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Episode 11: Reasons why managing managers is not for everyone and so much more with Katie Wilde

    Guest Biography

    Katie Wilde is currently Senior Director of Engineering at Snyk Cloud and has played other roles like VP of Engineering at Ambassador Labs and Buffer. She co-authored the O’Reilly books “97 Things Every Engineering Manager Should Know” and “Atomic Migration Strategy for Web Teams” and is also co-author for the Holloway Guide to Remote Work.

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    Transcript

    Patrick Kua: Hi everyone. Today we have Katie Wilde and Katie Wilde is currently Senior Director of Engineering at Snyk and has played other roles like VP of Engineering at Ambassador Labs and Buffer. She co-authored the O’Reilly books, 97 Things Every Engineering Manager Should Know and Atomic Migration Strategy for Web Teams and is also co-author of the recent Holloway Guide to Remote Work. Welcome Katie to the podcast.

    Katie Wilde: Thank you so much for having me Pat. I’m very excited about this podcast.

    Patrick Kua: Me too. You’ve got such a fascinating background. You studied philosophy, economics, have a Masters in management and strategy and before I understand it right, a certified financial analyst, and ran your own digital agency. So what’s your story about getting into tech and starting to lead?

    Katie Wilde: Gosh. Well I would say that I’m a curious person and so I think this industry is a great fit. I meet a lot of people who have the same fundamental curiosity. And that’s what got me into tech. It’s just neat that you can think of things. You can build them. You can make things come to life and I’ve really found that translated even more strongly into leadership where that kind of curiosity of what is happening here? Why are people behaving the way that they are behaving? What is everyone optimising for? It might not be what I am optimising for. That kind of a curiosity I’ve just found is grist to the mill when it comes to managing people and then managing managers where there’s just so much more to investigate and debug.

    Patrick Kua: Yeah I love that. I think you’re right is that our industry is so great for curious people. There’s always something new to learn. There’s always the people element which is always a challenge. And I could definitely see how that led into leading and managing people. What’s your story about getting into the management track and how did you start getting into, say managing people and then managing other managers?

    Katie Wilde: Well, I would say it’s a common story. I was working at Buffer at the time and at this time, Buffer was self-managed. There were no managers and it wasn’t going brilliantly. Which is a whole separate podcast that we could go into. But anyway I just joined. I was some roughly like lead-ish shaped engineer and I started doing a lot of things that it turns out are kind of fairly typical of engineering management, just for my peers. So because there was no management structure. It was emphatically self-managed. There were things like you had to write your own promotion cases and argue for it yourself. We had to get consensus on roadmaps and so I ended up playing a lot of these roles where I would go and talk to a PM. What are you thinking? What can we build and is this feasible? And oh I’m going to help my friend now. Like yes, you definitely are ready for this promotion. Let’s write this document. Let’s make the business case and after a few months of doing that, the organisation realised, well, maybe self-management and in various areas isn’t going the way that we’d quite hoped. I then took on the official role of engineering manager. At no point did I really receive much formal training and I’ve since then spoken to my peers. I don’t know if it’s the case today for engineering managers, you’re having their first management job, but you seem organised and like a fundamentally decent-ish human. Have at it. Like I don’t know. The first time I had to let someone go, I had to Google how to do this. It was like the Harvard Business Review was my number one resource and I have to give a huge amount of credit to the coaching that I got along the way. So I decided well, I’ve been thrown into this. I don’t have a boss. I’m reporting to a technical co-founder, who’s not much older than me and this is their first job. I don’t have somebody that can really tell me this is how it’s done. So I told myself last year I’m going to hire myself my ideal boss and I managed to get some very wonderful coaches. I’ve had a series of coaches and that was an absolutely massive career accelerator for me. Because you need somebody like that, it’s their job to tell you no, that’s a terrible idea or I think that you’re wrong in the situation. That you can listen to.

    Patrick Kua: Yeah.

    Katie Wilde: And if you don’t have that in your environment I think it’s quite difficult to make progress. So that’s something that I’m just so so glad I did. I can’t take credit for it. Actually I saw a tweet from Lara Hogan saying the biggest career accelerator for her was to hire a coach. People hire personal trainers all the time if they want to get fit. Or they go to the doctor if they’re unwell. I was like, oh yes, this is my exact situation and so and so yes, so that was very important.

