Making intentional career decisions w/ Ali Littman & Ali Irturk #96

I view my relationship to people that I work with, or people that I manage right now, is actually a lifelong commitment. And I think because of that, I end up with these really strong connections, even beyond past opportunities. Our show shares the most critical perspectives habits and examples of great software engineering leaders to help evolve leadership in the tech industry.

Welcome to a verified career framework jam session. In this conversation, we discuss a ton of different approaches and frameworks to help you intentionally create and select new career opportunities. With long time community members, Ali Littman & Ali Irturk. And in this conversation, we cover a pretty wide variety of approaches here. So we're going to talk a little bit about creating both internal and external career opportunities, how to assess, filter and prioritize those new opportunities.

We get into identifying your personal values. Plus, we just have a ton of fun sharing some of our favorite frameworks that we apply to engineering leadership. I told you, this is a framework jam session. Ali Littman is the interim head of engineering at modern health and formerly was director of engineering at Omoda Health. Ali Irturk is VP of engineering at Commerceub and formerly was VP of engineering at Workboard.

I've known both of them for several years through ELC and have always admired their intentionality behind their career decisions and their thoughtful approach to leadership. Career decisions, as you probably know, can be a murky and confusing world. And I've thoroughly enjoyed learning how they've navigated many of these big career decisions in their life. Enjoy our conversation with Ali Littman & Ali Irturk.

Ali, Ali, welcome. Thanks so much for joining us. How are you both doing? Super. Very excited to be here. This is going to be a fun conversation mainly because the three of us have known each other for a little bit of time now just to give a little bit of the high level for how I know you both and how we're all sort of connected. Ali here, Ali Littman has helped us shape our leaders, some of our leadership programs, namely the peer group program and some of the moderator experiences.

So she's been involved in the community for a really long time in helping us make sure that the experience is great and meaningful. So Ali, great to have you here. And then Ali related to peer groups, him and I are both in a peer group together. And so we jam once a month on all of the big existential challenges that Angel leaders face.

It's fun to bring this all together. But over the last few years, I think what's interesting and how this all sort of comes together is both of you in different ways have navigated both internal and external growth and different career opportunities.

What I've admired is the thoughtfulness and the intentionality that both of you take in almost everything that you do as an engineering leader. And that every time we talk, usually I'm learning about a new principle, a new idea or concept or definitely walking away with new book recommendations. And so today, a lot of what we're going to be diving into is that massive archive that you both have with the ways that you've approached and navigated some of these different opportunities.

And so this is a fun time for us to jam and talk about all of the whole world of navigating new career opportunities. You just set the bar so high. Everyone's like, oh, great. There's going to be some good stories here to bring us into this conversation.

We're going to talk about, I think the way we structured this conversation a little bit is we're going to talk about some different specific moments or phases of someone's transition and we'll jam together and share some of the different frameworks or approaches that we've taken in these context on the things that have made a big impact for us.

So with that, like let's start at the beginning when both of you are thinking about creating a new opportunity, whether that's internally within your current company or externally in beginning to navigate a search. Like what's your approach? Like just from from the very beginning, how do you begin to even frame how to think about that?

It's a really big thing to be considering taking that next step and it's something that, you know, some people, you know, they're on this path and they're like, okay, I see what the next level is.

Like I'm just going to go after that, but really what's important when you are considering changing things up is to take a step back and get a strong understanding of really what you want and why and you can walk yourself through some questions that I often coach people on as they're going through this thought exercise. What actually gives you energy and what drains you, you know, what makes you feel accomplished or aligns with your personal mission values.

This is something that I went through as I was thinking about my next career move a few years ago and I worked through that with a life coach actually, which is very helpful for me. But ultimately, once you understand some of those things, you can then figure out, you know, what's important to me in terms of, you know, my growth in terms of the mission of my next opportunity or the next company.

Maybe look at mission culture management, all of those various things, because those things are always going to be really important, you just need to make sure they align with what you need and what you want. I think getting a level set of what those things are for yourself is very important and then partizing from there. So for me, what that looked like a few years ago when I went through that experience was prioritizing managing managers.

That was the experience that I really wanted to make sure I maximized and that's where I felt most energized where I felt like I could make the most impact and aligned with my personal mission for how I, you know, grow people from various backgrounds. I love it. I was going to ask you like, what was the answer for you? Like what were you prioritizing, but understanding that it was the experience to be able to manage managers.

And that was where you got your energy from. I think it is a great understanding of how that applied. I'll leave you. You look like you're about to jump in. Yeah, yeah, definitely. I definitely agree. So in my mind, I love the number three, right? One, two, three. I have these three steps. The very first one is actually exactly what Ali mentioned, the Y part. And that's the part where you're just exploring yourself, things you want to do.

