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The Value of Being Direct

with Eisar Lipkovitz

July 9, 2020
The Value of Being Direct
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Eisar Lipkovitz - EVP of Engineering @ Lyft

Eisar is Executive Vice President of Engineering at Lyft. Prior to Lyft, Eisar spent 15 years at Google in various leadership roles, overseeing the tremendous growth of that business while streamlining operations and reducing product complexity. Since 2014, his team of several thousand engineers built Google’s Display, Video, and Apps Advertising products.

"At the end of the day, the main reason I think direct is effective is you actually get to the core of the issue where a lot of people dance around the details and they're conflict-averse."

- Eisar Lipkovitz

Previously, Eisar worked on the infrastructure behind Google Search, driving many innovations during a tremendous increase in scale and a transition from web to structured data. Prior to that, he worked for four years at Akamai during the explosive growth of the Internet. Eisar began his career at Israeli Air Force after graduating from Tel Aviv University with B.Sc and MBA.


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  • Why being direct is more effective and how to practice the art of direct communication (2:27)
  • How to overcome conflict aversion and the fear of being direct (9:16)
  • How to prepare yourself for a direct, difficult conversation (13:14)
  • How to balance communicating vision and strategy vs. the details (16:42)
  • How to navigate conversations when people don’t understand you (20:31)
  • How to make your conversation more direct when someone is speaking ambiguously or in code (26:07)
  • How to help junior engineering leaders grow (28:29)
  • Where people typically get stuck in the engineering leadership career track (32:59)
  • How inclusion creates environments for more direct conversations about real-world challenges (36:26)
  • What has brought you the greatest amount of joy as an engineering leader? (38:00)


Why being direct is more effective and how to practice the art of direct communication

Jerry Li: welcome to our podcast Eisar It's really exciting to have you here.

Actually have the opportunity to spoke to quite a few people at Lyft that worked with you in the past or right now. one of the things really struck me, is, How direct you are and how effective that is. So I think being direct is very important thing for a leader, especially the ones who are higher level.

Can you talk a little bit about your perspective on being direct and how that helped you to become an effective leader during your journey?

Eisar Lipkovitz: It's an excellent question. So actually directs and journeys is an important combination of things, right? Because, I have been direct, you know, for many years. and, I thought I was direct and only when I got better at being direct, I understood what being direct actually means. I think it is a lot more effective. I think majority of the people would appreciate it. However, it's a dangerous path to follow. and I also think that I have been helped by the fact that, in the past, it was less dangerous to be completely honest. and what I mean by that is, you know, things have changed, especially in the world, more so maybe in our industry and, and, you know, Especially in many parts where tech is concentrated in Northern California in particular, where people like honest and direct feedback, there's a lot of sensitivity . And it's very easy to accidentally or unintentionally being too direct with people and, get to a pretty bad outcome.

at the end of the day, the main reason I think direct is effective is you're actually sort of get to the core of the issue where a lot of people dance around the details and they're conflict averse, right? So they're trying to sugar coat stuff and they tried to be vague, hoping the person will understand. They're trying to avoid hurting people's feelings and all of it is actually legitimate.

So if you switch to no filter, it's, it's not very effective, right? so this is the art. I think what I would encourage people to do is try to be more direct, know what your initial bias is, . If you're very conflict averse, I think anything you will do to be more direct will land fine because ultimately, your bias is the opposite so you will be careful.

However, if you are naturally direct, I think you need to be careful in how you do that. You know what I mean is you need to learn the art and you also need to be paying huge attention to your audience. And the last thing I would say huge difference between private conversations, one on one versus public conversation. the key insight here is , praise in public criticize in private.

It doesn't mean that you cannot violate it . You can, but you have to start with that. So what it means is, you are in a sort of meeting with a large group of people . And , somebody did something that disappoints you, or you strongly disagree with a person.

