Jumping in the crazy pool - Isaac Perez Moncho

00:00

There are few rules I follow. First is, you don't know. It doesn't matter what you say, you're not going to know until you work there. So you have to assume that whatever your ideas, maybe some are right, but you'll know when you join. The other one is, talk to the people and see how they react and they answer the questions. More than what they say is how they say it if that makes sense. Trying to see their body language, maybe you ask, "How is it working there?" And no one is going to say, "It's not great to work here." But you could see in the body language, in their faces, that they're not very comfortable answering that question or they're trying to give a standard answer.

00:47

If your wife tells you to go and jump in the crazy pool or perhaps notices that you are jumping in the crazy pool. When was the first time that you jumped in the crazy pool and what happened?

01:00

Management-wise or career-wise, I think it was when I decided to be a manager and I thought, "This is going to be easy. I think that's going to be the path I want to take. Doesn't seem that difficult. I'm just going to put my hand up and go for it." And I think to compensate jumping in the crazy pool what I do, is try to over-prepare, which is conflictive. Because I say yes, then when I'm in the situation, I will say, "Okay, I need to reread all the management books I can find." And I join all the forums that I can find, and I talk to everyone I can find. But that first time when I said, "Yeah, I can do this, looks easy." And the manager at the time agreed and was pretty much a disaster the first time. It was not easy. So yeah, that was the first time that I said career-wise, I'll jump to the real crazy pool. I think coming to the UK may have been the first one, but I don't see that much of a risk. I guess-

02:16

You are a logical thinker and someone who deals in details. And yet the piece of advice you hold closest to your heart when you're allocating the most important thing to you, which is your time is, just do it. Just jump in the crazy pool. Why is that so powerful for you?

02:37

I think it's because you can overthink and if you don't do it, you either won't to do what you want to do, or you will get stuck in your comfort zone, and you may tend to over-prepare. I've seen as an engineer and as a person, sometimes we try to over-prepare a lot before we say yes, and then you delay the start of whatever you want to do. And that means that you're not learning. You may be preparing for things that don't matter that much, and you may not even do it. Because you may say, "Oh, I'm still not ready, I'm still not ready, I'm still not ready." And three years later, you're still not ready, or you think you were not ready, but you were actually ready to start. So I think it's creating the environment which is something I believe in, I create environment for myself to move forward, and sometimes that is like, I'll say yes and figure it out after.

03:38

How do you know when you are getting to the point where you're going to want to make that jump? And how do you feel that you are getting too far into your own comfort zone?

03:54

When I'm getting bored, usually is a sign. If I do the same things in the same way and I feel that it's not challenging anymore, and I can not pay that much attention. Think a good analogy would be, I do Brazilian jiu-jitsu, and that's very easy to see when you're in comfort zone or not because you have immediate feedback loops and are not very nice feedback loops. You can tell you're not paying attention, you're doing mechanically and you don't have to be alert and you don't have to prepare, and I see that at work. If I do the same thing several times, especially at the end, I'm not technical anymore or not supposed to be. And at the end of my technical career I was like, "Yeah, I've done this, created this system 20 times, I'm getting bored. I just do the same thing."

04:48

And I start feeling that I'm not engaged and I don't need to pay much attention to whatever the task is doing. It's like, now it's time to change but at the same time, the opportunities don't come whenever you're ready to change, they come when they come. And if an opportunity comes, no matter how I am in the cycle of getting bored or getting ready, I would say yes, if I think it's going to make me progress in my career because you never know when the next one will come.

05:17

Why do you think that you have to make this big leap when you're feeling that way. Because it sounds like it would be so obvious that you would feel too far in your comfort zone you'd be getting bored. So is there a need to rush that decision or to make that jump? Why do we have to go all that way in order to make the decision?