What's your mission, what's your career goals, what type of cultural values are important to you? What's your passion? What's your skill set and what things you're good at? There's so much analysis to do there. That's mandatory work to do before even starting to do any kind of internal external search. And then that kind of helps the understanding where you are today and where you want to get to and you draw a line and they say, this is the path that I'm going to take.

And Ali also mentioned certain exercises. You said, I think what gives you energy? There's a lot of different activities you can do. One of the things I learned during one of the SFLC podcasts, you might remember this Patrick. This is energy audit. Yeah, yeah, Brad Hendrickson. That was great. Right. Whatever works. So you can write reports to yourself like every day or you can just analyze your calendar or just go for a walk and take a week off.

Kind of analyzing writings or reflect so much. You need to better understand yourself. And then the second step in my mind, once you draw this line from where you are today and where you want to be, you're making a lot of assumptions. A lot of assumptions about yourself, a lot of assumptions about that role that thing that you're interested in.

Second thing is, it's very critical to do is to validate these assumptions. It has been very, very useful in my career. That comes in these information interviews. Did you create this like really good set of questions, wherever this like you want to get to the first level of management, managing managers, you want to get into product management, whatever this very powerful questions, figure out these people who are actually role model against.

And you can't believe how many times you reach out the people and they will respond. They say, I'll just spend half an hour to reach you. Just ask great questions, listen and then just take that feedback and reflect on it. I've done the multiple times in my career. At some point already in my career, I actually considered after my PhD a couple years in engineering, I consider maybe actually just moving to product management. Same model, right.

I just figure out the why first and then say, well, here are the questions that I'm interested in getting asked and talk to 10-20 people if you can. And I convinced myself that it is actually a great position to have, but maybe not the best fit for me at that point in my career. And then third one, if you figure out the why and if you validate assumptions, you possible already connect with so many of the people that you will be interested in working with.

And the other thing is just finding the best fit and that's very important that you solidify your pitch now, like what do you want to do, why you want to do it, why you're the best person to do it, you kind of get into the staccato, do you value it to make a decision to move to the right place for you at that time. So three steps figure out the why validate assumptions and find the perfect fit.

So follow question around creating assumptions and then validating those assumptions, what has been like your favorite way to define your assumptions around a specific opportunity. And then do you have like a favorite question that helps you validate those in some of those conversations.

The way that I would start figuring that out is understanding if this was a career move into managing engineering organizations. It's good idea to write down what do you think that looks like. How much do you divide your time between say coding and managing people. And clearly you don't want to ask questions directly in the information interview. You want to ask questions that release the answer, especially questions that come much to you code. It's kind of sometimes hard to answer on the spot.

So you want to come up with this question, they will kind of get you the answer so you can actually make a decision to an extent a bit indirectly, but figure out what the job looks like. And that's the reason that the last step is so important. Even after you validate you need to make sure that you're signing up with exactly what you thought it is, right, because there was always finer details in everything.

And then Ali, are there specific reflective activities that you found sort of in this in this sort of same area to help yield or help you identify or clarify what you want next. I think one of my favorite ones is really going through your own personal values and actually writing those down and understanding why they're your values and how those map to even your own personal goals.

And then from there, seeing how those might map to a particular opportunity, it could be the company's mission, it could be the role itself, but how do you get what you need so you can live your best life in a way. While also doing great work, right, that might actually align with the mission of the company. I think people talk about finding their dream job and it's perfect and makes them happy.

I don't know if anyone has ever found their exact perfect dream job, but you can really get close to that by looking very closely and doing that kind of self assessment and just making sure, hey, like, does this actually get me where I want to go in life if I spend a good chunk of my day doing this kind of work. And I think that's the best way you can find a nice opportunity for yourself in some of the last few different opportunities that you're evaluating.

I guess what are the personal values that were most important for you and filtering that decision? I think one thing that I value very highly is, I'll say two things, actually, interpersonal connection and growth and the growth can be for myself or for others. For me, finding opportunities where I can really mentor others is highly important in terms of what I want to be doing in my day to day.

That's why I prioritize roles where I can educate more junior leaders, for example, to teach them the craft of management. And that really makes me feel great. Or maybe there's a company that really promotes hiring diverse employees. And in that case, that also feels really great because that aligns with my own personal mission as well. And I think that I think that I can really help people with personal values to support others from underrepresented groups.

