The Happy Engineer Podcast

158: How to Minimize Regret and Maximize Success with Omar Halabieh | Tech Director at Amazon Payment Services

What does it take to be a Director of Engineering? Where do most engineering managers fall short? How can you maximize your career growth and progression… without regret?

In this episode, meet a global technology executive with over 20 years of experience on some of the most demanding teams and technologies in the world, Omar Halabieh.

If you want to make it Director level and beyond, this episode is essential. Omar is passionate about developing people and building high performing organizations.

Omar is currently Director of Technology at Amazon Payment Services, based in Dubai, UAE.

Prior to this, he led technology teams within Amazon’s Supply Chain Optimization Technologies organization based in Seattle. These engineering teams revolutionized what we consider “normal” in supply chain technology today.

Outside of work, he enjoys spending time with his active and inquisitive 4-year old son. You CAN have that time and balance with your family too.

Omar looked fear in the face many times… and discovered that regret minimization was more important than playing it safe. Discover the frameworks he used to make huge decisions and drive his success without regret.

So press play and let’s chat… it’s time to make courageous decisions that minimize regret and maximize success!

Ready for more? Join us in a live workshop for deeper training, career coaching 1:1, and an amazing community!  HAPPY HOUR Workshop Live with Zach!


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WATCH EPISODE 158: Achieve Director Level and Beyond as an Engineer with Omar Halabieh | Insights for Career Growth



LISTEN TO EPISODE 158: How to Minimize Regret and Maximize Success with Omar Halabieh | Tech Director at Amazon Payment Services

Previous Episode 157: Learn to Say More with Less Words | Executive Communication


The Top 3 Principles to Elevate Your Engineering Career to Executive Level

I had an insightful podcast episode on The Happy Engineer Podcast with Omar, a director of software development at Amazon, about achieving director level and beyond as an engineer. Here are the key takeaways:

1. Stay Up-to-Date: Understand business and industry, explore emerging technologies, and focus on engineering solutions that bring real value to customers.

2. Think Long-Term: Develop the judgment, intuition, and diverse network needed for success in higher-level leadership roles, and invest time in passive reflection for valuable insights.

3. Build Effective Organizations: Focus on strategic thinking, team culture, and organizational development to prepare for higher-level management and demonstrate readiness to senior leadership.

To go deeper and build an action plan around these points and why all this matters, click the podcast link below and listen to the entire conversation!


Omar Halabieh is a global tech executive with over 20 years of experience. He is currently Director of Technology for Amazon Payment Services – based in Dubai, UAE, and has been in this role for the past 5 years. Prior to this, he led technology teams within Amazon’s Supply Chain Optimization Technologies organization, based in Seattle for four years. Omar is passionate about developing people and building high performing organizations. Outside of work, he enjoys spending time with his 4-year old son – which keeps him active and inquisitive.



Please note the full transcript is 90-95% accuracy. Reference the podcast audio to confirm exact quotations.

[00:00:00] Zach White: It’s going to be an amazing day. Happy engineer. You made a great choice to be with us Omar. I have been looking forward to this since our last chat so much. Thank you for making time and welcome to the happy engineer podcast, 

[00:00:11] Omar Halabieh: Man. Super excited to be here. Thanks a lot for the invite and looking forward to our conversation.

Expand to Read Full Transcript

[00:00:16] Zach White: Yeah, no kidding. I want to start in a place I hadn’t planned, but it came up right before we hit record and I think it’s too important not to address because it comes up with engineering leaders all around the world, all the time in my coaching and it’s vacation, it’s vacation. So it’s, uh, December 18th.

[00:00:36] As we’re recording this near Christmas time, lots of people thinking about wrapping up for the year. And I asked you, when was your last day for 2023? And I’d love it if you would just tell me again, how that looks for you in terms of your holiday schedule. When, when are you done for the year, Omar? 

[00:00:55] Omar Halabieh: Sure.

[00:00:55] So I actually started my vacation last week. I believe it was starting December 11th, and I’m basically coming back to the office after the first full week January. So this is something that I started about years ago, where I pretty much saved most of my vacation through the year and ended up taking a bunch of time at the end of the year.

[00:01:16] it works for me in a number of different ways. I think one is. there’s never a good moment to take time off, but I feel like just from the business cycle standpoint, it’s probably the best time out of all the time. Sure. To really be able to, to disconnect and then I think the fact that it’s at the end of the year and before the beginning of a new year, I think it really helps me take time off to reflect, whether actively or not.