If you do it in this forum , when you give direct feedback, it ends up being criticism of a person, right. Most people can't take it because essentially you humiliate them in public. That's the only thing they can think about right?

I think it has multiple implications , to the person, they feel that they got humiliated in front of other people. It often is the case also at a larger meeting. There's like the boss, if you're the boss, there's some people work for you and other people, so essentially you create this situation where somebody is working for you as being humiliated by his or her boss in front of his or her team.

Jerry Li: And that could send a real message to the rest of the team.

Eisar Lipkovitz: Yeah. I mean, that's the other problem. I was like, even if the person can take it right. And he, or she has sort of like totally comfortable with that. The team just by virtue of being more junior, don't actually . Understand what happened. Right.

Now what then usually happen is most people are not , failing there. Right. You know, there was sort of very careful not to criticize people in general. Especially in the large group. What they don't do is they don't do the criticize in private. whether it's because actually as a leader, you thought the meeting went well, it's fine. I don't know why, but let's pretend that there was something you didn't like about the outcome of the meeting with the decision or, you know, how that person held on to stuff or whatnot. Right. You need to follow up! And that's where most people fail. . Because you'd only just need to follow up. You need to follow up in a time and the fasion, Because. You know, can talk about later, but if you give people feedback, the first thing anybody would ask is, can you give me an example?

And you know, for what it's worth, I have no idea if this is because the person have no idea what you're talking about or, you know, and they actually want example, or they're trying to argue with you and they're, you know, they're trying to, you have to prove them that your feedback is based on examples, but it's like standard, right.

There's two things I learned in my career this is one of the feedback. People want an example. And if you start a war, every body wants to know what's the exit criteria. So, two different things, but just humans are very predictable. So why it does it matter? Because if you want to give people feedback, you know, you need to do it as soon as you can, because otherwise you will forget, they will forget. And then you go into this sort of a complicated discussion of, " it's your opinion And it's not very timely.

so I think that's a pattern. And by the way, I'm not saying that every meeting we'll have to have a followup meeting, right. It's just time consuming, but, , I think it's a thing that you need to do. And to be clear, I was mostly talking about sort of. Situation where people were pointing to, but the same with, like peers, or just people you work with. and it's not even necessarily a disagreement, they just piss you off or whatever.

you schedule one-on-one and you can do and follow up. Right. and the other thing I would say on that one is the sort of the "I" sentences, It took me years to understand it's another standard procedure. It's not what you did. It's how what you did make me feel...

Because, you know, at the end of the day, it's the same thing. It may sound to some people like touchy feely, but it's irrelevant. The point being is it's not whether you did something wrong. It's like, what, what you did made me feel that way... and you can't disagree with that now. Now whether you wanna do anything about it, is your choice. But that's another thing that I strongly encourage people to use.

probably the most useful leadership skill, I think I've learned is to be flexible and adaptive. People have biases, but you need to be able to work with a lot of different kinds of people. the ability to know how to work with them is prerequisite, you know, and then you need to know how to do it, and then you have to choose whether you want to do it.

Jerry Li: And that's a hard thing. It can be a piece of art. So how do you get to know who that person is? And how do you adapt internally? Do you have a like example we can sort of expand on?

Eisar Lipkovitz: Yeah, that's an excellent question.

I think that, Now that I know what I know... when I sort of get to work with new people, I try sort of at the beginning of the relationship, try to have these conversations,

the more senior you get, you would find yourself when you people that some of them are sophisticated enough to try to tell you upfront, how they like to work with you. Or they ask you, how do you like to work? With that's great.

In other situations, other people I need to initiate the conversations. and even if you initiate, it doesn't mean you can't reach an outcome. But in general, if you have an opportunity to have these metta conversation , it's not about a topic it's like, how do you like to work? It's a good thing to do. It's a good thing to do with one-on-ones with people in general.

