SaaStr Podcast #404 with Slack Sr. Director Engineering Arquay Harris: “The Secrets To Managing in All Directions”

 

Ep. #404: The benefits of managing upwards and downwards are frequent management topics. However, managing sideways and inward are also important skills for a successful leader. Learn new ways to build strong teams by managing in all directions from Arquay Harris at Slack.

This episode is an excerpt of Arquay’s session at SaaStr @ Home 2020. You can view the full video here.

 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
SaaStr
Slack

Transcript:

Announcer:

This is SaaStr’s Founder’s Favorite Series, where you can hear some of the best of the best from SaaStr speakers. This is where the cloud meets. Up today, the secrets to managing in all directions with Arquay Harris, senior director of engineering at Slack.

Arquay Harris:

Okay, so my name is Arquay Harris. 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 going to lead you through some lessons that I’ve learned along the way.

Arquay Harris:

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 your own behaviors. So the first thing that I like to say is that your brain is not a cup. I’m sure you’re thinking, “What even does this mean? Your brain is not a cup?” A lot of people have this view of knowledge that it’s finite, that I can only learn a certain number of things, and that 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 can not fill it up with facts. It will not overflow. It really is just about your ability to learn new things.

Arquay Harris:

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 learn and grow as a manager. The second thing is we are not making rockets for NASA. 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’re doing really important work. It doesn’t really matter what team you’re on, you’re making contributions to the company. However, nothing should be so important that you sacrifice your own wellbeing, that you can’t function. Because if every single thing is important, then really nothing is important.

Arquay Harris:

So it’s really important to always have that perspective because at the end of the day, 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. Ketchup is mustard. This is really obvious. Ketchup is mustard. The comedian, Chris Rock, used to have this show on HBO, 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.

Arquay Harris:

He’s like, “Ketchup is mustard.” And Chris Rock is like, “What are you talking about there? Ketchup is not mustard.” And Tracy Morgan is like, “It is. I can prove it. Ketchup is yellow mustard. You put them both on hotdogs. 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, “All right. All right. 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 that a lot of times when you’re working on a project, let’s say you’re six months into what should have been a two-month project, you’re super burned out and you get really frustrated.

Arquay Harris:

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, many years ago when I was an 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. 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 in the top navigation. That’s not a good idea.”

Arquay Harris:

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 want to 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. Literally physically walk around the block, take a breath, think about the problem because you really want to avoid the situation where you’re just super frustrated and you just can’t work with someone else because of your frustration.

Arquay Harris:

So we’ve talked a little bit about managing inwards. And now we’re going to talk about managing sideways. The 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.

Arquay Harris:

And so a lot of times, there’ll be times where I’ll see conversations in Slack where people will say, “Well, we could do A or we could do B or this or that.” 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.” Because again, I think somehow people are reticent to really have a strong opinion about a thing and so they 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 fear, you should not be afraid to escalate.

Arquay Harris:

There will be times when you’ll work on a project and some decision will happen and in your gut, you just feel it. You’re like, “I’m not quite sure this is the right decision.” Now I say sparingly, because you don’t want to just be running, especially if you’re in a senior leadership position. You don’t want to just be escalating or hyper-escalating all the time. But you also don’t want to be the I-told-you-so person who says, “I knew this was a bad idea.” Well, you probably should have said something earlier. But I think people have a misperception about escalation and they think that it’s tattling, and that’s not really the point.

Arquay Harris:

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 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.

Arquay Harris:

But 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 can 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, “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, “Should we do a thing?” before actually doing it.

Arquay Harris:

This is one of my favorites. Most people say they like feedback, and most people are liars. Spoiler. I’m really sorry. They’re good people, but they’re also liars because… This is the funniest. Sometimes when I ask questions like this, I’ll say, “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”? 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.”

Arquay Harris:

That’s really what… Because real feedback is hard to take, and not only is giving feedback hard. There’s a lot of material and classes and seminars about giving feedback, very few about receiving it because 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’re in there and you’re just like, “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.

Arquay Harris:

I often say to peers and definitely people who report to me that if a 360 comes around or some 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, “That thing you did five months ago.” And you’re like, “What? You’ve been sitting on this for five months? You should have told me five months ago.” And so I think, really, you shouldn’t save it up and it should never be a surprise to the person receiving it. Another thing that I’ve seen that’s very common that people do is, tell me if you’ve heard this one. You’re working on a project with someone, let’s say you’re an engineer, and you have this really, let’s say strident, PM, hypothetically.

Arquay Harris:

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 because you’re not working on that project anymore. So then you don’t give the feedback because you’re like, “Well, it’s getting better. The person hasn’t done that again.” And I akin that to being buried up to your hand in quicksand. You can still move 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 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.

Arquay Harris:

And now they are a repeat offender. 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 just taking the opportunity to say, “Hey, that thing that you did, I know it was a couple of weeks ago, but I’d really like to talk about it.” Nothing matters if you drop the baton. 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.

Arquay Harris:

And so how that relates to leadership is if you can’t work together, really, nothing else matters. And one of our executive leaders at Slack, he was quoted as saying how we work together will be our competitive advantage. And I know a lot of you are in hyper-growth 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 they will often be this narrative of, “They just couldn’t work together,” or, “They weren’t able 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 worse when you have 500 people, 5,000 people.

Arquay Harris:

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 common misperception. People think that talking about your accomplishments, it’s bragging or it’s being boastful or it’s really 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.

Arquay Harris:

So I think a way to think about it is that you’re hoping to paint this complete picture. So for example, I consider myself a pretty good manager. Don’t fact-check it. Just take my… I’m 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 built. I’m not going to know every single piece of code. There’re just details that I won’t be able to have access to. Think of it as you are helping provide that context. And so it’s not bragging. It really is, again, information providing.