So that's one thing that I definitely prioritize in my own personal job search knowing that those are some things that I value. That's great. Thank you. I think it's always helpful because I find sometimes when folks talk about their personal values, it's really helpful to hear what's important to other people.

So I know we want to talk about validating a decision. But before getting to that part, one thing I want to point out, Ali, one of the things that's come up in some of our different conversations with folks and one of the challenges that people face is like when they're beginning to become interested in pursuing different opportunities. Usually there's like this question of, well, I've never had to look for a job before or I've never had to entertain that conversation.

I think every time walking away, people are always blown away by like the level of thought or like the infrastructure you have in place to just have really great conversations with tons of different people, regardless of you're looking for an opportunity or not.

So I was wondering if you could just give a couple of the practices that you do to just build great relationships with people over interesting stuff because every time we've talked about that, it usually is like exploding people's minds as we're talking. This is one of these areas that intentions that not enough right unit ever process in place. So in a grander scheme, I think people should be always looking for opportunities at whole times.

Internally, externally, and that's part of the network in peace comes in mainly because unless you think about this all the time and continue to have the conversations, you really don't know till that moment comes. But most of the time this moment shows about it over and you're not ready because you have not even know your valuations that there's a famous saying says the best time to eat orders are there being passed around.

And if you're not ready to eat now, you're going to miss that one reaching out to people having these coffee chats my MBA network Berkeley is very helpful. Staying in touch with your network, taking time like not eating lunch alone or finding opportunities for dinners and outside of your network, maybe having good connections with investors who invest in your companies or recruitment agencies.

There are so many great ones that are working with kind of a philosophy very closely introducing yourself to them. You just need to stay constantly in the loop with people. The second part, I think getting out of your comfort zone going out there and reaching out. So just choosing courage over comfort and not really just saying that well, I'm not ready. If you keep doing that eventually, you're thinking changes, the environment changes and opportunities arise.

So instead of just like act of now you've just started searching for is just something always happens. Do you have any any thoughts around around this? Yeah, well, first of all, I think I can learn a lot from Ali about how to best network. I do think, you know, staying is engaged as you can in a variety of communities, which I think is, you know, quite difficult right now considering a lot of a sort of remote.

But you know, it means that we still should make that time to lean in. I view my relationship to people that I work with are people that I manage right now is actually like a lifelong commitment in a way. I often find that those relationships that you build with people that you've worked with very closely and, you know, if you're already supporting one another, even after you move on, you know, that ideally should continue.

If you have that kind of relationship with that person and so that's as like a leader, that's something that I often employ. And I think because of that, I end up with these really strong connections, even, you know, beyond past opportunities. And considering I work in, you know, a very particular industry, I'm very focused in healthcare tech that often pays dividends when I need to go reach out and, you know, maybe it's like help with the particular vendor, even, or something like that.

Basically, so in a situation where opportunities end up presenting themselves through past networks that maybe I even help support people often, you know, want to give back to one another. And so I think that's a great, a great path. I love that mindset of viewing like your relationships and your commitments as like as lifelong and then the impact that has.

Okay, so we talked about networking. What's your favorite message to send to somebody in like a cold outreach? Like to say, maybe this is you're not looking for an opportunity, but you just want to talk to them about their cool startup or, or like their fund or something like that. Like what's your, what's your message to do that tactically?

There's really nice book called to our job search, which not only helps with how to message these things, but also how to create this process about reaching out to people and getting the feedback and understand their intentions. You clearly want to have if you have an affiliation with the person, you want to just mention that one. If you graduate from same school, it's good idea to bring that up, especially they will value that.

And understanding where they're coming from, it's a lot more valuable to reach out to a person if they're, if you read their article, if you read their book or if you looked at their code, that's a lot more encouraging for someone to respond. So number one rule, I would say do your research, just don't send something out. And once you do your research, your message looks pretty custom tailored for that purpose. And that's what makes the person want to respond.

But there's also a bunch of activities you can go to. You can go to your alumni networks gathering together, which is then, you know, it's a bit easier to get to know the people because everybody's there for networking. But you need a really good reason if you're going to just send some on a message and ask them to pay attention to you. I love it. The framework there is really interesting mentioned the connections do the research and mention the things that you value appreciate.

This is day one from Drew Dudley that focus is phenomenal in terms of setting the perfect framework to go through. I'm going to read down all these book recommendations you've been dropping during the year. I can I can plus one Drew Dudley. This is day one. I think even I talked about that one. Yeah, you know, in my period of taking a sabbatical, I read this is day one and probably spend about a week going through the book, identifying my personal values.

