see in so many people because the problem is when you’ve stopped doing energy management and you’ve gone into time management, everybody in that place is in a bad place emotionally.

Allen: And energetically probably.

Cate: Yeah, exactly. They’re tired and they’re beating themselves up for not doing more.

Allen: Yeah. And then because you’re beating yourself up, you get less done and then you beat yourself up more. Like I have been there.

Cate: I think because you’re miserable. And your coach made you both happy and productive.

Allen: Yes, and it’s great. And I’m all new person now. Reflections on writing a book. It’s hard. You did it. Congratulations. Any lesson learned or reflection for either past you or the people in your that are considering taking that path for going from blog writing to book writing?

Cate: I think if I could go back, I would not think about writing a book. I would think about finding my book sized message, which I think I spent too long before I started writing books, thinking about writing a book, and that was not the problem that I needed to solve. The book sized message was the problem. And then there’s a lot of advice about how to write a book and it’s generally like make a very detailed plan and then work on it at five o’clock every morning. Five o’clock in the morning is not a knowable time to me, but that’s not the only problem with that advice. I think that’s great advice for writing a blog for somebody who can get up at five in the morning, because you can write a blog post in 30 minutes to an hour. You can edit it in another 30 minutes to an hour. You can put it in your head and you can reason about it and you can think it through. And writing a book is so much, like having a project of that size in your head for a long time is very taxing. And I personally just couldn’t work on it in 30 minute increments. I carved out entire Saturdays, week in, week out to work on it. That honestly worked really well. But now I’m like, I should go back to blogging again. In many ways, I would like to go back to blogging again. I have ideas about blogging, but really it was a struggle to shift into the book mindset. But I think once I had the book size message, and especially once I had a book deal, that was just going to have to happen, but there’s nothing really to make me go back the other way. And I think my relationship with writing has changed in such a fundamental way. As a part of this, I always used to write to process my ideas, and at some point I was writing in a more like, this is one way to ship a book, and I really want to go back and find my joy of writing again and find my creativity again and return to blogging and writing small things regularly. And that is a huge struggle right now. So I’m so glad I wrote a book. I’m not, but yeah, I think people think they’ll be happy when it’s done. And actually, I’m happy. I’m happy that it’s done, but on some way it feels like, I don’t know, moving health or something. You’re like, “Okay, I’m in the new place, but shit, where’s all my stuff? It’s in boxes.”

Allen: And that’s a energy recovery. So I hope you find that love again. I am faithful and optimistic that you’ll get back into it, but I think it’s also, cut yourself some slack. You just spent a couple of years writing the book. You can recover for a while.

Cate: Well, thank you for reading the book. Everyone who reads the book makes me feel better about it, so super mad appreciation for that.

Allen: Thanks, Cate, for coming on the show. Where can people go to get the book and also to learn more about you and your book?

Cate: So the book is available everywhere that people buy books except in Australia and Brazil. Yeah, it will be available there soon. Apparently it takes longer for some book logistic reasons that I can’t find it in me to care about. You can find me on my website Cate.blog, and I’m on Mastodon.

Allen: Excellent. Thank you so much for being on the show. It Shipped That Way is brought to you by Steamclock Software. If you’re a growing business and your customers need a really nice mobile app, get in touch with Steamclock. That’s it for today. You can give us feedback, follow us on social media or rate the show by going to itshipped.fm/contact. Until next time, keep shipping.

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