    Patrick Kua: So just to reflect on what I’ve heard it’s like a) it’s really amazing because I think what you were demonstrating in that role before stepping into that EM role was really a lot of that leadership potential. Or the actions of what people would expect. So I guess that’s that formalisation and I think that journey that you talked about of being given that title, by then realising I don’t have any training am I doing the right thing is a very common experience for a lot of people. I have a little bit of selection bias because I obviously do training for EMs. But I know that there’s a whole bunch of people who don’t get that. I think everyone is looking for resources. Like HBR, Harvard Business Review or many other places today. But you’re right, a lot of people really struggle with that transition and I think it’s also very great that you also did reach out to get a coach because I think there’s also that difference between, oh yeah, this is a good idea versus actually then finding somebody and then doing that. So I’m really pleased for you.

    Katie Wilde: Oh thank you so much. Yes, and I love that you do management training because it’s something that I’m very passionate about where this is a separate profession and you should get trained. If you’re not being trained then you must train yourself. Absolutely.

    Katie Wilde: And I think I’m very grateful to have become a manager in an environment where management wasn’t the default. The alternative to me being a good manager was we won’t have any managers. And that was very important because it wasn’t the case that, of course, they’re managers. You get promoted into management. You’ll always be the manager. Now you’ve got power and you can do whatever. It was like, no, you have to prove your value to your peers, that are engineers. You need to be useful because there’s a very real chance that if this engineering management situation wasn’t meaningfully better than self-management, we would have just gone back to self-management. I think that that’s a fairly unique experience. A lot of people will say servant leader or like the job is to empower and support. But when you’re given a new role and you know, well either you figure out how to empower and support, or this entire situation, we’re just going to undo it, it gives a… it makes it very real. Let’s just say yeah.

    Patrick Kua: Yeah. Yeah, there’s definitely that credentialising. The proof and that pressure, as you say, of well this is maybe an experiment for the organisation. Did we really make the decision and that willingness to want to really make a big difference? Positive difference as a manager? Absolutely.

    Katie Wilde: Exactly.

    Patrick Kua: So you became an engineering manager and at what point did you start managing other managers? What did that journey look like for you there?

    Katie Wilde: It was a chaotic and difficult journey. It wasn’t something that and then I naturally stepped into it. And it was all wonderful. And I think it’s very important that the listeners know that this is a difficult transition, at least for me. I started managing managers when the CTO at the time decided to move on. At that point there wasn’t really a replacement and so I was in an interim leadership role. I think that was both a difficult situation and also in some ways a blessing because there was an out if I decided this is all but I can’t do it. There was a plan on paper. Well maybe we’ll go and hire a “Real VP of Engineering.” But I suppose the flip side of that, is you’re in an interim position and you don’t necessarily have a) the skills and training yet and b) the explicit organisational backing. So that was the environment with which I went into managing managers who were very aware that they’re being managed by somebody that’s never managed a manager before. Like there’s no hiding that. I must say Pat, it was much more difficult for me than the original engineering engineering lead/EM transition. The transition to managing managers. It was so much harder. And I remember my counterpart at the time, who then later on became the CEO, Dan Farreley. Yeah I was saying to him I’m really struggling with facilitating this meeting and I don’t know how to do this. And he said yeah but your management style. It’s like you walk in and you turn off the music and silence. And then you read everyone the thing and it’s like, “What are you doing?” I just remember being like, I see that. But I don’t know how else to do it. I think now, I love it. Now I actually I love the job of managing first-line engineering managers. It’s absolutely my, I don’t know if I’d say it’s my passion in life, but I just really love it. I was thinking the other day would I ever want, say, my boss’s job, say at Snyk? Where you’re only managing directors. It’s very much M&A. It’s very high level, strategic. I was like, I think I couldn’t. I couldn’t handle not being in it with managing EMs that are leading engineers. So I love it but the difficulty is you have to learn to manage without really knowing what the outcome is at a short level. And you have a very long feedback loop and that was what was so difficult for me compared to managing ICs (Individual Contributors). With an engineer. If you’re an engineer and they’re an engineer, and now you’re managing them, you can go to your Git repo. And you can go and look at the code they wrote. And so you can answer basic questions like is this person productive? There’s a factual answer. Is this person a good mentor? Again, you can look at their PR (pull request) reviews. You can see how they give feedback. It’s typically public. So there’s factual answers. And then suddenly, you get into managing managers and you’re thinking, does this person give effective feedback? You can’t join their one to ones.