And the best part about it all is that it helps you create operationalized questions. So you can ask yourself these questions throughout the day that then prime you to make decisions that are more in line with your personal values. What a mind was courage, which I didn't think about beforehand, but I realized that I was more in line with who I wanted to be as a person when I chose to act despite fear or I defined it as like fear or emotional risk.

Because I found like anytime I acted despite any of those things, I felt more in line with the type of person I wanted to be. And so it's cool. If you start asking yourself these questions of like, what have I done today that scares me? Then all of a sudden you're on the phone with somebody and they're saying some nonsense and you could have a critical conversation with them.

And then you choose to do it because you've been talking to yourself about that all day. So it's just like it's amazing Drew Dudley's book can't care or make it recommended enough. So speaking of frameworks, I want to talk a little bit about making the decision. So Ali, you mentioned personal values as like a first filter. I was wondering if there were any other ways that you go through filtering or assessing a decision.

And then I guess the other part of that is, is have those changed at different points of your career, depending on the opportunity that you're looking at. Yeah, I think everyone's filters are going to be a little personal, but there's some that you might be prioritizing over others. I do think there's some that are static almost everywhere, which could be quality of life, culture, you know, opportunities like those sorts of things.

But I think the very first one, which might be hard to filter on like early on in the in the process, but you know, making sure you've got the right manager. I totally have the opportunity. You want to pick your manager and that actually can have the biggest impact on whether or not you actually get what you thought you were getting when you were doing this assessment.

I think another big one that was a good initial filter for me when I was thinking about what exactly do I want was understanding my own personal risk tolerance. And so that can show up in a few different ways. You know, it could mean like looking at the phase of the company and understanding, you know, how risky would it be to join.

It could mean, you know, is this going to be a tumultuous environment or stable environment, you know, what feels better right now or maybe is this opportunity to stretch me in a brand new way? Or do I feel like my skills are perfectly aligned? And I'm going to knock it out of the park and understanding kind of where you are on some of those various things will also be good because those might change also over time coming out of COVID for me personally.

That's around the time that I was looking for any opportunity. I definitely wanted something that was going to give me the right next opportunities, but I still felt like, you know, had some level of stability and I could knock it out of the park knowing that I mostly work at, you know, in the startup space. So it was definitely looking looking for that, but that might not be the same thing I want for my next job.

So being really, really honest with yourself about where you're at with your risk tolerance is great. And I think one of the things I recommend for people tonight, I definitely have this as well to identify what are those filters are create a decision grid. So literally, you know, a spreadsheet. And as you're going through various opportunities, start to figure out like what are the things that you might tag each one with.

So maybe, you know, some straightforward ones could be, you know, expected compensation. If that's important to you, probably a little bit important to everybody could be, you know, what level, you know, just give me the level that I want.

Does it give me the quality of life? Do they have flexible vacation or is it two weeks? Like what are the things that matter to you and start making those assessments? And it actually, as you make and start tagging these opportunities, start making these various filters.

You'll understand which ones are actually giving you data that's causing you to prioritize your desire for one opportunity over another. So often find the exercise itself allows you to learn more about what you actually care about. And then you end up with a few different opportunities that you might be aiming for. And it can help you start to actually apply those filters to other searches you might be doing.

I think it's really cool that it's almost less about the data or the tag itself, but rather about the exercise of doing it helps you actually discover what you want. And I think that's really cool. So just like the process of doing it is what matters less about that. Yeah, absolutely. And I think that's been the experience for me and for others when I've suggested that they do that, they learn really what matters because there's so many different things that you could be assessing on.

When you've gone through this decision grade, were there anything that surprised you in going through it? Like for me, when we were talking about Drew Dudley, like courage as a personal value was totally off my radar. That one definitely surprised me. Were there any surprises for you? Yeah, I had one that was a little surprising to me related to my assessment of what quality of life meant relative to work time zone selection.

I didn't realize that which time zone a company was had courted in actually had a big impact on whether I wanted to work there. And so as I was thinking through, do I care that this company isn't Atlanta, even if I can work remotely from California, let's say the answer as I was going through the assessment on my grid.

I realized I actually kind of cared because I'm a morning person. And so I wanted to have mornings to myself to catch up and give Nege on work and do the things I needed to do for myself. So I felt like working for a West Coast company in this most recent job search was actually something I prioritize lot more. And I did not realize that until I really started to compare companies and think about like, do do I care about this or not? And the answer turned out to be yes.

