Episode 19 | Transitioning From a Holacracy to a Strong Engineering Leadership Culture with Katie Wilde from Ambassador Labs

Eiso: [00:00:00] Welcome to Developing Leadership, the podcast where I, Eiso Kant, and my cohost, Jason Warne, share our thoughts on lessons learned on engineering leadership through the years.

Today, we have Katie Wilde on the podcast for one of our most fun conversations to date. Katie is the VP of Engineering at Ambassador Labs, a cloud native developer experience platform, and was previously VPE at Buffer. She joins us to spill the tea on holacracy and decentralized management systems, find out why companies adopt this type of organizational model, in what conditions do teal organizations work, and how holacracies could drive your best people away. Katie will also walk us through transitioning from a holacracy into a strong engineering management and leadership culture. You thought implementing job levels was easy? Think again.

Also, today, I'm going to give a special shout out to Automatt for leaving a very kind review on Apple podcasts saying how essential this podcast is to anyone building software.

If you enjoy the episode, leave a review on Apple podcasts or Spotify and share it with another engineering leader. As always, this [00:01:00] episode comes with accompanying show notes featuring our favorite moments from the chat and a deep dive into today's topics. Find them at developingleadership.co or link in the description.

Hello, everyone. We're back again with another episode of Developing Leadership. Jason and I are really excited to have Katie Wilde with us today. She's currently the VP of Engineering at Ambassador Labs, the cloud native developer experience platform that enables developers to code, ship, and run applications faster. She's into dev tools, one of Jason and I's favorite areas. And previously, was the VP of Engineering at Buffer, a company that many of us know due to it's very visible product and even more visible policies about remote and holacracy.

Katie, thank you so much for taking the time with us today. Jason and I have, probably on multiple occasions on this podcast, been quite vocal about [00:02:00] holacracy and our, well, lack of belief in it. And so you came from an organization where that was originally part of the culture, and I know you- you took some changes to it. So, I'd love to kind of, you know, kickstart with hearing your experience and what you did to to change the engineering organization there.

Katie: Yeah. So holacracy is, I believe, a reaction to bad management, where people see organizations that have been run into the ground by incompetent leaders, and then they say, "You know what? Management sucks. We don't need leadership at all. We should get rid of that completely, and we're going to replace it with holacracy or teal organizations or, you know, whether you're going to have some kind of, formation of the above." So, Buffer had got... sort of gone through phases. It was very experimental culture, you know, very early to remote work. You know, 10 years ago, it was globally remote which was unheard of at the [00:03:00] time, pay transparency. So, this high degree of openness characterized the Buffer culture overall. And that meant that's the- the leadership and the team were- were very easy to embrace holacracy in the form of Patrick Lencioni's Reinventing Organizations. And, now, the idea is that organizations are not doing well because they are at various stages of dysfunction, because their leadership is not good and he has this framework of why it's not good, and what we need to do is we need to reinvent them and we need to dramatically change leadership to make it that everybody is a leader, i.e., nobody is. And we're sort of in this holacracy/teal organization is what it's called if you want to look up what that is.

And so, you know, we- we tried that and we worked in this manner for about six months before we realized that we literally [00:04:00] could not sustain it anymore. And the reason that happened was we ended up losing some very high-performing teammates. Our best people actually quit. We were left with our best people leaving and then people who were perhaps not quite as great, you know, really enjoying holacracy because it absolutely allowed them to do whatever they want and sort of set their own salaries and- and kind of crazy things. And high-performers would be there, you know, feeling like they were carrying the full burden of keeping the lights on and, you know, doing all the things that had to happen to serve the customers, absolutely burning out, feeling incredibly frustrated and not really being able to have the impact that they wanted.

So, we ended up with high performers leaving and then we ended up as a relatively small engineering team, massively duplicating effort because, of course, there's no strategy, there's no alignment, there's no goal setting. It was just like, "Okay, well, people just come together and work in whichever organic ways make sense." And so we had two groups sort of [00:05:00] emerge to both develop and ship the same product. So, clearly there was consensus on the problem and on the solution, so it has a win. However, in a small dev team that was about, I think 14 developers at the time, you know, duplicating effort like that is something that will kill a startup, you know, like you just can't do it. And so we were losing our best people and were duplicating effort to a massive degree, and, you know, ut was very much like, "Well, this is almost gonna... this is gonna take us out of business, like this is not one of those like fun experiments and we need to stop right now.