05:43

I don't think you need to go all the way. And it's more of a timing thing so not necessarily wait, and it depends on the situation. It's like, how big or how deep the crazy pool is. Some crazy pools are not that deep, they'll be shallow. So you can jump without thinking too much. Or they are like, "Okay, jumping into the ocean. So now maybe I need to think a bit more about this one." And it really depends. I don't have a master plan of crazy pools to jump. I have an idea of where I want to be, and if I see the next crazy pool that will get me there, I'll jump into it whenever that happens. And sometimes it will be, "Yeah, I need to do the jump now because otherwise, I'm not going to get anywhere." But I think for the last seven years, that has not happened. I always seen opportunities before I was ready.

06:37

How do you work out which crazy pools are shallow and which crazy pools are deep?

06:42

Probably not very well. I would say how far out of my current comfort zone they are. Let me give you an example. Let's say I'm managing a team and I see opportunity to manage two teams. It's not that different depending on the team sizes that I can say yeah, this is like, "I know I haven't done it before, but I could do it because it's just replicating what I did in one team maybe, with some differences, depending on the people." Or the opportunities to manage four or five teams. These are scale, our order of magnitude difference, and this is going to be a much harder time. I still do it. I'm just conscious and I try to get ready for that jump. So maybe I need to get floaties or whatever, and then I'll jump. But it's more how far it is and how much experience I have in the domain.

07:50

I want to try and see how far I can take this metaphor. What would you class as a floatie?

07:59

That would be things like mentor, support groups, resources, podcasts, books. Those are the main ones I use, for other people's maybe also videos, attending in-person meetings, which doesn't happen that often anymore but I did in the past. That I would consider a floatie in the... Well, there's two kinds of floaters let's say. There's the floatie of getting help like what I said. Mentors, support groups, resources, and then is the floatie that prepares you. So something I like to do is called... I don't like the name especially, but it's called a premortem. And I would say, these are all the things that can go wrong. What do I need to do to mitigate those risks? And that's another kind of floatie that gets me, maybe the right kind of floaties to say it that way. I can get this floatie, this floatie, this floatie, but this one will help me more because those are the risk that I see when going into that crazy pool.

09:05

Do you have any other thought experiments like the premortem that help you make this decision?

09:11

It's not as well-

09:12

For anyone who hasn't done a premortem well, how do you do it?

09:18

So a premortem, the Wikipedia entry is quite good but what I do is, let's say that I'm going to do a project, a promotion or something for myself, I would make the goals, I would create three goals, for example. And then I would list all the things that I can think of that can go wrong. For example, I'm trying to think of a premortem of a situation that I'm experiencing now. I manage several teams, one thing that could go wrong is, I don't have enough time to do proper one-to-ones with everyone. And for me, one-to-one are very important. So what am I going to do to mitigate that risk?

10:04

Another thing is, I'm going to have too much change of context switching because the teams work in different world streams. How I'm going to deal with that? Do I need to prepare? Do I need to do template for reporting? Do I need to do anything that will make assimilating different sources of information easier? And I do as many as I can think of. And sometimes the risk are not that... You cannot do anything about them or are too big. And it's like, okay, if that happens, then it's fine. Or you fail, I guess.

10:38

It sounds like the way that you're trying to manage it is by more deeply understanding the risk.

10:45

Yes. Yeah, that's correct. And making sure I have some mitigation measure before I go into it.

10:51

What have been the biggest risks that you've faced when you've moved from one job to another?

11:00

It's a very cliche answer. So for me, it's risk of failure of not doing well the job, that's my worry. But that's not very concrete. So in the last jobs yeah, it would risk of not doing a part of the job or maybe, I don't know, screwing it up so much that I get fired in a month, and then that's very hard to explain in your career. For example, that would be the biggest risk, I never been that close. I don't know into that, crazy pools are not that crazy for me. I have still a bit of common sense when I do these things. But yeah, it's a risk of failure.