How to overcome conflict aversion and the fear of being direct

Jerry Li: Going back to the first topic we mentioned of being direct. And you mentioned, a very useful fact that there's a spectrum of how people are being direct. Some people are naturally, conflict aversion. And for them it's important to be aware that they probably need to be more direct, but there are other people they have less filters. and the thing that they should watch out is being too direct.

So, when I talk to, especially the more junior engineering leaders, I think a lot of them have the, issue of being afraid of being direct . they see themself, as you know, we're nice people . but there are cases they have to have a conversation, deliver the bad news or, critical feedback. But this is always hard and they have internal dialogue that should I do that? Should I not do that? the longer they waited, the more difficult that conversation become. Eventually, probably just not having that conversation at all.

what kind of suggestion do you have for them and, what kinds of internal dialogues that you have, when you struggling having that conversation?

Eisar Lipkovitz: so let me actually start with the first thing you mentioned about how to be direct ineffectively. I think the three things is I want to avoid. I think if you are direct, you have to be least emotional as possible. So if you're angry it doesn't lend very well. Right. So you have to be neutral.

I think that if you want to be direct with people, you should choose what to be direct about. And it's just generally things that people can change. That's the other thing. so just focus on the least that you can, and just try to be neutral. It's very important, right? So if you're not in that position to do that, just don't do it.

but back to your question about people not feeling comfortable, you know, I think a lot of people are not. I was watching, Chris Rock, just the other day, I missed that 2018 Tambourine, piece, he has a piece afterwards about, schools have , no bullying policy. , I don't want to steal his thunder. But he does a terrific job of basically pointing out that if you eliminate bullying from schools, you don't actually fix the problem because people deal with bullying in the real world later, and they don't know how to deal with it. And it's much better to expose them when they're young.

I mean, it is an exaggerated point of view, but I still think that as a society, we, you know, became a lot more sheltered. So therefore, when people see a behavior they don't like with another person, they know what to do.

So it's challenging for people to be direct. I also think that, given that our industry has a lot of introverted people, you know, more so on average, I guess... those folks that are moving into management are often self-selected a little bit more, kind of easy to work with kind of people. I can see why that's a big challenge.

To answer your question, you sort of have to try and you need to get better and get more comfortable with that. And like anything you should try when the stakes are low, it's the same thing about public speaking or whatever, just do it. Do it in situations that if you screw up, the cost is less. See how people react and get better at that.

so I will try to do it all the time and just try to get better that and tried to like fight your biases. And you also can start slowly, when you have conversation in person, and you should just say, well, I want to give you a feedback out. I want to have a conversation. You know, forgive me. I'm going to be blunt or direct.

You have zero downsides from prefacing. It actually helps people do understand what you're about to say, rather than guessing where this is going . I think these are some basic tricks. We just do it and then look at the person and be ready to back off.

Jerry Li: Yeah, so start by pointing out the direction of the conversation but meanwhile also be willing to calibrate

Eisar Lipkovitz: yeah. people have a hard time with it, but you know, life is not a popularity contest. Like you should be ready to the outcome that, some people don't like you. It is what it is. You know, if you want to make sure everybody likes you, you could be successful at at that. Whether you'd be successful at anything else? I don't know.

How to prepare yourself for a direct, difficult conversation

Jerry Li: So I think that if you get to the bottom of that is the fear of not being liked or the fear of like hurting your identity.

So how do you prepare yourself for those? Are you just ready for that?

Eisar Lipkovitz: So I think that, This sort of the process of learning, right? I mean, I'm going to go a little bit abstract here, but , the general process of learning and , improving in something involves this sort of obsession and fear of not doing something cause you think it's going to be difficult. You think it's going to be something you want to succeed in? You get such stress out or whatnot. public speaking as a classic example, I've seen people that are do it. half an hour before the event, you see them pacing and trying to keep themselves busy and.

You know, like it's just natural. I'd like, you need to be top of your game just could be a better outcome. but so there's a lot of opportunity to spend too much energy preparing and then you just stress yourself the heck out.