Yeah, I did a little bit of research into why it didn't work. And what's interesting is that if you look at the organizations where holocracy or teal organizations have been successful, what is true about those organizations that can succeed. But the organizations where it succeeds and a tomato canning factory, what do you do? You take tomatoes, you put them in cans, that's it. Favi, they make gear boxes, same gearbox for, you know, a hundred years. What do we do? We take the gears, we make them into gear [00:06:00] boxes, and so we go. Buurtzorg, which is the Danish nursing organization. Well, they're a loose coalition of freelance nurses that know their job. They go to people's houses who need nursing, and they do the nursing, like they know what to do. 

Where do we not see holacracy work? Well, organizations like Buffer, which were not hugely simple, mechanized, predictable industries. So, the promise of holacracy is you're gonna tap into the creativity of your workforce. So, it's very attractive for industries in tech. It's very nice to think that, "Oh, well, we're going to have everybody put their thinking caps on and that'll be exactly what you want." But the problem is that we actually don't have records of holacracy succeeding in complex organizations because complex organizations, they need goal-setting and they need alignment. And what holacracy doesn't do well is alignment.

Jason: I... as Eiso said before, we could bash out holacracy all day. I think holacracy is the [00:07:00] exact example of a system you would create if you never wanted to get anything done. And there are so many examples out there of this. And I think if anyone listening to this podcast wants to understand what I mean by that, just go read The Tyranny of the Structuralists, which is an essay that came out of, I think, the 1970s feminist movement and what is entailed. But effectively, what you described is exactly what is described inside that essay too, which is when everybody's in charge, nobody is. When you have to consult with 100% of all the people to make a decision, you will never make a decision. And if you also combine that with this 1944 CIA manual called The Subtle Art Of Sabotage, you will understand how organizations that adopt this type of working will never get anything done.

Katie: Yeah. And the thing is, if you never get anything done, you know, who will leave? The people who wanna get stuff done. You know, who will stay? The people who enjoy getting [00:08:00] nothing done. So, what have you done now? Well, we've managed to very efficiently select for the least competent people on our team. So it's just like a complete disaster. You're doing the absolute opposite of enabling your high performers.

Jason: I think this is incredibly important for people to actually internalize as well because there'll be folks in my sphere who will point to, "Well, this is how open source works," and now in the crypto web3 world, well, this is how dows going to work." And my counter point is you need to study those examples to understand that none of those things actually work this way. There are always people who are making prioritization trade-offs, roadmap decisions or there- there's a power structure at play or hierarchical decision-making matrix inside all of these distributed things. And it's the fundamental reason why if you have experienced, and this is presented to you, you'd push back and say, "Oh no, this- this is a perfect recipe for us to kind of go out of business sooner. Is that your objective? Great job. You found the perfect example of how to do that for us."

Katie: [00:09:00] My sort of one answer to the... "but this is how open source works" is I go, "Do you know who . It's I go, do who Linus Torvalds is? And people go, "Yes, of course," and I say, "Exactly." And it's like, "Why is that relevant?" Well, because he is de facto in charge. He's the de facto CTO of Linux. Right? If this truly where a decentralized teal organization, we wouldn't be able to say, "Oh, I know who Vitalik is. I know who Linus Torvalds is. I know who holds the keys to the queendom because nobody would." So just the fact that these people exist, the fact that they are household names in our industry shows that's not really how open-source is working or how blockchain is working.

My partner is actually the CTO of a decentralized identity startup, and does a lot of work in the space. And the most difficult aspect of being in this environment for people that are in the environment is the lack of decision-making. And that is what everybody is trying to solve. You know, it's like... it's not like, "Oh, this is working so well. We love herding cats." It's like, "Who's going to [00:10:00] be the cat herder? Me today, great. It's your turn now." "Who's the maintainer here? Who's gonna like corral the agenda?" It's a job, and they get that job done. There are leaders in these communities. 

Jason: Some of the more important aspects I think people should take away from this too is that, at the end of the day, a lot of people come to holacracy or some of the other ways of working out of maybe good intentions or a spirit that they say "this is maybe how we should like Montessori school collectives and co-ops and things of that nature." And you don't wanna push them too hard on that. But what they need to understand, is just at scale? and scale, I just mean more than 10 people in this case here because you don't want to stop progress to talk about process 99% of the time. And that's what happens in a lot of these situations. And you love them, the best of intentions, but it's almost extreme, extreme to the nth degree naivete.

Katie: Absolutely, it's well-intentioned but [00:11:00] very naive. And we need people like us. We need people who can sort of dream of the best of worlds and like that- that's wonderful, but please don't do it in the form of holacracy. You know, there's- there's many other areas where you can Dream. And I would say that, you know, if you, if you are attracted to holacracy because it seems more autonomous or more creative or it's a better way of work, it's more transformative, those are all noble things. 