    Patrick Kua: Yeah. Kind of awkward right?

    Katie Wilde: How does this person run their team meetings? Like you don’t know. Is this person? I mean, you can see the outcomes of the team. But I’ve seen teams that have had very strong engineers and a very strong PM that have been very successful despite an engineering manager who turns out was really failing. And then I’ve also seen teams that were really struggling for a variety of reasons and had that engineering manager not been extremely strong, that team would have been struggling 10 times more. So it’s just very very difficult and we can go into how do you know? How do you find problems? How do you know if a manager is doing a good job? How do you help them if they’re not doing a good job? Yeah. I love talking about all that stuff. But it’s something that was really hard for me to learn and it was really hard for me to find resources at the time.

    Patrick Kua: No, absolutely. And this is one of the reasons I’m doing this podcast. I think a lot of people have a very similar experience to you, which is, oh managing managers is the same, and then they’re actually, oh, it’s really different than what I was expecting to do with managing individual team members. I think also similarly, when you’re in that role, you’re often, once again, not given a lot of support. Maybe you’re ready for this and then here you go. bBut nobody’s helping you understand what are those differences and preparing you for some of the challenges that you’re going to have. A common theme that’s definitely come up is that long feedback cycle. The signals that you get are more subjective, tenuous. Like you said you can’t already join somebody’s 1 to 1. You can’t really evaluate how somebody gives effective feedback. And that’s a very common challenge for a lot of people who are stepping into this managing managers for the first time. Thank you for helping us understand what your journey was like and let’s hear about some of the things that you’ve learned along the way then. One of those things that you said is how do you start to evaluate how good an engineering manager is. What are some of the signals that you look for these days?

    Katie Wilde: One of the big signals that I look for these days is, is the team able to incrementally make progress? This is not to be confused with how much they ship and how fast they ship. Are they able to do milestone-based development and deliver vertical slices of value? I can just imagine I hope no one from Snyk listens to Katie-vertical slices-Wilde. But that’s one of the things that I’ve, when it comes to the job of delivering software in how incrementally are they able to break it down? When I ask an engineering manager, how’s the project going at what level of detail do they answer is very important. If you ask the manager how’s the project going and they say it’s going great, I get very worried. If they say we’ve finished take a 2.3.49 and we’re on milestone 1.4.1b sub-section I, I get even more worried. I’m like, you have lost the forest from the trees. What I want to hear is something on the level of what I would call medium detail.

    Katie Wilde:

    If somebody tells me, well, we’re able to ingest assets now. That seems to be working for this type of container image. We don’t quite know how to make it work for a different type of image. But we’re working on that and our next milestone is going to be deduplication of the assets that we’ve ingested. That is an answer that gives me confidence because I can see that the engineering manager sees both the forest and the trees. Sometimes they see only one or the other and that’s a problem. So that’s the first thing is when it comes to delivery and it took me a while to figure out what is success and what does it mean to do a good job. Because there’s just so many things that are really important. For me, it’s come down to what I tell engineering managers that that I work with, your job is to get results sustainably over time. It is your job to get business results. You are here to make the business successful. But you need to be getting these good results sustainably over time. So that means you’re not going to get an amazing result this quarter by absolutely burning your team out and then everybody leaves. Now there’s no team. That’s not results sustainably over time. You also can’t be so protective of your team that you end up going to the other extreme where that team never actually ships.

    Patrick Kua: Yeah, the happy happy team.

    Katie Wilde: And I have had that where the engineering manager mistakenly tries to create a happy team by creating a very protected team and, Pat, you will know this more than me, but I personally haven’t seen a team over a longer period of time that is happy and fulfilled that isn’t shipping. Because typically engineers want to do a good job and they want to feel pride in their work and if you don’t actually make a dent on the world by getting some of your work out there, it’s very very difficult in the long run to maintain any pride, fulfilment, satisfaction, etc.

    Patrick Kua: Yeah, absolutely. Totally agree with you. I love the succinctness of how you bring that together, which is the business value but the sustainability over time. Also what you were emphasising was improvements in progress over time. So really great heuristics that I think a lot of people can look out for. Each team, as you mentioned, is going to be in a different state from that perspective. Which does bring us onto engineering managers because when you have a pool of them or a set of them they’re also going to be at different stages. Some are maybe more experienced. Other people are really new to this. How do you work out the right level of support per engineering manager?