I actually think that, you know, finding a time, before this conversation to think about what you want to say is a good thing, but maybe, in, in general, like so busy before works for me better. , because otherwise by the competition starts, you're just super nervous.

Right. So, you know, like make it concrete example. you look at your schedule, you see, you gonna have this conversation with the person tomorrow. You think about what you're going to say. Right. , then I would literally try to pack my day with meetings before. So I won't be sitting there, you know, stressed out about that meeting. , let's say I'm meeting this person at 11. I'm not going to make my nine and 10:00 AM am like crazy stressful meetings. It's not a good idea, but just, you know, keep yourself busy.

Patrick Gallagher: the pacing example you shared just makes me laugh because that's exactly what my routine looks like before going up and introducing our different events. I'm manically pacing in the background, frantically rehearsing what we're going to say, but I really appreciate what you said about like stressing ahead of time. Isn't helpful because that's going to make you, you know, say something and be rigid and not communicate well up there. And I think you boiled it down. So simply it's just really about just know the quick things, the bullet points that you want to say. And the thing is, is like, if you are clear with that, the message is gonna be a lot more natural because you'll be using more of your words and language.

Eisar Lipkovitz: That's right. You wouldn't need to prepare them to think about it. You know, like public speaking like it... especially if you're doing presentations, which I do not do, like I'm much better at like what we're doing here. So that's the one off I have a general agenda. I'm happy with Q and A. But if you, for example, if you do these like big events, these kind of Google IO or whatever, Dreamforce, why'd, you come in and it's a bigger keynote , like 10 minutes, everything is on. You actually have to practice the heck out of it. I've seen a lot of very well known people that are very good public speaker. They practice, there's no way around that. But before the event, they, they just try to distract himself.

I mean, the other thing, which is sort of a digression here, but, I used to meditate. I don't do much of it now. I mostly do yoga. But this whole act of, of sort of getting, distracted and not letting your thinking process just drive you nuts. Because you're just trying to calm your mind and do something else. You can do it by walking. You can do it by riding a bike or whatever. Its actually incredibly important for people in general that have high stress job. But it's like, especially in moments, you know, when you prepare yourself for that. So anything to keep your mind off it is good.

How to balance communicating vision and strategy vs. the details

Jerry Li: So transitioning the topic a little bit, talking about communication, last time when we had a conversation, you mentioned about the balance between, being abstract and also being detail oriented while having a conversation with, especially with upper management.

can you share your perspective on that?

Eisar Lipkovitz: Yeah. that's an important tension. So, what I found is in general, most people when they listen to a person, describe something, right.

Have bias or a tendency to prefer the people that sound, sort of more high level abstract, visionary, you know, strategy... Different words that essentially when, you described the topic , you sort of start top down.

Practically speaking. it's always better. it's better to be optimistic and pessimistic. There's just things that unfortunately, or fortunately, whatever you're looking at are just truths, right? The trouble is a lot of the people who are naturally good at that are often unable to explain anything in details. Either they just don't think it's important. They only don't understand any of these details.

if your job is to set strategy or vision, that's great. But , if you're in a smaller group of people and you're just telling them what the plan is, and they're like, okay, fine. So, you know, what next step would you do next? And you are stuck. It's not actually useful.

Now conversely, the people who are often most close to the details and the weeds When they describe stuff, very bottoms up and it just comes across the scatterbrain. It's just like people can follow.

you get into these traps, because, You know, especially in a business meeting, not where you have cross-functional is like, let's be honest, right? If you have like a product manager and engineer and a sales person in the meeting, you know, the odds are, is the engineer will be the one that will go into the details way too fast. Right.

And the problem with that is the other people can't understand by worse. you know, you would be looked down upon, right. You know, one of those engineers or whatnot, and people won't even understand what you're saying

I've found that in general, you want to sort of start, higher level. Make sure You've been touching on the right point and then go down into the details. And this art of going up and down, this sort of stack is, is, is very difficult. especially if you talk to people, it doesn't matter if it's public speaking or sort of meetings, or 1:1 conversation, you just check that they understood what you said.