But what you're really attracted to there is a certain leadership style, a transformative leadership style. And if you Google transformative leadership and generative culture, you will find a lot of resources about how to do that well, and that is a- that is a wonderful thing to do that does work. You know, the book accelerate, which many people, you know, really love for being good at helping us get things done, has a great section on transformative leadership. So, I'm not at all against good leadership and transformative leadership. These are excellent things. It's just that holocracy isn't it. Holocracy is an abdication of leadership, and that doesn't work very well for any of us.

Jason: Thank you for using the word advocation. [00:12:00] That is exactly what I view this is. And it's a 100%, as you mentioned before, reaction to atrocious leadership in most cases. So, you go from atrocious to abdicated as opposed to understanding and trying to find the good examples. I love the way you framed that. And Eiso and I have talked about this a lot in the podcast too which is one of my strongly held views is that there generally is a lack of leadership in the tech industry and particularly on the engineering side of the fence, product engineering CEO side of the fence. yeah, yeah, I could not agree with everything you said more. 

Katie: Yeah. We have a terrible leader. So, what do we do? We should get rid of leadership. Okay. 

Eiso: I'd say Katie, this was probably the most eloquent rebuttal anyone could have given on holacracy. This has to be written out to share with the world. This w- was- was very good. You then found yourself having to transition away from it. Some of your best people sounded like they left. How did you go about this? I know you ended up going through quite a bit of growth afterwards. What allowed you to rebuild the engineering org into a [00:13:00] high-performing one?

Katie: Yeah. Well, it wasn't difficult to transfer, you know, the- the engineering organization away from holacracy because it was very clearly not working, and people were very upset about it. So, there- there were a couple of people that, you know, wanted to give it a little more time, but that actually wasn't difficult to- to get by and for, basically followed a- a method of like, "Well, these are the problems that we're having right now. Correct?" You know, we're... People are overworking, things feel unfair, it's very unclear what your career path is, you don't know how you're going to get promoted. We're not doing well as business.

In fact, we'll probably go out of business. These are the problems." Yes. I would say, "Okay, well, what are the things that, you know, we want to solve?" It's like, "Well, we want a sense of, you know, plan. You know we can say strategy is a fancy word. We want some sort of plans and not go out of business." Like, "That sounds good." We would like to you know, like- like all understand, you know, what our jobs ask and, basically, we would like to subdue them. That'd be great. If we could get personally promoted, that would also be very nice. If we could have it more equitable where we don't have, you know, Alice is working a hundred hours a week, and Bob is like reading books in the sun because he's sort of like ideating.

You know, if we could move away from [00:14:00] that, that'd be good. I'd be like, "Great." And then it's like, "Okay, engineering management is like the, you know, search term to Google, and that's the thing that solves these problems. So, we're going to do that." Everyone was like, "Sounds good." 

One thing I will say is having come from a no-managers organizational background, the bar for leadership was high. It's sort of like being in a democracy for the first time and you're remembering the guillotine, and you're remembering the people coming in the streets and they're going to go off with your heads if you go and Marie Antoinette them now, you know. So the bar for leadership was extremely high and managers absolutely had to do a good job in showing the value of leadership. And I would say that pushed us very hard to develop a strong engineering management and leadership culture, me, the other engineering managers, because it was a real sense of, if we go from abdication [00:15:00] to atrocious, we'll just get back to abdication, you know. We'll all be out of a job. So, there was this very, very real sense of accountability to the team and to the business, that I've really never felt anywhere else.

And that was interesting. I don't think you need to experience holacracy for six months to get it, but there was a very real sense of, "We need to prove that leadership can be good because, otherwise, people are just gonna say, "Well, this leadership thing doesn't work either. Back to holacracy," you know.

Jason: That is really interesting that you say that because, in my own experience with going in order canonical to Heroku and then, in particular, GitHub, all three didn't have managers. And at various stages, they introduced them for the first time. Though at GitHub, in particular, when they started to introduce them, they had a- a terrible experience with some of the senior-most leadership at the company. And as I joined, one of my personal and private comments to one of my friends was, "This is the most trepidatious environment I've ever entered before." I have to be so far and [00:16:00] away better than at- at another peer organization, that there is no choice. 

It's so obvious that this is the way that we're gonna do it. If I was average, I would have been out and the company would have gone back to whatever way it was. And even if I was above average. But I had to be exceptional in that one circumstance. And it was stressful, obviously, as you- you navigate that, but you understood the stakes for the organization. But it is funny how the pendulum swings. It doesn't swing back to the middle. It has to swing all the way.