And so true that because I've worked both West Coast East Coast and and Jerry Jerry and I are primarily the ones talking to each other and he's been mostly West Coast. And so I've had the experience of being the same time zone with him and working together on the West Coast. And you know, that's great. Like them. We're kind of interfacing pretty early. But I am totally like you. I'm a morning person. And so having like that eight to 11 a.m. time frame as just like me time, like pushing forward, whatever I want to push forward.

It's been great. So actually the East Coast has been what more like me living on in Washington DC has been more well suited to that relationship because then I'm pushing forward a bunch of stuff before Jerry even wakes up.

Even though he's a he's a ridiculously early riser. And so I think that time that is such an interesting surprise to realize that that has such an important weight in terms of the style and light the lifestyle of how you want to work. Ali, what about what about you? Any surprising things from your assessments or filters are guess what's what how do you how do you filter your decisions?

I feel like how Ali mentioned pretty much an excel sheet, these raw items are things that you care about. And there are lists you can start. There's some of them are kind of comments and some of them are very specific to an individual and then look at where you are where you want to what your options are.

What I like to do every time I had a significant change. I always have this same process done with my significant other. And since she knows me so well, she also kind of ranks the things I give a certain score. And she gives us a certain score. And that kind of starts a separate discussion because sometimes it's hard to be extremely honest with yourself because something maybe so exciting some other ad to really kind of just underestimate and that seems to keep me honest.

You know, again, in this case, who you know matters a lot to people who have done this job or similar jobs maybe sometimes in the same company can actually help at decision making you can get that information provided. I love the idea of coming up with certain decisions and I'm sleeping on it. And I felt like this is the biggest marker for me to see if this is the right decision or not. How energized I feel the moment that I start imagining myself being there.

And just jail and never fails me. And that's kind of like the litmus test. If as long as you keep maximizing that energy, excitement and comparing to things, it can tell which ones giving you more energy. And you also mentioned it does this change over time. I feel like I know about myself a lot more now than I knew say like 10 years ago.

And I knew like 10 years before I just like significantly changed my priorities have changed my how I look at life has changed, you know, my values have evolved. And very frequently this needs to be kind of reevaluated. It's just part of the process. There's really no work around it is not like you can just say this is it this is who I am.

It's the adaptable one of the survives the longest and other and other maybe the last thing I can say but this is if this does not feel right to you, it's possible not right for you. Right. It's just if it doesn't feel right that pass me so I think just having some got check will definitely bring one to closure. That's great. Ali, what do you you mentioned you had some thoughts about how the decision making filter or your priorities changed over time. What are your thoughts there?

Yeah, I couldn't agree more with Ali's assessment, you know, you learn about yourself throughout the process. So totally changes me, especially early in my career, I had a very loose idea of what I wanted to do. And I felt like I was just looking for the right job, but I didn't really know what that was. And so I felt like almost like the job kind of picked me, which I think is, you know, best case scenario for recruiting, but I was looking for the right job.

And I ended up with that the right one for the time learned a lot what I want to do that job forever. No. And then I felt like the next phase for me was more about, you know, making the next big tweak where I had to get my foot in the door in another direction. And for me personally, that was breaking out of like a very niche industry into a different, a different industry. So a different section of health care tech.

For me, I was like, that's what I care about the most. It was a little bit less about the role at that moment. It was more about getting my foot in the door. So I could get access to the other opportunities that maybe I wanted. But as I've grown from there, I have higher and higher knowledge and standards of what I need in my role.

So now I can be significantly more thoughtful and, you know, it's not about like, oh, I'm going to take the first offer because that's giving me that opportunity. I can really be so much more thoughtful and selective with what I want, which I think comes with both learning about yourself and also experience in your role.

And just add to that because I think it's it's very important what you mentioned. And this is what it might be debated topic, but I generally encourage people, especially earlier in their career to experiment a lot more. So they actually kind of evolve the world is understanding about yourself and about the industry and whatever this. And you can actually go out of our wherever you've been trained, right, educated for you can even get out of that.

Just explore see if you will like a door. Because it's cost of doing that later in your career is a lot higher. Nothing possible. Anyone can do anything anytime. But kind of it easier in the very beginning.

I think in response to both of you shared like in kind of connecting the dots from a couple things we've talked about. So we talked about like making some assumptions about about the role. We talked about kind of filtering and all you when you're talking about experimenting and using that as a as a frame of reference.

There's been one framework that I found particularly helpful in terms of validating like your assumptions around a role or giving some direction to the types of experiments that you take on for a role. So it's kind of a mashup between two frameworks. So you know, I've got a lot of internal ego and pride around this concept. But it's a mixture between like Jim Collins's headshot concept and then Malcolm Gladwell's outliers.