11:48

Like if I'm managing a team, let's say I take over a team. For me, people are very important, and the good thing about management is, you impact more people and you can benefit more people. If you do that wrong, you also negatively impact more people. So for me, the bigger risk would be, I join a new job, I manage 1, 2, 3 teams, I screw up, everyone is unhappy, half of the teams leave and my has been magnified by everyone I touched. And for me, that's the biggest risk.

12:19

What are the upsides that you're trying to optimize for?

12:22

For me, it's two dimensions, and you could call it selfish dimension, which is about me, what I want, and then the non-selfish dimension. I'm trying to optimize both, I think they correlate, but selfish dimension, it's career progression, get where I want to be and that may mean managing more teams, have more impact. I see the number of teams that I can impact as the impact I can make and how many people I can benefit, which is the unselfish direction. So for me, it has upsides because where I want to go in my career and it's not good or bad, it's what I want to do. And you also get more money when you do this changes. People don't mention it, but it's important.

13:18

And then the people I can impact. I've seen bad managers and bad leaders at different levels. Not only first-level managers but maybe lead of leads and lead of leads, of leads. And to me, the ability to do a good job at that level and impact 20, 30, 40, 50 people, it's what I'm looking for, and the learning that comes from it. So I like learning new things and as you may have noticed like getting out of the comfort zone and that's always pushing the comfort zone further.

13:58

Throughout your waiting, however you decide to wait each one of those, is there an outcome that you are looking for, or a singular thing that you are searching for or looking for? Well, I guess I could ask this question in another way which is, when's the moment at which those things combine and you know that that's the decision you want to make?

14:27

It's two dimensions. One would be again, when the opportunity appears, because that's going to define the moment more than anything else, and then how far from ready I think I am, or how bored I am in my current position. I worked for startups for the last seven years, so the boring part doesn't happen that often. So it's the opportunity there. And then I said, yes, because the last companies I work for, they move so fast that you don't really have time to say, "Yeah, I'm bored now, I want to prepare for the next thing. It's more of I see it coming, I better get ready and say yes before the opportunity passes. In previous jobs, in bigger companies, it was more of a push and asking for it.

15:27

For example, the last big corporation I worked for, things moved quite slowly. So there I had to push my manager, "I want to lead a team. I want to lead a team. I want to lead a team." And I did anything I wanted because I saw that I could have a bigger impact and benefit more people by going into management than just solving technological problems. And in that sense, I had to ask for it and I was not ready at all anyway, but I thought I was. And I pushed for it much harder than in startups when I just said, "Yeah, I'm interested." And it happens straight away. Or it happened very quickly because of the needs and the nature of fast-moving companies versus big corporation where you have to ask for something 20 times before it happened.

16:13

How do you about understanding? What was the process that you go through in order to understand whether the crazy pool you're jumping into is shallow or deep? The thing I'd love to know is, what are the tangible things that you are using in an interview or the research that you're doing on a company before you go in or to try and get to the detail of it?

16:39

The job definition, which is usually quite vague, but gives you a view of the company and how many of the skills required. I think I can do very well on how many are... Okay this bit, maybe 50% I can do well and 50% will be a challenge, or 30% I can do pretty well and 20% I've never done before. So that percentage, and I try to keep a sensible approach to not say, "Yeah, I cannot do anything, but I want to do it." So I have to keep the mix of things that I can do well, versus things that I can do decently, and things that I will be challenged by. The other part is the business and how much they're growing. So different scales bring different problems and if you know that a company has done a massive round of funding and they're going to start hiring, you know more or less the number of people they have at the moment, and you know they're going to want to double or triple that. You know that comes with that certain challenges.

17:58

So I would say, "Are those the challenges that I want to have now?" Then I would go for it. If not, maybe you see they got funded like three years ago and the more materials that brings another set of challenges out of the challenges I want now. That's pre-interview work. During the interview, I would see the things they ask which may mean those are the problems they're having, or if they're not the problems they're having, the interview process is not great in my opinion. And then I try to figure out the problems they're having, the culture they have, and technical and people problems they have, based on the questions they ask. And if those questions relate to real problems. I sometimes ask in interviews like, "Okay, is this something a problem that you have, or is this not a problem?" And if nothing they ask is a problem for them, I wonder why they're asking those type of questions.