Katie: Absolutely. It swings all the way to, "Okay, so your leadership must be flawless. And if there's ever a mistake, there's that, there's that large cohort that's gonna say, "You see, leadership's atrocious. You know, holacracy might've been bad but, like, abdication is better than atrociousness so it- it becomes completely there's no, there's no security of like, "I'm the boss and they're never going to get rid of bosses." It's like, "Oh, yes, they will. You know, they- they very easily will." So, it does... I- it [00:17:00] does really put engineering management on its toes. 

Jason: You and I have some shared experiences here that I'm sure, at some point, would be rather amusing to have conversations about. 

Walk us through a little bit about how you did that because I'm sure there's a- a common set of things that you said, "Okay, here's how we're going to go do this. We're gonna do X. We're gonna do Y. We're gonna do Z. We're gonna layer on As, Bs, and Cs, and then, you know, we're gonna bring it all together with the MNOP type of stuff. Do you have a- a framework in your head that-

Katie: Yeah, like how do you implement engineering management now it's gotta be good because, otherwise, you'll be overthrown in a revolution. Right? Okay. Absolutely.

So, the first thing to implement is one-to-one's. So, we did this, every manager was having one-to-one with every person for one hour each week. Now, that- that's a lot of one-to-one time, you know, where I'm at currently, we do a half an hour every week. But it was a lot of time because the number one thing is people need to be heard. And I'm not saying listen- listening is an activity and that's not... Y- you know, sure, you can do the listening. The outcome you need is people must feel heard, [00:18:00] and that was the number one thing that they needed to feel in order to trust this new, you know, leadership situation. So we did one-to-ones. It was an hour a week. It was every week. They were completely inviolate, and it is outcome-orientated, but it's the manager's kind of like hop on Twitter like, "Yeah, yeah, how you doing? You're fine. Cool, cool," Like, "Sounds good. Yeah, you're doing good job." No, no, these- these people have to feel deeply heard and understood. And so there was, you know, training there in active listening and nonviolent communication reflecting back and really making people feel like we hear you, we get you.

The next thing we needed to do was address the feeling of being stuck in a career. So, we brought in, you know, job levels and that's a whole separate podcast. But what I would say is making job levels is very easy. You can copy and paste them off the Internet these days. Deciding who on your team is in what level, that's also very easy. We generally know who's a staff engineer, who's like actually not that great. Rolling out the job levels is a complete kettle of fish. [00:19:00] That was the most difficult thing because everybody would be like, "Yeah, these job levels look great. I love it. I'm here for it," and everybody will immediately figure out where they think they fit and then become extremely attached to that, and then think that you're all being extremely unfair when you explain to them why they're not actually a senior engineer because, technically, a senior engineer has done da-da-da-da-da.

So, that's very difficult because people are, you know, coming up against all kinds of basic needs. So, you need to have the job levels and there'll be pressure. People say, "I want job levels." Yes, you do. And... But the reason is because they all think that they're going to get staff engineer. They all think they're gonna get a massive raise, and I've been so under appreciated. Then the reality is that, you know, you've got the bell curve of your organization and, you know, most of them are not going to be staff engineers. So, rolling them out, that was really tricky, and that took time. That took significantly more time than creating the levels in the first place.

And, okay, so we did one-to-ones. We did job levels, and then we, you [00:20:00] know, got managers to really help on teams be... you know, you were managing everybody who obviously reported to you but you were also managing the team and the outcomes of the team. So we did away with sort of the- the matrix structure that we had before where engineers worked on all kinds of different projects and they had a people manager they talk to once a week. And the reason we did that is because it was very important for people to feel that my manager, you know, listens to me. My manager is technical enough to appreciate it and praise my work. And then, thirdly, my manager actually knows what's going on, like they're managing my project. So, we- we- we try to keep the situation where everybody working on the same team, report it to the same manager, and the manager was responsible for that team climate being a healthy team climate. And you can go an, you know, have a separate podcast on healthy team climate.

The trade-off we made though is that's not flexible. You suddenly realize, oh, this other team over here needs two more engineers. You- you can't just floating mosaic them around, [00:21:00] but we made that trade-off because we wanted to give people the best possible experience of management. And the best possible experience with management and leadership is your people manager also understands your projects and also understands technically what you're doing. And you've got this deep level of understanding. And then we really focus management on progressing through the job level. So, we actually tried to make it very, very focused on how is this management thing good for you personally today? And overall, I would say that it went mostly quite well. The hardest part by far was the leveling people into the career framework and getting them to accept management's decision of- of where they were currently at.