So the headshot concept for folks unfamiliar with that is like the intersection of three things. What are you passionate about? What could you be the best in the world at and then what drives your economic engine? And the idea is that like this sort of sweet spot where you're both feel purposeful and you're also like economically successful is the intersection of like your love and your ability and then like something that is like economically valuable.

And then the other side like Malcolm Gladwell's outliers the kind of TL the arc of this is like there are certain things that like certain things that allowed people to have outlier performance and sometimes it's related to timing and sometimes it's related to unique experiences earlier than others.

So like one of the examples was Bill Gates getting access to a coding lab at Berkeley when he was like 16 years old or something like that, which then gave him the early experience then build all these other amazing things far earlier before anybody else was interested in that particular stuff.

So with the headshot concept when you're thinking about what are you passionate about that's an easy list you can talk about all the things that you love like I love surfing or I love knitting or hiking or whatever. And then in addition to like the things you love about your job and then when you think about like what could you be the best in the world that the truth is like especially if you are younger in your career, you are probably not the best in the world at a whole lot if not anything.

So when I was answering this like there's nothing on the best in the world that but how I wanted to reframe this question which I thought was really important was what could you be the best in the world that if you chose to invest in growing and training and developing your skill set in that area and then pairing that with outliers like what's something maybe that you have had more experience with and other people that's interesting or unique that if you continue to invest in that it'll help you become the best in the world that are a reason we like top five or 1% or whatever.

And then you answer all the other questions of like what are the different like permutations of what people would pay you for like what's valuable skill set that you can cultivate. So the intersection of that then like you start to experiment being like okay I love this this is economically valuable and if I invest in this I'm pretty good at it and you can start to check off those experiments.

So that's my mashup concept served me directionally it's helped me cross off a lot of things on my list but also open up opportunities and different things.

I love it. I love how we merge them so that when it comes to passion the way that I approach that one is a very hard one right how be you figure out what your passion is like Stephen Coplar talks a lot about this so the best model that I found so far is actually to find your passion is just searching for the flow how do you achieve the flow the most right what's your way to go generally I feel like that's very well correlated with the passion part and I also like what you said like what you're good at that's also very hard to do.

The one way you can do actually reach out to other people and ask them to tell you what they didn't do that but also like you said trying to do certain interesting skills for me I come from military and I have a lot of leadership experience and then I'm very well trained in engineering so it's a unique skill to have like have both leadership and technical merge together so that's actually how I explain people by I love engineering leadership roles and what others pay you for is actually a very important point as well I completely agree.

That reminds me of the triple threat framework where it's like you pick three skills and if you can become really good at that then like that also create success so like you were talking about like the double threat was leadership and engineering then the triple threat being like what's that third skill in the combination of those three make you super professionally skillful all you've been jamming what's what's come up for you is there been another another framework or concept reflective exercise that you found valuable one of the main things is just reminding me of is you know kind of that that tension and

as you're going through this process of like what do you want to learn and what are you already good at and identifying what you want to learn like how that opportunity is going to really get you there because that's at the end of the day a lot of the reasons why and I personally pick various opportunities but you almost need what you're good at to kind of stabilize the ability for you to actually have an opportunity those two things I think are actually really important when thinking about like how is this the best fit for me right now for exactly what I want where is my gap and where is my

strength and then how do I get that out of this opportunity so that came up for me and relations and things you're just talking through I love it okay we're reaching a transition point in our conversation and so I'm counting the list of topics I have on our list there are 12 discrete topics we can get into and I think we have probably

about 10 minutes left what I am inviting you both into is that maybe we we have a part two in terms of like the other phases of transitions but I want to open up a random grab bag of engineering leadership frameworks and approaches because like it's been so fun jamming with you both and hearing the things that have been

made the biggest impact on you when it comes to assessment filtering cultivating opportunities so this this next question is just going to be an open explosion of what are your other favorite frameworks or approaches to engineering leadership so when you're thinking about like principles that you've applied or frameworks that have helped change how you

approach leadership this is just an invitation what are your favorites let us know the one thing that the significant impact on me in terms of leadership is the moment that I realize that it's just not one thing so there's a favorite question they ask you what's your leadership style right it's a lot of interviews we'll talk about a lot of people who's interested in the

question but there is no one's that there's this it's almost like this hats you get to wear them depending on the situation and it's your your inventory what matters but kind of you matters for your leadership style so you have this a coaching hat that you need to be really observant and you put the hat on and the time is right and you need to be

really very smart democratic you kind of put that hat on and there's this pay setting like you realize the team needs now you put the hat on there I think you know studies that tells us what type of leadership works for say engineering organization most efficient effective ones and if you were to just wear a pay setting hat all the time you pass a burn you and team up but kind of just realizing that's actually not one thing and many things and