Arquay Harris:

It’s also very important, when you do this, to provide clarity. So if you have this internal goal where you’re thinking, “Someday I would like to be principal engineer,” or, “I’m a senior manager and I hope to be director someday.” 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 could be like, “Well, maybe you love being a senior manager. That’s your sweet spot.” So providing that clarity is very important and stating your goals is really important for your personal trajectory.

Arquay Harris:

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 proceed 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’m performing at a G06. I’m a principal. I’m staff.” And I’ll be like, “Nope, you are not calibrated. You are maybe a high four.” And I don’t say that in a mean way, but I think a lot of people just 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.”

Arquay Harris:

It really is making sure that you are demonstrating 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 a year and a half. If you’re trying to go from senior manager to director, sustain can mean years. 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 it’s easy to say that. So how do you do it?

Arquay Harris:

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. So 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? Am I really doing everything that that person is doing? Or am I just comparing myself to…?” 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.”

Arquay Harris:

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 will grant you some time. If you go to someone and you say, “Hey, I really loved 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? They take radical candor to just a high level. Seek out that person.

Arquay Harris:

Be like, “Hey, I’m really thinking about doing this thing. What do you think about it?” Because maybe it’s a terrible idea. You should definitely not do it and you’re 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 things and some knowledge that you can share with someone else. So 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.

Arquay Harris:

If it is important that I be there, it is important that I pay attention. Anyone who is on my teams know that I 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 is not. You may devote some partial attention to many different things. And I know, you’re all special. I know you’re special and you’re able to do that, but most people are not.

Arquay Harris:

And I think that 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 anytime that I’m doing something, anything, I’m not doing something else. And so think about the leaders who you really admire. There’re exceptions that prove the rule, but most of them, in meetings, they’re 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.

Arquay Harris:

And then there 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 with execs or someone who, I don’t want to say outranks you, but someone who is higher in the management chain, the message that you’re sending is your time is more important than everybody else in the room. And that you’re just so busy. You got to answer this email right away. And so one of the things that prompted me to make this quote on 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.

Arquay Harris:

And the poor intern, 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 promise you, other people notice. If you’re in a room and everyone’s eating an apple and you’re eating an orange, people notice. They’re like, “Who’s the orange eating person?” And so I think it’s really important to have just that level of situational awareness. I understand that every company is different and culture varies, but you really want to just be really cognizant of that when you’re managing up and then you’re in these situations.

Arquay Harris:

So now managing downwards, this has to do with managing your team. How you position yourself as a leader really impacts your ability to have a successful team. The first one is lead like people are following. I think that people don’t listen to… If I ask someone on my team to do something, they don’t do it just because 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. I’m in charge. People better listen to me.” That’s really just not how human nature works, because ruling by fear is not a durable mechanism.

Arquay Harris:

People have to want to follow you. And 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 I belittle them, their team’s going to do that too, because it’s 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 lead like people are following, you have to really be cognizant of the decisions that you make.

Arquay Harris:

And the fact that, particularly if you lead a large organization, that the way that you behave really trickles down to your org. In a crisis, blame doesn’t matter. True words. So true. So years ago, when I was a young developer, I made this really bad coding error. And it broke things. It was really terrible, and I was terrified. All right, sure. I could have written tests, but people didn’t really write the test back then, trust me. But 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 sensitive, touchy-feely boss. He was a stern guy.

Arquay Harris:

And it really made quite an impression on me because it’s something that I’ve carried with me and I’ve tried to implement on my team since then. And 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. Maybe we should have had better linting or maybe we should have had a different quality process or whatever it is.

Arquay Harris:

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 tempting to point that finger and be like, “Who broke this? Who checked in this bad PR?” But it can be really destructive in a crisis. 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 a 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 think, “Really, I’m not that funny.”

Arquay Harris:

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 a director and you’re talking to someone else, there is a certain level of reverence that happens. People are going to look up to you. And so there is no such thing as an offhanded comment. I tell my managers this all the time. So if I say an offhanded thing like, “Maybe we should change these 404 pages,” you are setting a thing in motion.

Arquay Harris:

People are going to strike up a committee. They’re going to start looking into whether or not, and you were just like, “I was just spit balling.” And so you have to be really clear about, “Hey, this is a directive. I’d really like you to do this,” or, “It’s just 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. 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 senior in your leadership chain, you were a little freaked out by them.

Arquay Harris:

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. The occasional lunch or holiday thing or something like that, but my very presence changes the dynamic. It goes from, “We’re all just relaxing and having lunch,” to, “The boss is here and we got to stand straight in.” And that varies 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, technology brings us together and there’re not these bureaucratic levels that you might’ve had some years ago.

Arquay Harris:

But for me, I think I became an engineering leader the way that a lot of people became an engineering leader, which is 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.” And so then what happens is all those people who are your besties, you’re hanging out at Katie O’s every night, you’re just having fun, and then now you have to tell these people what to do. And it’s really hard because I think it’s very important to establish boundaries.

Arquay Harris:

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, “I can’t. Scott’s my best friend. I can’t say something bad about Scott.” And so it was important very early on to establish those boundaries. And that’s why I say be friendly. 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 how it goes, because I actually do you a disservice.

Arquay Harris:

If I allow any personal feelings that I have for you to impact the way that I helped you in your career and help you grow, then I am actually cheating you out of your own advancement. So I think it’s important also to develop that community because your first 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 you work with. And because at the end of the day, it really is more important to be respected than to be liked because that implicit hierarchy exists anyway. So I think really the main point is that it’s important to just really establish those boundaries.

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Published on December 3, 2020

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