Jason: We had similar experiences and I would... I was laughing while you were talking. No one in the podcast is gonna see that because it's an audio, but it was same thing. Rolling off those levels was tricky because exactly what you said; everyone always put themselves in the staff, you know [00:22:00] level levels and saw themselves that way. And you had to have some conversations with them.

And I also was laughing when you said they had to be deeply heard. And it's funny because when you're rolling these things out, you have to do that. Then there is a- a gentle way that you have to start giving people feedback along that spectrum too, so that you have to feel heard for the first time, if they've never been heard before, so you have to do that. Then you have to actually start transitioning to giving them feedback as well, as managers do, because growth comes from feedback and being challenged. 

Did you, in your experience, find that there was an intentional switch to like, "Hey, we're in listen mode," "Hey, now we're going to be in... this is gonna to be a bi-directional mode now," and then that sort of thing?

Katie: Yeah, absolutely. So you first need to be in listen mode, but then if you're just endlessly listening and nothing's changing, people will quickly become frustrated. So, you can't stay in that listen mode for longer than, I don't know, a couple months max, you know. You- you have to start giving people feedback.[00:23:00] 

The mistake I made was, you know, I was doing surveys, I think I... like Google Forms, how there's much better ways can use that as a culture app or whatever. But I was getting feedback, you know, from the organization of how those management situations going, and I was hearing very many comments like, "I want more feedback." I was like, "Great. You're ready for the feedback part. This is exciting. Let me tell you all the things that you could be doing better." That was not what they wanted at all. They want to praise. 

 Yeah.

 And so that was a, that was a major mistake. So they firstly wanted to be listened to, then they wanted to be praised and told how they were so fantastic. And then they wanted to grow but people don't actually want to receive corrective feedback or critical feedback, but you need to give it because if they don't end up changing and growing, then they will get frustrated with you. Right? So, it's a difficult thing where they- they want the result of what you're gonna provide, but they don't actually want you to provide it.

So, one of the things we did was try to maintain a ratio of about five praises to every one piece of corrective feedback. I [00:24:00] have no idea if that's a scientific ratio. I think I might've got that from some dolphin training podcasts, like it's- yeah, I don't know but I- I can say it did sort of work because it, you know, gave people a lot of praise and then there was, okay, now there's one piece of critical feedback.

The next thing was we did a lot of feedback training and giving feedback in the most non-triggering way possible where it is, "Here is a very factual observation. Your PR descriptions often contain 50 words or less." It's not a statement. It's not like, "Hey, you have terrible communication skills that your PR is running at 50 words or less." Then you have the impact of that, you know. "As a result, it's difficult to know what your code is going to do. So, you know, it- it's difficult for people to, you know, understand what the point is. And so, here's how it affects you personally and holds you back," the thing they care about, not like your teammates, the staff, the organization of that. No, no, "your coworkers are going to find it really difficult to like, really appreciate your ideas. [00:25:00] You're gonna find it hard to say, you know, that's a great idea. Can you tell me more about what you're optimizing for with this 50-word PR description?" they'll be like, "Oh, I was trying to get it done fast," like, "Oh, maybe we wanna to do something different." That's the- that's the lightest, softest feedback. And then you have the same formula but instead of, "Can you tell me, you know, a bit about why you're doing thing I wanna change?" you can go, "You need to change X. I need you to change X." That's when you start getting into the- "I need you to understand that X has got to change. The behavior must change. You're not a bad person. You're a great person, but this behavior must change," and then you get stronger from there, so.

Jason: There are two things you said that are going to help me a- as well if I ever go back to get- get a real job, which I hope I actually don't do. ... but it was funny. I was having a s- similar conversation with someone a long time ago about something very similar to this. And I made a massive mistake, which was I tried to convince, at some point, as opposed to just set expectations. I wanted this person to believe something different [00:26:00] because there's a fundamental I thought. And I changed it towards the end of the... this- my tenure with this person. I said, "Hey, you know what? I actually don't care what you believe. I just need the behavior to change. So if you believe that I'm wrong, I actually don't care anymore. I just need this behavior to change. And my expectation is that it will or we're gonna have a different conversation."

And that transition that you also talked about earlier, I call it going from coaching to expectations. And many of the coaching scenarios, you're gonna be a little gentler, you're gonna be a little beat around the bush because, sometimes, people aren't ready to understand where they actually sit in the moment where they are on that growth curve. If they can slowly transition into it, I just call the expectation setting, "Here's my expectations about what this role entails. Here's what my expectations about what we do on PRS. Here's my expectations about what we do." that's when you see the bell curve really come out, the senior folks and not senior in terms of just pure technical but senior in terms of social, understanding, growth, technical. They're like, "Yup, makes total sense," [00:27:00] and everyone else then starts to, you know, who's lower on that. Their growth journey themselves starts to react differently.