19:10

How do you account for the abstract nature of an interview, because it is so far removed from the day-to-day work that we all go through. It can act as a certain proxy to give us a bit of an idea about what a company is like, but it is pretty well removed from what the actual day-to-day is like. How do you know whether there are some bits that might be truthful, other bits that might not be?

19:41

There are a few rules I follow. First is, you don't know. It doesn't matter what you say, you're not going to know until you work there. So you have to assume that whatever you write there maybe some are right, but you'll know when you join. The other one is trying to talk to the people and see how they react and they answer the questions more than what they say is how they say it if that make sense. Trying to see their body language, maybe you ask, "How is it working there?" And no one is going to say, "It's not great to work here." But you could see in the body language, in their faces that they're not very comfortable answering that question or they're trying to give a standard answer.

20:32

And try to understand companies in the same industry with the same challenges, more or less how they are, but everything is very proxy related. You don't have anything that's going to say "Yeah, I'm sure it is like that." Because I said, you don't know. So how the people react in the interview, what questions they ask, my own research about the industry and the company. And that's pretty much it. And I know it's not going to be very accurate anyway, so.

21:09

It strikes me that a lot of the process that you're going through there relies on a certain level of self-understanding. Where you have grasped what it is that's important to you in order to ask the questions, to understand what it's like, to figure out if there's a match or not.

21:32

Yeah.

21:32

Is that level of self-understanding something that you proactively work on somehow? And if so, how?

21:41

I try to do it, I don't think that proactively. I think comes naturally to me for some reason I don't understand. The only thing that I did that for sure helps is, I do mindfulness meditation. Not as often as I like, but I try to do it and I did few courses and retreats to get better at it. Well, not to get better at it, to do it, basically. And that's the only thing that I did that I'm sure it was for that. Other than that, don't have any practices, I just do it. Which is not a great answer, I know. I did a lot of sports in my life. Most of them, the main one when I was growing up were cycling, running, and swimming which is [inaudible 00:22:36] lately.

22:36

So I think that gives me time to think and to reflect. Other sports that I did, they also have very quick feedback loops and especially jujitsu, as I mentioned. If you go, you're going to find someone, you have to be aware of yourself before you go have a chance to win. So you have to be aware of yourself, of the other person and be really aware of your strength, your weakness, how to do the strategies. So self-reflection and trying to understand the other person or the environment, probably from sport that I take it, but it's probably my personality too, so they both match. And I don't have any extra exercises that would be great. You do this, you do that. I heard about daily decision logs or journals. I tried a few of them, I never stuck to any, but I do it naturally, so I think that's why I've been lucky and I have not need that much extra help on that part.

23:49

Are there any other parts to your own personal life that you think play a big role in the way that you pursue your best work? In the same way that sport helps you be that more reflective self or just by being on your own, what other things in your personal life give you that inroad?

24:15

There is this quote I really liked from... Well, I'm going to botch the name, but Amos Tversky, the one who was partner with is Daniel Kahneman, who wrote Thinking, Fast and Slow. And they said that the work that you do, is depending on environment. And you can be a carpenter, you can do whatever, depending on where you're born and how you grew up, but how you do it is to your personality. So I think everything I do is and how I do it, it's related to my personality and how I like to learn and self-improvement. And that's very important because I do try to learn from everything I do, and I do it outside work, at work, everywhere, in sports.

25:09

Everything I do, I try to have continuous feedback loops that make me improve as fast as I can. I mean, if I start that doing it, whatever I do that well but if I can improve, then it will get to a better point that if you start well but don't improve. And the wanting to learn more and being empathetic with people, I think both are core parts of my personality, and they help me in anything I do, really. And work is one of them. One of those things that I do.

