The Secrets To Managing in All Directions with Slack Sr. Director Engineering Arquay Harris

Okay. Okay, so my name is Arkhlay Harris, and today I'm the Senior Director of Engineering at Slack, and today I'm going to be talking to you about managing in all directions. I think it's always really good to start your presentations with a quote by a really smart person. And this quote is, "Management isn't just telling people what to do." I think a lot of times when we talk about management, we talk about managing upwards and we talk about managing downwards, but managing sideways and inwards are also really important to success. And so today, through a series of quotes and anecdotes, I'm gonna lead you through some lessons that I've learned along the way. So first we're going to start with managing inwards, and that's how you can really look inside yourself and be able to be successful and understand how to manage what your own behaviors. So the first thing that I like to say is that your brain is not a cup, right? I'm sure you're thinking, what, what even does this mean? Your brain is not a cup. A lot of people have this, this view of knowledge that it's finite. That I can only learn a certain number of things and that if I, if I just learned one more thing, it's just going to be really incomprehensible. When really your brain is more like a muscle. You cannot fill it up with facts. It will not overflow. It really is just about your ability to learn new things. And so I think that if you think about the more that you exercise your mind, the more that you're going to be able to, you know, learn and grow as a manager. The second thing is we're not making rockets for NASA. So this is something that one of my old bosses used to say. And the idea here is that every single thing that you work on day to day is really important. You do— you're doing really important work. It doesn't really matter what team you're on. It's— you're making contributions to the company. However, nothing should be so important that you sacrifice your own well-being, that you can't function. Because if every single thing is important, then really nothing is important. So it's really important to always have that perspective because at the end of the day, like, we aren't building rockets. Nothing is life or death. And making sure to keep that focus and perspective can be really important for your success. Ah, ketchup is mustard. This is really obvious, right? Ketchup is mustard. So the comedian Chris Rock used to have the show on HBO called— and Tracy Morgan, who's also a comedian, he was on 30 Rock. He went on the show and they did the sketch, and the sketch was basically called The Loud Wrong Guy. And Tracy Morgan goes on the show and he starts talking about how ketchup is mustard. And he's like, he's like, ketchup is ketchup is mustard. And Chris Rock is like, what are you talking about there? Ketchup is not mustard. And Tracy Morgan is like, yeah, it is. I can prove it. Ketchup is yellow mustard. You put them both on hot dogs. You go to the grocery store, they're in the same aisle. I promise you, ketchup is mustard. And finally, Chris Rock just gets really frustrated and he's like, okay, all right, all right, fine, fine. Ketchup is mustard. And I'm sure you're wondering, what does that have to do with leadership or management, Arquay? The point is, is that a lot of times when you're working on a project, let's say you are 6 months into what should have been a 2-month project, you're super burned out and you get really frustrated. And your frustration begins to lead your decision-making. And so I think that when you have those situations, you really should take a moment and do these things. You should align on what the common goal is. What are you trying to solve? For example, there was many years ago when I was in IC, I was working on a project with a stakeholder and we were just both so tired, probably pretty sick of each other at this point, working on this project. And she, I think her suggestion was something like she wanted to add this feature to the top navigation. And I was like, "No, we don't add every feature at the top navigation. Like, that's not a good idea." And so finally I looked at her and I said, "What are you trying to do? What are you trying to accomplish?" And she said, "I really just want to feature this thing. I really wanna give more visibility." And so we brainstormed, we aligned on what the problem was that we were trying to solve, and we ended up coming up with a really good solution. And so the key there is that sometimes that alignment, that realignment, and that focus is really important. And then also sometimes just take a breath, right? Literally physically walk around the block, take a breath, like think about the problem because you really want to avoid this, the situation where you're just super frustrated and you just, just can't work with someone else because of your frustration. So we talked a little bit about managing inwards. And now we're gonna talk about managing sideways. Peer relationships that you develop, those relationships that you build really are important to your growth. In addition to keeping you calibrated and centered, it also just shows your capacity for collaboration and teamwork. So the first one is that you should always have a point of view. Now, it doesn't matter whether you are an engineering manager or an IC, you are most likely the domain expert and people are going to be coming to you for your opinion because you are the domain expert. And so a lot of times there'll be times where I'll see conversations in Slack where people will say, Well, you know, we could do A or we could do B or this or that, you know, sure. Because as previously mentioned, we're not making rockets for NASA. We can technically do anything. But you should say something like, we could do A or B and I think we should do A and here's why, right? Because again, I think sometimes people are reticent to really have a strong opinion about a thing. And so they kind of like, you know, equivocate. And I think that you should always have a strong perspective and that really helps with your peer relationships. And then also speaking of this, you should also not be afraid to escalate. There'll, there'll be times when you'll work on a project and some decision will happen and you just, in your gut, you just feel it. You're like, ah, this isn't, I'm not quite sure this is the right decision. Now I say sparingly because you don't wanna just be running, especially if you're in a senior leadership position, you don't wanna just be escalating or hyper-escalating all the time, but you also don't wanna be the I told you so person who's, who's says, "I knew this was a bad idea." Well, you probably should have said something earlier. But I think, you know, people have a misperception about escalation, and they think that it's tattling, and that's not really the point. The point is to make sure that the key stakeholders or the key decision makers or DRIs have all of the information that they need in order to