    Katie Wilde: You know every engineering manager I’ve worked with has wanted a different level of support. I’m a very big fan of the first 1-1 questions. How do you like to work? Bearing in mind that a lot of people how they like to work and how they think they like to work are not actually the same.

    Patrick Kua: Love it.

    Katie Wilde: So very much. The first thing is asking explicitly what level of support do you need? Some managers do very well with a much kind of looser rein. Typically if they’re more experienced, that’s something I’m very comfortable with. Others have wanted to check in with me daily or even multiple times a day. Then there’s a balance. At what point is that I’m literally unable to support that level of constant checking in? But, like with engineers but even more so you need to really tailor your approach to be different to every different manager. Learning how to do coaching is really a valuable skill. Then the other thing that I wish I’d figured out sooner was there’s coaching and there’s straight up giving advice. You need to be very explicit on when you’re doing one or the other. When you switch into, I am giving you advice now, I say it. Or if I’m saying, okay, I’m coaching you now, to work through how we’ll think about this, if at any point you want me just to tell you what my opinion is, ask me for that. If something’s sufficiently off the rails I will not go through a massive. So for example, I think an engineer is about to get unfairly fired. If there’s something dramatic I might go straight into, this is my suggestion. This is my advice. This is my expectation. It gets stronger and clearer. But that was really helpful because then I found some managers saying I don’t want you to coach me through how to do retros because I’ve never done a retro. I have no idea. I want you to tell me. Give me resources and give me the information and I’ll be like, oh this here’s the information. Other people, they don’t want to be told how to do a retro because they know very well how to do retros. It’s very patronising. They have some specific issue with their retro. So for example, the team just looks at me blankly and I say well what made you sad and the team just looks at me. They don’t necessarily need more advice. They need a co-explorator. That’s really something that’s helpful. Is adjusting your style and being comfortable in switching between coaching and advice giving. Kind of demarcating when you’re doing that and then when you’re going from advice mode into expectation mode, again, demarcating, this is no longer a tip for something you could try. This is, you have to do your performance review. You have to give this feedback back objectively.

    Patrick Kua: Yes, no I love it. I mean I think there’s a deliberateness and I think I’m hearing the emphasis of communicating which mode that you’re working in. Either through your coaching or advice giving or through expectations or feedback. I think that’s such a useful tool for people who are managing other managers. Of course knowing based on what that person wants, or what they say they want, knowing what you just talked about is the incongruence, of course, of how people say things versus what they really need. Which is of course a very human thing. Have you had to grow people into being an engineering manager? Like people who are going to become a new engineering manager?

    Katie Wilde: Yes

    Patrick Kua: How do you spot those people and what do you do to support them in that transition?

    Katie Wilde: Several times and that’s something that I really really enjoy is the growing the new engineering manager from being in an engineering role. So the first thing, which was counterintuitive, was making sure that they understand and are okay with the manager’s schedule which is very different from the maker’s schedule. So one of the first things I do, there’s a new engineering manager role opening up, I would always post that internally and often I know because I’ve been having skip levels with my team, I know who in my orbit, might be interested in management but it’s very clear that there is this role. And I would like to promote from within. From the roles of engineering.

    Katie Wilde: One thing that helped was when I would say, well, what’s it like to be an engineering manager? I’d give a little blurb of what things are. Then I would post a calendar screenshot of a typical. I would find someone who is a current EM and I would be like, who here has a calendar that looks normal this week or find a week. We can obscure anything confidential. But we post a screenshot and be like, this is what your week will look like.

    Patrick Kua: I love it.

    Katie Wilde:

    That massively helped. A very practical way to help people understand, okay, you’re going to wake up, you’re going to go into a standup then you’ll have a stakeholder meeting then you’ll go and talk to a PM then maybe you’ll have two 1-1s. Then you’ll have an hour free. But at some point you have to eat. That helps a lot because a lot of people don’t realise how difficult just schedule transition can be.

    Patrick Kua: And you still managed to find people who weren’t scared off?