25:44

You have a really interesting background because you've looked for work both as an individual contributor but then also as a manager and a leader. What are the differences between the two? And what I mean by that, sorry, is what's the difference between looking for work in those moments between the two?

26:02

The types of challenges I would say, when I was looking for work as an individual contributor, I was more focused on which technology I'm going to work on that's challenging, that's model, that will help me, and I'm really excited about the technology and maybe not so much about the industry. Especially in the infrastructure side, we are a bit isolated from the product because we run product and it doesn't matter its financial services or marketplace. It always runs the same way.

26:40

And when I'm looking for a job as a manager, that's important but secondary, what I'm looking for is, what's the organizational structure, what's the culture, what's the industry? I think that plays a bigger part as a manager than as an individual contributor because certain industries will have certain cultures. Not a hundred percent, but they correlate. And who I am going to work with, who I'm going to report to, how's the org chart which it's not great but at the end of the day it matters. And how is that going to help me work with people? And then the technology is not that important anymore. Even though I have some technologies I like more than others for companies, because they imply certain things, but they're secondary now.

27:39

Almost as if culture sounds more important to you now. Before it didn't, but in some ways wouldn't it be better if you could have both in those circumstances. Is it that you would... Don't know how I'm trying to ask this question really. But seems like in some way there's a priority order to it, which is when you're more junior, naturally you want to make sure that you're working with the right technologies. But as you're more senior, it makes a whole lot of sense that you'd want the cultural. But then at the same time it's like, "Well, it'd be great if you could almost have both from the beginning in some way."

28:20

Yeah, I agree. It's just what you said, priorities. So it doesn't mean that I would have gone to a culture I didn't like, it means that I was looking for technology first and culture that I could work in. Now could be the other way around, it could be culture that it matches and technology that I can work with. If that makes sense.

28:43

I'd love to dive into what happened when you first went into management for the first time. It sounds like you had to ask for it in that larger company. Why did you have to ask for it in the larger company, and why did you ask for it instead of leaving that larger company and going somewhere else?

29:07

In larger companies, I feel you have to ask for anything you want to do that's not specific in your role on your definition. Some things I did not ask for which were more technical, I just didn't need them. But to manage people, you need a process, you need approval, there may be more candidates. So you need to ask for it more because things also don't happen fast. So maybe you ask your manager and they forget, or they get pulled into other direction or something. So you keep asking until it happens, at least that's why I did it.

29:50

And it was the easy path. If you go into management to your company, it's easier to get a management job later than be hired as a first manager in another company. So that was the main reasoning. So it was much easier for me to go into management inside the same company, even though it was a bit painful and it took some time, but I don't think I could have gotten a job as a first time manager in another place. I think the gap is bigger.

30:23

Did it feel like jumping in the crazy pool when you made that internal move?

30:27

I think it was too naive and it didn't, but it should have.

30:36

What do you mean by that?

30:36

I thought it was like, "Ah, this easy, I've seen what these managers do." I don't think I have great examples so that's why it looked easy. And then I was like, "I'll have some one-to-one." Whatever that means, and that's enough and was not like that. It was also a smaller team, it was three people only. So it was like, "Okay, I've been working with them, they respect me as an engineer so I have good relationships. This management thing doesn't seem too difficult." And it doesn't seem that crazy pool jump at the time.

31:18

How has reading helped you decide where to work?

31:22

That changed quite a lot from me more reading about management books. Those have changed more where I decide, because now I know when you call best practices from the industry of management engineers, and now I look for places that share those values or those practices. I can ask about those during the interviews, and I have some expectations of what good management it is and good culture and good organization. And as much as I can, I try to get that of out of the interviews. But reading management books, it's been like, I don't know... I read quite a lot so it's pretty much everything I do. Has some component of having read about it and definitely reading management books has helped me think about what I want in a company from the engineering management.