make the best decision. We should ask, "Should we?" not "Can we?" I really don't think that we ask this question enough. I think that a lot of times, particularly in the tech field, we get really infatuated with all of the fancy things that we can do, but we don't often stop and ask whether or not we should do a thing. So, so just because we can do something doesn't mean we should. And we should always, always, always consider the cost. And now cost doesn't mean dollar amount, although it can, depends on your industry or what you're doing. Let's say you want to add this new feature and it adds a considerable amount of code complexity. Now the cost of that is if someone has to come behind you to look at that code or has to modify it later, that could be an incredibly costly decision. Or maybe you can rush out this thing in a month, but it means that you're going to have to work all of your developers every weekend. And that can have a massive impact on team morale and also attrition. And so then you might think, well, maybe the cost is too high. We maybe should not do this thing. And so I think it's always just something to keep in mind to ask yourself this question about, like, can we, should we do a thing before we're actually doing it? Ah, this is one of my favorites. Most people say they like feedback and most people are liars. Spoiler, really sorry. They're good people, but they're also liars because how many, oh, So this is funny. It's like sometimes when I, when I ask questions like this, I'll say like, how many people out there have heard? So we'll just pretend, I'll pretend that virtual hands are raising, but how many people have ever heard someone say, I love feedback? Yeah. Everyone has heard someone say that. And it's usually not true. When people say that, what they mean is I would like you to tell me the least offensive thing about myself and mirror it back to me in a way that mimics feedback. That's really what, because real feedback is hard to take. And not only is giving feedback hard, but we have, there's a lot lot of material and classes and seminars about giving feedback, very few about receiving it. Right. Because that's, I think that's even harder. So then what does that mean? The first thing that you want to try to do is really be direct. You want to talk to people, not about people. And it's really hard to resist that temptation because you're with your work bestie and you know, you're in there and you're just like, ugh, this jerk, I can't believe this person did this thing. But Because feedback is a gift and not a punishment, you really should take the opportunity to give that person the feedback directly. I often say to peers and definitely people who report to me that if a 360 comes around or some sort of perf review and anything on that is a surprise, I have failed you. How bad would it be to be in a situation where someone says in a review, like, oh, you know that thing that you did, that thing you did 5 months ago? And you're like, what? You've been sitting on this for 5 months? You should have told me 5 months ago. And so I think, uh, really you shouldn't save it up and it should never be a surprise to the person receiving it. Um, another thing that, that I've seen that's very common that people do is, um, tell me if you've heard this one. You're, you're working on a project with someone. Let's say you're an engineer and you have this kind of really you know, let's say strident PM hypothetically, and they're just constantly talking over you, or maybe they're dismissive of what you're saying. And then what happens? The project ends. And so of course the behavior stops cuz you're not working on that project anymore. And so then you don't give the feedback because you're like, well, it's getting better, right? That, that person hasn't done that again. And I akin that to being buried up to your hand in quicksand. Like, yeah, you can still look at your fingers, but you're also still sinking as well. And so I think that rather than save up that feedback, you should give it Because then, then what's going to happen, of course, you work on a project and you get to crunch time again, and maybe stresses are high and that person repeats that behavior and now they are a repeat offender. And so the resentment just grows higher. So I call this out specifically because it is just a very common thing that I see happen. And it's something that, you know, just take the opportunity to say, hey, you know, that thing that you did, I know it was a couple of weeks ago, but I really like to talk about it. Nothing matters if you drop the baton. You know, you can have the fastest runners. Anyone who's ever done anything with track and field, you can have the fastest runners, but if you drop that baton, nothing else matters. You may not be, depending upon the race, you may not be instantly disqualified, but you're most likely not going to win. And so how that relates to leadership is if you can't work together, Like really, really nothing else matters. And one of our executive leaders at Slack was quoted as saying, "How we work together will be our competitive advantage." And I know a lot of you are in hypergrowth startups as well. And I think every day you'll see startups for whatever reason, maybe they fail or maybe they don't perform in the way that you think. And there will often be this narrative of, yeah, you know, they just couldn't work together or, They were unable to execute on their vision. And that really becomes important, particularly as you scale. It becomes even more important because what was perhaps a problem when you had 50 people just becomes exponentially, you know, worse when you have 500 people, 5,000 people. So now we're going to talk a little bit about managing upwards. And managing upwards generally will take the form of advocacy. Either for yourself or for your team. But it's really important to master this skill, particularly if you have aspirations to progress in your level or your role. Talking about your accomplishments is not arrogant. This is a very, very common misperception. People think that, you know, talking about your accomplishments, it's like bragging or it's being boastful or it's really like in poor taste. And it really isn't true. You are really helping the decision makers, your management, you're giving them information and context that they might not have. So I think a way to think about it is that you are, you're helping to paint this complete picture. And so for example, I consider myself a pretty good manager. Don't fact check it. I mean, just take my word. I am a fantastic manager. It's true. But even if you consider yourself a good manager, I can't know every single thing that you've worked on. And even if I could, I'm not going to know the nuance. I'm not going to know every single relationship that you've built. I'm not going to know every single piece of code. There's just details that I won't be able to have access to. And think of it as you are helping provide that context. And so it's not bragging. It really is, again, it's information