    Katie Wilde: Well actually it did scare people. So then I had to say, well we teach you how to manage the schedule. Let me teach you how to adjust. But then the second thing is really understanding, why does this person want to be a manager? Is it because they see it as the next step? In which case, that’s really important to dig into what does the IC career track look like? Just make sure it’s not a upwards into management. Because management is a different job. It’s not just the next step for a talented experienced engineer. That, I found, has not often been the problem. And then when it comes to management, I want to dig into, will they naturally gravitate towards doing the types of things that are naturally EM-y. So ideally, if I know this person because they’ve been an engineer on the team, I want to know as an engineer did they gravitate towards what might be typically much more like architecture? Hands-on making decisions? Or did they gravitate more towards facilitating a group discussion? It doesn’t mean that somebody who went the hands-on way can’t be a great manager. It just means that they might be coming from a different place or looking for something different.

    Patrick Kua: Right. And are you getting this feedback through their manager or is this through you hearing about what they’re doing from other people?

    Katie Wilde: I would absolutely ask their manager. But, of course, you’re getting somebody’s opinion of somebody else. That’s a little bit third hand. So I interview them. Like I would with any external candidate. Tell me about a time when a project was going off the rails and did they swoop in and save the day by working an 80 hour workweek? Doing all the code themselves.

    Patrick Kua: I’ll just solve it myself.

    Katie Wilde: Yes. Then if they did do that, are they showing an awareness of, in hindsight maybe that wasn’t the best approach? That’s going in a better direction. And that’s why I think I should be the manager because it would be so great if all the engineering managers could just swoop in and save the day directly. And you’re like, well maybe you’re going to be more effective as a staff engineer. So that’s the selection process. And then something I’ve since changed my stance on is the tech lead/manager role. I used to be very against doing two roles. I still sort of am. But I now think that it can be, as a time-boxed role, with no more than 3 direct reports, the tech lead manager can be a very nice way to see, in practice, which way does this person go? With the explicit understanding that this is not a permanent role in the organisation. This is a temporary time boxed role. It’ll be 6-12 months at the absolute most. And then they will then appreciate naturally either into an architecture type staff/principal etc engineer path, or an engineering management path. That’s something that’s quite nice. The challenge with that is, of course, it’s very easy for that to be, oh we can just get all of our managers to also moonlight manage and code. So there’s all kinds of organisational messiness that worry me about it. But that’s a very nice way to allow somebody to explore, in a low stakes way, and in a way that allows them to save face because you can do a short term hybrid role. Then if you realise actually the people path is horrible, you can kind of veer away.

    Patrick Kua: Yep.

    Katie Wilde:

    Or if you’re loving the people part. I have seen that people naturally do tend to go one way or the other. I’m sure it’s possible that there’s somebody who that is their permanent lifelong role. But I’ve not encountered it.

    Patrick Kua: Got it. So if I understand it right, you find people who are looking to maybe step into this. Then you try to find an opportunity where they can play a tech lead manager role, where they’re leading a very small team of maximum, maybe 3 people. Where they’re both doing the technical leadership as well as the management stuff for a time-boxed period to see how well and in which way that they lean. If they’re going well into the people management space then you would then give them an opportunity to take on a larger team and drop the technical leadership side. Is that right?

    Katie Wilde: Yeah, that’s one way. With the big caveat that if the organisation supports that. Which is not always is not always the case. So of course when I was VP of Engineering in the past, well the organisation supported it because I got to decide that. Now I’m at a much bigger organisation, where I don’t get to just invent new job categories. So for better or worse. There’s also the, alright, now we’re going straight into engineering management and you will take on a team of 6 or 7. Which is not something that I’m at all against. It’s something that I’ve also done. The most important thing is skip levels. You need to do your skip levels. Like you should always do skip levels. But with a brand new manager, skip levels are the feedback loop. Getting good at them and having a relationship with the engineers, your skip level reports, is really important and making it very clear that it’s your job to make their manager successful. We all know that their manager is new at this and so therefore you are much more involved. You will be attending team ceremonies to see how it goes and provide active feedback. I sometimes provide feedback throughout. I might say I’ve noticed that Mary-Anne has been talked over 3 times. You need to do something. So that sort of thing. So I will attend their group ceremonies, however you’re using it. Whether it’s a kickoff or retro. So I’ll attend it. Give the manager feedback. I usually turn my video off and everything.