Katie: Absolutely, yeah. I completely agree. And that's why, you know, managers have... Well, I- I see it as there's- there's four skills. So there's coaching, sure, you know, there's sponsorship where you could say, "Oh, here's a great project. You should be in charge." There's mentorship, "Let me teach you all the stuff," and then there's feedback. And in this case, wherein feedback is like, "This job entails you achieving the following outcomes and doing the following things." And the next job entails you doing the following things. If you want to get promoted, here's the things to do. If you want to be not fired, here's things you need to do.

 And eventually it just comes down to really like, "Listen, this is not personal but, like, for someone at your position in this role, I need to da-da-da-da-da-da-da. And if you can't or won't do it, like you are going to need to find a more compatible organization/I am going to need to fire you."

The biggest mistakes I've made have been firing people, and then it's like they're coming as a surprise because I was [00:28:00] coaching them, and then I was trying to train them, and then I was trying to, like, understand them. And at no point did I say the job requires X, you are not doing X. Therefore, there's a risk you won't be able to do the job. And then, okay, you can't do this job anymore, you're being fired because you know how you need to do X and you know how you didn't do X, like, yeah, that was a deal breaker.

And some people are very, very gentle and they're gonna respond right away to that, "Can you help me understand?" you know, that coaching. Some people respond right away. They're very sensitive. They're very responsive. Some people are going to need it spelled out and there's... I've seen a lot of managers kind of have this attitude of like, "By the time I need to spell it out for you, like, there's no way you're going to do it."

And I completely disagree with that because you got a lot of people and a lot of cultures, especially in this global remote world that are way more direct than the North American, you know, "Hey, don't you wanna to do thing that's actually mandatory.?" you know. I mean, an Israeli person is not going to react like that, you know, they're going to be like, "Do X. It's your job." They go, "Yeah, very good. Okay, fine." Nigerian culture [00:29:00] is a very, very direct. And I think that's an important point now that we're all working in remote organizations, and we're all hiring globally is that we- we can't skip out on the direct expectation setting and the direct, "Well, this is where you are." And as long as you keep it about the work, you know, you're not being mean or just being candid. The mean thing is somebody gets fired and they don't understand why. And I've done that, and everyone.

Jason: It's interesting you mentioned that. This is a personal comment in that my- my... I have three kids but two are on the spectrum and one of them is pretty on the spectrum. And he does not understand when I do the... it's a directive, but I'm gonna to ask you in a nice questiony sort of way , like, "Hey, don't you think you should put away the milk?" and they're like, "No."

 No.

 I'm like, "Oh, no, no, that wasn't a question. That's my North Americanism coming out about trying to be kind in a subtle, subvert sort of way to ask you to do something," and he's like, "No, that's, that was a question. I told you the answer to that question." And interestingly, I've... I took that to work [00:30:00] when I started to realize what was happening there and I- I adapted my own way of doing this which was if I was working with somebody, I would coach and do the expectation in the same moment with them too. I would say, "Here's how I might approach the situation. Here's something I might do. Here's something... Here's my expectation." And if there was any question about any one of those, I'm happy to go into it, but I was also gonna set the... what was going to happen outside if- if the expectations weren't met. And, obviously, you start to enter a phase that looks like that. You actually do want to be more direct to saying, "Hey, if these expectations aren't met, this is the result of those expectations."

And you mentioned your mistakes. My biggest mistakes was not doing those exact same things because I wanted to be kind. I thought I was being kind when, in fact, I was not helping this person to understand how they were about to not be fired.

Katie: Yeah. Like you think you could give them a heads up, you know, like, "Do you want to not be fired? Like, change this one easy thing," or maybe it's 10 difficult things, but like, "Here's the things to change." Absolutely.

Jason: Yeah. [00:31:00] if I could give myself any advice in my 20s... you know, I'm in my forties at this point, but if I can say in my 20s like, "Don't do that, Jason," start to become a more directive person. You can still be the kind, gentle person on this side, but you have to marry it with the other side of the coin in the directive expectations setting. They could be together in the same package, but you can't have one without the other."