providing. It's also very important. When you do this to provide clarity. So if you have this internal goal where you're, where you're thinking, oh, someday I would like to be principal engineer, or I'm a senior manager and I hope to be director someday. And you haven't, if you haven't articulated that to your manager, if you're just thinking, well, I'll just keep working and someday my manager is going to anoint me with this next role. Nope. Because they, they could be like, well, maybe you love being a senior manager and that's your, that's your sweet spot. So, you know, providing that clarity is very, very important. And stating that your goals is really important for your personal trajectory. This is definitely, I think, one of the most important quotes if you want to do any sort of managing up. So self-calibration must absolutely precede self-advocacy. I hold weekly office hours here, and often someone will come to my office hours and they'll be like, Arquay, I am crushing. I am, I am, I'm performing at like a G06. I'm a principal, I'm staff. And I'll be like, nope, you are not calibrated. You are, you are maybe a high 4, right? And I don't say that in a mean way. But I think a lot of people just aren't, aren't calibrated. And advocacy, particularly self-advocacy, isn't about just blindly stating I'm the best, I'm the best, I'm the best, promote me, I'm the best. It really is making sure that you are demonstrating the the requisite level of excellence for a sustained period of time. And this is important too, because what does sustained mean? That very much depends on your level. If you're trying to go from associate to maybe engineer, sustained could be a few quarters. It could be, you know, a year and a half. If you're trying to go from senior manager to director, sustained can mean years, right? So it's very important to understand the expectations of where you're trying to go and to really make sure that you're calibrated as you advocate for yourself. So then that's easy to say that. So how do you do it? Right. So the first thing is that you really have to ask yourself the hard questions. And similar to receiving feedback, it's really difficult because it will make you question your perception of yourself. Right. So, so if at any role that you have, it doesn't matter what you do, there's probably someone at your level who is just doing everything right. They're excellent. And you really have to say, am I making the same level of impact that this person is? Am I closing the same number of deals? Am I writing the same pristine code? You know, am I really doing everything that that person is doing? Or am I, am I just sort of, you know, comparing myself to, you know, it's easy to compare yourself to, if there's a spectrum, it's easy to be like, I'm doing way better than that person who is maybe close to being on a PIP, right? Like no one, no one No one compares themselves to the upper part of the spectrum. But I really do think that if you want to really be serious and get to the next level, you really need to ask yourself those types of questions. And so then after you've done that, you should make connections. I think most people, most people will grant you some time, right? If you go to someone and you say, and you say, hey, I really love that presentation that you gave. Can we get a 30-minute coffee? People will grant you that. And I think there's a lot to be learned. And I also think it's really beneficial if you go, who is the person who is just brutal? Like brutally, they take radical candor to just a high level. Seek out that person. Be like, hey, you know, I'm really thinking about doing this thing. What do you think about it? So just, you know, because maybe it's a terrible idea. You should definitely not do it and you are not calibrated. And knowing that is going to be really helpful to your own personal growth. And then also I just like to say pay it forward. Even if you're at a more junior level or starting out in your career, you probably still have some, some things and some knowledge that you can share with someone else. So, you know, just as you want to help other people help, just as you want help with your own calibration, it's important to pay it forward for those who also need that level of help. Ah, if it is important that I be there, it is important that I pay attention. Anyone who is in, on my teams know that I kind of have a thing about laptops. Laptops are great inventions. We love them. Not so great in meetings. And many studies have been done on this. Feel free to Google it. But it is honestly not possible for a person to devote full attention to two things. It's just not. Like you may devote some partial attention to many different things. And I know, I know, I know you're all special. I know you're special and you're able to do that, but most people are not. And I think that this, this whole thing about things being important enough for you to be there is really important because time is the most precious commodity to a leader. I don't know about you all, but my calendar is just packed every single day. And time is so precious because any time that I'm doing something, anything, I'm not doing something else. And so think about the leaders who you really admire. All right. There's exceptions that prove the rule, but most of them in meetings are pretty engaged. They're paying attention. They're asking really hard questions because they could be doing anything else. And so I think that's really important. And then it also is a level of self-awareness that is involved because if you are not fully paying attention, particularly in a situation where you're main— like if you're with execs or, you know, someone who, you know, I don't wanna say like outranks you, but someone who like is higher in the management chain. That the message that you're sending is that your time is more important than everybody else in the room. And that, like, you know, you're just so busy, you gotta, you gotta answer this email right away. And so one of the things that prompted me to sort of make this quote or the slide was many years ago, we had an intern and we have this thing called workshop and the intern came and everyone's paying attention and they're engaged and the poor interns, they're at the table and they're on their laptop. Now, This is where the situational awareness comes in. If you're the only one doing anything, I'm, I promise you other people notice. If, if you're in a room and everyone's eating an apple and you're eating an orange, people notice that. They're like, who's the orange eating person? Right? And so I think, uh, it's really important to have just that level of situational awareness. I understand that every company is different and culture varies, but, um, you really wanna just be really cognizant of that when you're managing up and then you're in these situations. Um, So now managing downwards. This has to do with managing your team. How you position yourself as a leader really impacts, you know, your ability to have a successful team. The first one