32:26

As you spoke earlier about the jump into the pool, it struck me that maybe there was a part to that where if you make that decision quickly, you avoid having to face on with imposter syndrome. You make the call, you go through it, you can ignore the doubts that are happening in your mind and just go with it. Is there an element of truth to that?

32:57

I think imposter syndrome kicks in later. So it kicks in when you actually start in the job and you're like, "Oh, maybe I should have thought about this a bit more before saying yes." But that's what I like, and it's risky. But what I like is, I'm already in that position, so I don't want to back off. And I gave my word that I'll do this work and I'll try to do it the best that I can. So it's a bit too late and impostor syndrome kicks in, but well, it's a bit too late to impostor syndrome. So you have to deal with it in the situation. If you wait too much to decide, maybe kicks in before, and you cannot... Yeah, you won't decide or say, "I'm not going to be good enough for this role or for this provision or this challenge."

33:48

So maybe a better way of thinking about it is, rather than in that moment, you're making the faster jump to get over imposter syndrome, you're making the faster jump to just quell the inner voices in your mind who might question whether this decision is the right one to make.

34:08

I like to think more about it being that I put myself in the environment that will get me to the next step. And I don't have that... This inner voices is not very strong with me. Or sometimes I have them, but it's not that I'm constantly thinking, I'm not going to be good on this or anything like that. Thankfully, I don't have that problem. So it's more of, before I not do it, I'll say yes, and then it's too late to say no after.

34:42

And is that because you think that you as an individual, are more susceptible to the environment that you in? So therefore if you can latch yourself onto an up-and-coming environment, your natural character will flourish there? Or is it that you think that just generally we should all try and be in that right environment to improve. And it doesn't matter how well our own character is suited to that?

35:10

I think the environment definitely helps. And if you're in the right environment, you will flourish faster than if you're not. And it depends on you. Maybe you can still flourish in the wrong environment, but it will be not as much as in the right environment. For me, I think well yeah, in the wrong environment is quite hard. One example would be last big corporation I worked for was very hard to do anything especially at the end, when it was clear that my team was being dismantled, and I was the last one and I was not even getting new work assigned to me. And I'm like, "Okay, it seems that I don't have anything to do. And that environment [inaudible 00:35:56] been really, really hard for me to advance. Even though I tried outside the war, you can keep reading and all that, but it's an uphill battle, very uphill. And some people may still push a bit, some people a bit less, but definitely if you're keen on improving and you have the right environment, is much, much better, you progress much, much faster.

36:20

My last question is about your motivations and where they come from. I think we are all so deeply driven by our childhood, but also our parents and perhaps the work that they had in mind for us inadvertently or directly. Were you in any way... Where do your motivation stem from?

36:55

From two. One is the desire to learn and try new things, and the other one is to help people. And I think engineering it's really good for both because it's always changing. So you have to learn you like it or not. And if you go into management or even you're an individual contributor, you still can help people because you can and make better tools, easier to use services and improve people life, or you're in a company that's doing some health tech or there's a lot of... It's not the only field of course, but I think it combines both pretty well. And I think those are my motivation. I could have landed in any other environment. At first, I wanted to do science, I studied C science and I wanted to study a sonography and investigate there, which was more on the learning side. But then I realized computers also allow you to learn quite a lot quite often and you can't stop. So I changed and I think those are the two core things that drive me or the career. And any career I would do they would still apply.

38:13

I'd loved learning about your own journey. Thanks so much for sharing and being so aware of how your... That jump into the crazy pool makes such a profound difference. That's amazing.

38:35

Thank you. And can I tell you where it comes from [inaudible 00:38:40]? So when I met my wife, we started dating and we moved in the first week that we started dating, so she said, "Oh, let's jump into the crazy pool and see what happens." And then since then it was like, that was the first crazy jump into the pool that I did. And it worked out.

38:57

The craziest.