Katie: Absolutely. And it's such a good point about the neurodiverse. You know, if you're thinking about, you know, DEI, what Jason's saying is very important for inclusion, whether it's including people that are not neuro-typical, and might be on the spectrum and, you know, any way, and- and there are many people in our industry who are all people from different cultures, different backgrounds. You know, if you want to be an inclusive leader, that actually means you're a clear leader. 

Jason: And I think on the flip side of that too, maybe this is a particular... I don't know if this is a particular to like North American cultures or in U.S. in general, maybe West Coast U.S. in some, in some cases too. But there's a lot of times when people will overreact and [00:32:00] say that we need to implement somebody's feedback because we're gonna be inclusive. In fact, what I think is most people need to be heard and that they have to feel heard, and that- that was taken seriously. Your job as a leader is not to 100% amalgamate every piece of information from your organization and somehow mold the perfect sculpture with all of those bits. You're supposed to take them in, make something out of it, and make a direction or an X or Y or Z.

 But it doesn't have to incorporate every single thing. The obviousness of that is because you'll have 180-degree pieces of feedback, which is "we're too slow" and "we're too fast" given at the same time. And obviously, you can't incorporate both of those. So, once you understand that, it's not that everyone's feedback is included in the final direction, it's that they're heard.

Katie: Absolutely. One of the- the few times where I felt like, "Gee, I did a good job on this leadership thing, you know." If I think about successes, they've actually been when I've been very [00:33:00] upfront about, not including feedback. So, I remember one case is I had a contingent of engineers who wanted to be senior staff engineers but did not want to mentor and teach other people. And they were saying, "I should be a senior engineer because I'm brilliant. You should pay me more for that." And so I called an all-hands and I got up at the offside, and I stood up in front of them, and I said, you know, "This is what you want." And they expected to get it. They were like, "Yes, great," lots of smiles.

I was like, "So, we want to have senior engineers that can be senior without mentoring, without teaching, without sharing knowledge, just because you're very, very technically- technically qualified. That is... I hear you. That's what you want." And they were like, "Great. I'm so glad we got it now." And I was like, "I'm not gonna do that, and here's why, because we're a small organization and we have to teach people, otherwise, we'll not succeed, we'll not be effective. And so the business needs you to actually mentor and teach and train. So, we're gonna to keep the career level like this, and we're not gonna have senior engineers that are, you know, purely by themselves being highly technical because that's actually [00:34:00] just not a good thing. And so I'm not gonna pay you more for doing something that doesn't help." And they were sort of a little bit stunned. And afterwards, a couple of these sort of engineers who were very much in this camp of like, "Hey, I should get the promotion because I'm great. I'm not going to mentor," they come up to me and they said how much they appreciated that, that kind, they still, they still disagree, but they sort of saw my point, and they were kind of gonna like drop it a bit now.

So, it wasn't that I convinced them, and it wasn't a convincing game. I was just saying, "Listen, you want X and the business needs Y, and I'm in the job of making sure that we align them as best as we can, and I just can't of align what you want for what the business needs, so I'm sorry that's the situation." And they were like, "You know what? I appreciated that. Like, I get it now. I get why you're not doing it. I still want it, but I accept." And that's really... that- that was like a disagree and commit moment. You know, it's like I- I disagreed with them and got them to commit by being upfront about that. So, I'm proud of that one and I wish I'd done that more.

Jason: Love it because I think it also empowers people in that situation too [00:35:00] to say, "Am I opting in or opting out if this is a deal breaker for me at some point too," which, you know, again, being clear is a superpower, being communicative in direction and process or scope or XYZs can be a superpower, and it allows people to make rational decisions or at least opt-in/opt-out decisions.

Eiso: It reminds me a lot of something I was, I was taught early on in my career, which was that everything that we're defining as our culture within the team and within the organization shouldn't just be the thing that makes people say, "I absolutely belong here," but it also should be the thing that some- make someone say, "This is why I shouldn't be here," and I think it's exactly these kinds of things that you're mentioning that when someone says, "Hey, I either disagree and commit or this isn't for me." And I think if you have a culture that is only, "We are transparent and, you know, we trust each other," and it doesn't have anything that actually sets the boundaries for who should be inside and who not you end up with pretty words on the wall, but not [00:36:00] anything that actually defines who you truly are.

Katie: Absolutely. Yeah, good, strong cultures are one that people look at and they go, "Yeah, I can see how that would appeal to some people. Not me. This is not for me." And I'm like, "That's great. Like, that's helpful. That helps everyone. It helps us all find a better fit," you know.