is lead like people are following. I think that people don't listen to— like, if I ask someone on my team to do something, they don't do it just because because like I asked them to do it. They do it because in most situations I've earned their trust. And I think a lot of times people have this idea that, well, I'm in the big chair, like I, you know, I'm in charge, like people better listen to me. And that's really just not how human nature works. And so, because ruling by fear is not a durable mechanism, people have to want to follow you. If you think that people— no one, not a single person listens to what you say. They watch what you do. And so when I say lead like people are following, if I am the type of leader who I yell at people or I'm super rude or, you know, I belittle them and it's— yeah, their team's going to do that too, because it is very true that culture is what the leader allows. And so when you look at organizations that have a high level of dysfunction, I guarantee it's because at some level generally at a high level, that behavior is not only tolerated, but rewarded in some ways perpetuated. And so I really think that when I say, you know, lead like people are following you, you know, you have to really be cognizant of the decisions that you make. And the fact that particularly if you, if you lead a large organization, that, that the way that you behave really trickles down to your org. In a crisis, blame doesn't matter. True words, so true. Years ago when I was a young developer, I made this really, really bad coding error and it broke things. It was really terrible and I was terrified. All right, sure. I mean, I could have written tests, but people didn't really write tests back then, trust me. But yeah, it was a mistake and I was terrified. And my boss at the time, he said this to me, he said, "In a crisis, blame doesn't matter." And now this wasn't this kind of, you know, sensitive, touchy-feely, like, boss. He was kind of a stern guy. And it really made quite an impression on me because it's something that I've carried with me and have tried to implement on my team since then. And, you know, what he really meant by this was in the moment, It is really important to fix the issue. Even accountability doesn't matter in the moment because you can always assess the crisis and figure out what happened later. Because the other thing is that when you have situations like this where it's an incident or whatever, there's generally some systemic reason for why that mistake was allowed to happen. Like maybe we should have had better linting or maybe we should have had a different quality process or whatever it is. And that's just always something that you can assess later. What's really most important is that you just learn from your past mistakes because it can be really, really tempting to kind of point that finger and be like, who broke this? Who checked in this bad PR? But it can be really, really destructive in a crisis. Okay, perfect. I'm not that funny. I love this one because I took one of my teams out for lunch a little while ago and I was sitting in the middle of the table and I noticed that every single time I started talking, people would just naturally look at me and then I would say something not even really that funny and people would laugh and I'd think, oh, really? I'm not that funny. And that's very clearly because the hierarchy had set in. And I think once you get to a certain level, or even if you're just starting out, if you are in charge, you have to remember that your words have weight. If you are even a staff engineer and you're talking to an associate, or if you're, you know, a director and you're talking to someone else, there is a certain level of reverence that happens. People are gonna look up to you. And so there's no such thing as an offhanded comment. I tell my managers this all the time. So if I just, if I say like an offhanded thing, like, ah, you know, maybe we should change these 404 pages. Yeah, you are setting a thing in motion. People are going to like strike up a committee. They're going to start looking into whether or not, and you were just like, oh, I was just spitballing. Right. And so you have to be like really clear about, hey, this is a directive. I really like you to do this. Or it's a suggestion. I'm just saying it. So really consider that. And then never forget what it was like to be junior. I think a lot of people, especially when they first enter into management, they think, well, we're all the same. I'm one of you. You're what? We're the same. We're on the same team. Nope. No, you're not. And also think about when you were just starting out. I guarantee that probably the person who was, you know, the senior in your leadership chain, you were a little freaked out by them. You sit a little bit straighter when they came around. And it's one of the reasons why I, for example, don't socialize with my team. Occasional, like a lunch or holiday thing or something like that. But, but my very presence changes the dynamic. It goes from, oh, we're all just relaxing and having lunch to, oh, the boss is here and we got to stand straighter. And that varies from people from person to person, team to team. But for me, it's very important because I very much believe in be friendly, not friends. This is a hard one because especially the way that we work together today, we all, you know, technology brings us together and there's not this like bureaucratic, bureaucratic levels that you might have had some years ago. But for me, I think I became an engineering leader the way that a lot of people became an engineering leader, which is, uh, people were like, my boss was like, you're the most technically proficient person on the team. Have you ever thought about management? And I was like, no, let's do it. Um, and so then what happens is all those people who are your besties, uh, you're hanging out at KTOs, you know, every night you're just having fun. Um, and then now you have to tell these people what to do. And it's really hard because, um, I think it's very important to establish boundaries. And it took me a long time to learn that in my career, because if someone messes up or you need to give that person hard feedback, you're going to be like, ah, I can't, Scott's my best friend. I can't, I can't say something bad about Scott. And so it's important very early on to establish those boundaries. And that's why I say friendly, be friendly. Like I love my team. I have right now, I think the best team I've ever had, but I'm not friends with them. And that's just, that's just how it goes because I actually do you a disservice if I allow any sort of personal feelings that I have for you to impact the way that I help you in your career and help you grow, then I am actually cheating you out of your own advancement. And so I think it's important to also develop that community because your first team, your first team is not your team, is not the people who report to you. It's your peer managers, your peer directors. It's other people who are cross-functional