    Katie Wilde:

    I do skip levels really frequently, like every 2 to 3 weeks. That phases out. That achieves 2 things. Firstly, it gives me. It shortens the feedback loop so I can actually give the manager feedback on how they’re doing. Secondly, if something were to go quite wrong, I have a relationship with the manager’s reports, where they can come to me with the problem. They actually trust me enough. Which is always important. But particularly in the case of a new manager. I’ve not had a new manager go on some kind of wild power trip and be a terrible person. That’s not the worry. My worry is more, there’s somebody on the team who is really a bit of a toxic character and this new manager is having a really hard time reining them in. It’s starting to really affect the others. These kind of manager challenges. You want to hear about it as soon as you can so that you can help them through it. Help them to solve it and not let it fester. I mean I’m sure everyone’s been asked, what were your mistakes as a new manager? People usually say I took way too long to fire somebody. I was afraid of getting rid of the brilliant jerk because I didn’t know how we’d maintain the system. All of those mistakes. So it’s not that those mistakes won’t be made. We just want to make them sooner.

    Patrick Kua: Yeah.

    Patrick Kua: No, that’s great and I think what you talked about with that more frequent skip levels, of having that faster feedback loop and also that gives you a chance to really work with that manager. As you talked about use coaching or giving advice about how to deal with those particular situations and help them grow so that they’re not feeling like they’re by themselves, which I know a lot of managers feel when they’re thrown into that role also without a lot of support. It sounds like a great environment for a lot of new managers in that world. If we talk about your current role, how many managers are you currently managing and how do you split your time across the teams?

    Katie Wilde: Well currently, right now I’m only managing three managers which is the lowest I have managed in a while.

    Patrick Kua: What’s the most?

    Katie Wilde: The most I’ve managed is seven.

    Patrick Kua: Wow.

    Katie Wilde: And that was exhausting because they all had a full load of 6 to 8 reports. Then the limits of my system, where you do skip levels and you pop in on team managers, I really started to see the limits of that. That was when I could see, this is when you would want to bring in the director layer, where you now have these 3 managers report to this director. They are going to do. Because it gets a point where you just can’t do anything else because your calendar is just full of all the skip levels. So yeah, exactly. So that, now I know, is where the breaking point is of when do you bring in the additional layers. Of course there’s a pro and con where if you were to bring in another director, well then these managers get much more support, but then, of course, you’re now dealing with another layer of indirection which further massively complicates things.

    Patrick Kua: So if I understand it right, you have three managers right now.

    Katie Wilde: That’s right.

    Patrick Kua: We’ve talked a little bit about where you spend time with skips, going into the organisation. How do you think about your time with your team versus other parts of the business today?

    Katie Wilde: Right? So my team, I actually consider my team to be my peers. Then there’s the team or group I manage. So my team would be my product counterpart and then the other directors in my group or division and what is it that we need to jointly achieve? So that’s what I regard as my first team and how do I make the organisation successful? How do I make the group successful? How do I make them, the team, I manage successful?

    Katie Wilde:

    In terms of splitting my time? I have a habit of spending too much time with the organisation that I manage and too little time ensuring the success of the organisation that is my first team. So that’s something about myself that I’m currently trying to change. Part of it is just because I love it so much. I love managing managers. My favourite thing. So that’s something that I think very candidly, Pat, it’s important not to fall into the trap of then, you’re doing a great job with the organisation that you manage, but you’re not giving as much input and direction to aligning our joint roadmaps and making sure that we all headed in the same direction and so on. I think the ideal there would be if I could spend perhaps 30% of my time at that level. That’s something that I’m actively trying to do right now. It is so important for the success of the team you manage that you have strong working relationships with other groups. Whether you’re like me, where you’re now in a larger organisation and it’s the other directors. Or whether you are like me in the past where I was VP of Engineering but then of course there’s the VP sales, there’s the VP product. I actually found it easier to spend time with my peers in that environment because the cost of not doing it was so high. If you end up not spending enough time with sales… we all know what happens when you then suddenly get hit with what do you mean, you sold whatever whatever?

    Patrick Kua: Oh yes.

    Katie Wilde: So that’s very important and I don’t know. It motivates someone like me who cares about the team I manage and being like for them to get results and for them to be successful, I need to be smoothing the waters in my first team layer.