Eiso: What you mentioned earlier, right, the- the notion of a style of communication between different types of people, I've actually come across this from the complete opposite side of my career. I'm from the Netherlands originally, and we have a culture where being direct is similar to the Israelis and- and to many, and we're quite known for it. About five, six years ago, I started first building a global remote organization. I found myself hiring more and more people in North America. And I realized very quickly and still to this date, it slaps me to face once in a while, that it's really important early on to preface. Now we do it as part of the interview process even like, "Hey, we have a culture in this company where we are going to be speaking very clear, very direct." And I remember the [00:37:00] first time I- I had hired a VP who came to me and said, "The fact that you spoke up in that meeting made me lose face. This should never happen." And it, like, to my core, bothered me. It both bothered me that I made someone feel this way, and it made... it bothered me that someone in the organization felt that speaking directly isn't... wasn't okay. 

And they were giving me these examples of Asian culture. This was a North American VP. And we really had to realign afterwards like, "Hey, this is who we are." And so I've seen it from both sides work, but I like what both of you mentioned that the marrying of the coaching and the mentoring with the expectation setting, it seems to bridge these cultural gaps but still it's something that I think is- is more and more challenging as we we build teams from people from lots of different backgrounds, no matter if that's nationality or- or neurodiversity.

Katie: Absolutely, yeah. And you've- you- you've got to have one of the most useful, you know, DEI training sessions. We kind of talked about this thing of like, "Oh, what if somebody says your [00:38:00] way of working is against my culture?" And the facilitator said, This is why it's so important to have a clear culture with clear values where you say "this is the company culture, that it supersedes national cultures." So," if in your culture, women are not allowed, yeah, outside of the home and should not be coding, well, our company culture supersedes that. Or if in your culture, direct feedback is unacceptable, we have a culture of candid communication, so it supersedes that. And you don't have to work here." 

Jason: This to me is actually one of the cruxes that I think in- in the current environment which is we think of DEI and inclusion as a 100%. That's my own framing of this is that it should be for everybody in the world. It should be for all those sorts of things. But it's as simple, it's a fallacy. It can't be. It can't... because if you're for everybody... again, if you're for nobody, if you have no lea- if you have no bosses, whatever, you have no- no leaders, whatsoever, that's how you're gonna end up. And so it- it's about being explicit and this is what we're going to emphasize.

And again, like I know, as an [00:39:00] example, that I don't want to ever work at Apple. I use this example because it's a big company that everyone understands, but just their way of working just doesn't jive with mine. Okay, so great. I know that, but there's also a thousand other places that I- I could work. Now, if I went in with the expectations that I don't wanna work at Apple and I- I don't like their way of working, and I was adamant that they need to change to do that's not... There's a mismatched expectation going into it, and I just don't understand how we can really live in this world where we think that everything has to cater to an individual. The place needs to actually have its own ethos.

Katie: Yeah, no, I completely agree. And it's funny you say that about Apple 'cause I'm like a naturally very transparent person. I just wouldn't be able to be in a, at a secretive environment, like I just couldn't do it. It would just... I would just mess up so much and be so unhappy and that's fine. Apple's not wrong, you now. It's like they're not wrong to keep things very tightly under wraps and to be very secretive. It works for them, and they would arguably be very much [00:40:00] less successful if they were to accommodate me. I just need to pick the organization that works for me, that fits my values and my culture, you know, what I'm looking for. 

Eiso: Katie, we- we have, we have about one or two more minutes. Is there anything else that you'd love to leave our audience with? A lot of them are engineering leaders that I know have taken a lot of this episode today. What are some of the things maybe that you wish you would've known earlier in your career that it can be shared in- in bite-sized quotes?

Katie:  Often leaders think that their boss should manage them even better than they are managing their direct reports 'cause their- boss is ahead of them and so should be this kind of super power manager. And I think it's important that you realize that the higher up you go, the less management that you're gonna get and that that's normal, and expected and the more it becomes your job to manage everything, including manage your boss. That's the number one thing that I see holds engineering managers back when they're becoming directors, it holds director's back when they're [00:41:00] becoming VPs. It's very difficult for new VPs now to work with a CEO who, actually, isn't going to sit down every week with a career development plan. That's kind of the number one thing that I'm currently on the... beating the drum about the public service announcement. It is, in fact, your responsibility. And the- the- the higher up you go in the organization, you know, the less you're going to be managed and led. And the more it's going to start to look like, dare we say it, holocracy where you kind of have to figure it out, you got to have to take responsibility , you know. Once you're an executive like, yeah. It's... You- you are the person who is going to be, making the- the goals and creating the alignments and figuring that out. So that would be my number one thing.

Eiso: This is gonna be the perfect place to end today's episode on today. Thank you so much, [00:42:00] Katie.

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