stakeholders that work with. And because at the end of the day, it really is more important to be respected than to be liked. Because, you know, it's really— that implicit hierarchy exists anyway. So I think, I think really the main point is that it's important to just really establish those boundaries. And this is my most favorite management chart. And I'll kind of end, this is like the last of the managing in all directions slides. And the source is, it's pretty well known. Sylvia Duckworth did the illustration. And as you all, as many of you all are doing, you're working at these hypergrowth companies and things are changing all the time. And it is a rare, rare management scenario where you have every single one of these things accounted for. But I think it's important. I refer back to this all the time. When I'm rolling out a new thing or trying to, to, you know, introduce a new change. Because even if you don't have all of them, you can kind of think about it and be like, okay, well, which ones don't I have? And which one— how can I fill the gaps? So for example, I'll start with vision. If you roll out something or you try to introduce a change and you have not clearly communicated the vision, that's going to lead to confusion. So let's say that you're like, Well, we're going to do this new internationalization strategy. And then you're like, we're going to start in Belize. And then everyone's like, well, why Belize? And you're like, well, okay. Or like, how does this impact our goals? Or what is the currency in Belize? Or you just haven't explained anything. You haven't explained what the vision is, how this fits into the company. I mean, maybe the reason is that you just want to have a really killer offsite in Belize. I'm not really sure. But the whole point is that that will 100% lead to confusion and questioning if you haven't no one really communicated what that vision is. Second one is skills. If you, let's say that you say to an iOS developer, "Hey, you know what? I'm gonna give you a new task. I want you to rebuild the job queue." Now, maybe you have that rare developer who can just do everything, but that person generally does not have the requisite skills to do that task. And even if they did, you know, because it's just a totally different technology and that's probably not what they do every day. So that person's gonna have a lot of anxiety. What you'll hear managers say a lot is they'll say, no, no, no, this is a growth opportunity. And you're thinking, that's not a growth opportunity. A growth opportunity is something I could grow into. This is a Kobayashi Maru. I have no idea how to do this. And you are giving me this task and I am very anxious about it. The next one is incentives. So if you were to say to your team, great news, everyone, we're now going to be working Saturdays every single Saturday. No, you're not getting any more money or bonuses or there's not even going to be free pizza, but yay. Yeah, massive resistance. No one is gonna wanna do that because you have not incentivized them to do that thing. And it doesn't even necessarily have to be a financial thing or any sort of monetary thing. It just like, you have to give someone some sort of incentive to want to do this kind of new thing. Resources. Oof, this is my favorite. I think this is the life of an engineering manager. You know, it is not uncommon where someone will come and they'll say, You all did really great last quarter. How about if you did twice as many projects as you did last quarter? Oh, more headcount? No, no, no, no. You're not getting any more headcount, but yeah, but can you just do twice as many things? Massive frustration. And I think, you know, sometimes you have to do this and this is what I mean about you're not gonna be able to address every single check, every box on this chart. Sometimes you do have to do this. Maybe it's really important for you to do this because just for this, just one quarter. Because we need to hit this deadline or we need to hit like some conference or whatever it is. But if that becomes a regular thing, there is likely going to be a problem. And then the last one is action plan. And I see this one a lot because I think sometimes in leadership positions we get excited by the idea and we don't fully think about the implications of that. A real-life example could be something like You want to roll out a new deploy process, but you know, you didn't, you don't have the tooling. It's all set up, or you didn't actually talk to the people who use it. And so there's just like a lot of problems or you didn't write down. So basically the point is like you're rolling it out, but then you have to be like, oh, we didn't think of that. Oh yeah. How does this work on this platform? Or, you know, you're sort of constantly, constantly false starting because you didn't fully think out what it is that you're trying to do with this kind of really complex change that you wanna make. And so I really, again, like, I really love this chart because it just really provides like a lot of, it just kind of refocuses and centers. And so when I think about making a big decision, I'll sometimes do an exercise where I'll run it through this to be like, have I checked all the boxes or which ones am I missing? Lastly, this is the last one. It's my job to listen more than I talk. Ironically, I've been talking this whole time, but you get my point. So I think whenever you are leading a team and you're managing in all these different directions, you're not going to get it right the first time. You're going to have to iterate. You're going to have to take feedback. You're going to have to situationally lead the people who report to you, and you're going to have to manage those peer relationships and those up relationships. Sideways, all around, 360. And so I think that the whole point is that listening more than talking is, is a surefire way to get to some good results. Key takeaways really quickly. 360 relationships are important, but it's important to not over-index on one thing. A lot of people spend a lot of time managing up because they think that that's the sure the surest and fastest way to success. But sometimes it's like a tree falling in the forest. If you don't spend any time nurturing those peer relationships, then did it even happen? Would you have people who would advocate for you? Do people actually know the impact that you're making beyond just the person who's, you know, above you and your leadership chain? You got to, you got to persevere. Trust. You're not just going to instantly get people to trust you or your team to trust you or even the people who you report to. It definitely takes time. And then the last thing is I kind of went into it in the previous slide, which is you got— you have to iterate. Because again, like, we should, we should be brave enough to experiment. Because again, we're not gonna get it right on the first time. All right. Thank you so much. I understand that we have some questions, so I'm happy to answer any questions that people have right now. So.