How to navigate conversations when people don't understand you

what I found is most people are uncomfortable admitting they have no idea what you just said. And it's anywhere from like, well, I was on my phone. I was thinking about my cat and I wasn't paying attention.

Right. Because it happens all the time , the funniest ones is when, you know, and I don't know if you had this experience in a meeting where, you know, there's a meeting with all those people, somebody. Like two people are talking about something let's say it's like the most senior person in the room with another person. And then the conversation goes into some other topic and you most, mostly listening to me go to this person. "And what do you think about it?"

And you know, the person had no idea what you're talking about. Right. And you can tell from the body language. You know, the reality is only a minority of people would say, I'"m sorry, I wasn't following. I wasn't paying attention."

Other people try to angle, you know, like sort of start rambling or ask followup questions to try to guess what the heck you just said. And this is terrible. Right. And, you know, I use this extreme example because, senior people, you can quote, you got caught. It is your boss. I can see why some people think it's terrible, but in reality, that's not the case. Right? you would be surprised how many people get so much credibility from admitting, anything from, I wasn't paying attention to like, I'm unable to understand what you just said.

Now the other issue here is the more common one is people talk a little bit abstract because it makes the conversation, crisp. And , people say they understand and agree, but they don't actually. No either because they don't understand what this expression mean or it's ambiguous.

Right? So these are the most common patterns. And, unfortunately if you're trying to deliver some sort of something nuance, you know, you actually have no idea if people understand what you are saying. one of the things that I find the most effective, . Is, let me play back to you.

So, you mentioned that the meetings where, and it's another pattern. I encourage people to adopt, where you're being talked to and somebody's asking you to do something and you want to make sure I understand. If you're the recipient, you should just say the following. "Let me play it back to you what I think I heard. And tell me if that's what you want me to do."

Now, if you're the person trying to deliver some information or communicate something, you know, you can actually demand people to do that. Right. How about you tell me what you think I said.

You can't always do it. Some people get defensive when you ask them to do that. But, you know, that's the best way. Cause if you just ask people, did you understand? It was always yes. You know, a number of meetings that I see people talk. You have a lot of people nodding? You have no idea,

Jerry Li: yeah and this is super risky because people leaving the meeting... assuming that we're on the same page, but they go off and doing very different things. And then later on when things are discovered that there are gaps, if you're like confused or angry, because that's not what I...what I took away from the meeting. and having those checks early on is, it's definitely going to be a lot cheaper , to correct.

Eisar Lipkovitz: Yeah. I'm actually just to build on that, I mentioned earlier that, you know, I get angry often. it's almost always because of that. and what I'm trying to say is even when I try super hard, right. I still end up with this outcome incredibly often.

Patrick Gallagher: I appreciate kind of underneath all of this that when you're direct and honest with people and that's coming from a place of goodwill and graciousness, you being direct is actually you trying to be really gracious to the people you're working with. These things become infinitely easier if you're honest and direct with people and that's agreed upon and how you're operating.

Eisar Lipkovitz: the key word you said is graciousness, it's an excellent word, which I should have touched on before and to be completely honest, this is something I'm still working on. Right. You know, and, and the people who know me even few years ago, I don't know would use the word gracious to describe my behavior. Right. So I, I, I think that, you know, for some people it comes more naturally, right? But these are the people who are usually not very direct. if you end up being direct, yeah, gracious is a very good, side adjective to accompany.

And I think using these sort of catch phrases, , like, "can you play back what I just said?" another thing that people do a lot, which I, like, is "tell me more?" somebody said something, you don't like what they said, you may be smart enough to understand there's a chance you missunderstood what they said.