    Patrick Kua: Yeah, no I love that. I think that distinction is very important. I think for a lot of people who step into that managing managers role, seeing their team still as the managers that they manage versus that distinction that you make. Which is your first team being your peers. The directors that you work with. Your product counterpart. And then the organisation that you happen to manage given your current role. So I think that’s a really useful distinction and I know a lot of people struggle trying to spend as much time as they would like with their first team, like a) each one of those directors and product people also probably have very full calendars and different organisations and teams they also need to manage. So the synchronisation problem is always an interesting challenge. How do you synchronise with your first team? What are some of the rituals like on a weekly or fortnightly basis do you have to spend time with each other right now?

    Katie Wilde: Right? I am very very close with my product counterpart. We’re luckily in the same time zone. So we talk every day and that’s wonderful. So that fits the easiest. When it comes to the rest of my first team, there are two types of touch points. The first is the joint project working group type touch point. So we are going to be working on this project. So we have the working meetings and that might involve a PM from somewhere else, or design or whatever. Then the second type of meeting is the recurring. Whether it’s the staff meeting, led by our collective boss. Or the other kind of recurring meetings that we have. I am a big fan… I am actually quite introverted which surprises people but I’m a big fan of 1-1 meetings. And it was a game changer to realise that you can in fact, schedule a meeting for 15 minutes. I don’t know why this didn’t occur to me before but it’s possible. So I have taken to scheduling 15 minutes, have a cup of coffee and just how are you and just knowing, like my peer is actually having a terrible time or like things are going quite well with my peer. Like they’re happy or it’s like I can’t keep up with the slack. There are a thousand sides. It’s driving me insane. And just knowing okay, well maybe don’t slack message Barry because you know… I’m going to find another way to get him this information. I’m going to book a 15 minute calendar. I’m like, this document. Read it now. That was a game changer.

    Katie Wilde: Then lastly, having cross-cutting projects. So my current pet project at Snyk, is incident response. So I’ve taken over the incident response guild and I love this one. Firstly because I just love incident response. Like blameless postmortems. I love that stuff. I’m a curious person. What went wrong here? How did smart, reasonable, well-intentioned people end up in this situation? I just love that. Then secondly, it’s such a wonderful vehicle to get together people that otherwise, we’re all busy. You can’t just say let’s get together and chat. Or maybe someone can but I’ve found it hard to pull that off. It’s been a wonderful vehicle to get together. We do that every two weeks with other directors in other parts of the organisation. We talk about what are we going to respond to in the process. We’re going to update how we define severities. We’re going to change how we train people in post-mortems across the whole R&D organisation. That’s been wonderful because it feels productive. People come to the meeting. You build relationships. You’re jointly building this muscle of wanting to all improve together. Then when you run into the inevitable tensions where it’s like, oh well, I need to do this to close some deal in my area but I’ve got a dependency on your team and your team’s not prioritising the roadmap. If you have no relationship with this person, it’s difficult to work through those gnarly problems. But if you have a relationship that’s built on a) knowing them and caring about them and b) there are projects that you have solved together, you’ve managed to improve how we use PagerDuty schedules, whatever it is, it just feels a lot easier to approach a different problem.

    Patrick Kua: Oh great. Love it. I love the pet project approach of being able to use that to make connections and build those relationships and then give you, not just the, hey, let’s just have a chat. But actually there’s also a reason to have a chat to connect across the organisation. So great. Great example that you gave us here. If you were to step back into your past when you first started managing managers, what would be one or a few things that you wish you’d known at that time?

    Katie Wilde: If I was to step back into my past managing managers, a few things that I wish I’d known at the time? Um. I mean there’s just so much. It’s not that I can’t think of anything. It’s just trying to go back to like what are just a couple of things. I think the number one thing I would have wanted to know is, how do I keep a weekly pulse on roughly are things on track or do I need to dig in? I now have various mechanisms for that, that I have trust in the system. That I know that, at a cadence of a weekly cadence I can see the team is operating within normal tolerances or not. And that was the skill that I wish that I’d learned earlier. So the mechanisms that I have now. So there’s the weekly summary of what your team did. I only started doing that two years ago. I actually don’t know how I did it before. What is the progress that your team made? What are the problems or challenges that you need to surface to me? You don’t have to have a solution to them. If you do great. But what are the problems and then what are your plans for next week? Then I look at what they said were their plans for last week and then look at the progress for this week and they often don’t line up. Things get pushed. But if I see two weeks, three weeks, ok, you’ve now told me for three weeks in a row that next week you plan to do x and there’s three weeks where x hasn’t happened, at this point I expect that section to move into problems. It’s not bad. It doesn’t mean you failed. It means that there is some problem. What are we going to do about the problem? So that’s the mechanism. How teams show progress. Are they able to demo and all of the rest? That’s the mechanism.