Great session so far. We've got quite a few in the queue. I'll start from the beginning. When considering costs, how do you handle senior executives pushing back on your decision to not follow through with a project?

And I wonder, I'm assuming that in this case, the person means like not monetary costs, but just like, like kind of general costs. I think that Generally, we don't do anything in a vacuum. And it's not like we can just kind of make it. And most people's working situations, you can't just like make a decision like that. And so I would say that if I was in the situation and senior executives are pushing back, if you just say, look, we can't do this, or this doesn't make sense, or I don't have the resources or whatever it is, I think I think the key is to think about the ketchup as mustard and try to see if you can align on whatever the goals are and really try to get some understanding. So if they're just like, if you're like, look, we just absolutely physically cannot get this done. Do you understand that? And they were like, well, we don't care. We need it done. So then you need to come to be like, well, I need more people, like, or something. Because generally when people like push back, there's a reason, right? Like maybe this is something that is really important to the board. Maybe it's important because you have some sort of ARR targets that you've hit and it's very, very important for you to launch this feature. There's always a why. And particularly if this is coming from the most senior levels of leadership. And so I think rather than approach it of a like us versus them or they're making me do this thing, I would just really, really exercise just an extra, extra dose of empathy and try to see from their side. What it is that they're objecting to and how you can kind of come to some consensus. And sometimes you can't, I'm not gonna be disingenuous. Like sometimes you just can't and you have to also decide, is this a situation where I just have to rally and do it? Or if this is just something that I'm really willing to just draw a line in the sand about. All right. Hope that's helpful. Great.