So instead of jumping into their own conclusions, just like, you know, force him to say more, right. Because, it, you know, and at the end of the day, it's either like a trick in some ways to , kind of, like I said, something very clear and somebody says same or because they don't like what I said, that's fine. I'll clarify.

I think it's another way to address the fact that what somebody said might be ambiguous. And somebody is literally telling you, like, you know, I think you need to clarify.

Patrick Gallagher: I think that's such a powerful way to get past the the ambiguity, like you mentioned, cause then that, that directly gets to the heart of whatever's being unspoken. Or if somebody is using code language to describe something or trying to allude to something. "Tell me more about that" opens up. Like, no, it's directly talking about that and really...

Eisar Lipkovitz: by the way, the funny thing about it is. I sort of gave up on trying to understand people's motivation, right? Because when people speak in code language, right.

You know, I used to think if somebody didn't speak direct they just sort of conflict diverse or trying to be vague intentionally. But I discovered is many people do that because they think it makes them look smart. they're more crisp, know, or they don't want to be come across as rambling or, or too, too in the weeds?

Or why do I need to even explain that? Right. Everybody knows what THAT is. it's just crazy. And I do think it is getting worse for what it's worth

How to make your conversation more direct when someone is speaking ambiguously or in code

Jerry Li: Do you have an example well, that sort of helping the audience to get a bit of color for that?

Eisar Lipkovitz: I'll give you an example. So, I sent an email to one of my folks trying to ask him if we can make some changes in UI. And he got back to me and he's like, "yeah, I agree with you. We should do it but were constrained." End of sentence. I'm sitting, this is an email I'm like, what does it mean? It's like, what do I do with that?

Like do you, therefore you didn't even tell me if we're not going to do it right. You didn't tell me what we constrained by. Do you want me to do something about it? I have no idea what you said. And you know, this is actually an example where I actually, it's a good example. I fell into the trap, right? Because you know, at this point you can try to. Get the outcome you want, which is what I do. I said like, "okay, I'm sorry. I have no idea what you mean. Like, are we constrained by what, like the code doesn't work? Marketing doesn't let you change the language?

I mean, they're all legitimate constraints. So I took, you know, something short and abstracting made it into multiple choice questions and spoonfed that person. And the reason I did it is because I want the answer in the email to be what I want, which is I'll get what I need to know , whether the person got it. I don't know, for all I know he was just brief and he was busy doing something else and, you know, typed constraints enter moved on. You know, I don't know why.

If he didn't want me to have this conversation. Cause here's the thing about that email, by the way, I've been in that situation. If I were sending that email, it could have been the last email on the chain. There's a lot of people who will be fine with that answer. And you have no idea if they don't understand that it doesn't mean anything. Or they just don't care.

Jerry Li: yeah. That's a good example. Is it felt like the email is, half completed. So there is things should be said, but not , being said

Eisar Lipkovitz: And the reason I know that I'm not alone with that is I've talked to a lot of people, especially for the junior people, say you're the director level, or whatever you're sitting in a meeting or whatnot, or you're on an email thread?

And you see this exchange and you know, you don't feel in a position to challenge the person who made that statement. And nobody else does, and you're sitting there like what just happened here? I don't know,

Jerry Li: and those examples, if not handled correctly, that just compounding to potentially some harmful cultures and people just follow the behavior.

How to help junior engineering leaders grow

So another thing I want want to talk about is, in terms of career growth for, engineering leaders, I think the are two folds of it. One is how do you see helping, people who are on your team or more junior engineering leader to to grow, to a more senior level. What are the challenges when people typically get stuck?

And also, what are the insights you've got, reflecting from your own journey?

Eisar Lipkovitz: I think I've helped people, you know, in that mission. but it's not something that comes naturally to me. if, I'm having conversation with this person, somebody needs help and asks a specific question, I'm happy to answer. and also, especially people working for me or maybe one or two levels below. I have given them advice and feedback in the context t hat hopefully made them a better person.