artists figuring out which one to use when it's not almost like whenever you're going just need to be careful which had to be a lot more enlightening for me so I deliberately think that way that I'm approaching leadership problems that's both

illuminating and I think we're leaving for a lot of folks because that also kind of reinforces the implication that leadership is not a single style or rather like inherited but rather it's a series of different skills or capabilities that you can you can learn and acquire

through practice and then the ability to be malleable and dynamic with being able to try on some of those different roles is is so that framework I tend to try to and it's it's hard to always have this one but try to enter a meeting first by centering and then

entering and when you're like centering right before the meeting just you know couple of questions you can ask yourself we could ask yourself like what does this meeting require from me from my leadership or like what the people I'm going to meet with require from me

so asking these type of questions will require to kind of understand what's needed and you can use the right style for the right moment so that's like how you can put it in applications hard of course you serve you know zoom surfing throughout the

day from one to another but like that's a very valuable and meant to spend I love that I think a lot of what's coming up for me from everything you're sharing Ali is that leadership is more of an art than anything and I think that is why there are so many leadership resources that no matter how great a leader you are how many years of experience you have it's always useful to cycle through those to get fresh inspiration for a new frame of looking at a problem or looking at how you influence or

how you support someone that's a great tactic that you just mentioned I can go bring that back I'm inspired I'm going to go try that you know and like that's a new way of thinking but you know maybe I'll get tired of doing that and I need something fresh to you find a new way

to make my teams feel supported have this reach our objective have people feel inspired all those different things there's no one tactic and I think that is kind of the beauty of leadership and also why there's a large industry out there of management books absolutely I'm definitely taking that question putting in the back pocket as a primer for for different meetings and even I think like even like events or experiences like what's required for me or who do I want to be in this particular event

I love it Ali what about you what are your favorite or if you have to pick you know a framework around engineering leadership that's made a big impact on you I'm going to go with the one that just feels like it's at the core of everything I do which is vulnerable leadership for me showing up as a human being and all of my interactions with people is something very core to how I lead and so for me you know a lot of my job is getting by and building trust building empathy and understanding

and community like all of those things require me to be approachable both you know in terms of you know communication but also you know emotionally so setting that stage for people so I can be a better leader and then they can meet me where I'm at

right because we're trying to build a team culture where they feel like you know they can be themselves and everyone can be comfortable and like feel comfortable raising concerns and creating space for that that's ultimately like what I want in my communities

I want people to be supporting one another if you don't have a culture of sharing your emotions or sharing your feelings or thoughts you're not going to get any of those inputs that you need and I strongly believe that you know emotions have a place in the workplace

and that those really drive flagging what direction you might need to go right if something like oh gosh there's this big technical problem really stressed out about it that probably means you should do something about it there's something behind that emotion

and so being able to express that and having a space for that is important and as a leader I feel like I need to provide that space for people and so I make a point of doing things like talking about going to therapy that's something that I want people to feel comfortable

sharing in the event that they need space for that at work or you take time off from work so yeah vulnerable leadership for me is really at the core of a lot of what I do and it's a strategy that works really well for me so strongly recommend it to anyone else I really I really appreciate that because there is one quote from our summit back in 2019 from Max Levkin and he was talking about how the biggest problems are almost always never code and always people

what you shared there like what came up for me was when you're thinking about like it's about people it's not only that but it's about being comfortable with the emotions around people and the ability to understand the emotions that people are experiencing and to be comfortable discussing them

and being in conversation being like emotionally fluent and so I think that's a really great priority and perspective to have it has been always important but especially now if you're working remotely COVID times there's no other way absolutely especially attention to it

this has been so much fun hanging out with you both I could jam about leadership frameworks forever we we do have a couple rapid fire questions to wrap this all up to kick this off oh gosh this is also another one of the things that could immediately you know this could be a Cambrian explosion of things for people to look up but what are you reading or listening to right now?

I I finally read staff engineer so well our sins book so got that under my belt and then I'm also at Ali's recommendation just finished up influence so that's a psychology of influence books the thanks for that and then I'm also listening to a cyber security leadership podcast which is important for me since I've taken over security at my organization so that one's called defense in depth that's been pretty cool

great recommendations Ali what's up? A guy to good life really never mind about stoic philosophy it's awesome and I try to read just two books at a time and I'm going really deep on Ellen Watkins books for the leadership coherence really good books I'd recommend it everyone

great I need you I need you both to have some great recommendations for people to pull we talked about engineering leadership frameworks we're going to take a different tack tier what tool or methodology has had a big impact on you?