We've got, how do you split your time to be close to your team, customers and stakeholders? Any advice that you can provide?

Yeah. I think that that very much depends on where you are in your, in your sort of leadership journey, right? Because I think, so for me, if I'm new to a company or I've had situations where I've taken over teams or gained new responsibility, the amount of time that I'm going to spend focused on that team is going to be increased because I'm really digging in. I'm trying to really understand. I'm meeting with people. I'm really trying to do what I call the 3 L's: look, listening, and learning. And so the ratio is very much going to, going to be different there. And then later, once I kind of am up to speed, I'm ideally delegating more things to leaders on the team that I can trust. And then I'm spending generally more time there doing kind of sideways management. I'm spending more time with my peers. I'm understanding how my organization can, can be more impactful cross-functionally. And so I think that that's kind of the answer. It's, I would, I would say like, and you would, you should probably assess where you are and then also assess what you're trying to do. If, if for example, like maybe you're on the team and you think, you know what, we really want to do this big, we're going to take this big swing by the end of the year. We're just going to go all in. And you might have this very specific goal that's going to also impact how you split your time.

Next question, for smaller teams who spend so much time together initially, How do you manage the be friendly, not friends, especially when you go from contributor to leader?

Yes, that is a very fair and common question. I think there's, there's no, um, there's no easy answer. And I don't want to make it seem like I'm just a mean, a mean old Grinch robot who just doesn't talk to my teams ever. I think, I think friendly can be, it's a spectrum, right? For some teams, friendly is we do Secret Santa and we have lunch together and we, you know, we have a knitting club, whatever it is. And, and, but I think where you need, it really just is about your own personal boundaries. If, for example, you find yourself making decisions that you wouldn't normally make because of your friendship with this person and not because of the professional boundary that you set as this person's manager, then you have a problem, right? Because what, what can also happen is that the other thing that I try to really be cognizant of is like the impropriety of it too. Like if I'm friends with someone, it takes a really strong person to be like, well, I know what this person can do. They're, they've just delivered. They're my friend. Let's give them all the good projects or let's favor this person. Or do I, do I instantly, you know, favor this person's opinion on a particular design spec because I know them, you know, like I know them. And so I guess there's no right answer because it really is going to vary from team to team. But I think you have to really do that sort of hard work and be honest with yourself and decide if you're making decisions and you're really respecting those boundaries. And here's a, here's a litmus test that you can have is like make a scenario like this person brought the site down. They, I don't know, they had a data leak, they did something really terrible. Would you be able to go to this person and say, you really messed up, or this person has really terrible communication skills and you need to tell this person like, hey, you need to fix this. Would you be able to do that and, and, and worry about, or would you be more worried about hurting your friendship? Right? If the answer is you couldn't do it, then you probably need to set clearer boundaries.

Got so many great questions coming in. Next one. What's been the biggest challenge on your team since shelter at home?

I think, well, it's a couple of things. The first is we have had now a lot of people who have started and spent their entire time working from, working remotely. Like, it just, you know, and it's been a little while, we have people who have spent their entire, an entire year working remotely, which is pretty mind-boggling. And so Making those people feel welcome and acclimating them to the team is pretty challenging because a lot of things that you do, you just take for granted. It's like, oh, we'll have an offsite, we'll do a team lunch or we'll whatever. And you can't really do that. So you have to be really creative in terms of the ways that you can, can have bonding and sort of community. So that's been really challenging. And then the other thing is, I think, I think there is something having to figure out these ways to replicate the tap you on the shoulder kind of thing. You know, there was a lot of time in the day where you're just like, you know, I'm just going to walk over to that person's desk and just ask them in 2 seconds. And you have to do the whole like calendar thing where you're like, okay, is that first free? Can they Zoom right now? So it's like, you know, there's pros and cons to that. I will say on the pro side, though, from working at home, Zoom, it has in certain ways leveled the playing field because even there's definitely remote people who work on my teams and you would have that just one person on the Zoom scenario, just the one, the one person in the box. And I, you always feel a certain level of empathy for that person because they can't hear people eating lunch and banging the plates loud and whatever. It's just a really awkward scenario. And now, you know, everyone is just can, you know, you have the same opportunities to speak, your voice can be heard in the same way. And then another thing that it does that I thought of the other day that is kind of an interesting byproduct is conference rooms, right? In the past, it would be like, well, you know, we can only have a room for 10 or this 6-person room or whatever. And so a lot of people's presence and meetings were really gated on your ability to find a conference room. And now what I've I've taken the opportunity of doing is if I have some of my senior managers and maybe they want to observe how a certain process goes, you can be like, oh, you can just be on the Zoom and they can even have their camera off and no one even knows they're there. And they're able to get that sort of additional access or, or learning that they maybe wouldn't have been able to do. And like, cause you're trying to find a room.