Now, the last thing, and then,I 'll answer the question more specifically is I think that, you know, setting a tone in meetings. You know, like even the examples we just spent on, you know, sort of tell me more, or what do you mean is actually an incredibly powerful way to get people be more successful. It's the lead by example kind of thing. Right. and, and you just give people an alternative approach to some management that I find effective. And, you know, at the end of the day people pattern match. Right.

now back to your question, I think that the biggest thing that you can do as a leader is to give people opportunities. Because like in the end of the day, Especially now a lot of people can look at their career growth as this sort of like promotion thing. You're right. I could stand on there. Like most people, you know, you can use this code career, but like when people want to have a conversation with me like 99% of the time, it was like, I'm at level X. How do I get to the next level? ,

but I, I think one of the things that we... I've seen happen at Google, and I know a lot of other companies sort of adopted it. And I know it existed before in the sort of the likes of Microsoft and Suns and whatnot. Is you, especially in engineering, you create a very clear structure around levels with numbers and meanings, and you start writing a bunch of at the end of the day checklist. so if you want to get promoted, you need do X, Y, and Z.

And unfortunately, a lot of people use that is what they consider the benchmark for career growth. I think it's a problem, right.

That said, many of these things, even if they're not about levels and scope. The best way for people to learn is to give them an opportunity that is sort of above your current capabilities. Either they swim or sink. So, as a leader, you know, my bias has always been to when possible to promote from within.

what you need to do is over time, sort of who is ambitious, who was interested, who has some potential. And when an opportunity opens up, take a chance on people. And by the way, the take a chance isn't just not hiring somebody else to fill that job. Job is also moving the person from what the heck they're doing.

That's another big problem that all of leaders fail on. so you have like two people, three people reporting to you. One of them leaves, you can go hire another person or give the job to somebody else. You have a hole... you know, and so people like, well, I can get some new talent from the outside. That's great. And I don't have to have two new leaders. Right. So they often, people who have an existing job get screwed. Right.

So to me, that's the best thing I think I've done too for people over time. And I continue doing that, but you know, the rest is mostly, mostly around just having conversations with people. I mean, I also think that using coaches and, and sending people to classes, is, you know, not all of them are great, but it is useful for many people.

Jerry Li: Yeah . Because as an engineering leader, first of all, we're very busy and also we're not an expert on everything. And, areas other people need to grow, or get better at, it could be, well beyond our capability

Eisar Lipkovitz: yeah. I mean, if somebody has communication problems, for example, which is pretty common, right? Whatever, it could be anything from even an accent or whatever. Right. I got, what am I going to do about it? I actually know about some people in the industry that have done that. I think it's worth it. But it's clearly not something I can help somebody with

Where people typically get stuck in the engineering leadership career track

Jerry Li: Yeah, yeah, that takes a lot of skills just to, to coach people on that. There's people doing that as a living for a long time. So better leave those to the experts.

Where do you see, typically people get stuck in, leadership, career track? what are the break through moments that are sort of important for them to go past that?

Eisar Lipkovitz: So I'll start with maybe a slightly different version of stuck, but I've seen that pattern a lot. I think one of the things that makes our industry quite unique compared to so many other professions, by and large, many of the most effective managers are also highly technical, right? There are some industries where literally somebody in a management job could even come from completely different. You know, they're just good management, .

I think it, with engineering and particularly for a difficult and often the people are most effective are actually very reasonably talented engineers. Maybe not the best, but you know, reasonably talented. And, then you know, some of them, get into management by some accident, maybe myself included and many of them in the middle of their career kind of realize that actually it's not worth it. the other thing which we have in our industry which is sort of weird. So we are this, if you rise up enough and you're the right company, you probably, at some point in your thirties, forties don't have to work anymore.

So then it's kind of like why? You know, cause this whole management thing, I I'll be completely honest. It's not easy. Right. Why bother? So that's, you know, and I bring it up cause it's not an obvious failure mode, but. It is incredibly common.