I will immediately go one of my most passionate about 20 minutes power naps change my life if you especially just like Marissa with the cappuccino what they call Mac Napichino a phenomenal so my day starts at high and I have to play a teller and not like I have another one

I have another one that many others who doesn't do the Napichino have I don't think there are enough people advocating for power naps and so this is a this is definitely a podcast first and in a non-traditional tool or methodology so thank you for for helping make history here and giving me permission to go take a nap like this is great are you still doing like the engineering floor right in the middle? Ali what about you?

Okay I was going to share something very different but now I want to talk about something very personal to me that has completely evolved how I organize my time for myself both work and non-work related things so every morning I make a list

of what I want to do for the day but it's not like this exhaustive list of all the things I have to do it's only the list of things that would bring me peace if I were to do them and also things that I'd be proud of and that allows me to really focus on what's most important for me

and make a balance to do list that I can actually get through in one day and the satisfaction for doing things that purely bring peace and and a sense of pride oh my gosh that's changed my morning routine thank you Ali that's wonderful all right next rapid fire question what's been one of the most meaningful in-person experiences with your team company or otherwise doesn't have to be the most but in kind of the ballpark of one of the most meaningful in-person experiences that you've had

so my team just did an all tech wide off site in Santa Cruz and the thing that brought me the most joy and that most meaning was an event that I didn't even want to go to originally but I cannot recommend more for your team or as part of an interview process

we had to we did a competition where we had to build boats out of cardboard I don't know if you've ever done that we had a limited amount of time to build a boat out of cardboard and then we had to race it in a pool I was the tribute to be in the boat for my team

but oh my gosh it was so meaningful because you know with a random group of people I got to figure out like in-person can we work together as a team can we collaborate can we support each other in ambiguity do I trust you to experiment it was an amazing experience and oh my gosh I would totally rehire everyone on my team even though my boat sank you were the first one or the last one did you make it all the way then?

so we made it further than other boats but I was definitely swimming and dragging the boat for a portion of the pool yeah we have a very similar team building activity there they are the best very similar so I'm very interested in these experiences where I got a chance to personally connect with others weddings going to visit them and they have kids recently I got a chance to catch up and meet everything there with one of my engineers that I broke together for a long time ago

personally I think it was a mechanical engineers now doing data science 10 years later that type of moments are the most meaningful experiences for me that's great Ali I used to be a lifeguard for nine years of my life and you better believe I have administered that event before and so that is a ton I can tell you a ton of fun every time I've seen it it's a total blast alright what is the trend that you're seeing or following that's interesting or hasn't hit the mainstream yet?

so I'm a big AI nerd and I follow open AI pretty closely so the one that I don't think it's caught up yet but I'm not on the most excited it's something called visual generative models and they release something called valley tool and it's like GPT3 allows you to create text out of text allows you to create images out of text so you can actually say some kind of text and art comes out and I think it's going to disrupt the whole visual art space that I'm very excited and interested in

so that's what I'm like to read and understand more I love it I'm so excited for that too as somebody who's not necessarily the most skilled at art the ability to come up with something like Ali, Ali, Patrick in a cartoon form writing dinosaurs with a volcano in the background and an amazing piece of art comes up from that that's a dream that's an FD and you're rich you'll be surprised next week when those NFTs drop so Ali what about you?

Yeah I think my example is very much just a recent problem that I had to deal with that got me pretty interested there's some new new companies out there that allow for cloud development environments to really minimize onboarding time and you know decouple computing power from the machine

so I think a lot of larger companies have developed these for themselves but a lot of startups really really struggle with this and help solve some of those scalability issues so that's been something that I think has been pretty cool and talk with some of those companies that's been interesting

that's a great one. Okay let's wrap this all up final question is there a quote or mantra that you live by or a quote that's been really resonating with you right now so my favorite one of all time I say it often is do one thing every day that scares you

think that came up earlier in the podcast at some point I think that's Eleanor Rosella but I know it from Boslermans everyone's free to wear sunscreen song and it is very very helpful to just realize what you're holding yourself back from and just decide to go for it instead

and it's fantastic. So mine is not just for now it's just in general until you make unconscious conscious it will direct your life and you'll call it fate it's a call for action to take control and analyze and there we have it two phenomenal quotes to close

and to send people into really important existential evaluations of their life but also to compel people to do things that scare you and to shirk fate and take ownership and create a more intentional career so Ali Ali thank you both so much for an incredible and fun conversation thank you both thank you thanks Patrick