    Katie Wilde: I would say the last one is having a very close trusting relationship with product because your product counterpart and the PMs involved in your teams will likely know sooner than you if things are either going very well or very badly. But often they don’t tell the engineering leaders because they don’t want to throw engineers they care about under the bus. Or they’ve had bad experiences where you go to engineering leader and with your typical like, “Hi, engineering! You’re too slow.” We’re going to complain and then they get a very negative response from engineering about how you don’t understand anything. Not having an adversarial relationship and seeing them as an asset of information and they can tell me from their perspective, how things are going. They’re not always right. But that was the other thing. I think if I were to go back into my past I had a very arm’s length relationship when it came to product. It was like, we will do engineering very well, according to all the things. Product was this abstract thing over there, which was different. You can’t really disentangle the two. I learned that lesson the hard way when it became an escalating situation of either this PM is terrible and must be fired. Or this EM is terrible and must be fired. I was like, “How did it get to this point?” That’s me and my product counterpart are like, well which one of our’s? They’re both saying that the other one is the worst in the world and isn’t doing their job. That was a massive wakeup call where if I’d been closer to my product leader peer and closer to the PMs, I think that wouldn’t have happened.

    Patrick Kua: Yeah, lovely. Amazing reflections. Lots of really useful things I think for people who are thinking about stepping into the role of managing other managers. Would there be anything that you would say to an engineering manager today that you would say okay, here’s reasons why you wouldn’t want to manage other managers?

    Katie Wilde: Yes. I would say that it can feel very abstract where you have a job that mainly involves talking to people who talk to people.

    Patrick Kua: Very meta.

    Katie Wilde: So it starts to get a little bit odd. So I have seen people really flounder because they are at that point, so far from actually building and influencing things. The second thing is if you think you’ll have more control and the ability to influence things as a manager of managers than as a line manager, you actually have less. You have these high level levers. You can change people. You can sort of change roles. But the further up in an organisation you go, the more control people think you have and the less control over any actual action you actually have. So that’s the other reason. If you’re thinking, well I want to manage managers, because then I’ll be able to like fix everything and make it happen, you may actually have less ability to affect change than when you’re closer to the decisions being made. I think the third thing is the amount of emotional labour you will end up doing is often really really high. As a line manager, there’s a component of that but you’ve very much focused as well what are you shipping? What are the decisions? What are the trade-offs? Talking about the problem to be solved. Really getting into a lot of the intellectual meat of the problem. As a director I actually have less of that. I thought I would have more. I have significantly less and the component of my job that is emotional labour. Aligning everyone’s motivations. Trying to figure out where there’s a way forward through all of the different agendas, etc. That’s a huge amount of my time. I happen to like it. But I think I also got very lucky with it because I didn’t think it would be like that. It really is.

    Patrick Kua: Yeah, lots of good reasons. You’re absolutely right is that I think a lot of people are surprised about what are some of the things that they think they are going to have, but they’re not actually true when they find themselves in those roles. So thank you so much. I’d like to wrap up now. Where can people find out more about you on the internet or reach out to you?

    Katie Wilde: Right? Well it’s a little bit difficult since Twitter first imploded. However I am in fact, on Mastodon and I am on Bluesky. So people can find me there. But really the most reliable way at this point in time is to email me at hello@katiewilde.com So honestly, emailing me is the best. Until we figure out where we, collectively, as tech people are. And if you all are somewhere that I should be and I don’t know, tell me.

    Patrick Kua: Old school email works very well. There is a website and we’ll make sure that all of these are also in the show notes as well.

    Katie Wilde: Absolutely

    Patrick Kua:

    Thank you so much for all your wonderful insights and yeah, really great lessons learned. Thank you very much for sharing your advice and your wisdom on the podcast.

    Katie Wilde: Oh I’ve really enjoyed this. I really do hope the listeners do get in touch if you have any questions. I genuinely do like it, so please do email me about anything.

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