I think what happened its usually lose the ability to learn, and I'm not sure what it is. And I actually found myself into that trap and it kind of scared me. I, you know, you just get older and you have like family and stuff. So if you become comfortable and you sort of realize you can't get to the next level. And you just don't even try, like, why bother.

And the third category is the people who are, it's almost the opposite. It's like the people who are not patient enough, right. So they essentially, They're running away from themselves. Right. So, you know, they get to a particular level and they go to their boss and they're like, you know, I'm X, you know, I think I should do X plus one. Make it happen for me.

And, and there's two failures mode. One is like, well, your boss doesn't have an X plus one job for you. We don't, you just have to wait. Like it's not even personal. The more common one is like, "no, I need you to work on something." And they're like, yeahhhh..." You know, like whatever.

And because we have this very you know, liquid job market, they running away from stuff. So they've gone, going to. Somebody else that will give them that job, right? Like Google, for example, is such a huge company that you can literally move between organizations every few years. And the problem with that is like sooner or later, like first of all, you're never going to fix your problems, whatever they are. And sooner or later people will form an opinion of you.


Jerry Li: Yeah. And that brings up the point...

Eisar Lipkovitz: the only thing that helps you is people are not direct. So there's a chance that you will piss off enough people, but they will not tell anybody else.

Jerry Li: and that goes back to the earlier point you mentioned. I think it's really important to be aware is that, so in terms of career growth, not just look at it, in the lens of the level. but more importantly it's your capability, like how do you improve yourself? And there's blind spots and areas of improvements. So it's really the real skills that need to be leveled up. the levels or titles are just a reflection of, the raw talent you have.

How inclusion creates environments for more direct conversations about real world challenges

Patrick Gallagher: Eisar one of the things that we were thinking about right now and talking about a lot of what we've been talking about with being direct and being honest. I think there's a big hunger from the tech community to be able to have really direct and honest conversations beyond just what's going on at work, but also what's going on in the world. And I think one of the things we were curious to get your take on, because we know lyft as an organization does an incredible job, about like addressing real issues within the organization, but also in terms of the impact that the business makes.

and so we were wondering if you had any thoughts or perspectives with what's going on around inequality or some of the big diversity gaps in tech. And if you had any thoughts or different things that you have done as an organization that you found to be really effective to help address and create places where engineering teams, engineering leaders can have more direct conversations about some of those challenges. So really just wanting to kind of open up and see if you had any interesting takes or insights or perspectives, about how to do that in an organization?

Eisar Lipkovitz: I am a huge fan of having an actual. Diverse workforce, and I mean it in the most broad way, right? It's like difference of opinions, you know, difference of perspectives and obviously different kind of backgrounds. So to me, the most important thing is inclusion, right? If you're inclusive people that work with you feel it, you know, they don't face microaggressions, they don't feel discriminated against, and that's incredibly important.

So as a leader, I just want to empower people to bring their whole self to work,

What has brought you the greatest amount of joy as an engineering leader?

Patrick Gallagher: We have one final question for you Eisar. What has brought you the greatest amount of joy as an engineering leader?

Eisar Lipkovitz: I mean, it happened multiple times in my career. It's this sort of being in the grind in a project for a very long time. And then you just sort of realize, "wow, how much we have accomplished." Right.

And when you reach this point, you know, it's not like, you know, if you worked for Space X Elon Musk you know, you clearly just had that moment Right. this is a rare example, but most software project, you know, especially if you're not building, like an actual consumer product, which I have rarely done... that end state is sort of subjective.

But there is a point where you're like, wow, gee, wow we have accomplished a lot or, you know, we sort of changed the world or whatever. And often it happens even later. It's very rewarding.

Jerry Li: It's the process that is enjoyable but , those moments are just really highlights and make everything worthwhile.

Eisar Lipkovitz: That's right. And, you know, sometimes you just remember these moments much later in your career, you look back like, wow, we have done that.

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