Very true.

Yeah.

Very popular question. Everyone would love to know your favorite leadership book. Books and podcasts that you recommend?

I can't pick a favorite, can I? Um, I, I don't know. It's such a hard thing. See, here's the thing, I'm gonna plead the fifth on this question because if I say, if I say a favorite, then people are gonna be like, why didn't you say my book/podcast? Um, but, uh, I think, I think SaaStr, for example, is a really good resource. I don't have a favorite. They're all my favorite. Is that— I read all of them.

Fair question. Fair question. We'll take one more because we're at about time. What are the challenges you've overcome in firing someone?

Ooh. Yeah, sadly, this is the very hard part of the job. I would say in early in my career, when I've had to let people go, the— I learned, I sort of learned a lot of lessons and I kind of developed my own North Star around performance management. And I always ask myself these 3 questions. I literally just had this conversation with yesterday. Like, I always ask myself these 3 questions. The first question is, was I transparent? And honest with this person? Meaning, is it not a surprise? Have, you know, did they know this is coming? The second question I ask myself is, did I do everything I could to support this person? Right? Like, was I secretly hoping that the PIP wouldn't work out the right way? Like the best case scenario of a PIP or any sort of performance management is like they come through it and I've definitely successfully managed people out of PIPs before. So the second question is like, you know, did I support them? And the third, and maybe the most important question is, did I act with integrity? Right? Did I, you know, was I like rooting for them? Did I talk about them behind their back? Was I disingenuous? You know, that integrity piece is really important. And so in terms of the challenges, I think early on in my career before I kind of developed this, this, because a couple of firings that I had, like they sometimes they don't sit well with you. And I noticed that what I've seen in some environments is that people will watch people fail. Fail, right? Like everyone will be in a situation where you have a person on the team and they're not performing and everyone knows they are not performing, but no one will say anything. It's that whole feedback piece where you're talking about a person, not to them. And so rather than— I vowed that I would never just watch a person fail. I would either be direct with them and say, hey, you need to improve in these other ways, or how can I help you? Or, you know, maybe because maybe they're oblivious and they have no idea. But, but yeah, it's the short answer is there's no easy way to fire someone. It never feels good. You always wish that you could do what you can. But if you, if I answer those questions and I feel like I've done everything that I can, I've tried to support them and it still just isn't working and I've acted with integrity, then, you know, I've done what I can and it's probably the right decision. Sorry.

We've got one final question if you're up for it. What are some of the games, competitions, and activities to encourage team bonding and motivate your reports, direct reports?

It's so hard in this remote world. This is a fun activity. This is a completely random thing, but it's something I just thought I've done. Hello?

Yeah, you're on. Sorry about that.

No, no worries. So this is a more like a holiday thing, but I've done this with every single team that I've managed and it is the best results. Everyone's so happy. It's not exactly like an offsite type thing, but it is a bonding exercise. So I grew up like pretty meager means and I really believe in like giving back and being of service. And so every year I would give my team a budget. Like one year it was like everyone gets $50 or whatever. And we go to a toy store and you can, you buy toys and then afterwards we donate the toys to Toys for Tots. And why this is such a great activity, one is because everyone just, you see people's personality, like the number of people who buy Legos or like, I, of course I bought roller skates, but you really see people's personality in the toys that they buy. But they also have so much fun because this isn't a thing where like, oh, I'm getting swag. You know that you're doing something that's really going to make a difference in a kid's life. And so that That is just something that is really important and a really good bonding activity that I've done.

Love that question and answer. We had some great questions and some great insights from you. Thank you very much. We're right at time, but we were able to take the majority of the questions that came in, which was great.

All right, thank you so much. Thanks everyone, had a great time. Bye-bye.