[00:01:41] Yeah. Passively, about how the year went, whether from a professional perspective, personal perspective, et cetera. And it helps me get a headstart in terms of thinking about 2024. What are some of the things I want to do? What are some of the things I want to do differently? And even for some of those things, maybe get them seeded and started.

[00:02:01] I always find it easier when you get started on something in December, rather than waiting for January 1st to get some of these habits kick started. and so it’s been it’s been great. Obviously, I’m extremely grateful for, the team, to be able to essentially navigate while I’m out of the office.

[00:02:18] and it takes intentional effort, both from the leader to build that team and then for the team also to step up and engage. So I’m very grateful for that and for the management support as well. But that’s kind of how I’ve how I’ve thought about it. And this is my third year running in this kind of model.

[00:02:34] And I’ve really it. Found it super beneficial last year for me and then also for the team. I think it gives them an opportunity step up to have some direct engagements that they usually don’t have. If I was there directly because those are conversations that I would normally facilitate. So I think in that respect, it’s a win win situation.

[00:02:55] And then, of course, like, as you come back in January, it’s a win win situation. there’s a lot of sprinting at the beginning of the year, whether in terms of goal settings, performance reviews and management cycle, et cetera. So I feel like you get in energized to go through that versus, coming off a whole year where you’ve worked so hard and then now you’re trying to sprint again.

[00:03:16] So those are essentially the ways that I’ve thought about the topic and grateful to be in a position to do 

[00:03:21] Zach White: that. skeptic, engineering hat on for a lot of the leaders who I talked to. They might be thinking right now. Yeah, Omar must not have a very important role within his organization or work at one of these small companies where there’s no deadlines or real challenges around the holidays.

[00:03:39] That’s not true at all. Can you really quickly tell us what is your current role and who you work for? 

[00:03:47] Omar Halabieh: I’m currently a director of software development for Amazon. So I’m particularly responsible for payments technology in the Middle East and Africa region. and so we enable, external companies, to use our services to process digital payments or online payments, uh, and various size, shapes, forms.

[00:04:08] and then we also support all the payment activity on Amazon storefronts, here in the Middle East region. So it’s a fairly large team, fairly large organization. 

[00:04:17] Zach White: Pay payments at the most. Busy payment processing time of the entire calendar year at Christmas time here, the whole world is buying everything right now and a huge percentage of that online, maybe the majority and and you’re on vacation for three weeks.

[00:04:35] So I just wanted to level set. That if anyone has a belief that it’s not possible to separate yourself from the organization for any extended period of time, it’s not true. That’s a mindset. That’s a belief. And you mentioned a couple of things that make that possible that we’ll probably come back to later in our chat on what it takes to become not just a director period, but a great director and how we break out of that middle management band.

[00:05:03] But before we go there, you mentioned active. Intentional reflection versus passive reflection. And I was wondering if you could explain what you mean by passive reflection, because that’s not something you hear about very often. 

[00:05:17] Omar Halabieh: Sure. So I always find it in terms of like active reflection.

[00:05:20] I think of it as Like you’re sitting there literally, you may have a pen and paper if you’re old school, like me, writing down some answers like what’s worked great. Well, last year, what things, you know, I want to improve on, et cetera, but I find that when you give yourself that, space, that mental space and you step out of your day to day, activities and responsibilities, your mind doesn’t just completely disconnect, in the back of your mind.

[00:05:47] There’s thinking that’s happening, ideas are doing things that you’ve worked on, et cetera. And I feel when you give yourself that mental space. A lot of passive reflection is happening sort of in the back of your mind, even though you may not be thinking about it and you’re here to get these spurts of like ideas, whether creativity things to try things to maybe do differently recalls of, you know, moments of achievements from the year.

[00:06:13] So I feel that giving yourself that, that mental space, is important because I feel like both aspects of reflection, whether active or passive play a role, in you understanding yourself better, understanding how you can develop, how you can become better, et cetera. But that’s kind of how I think about it and why that time is, important, 

[00:06:32] Zach White: Omar, I really liked that concept and it came up last week in a coaching conversation where one of my clients was. Expressing his desire for the holiday break to be a complete turnoff, you know, as far as work, like switch off work, switch on family and rest and recovery in the holiday season. And, like this really aggressive kind of black and white mindset about, I don’t want to think about work at all while I’m on the trip.

[00:07:02] And how can I make that happen? And one of the things I shared was, I really appreciate the heart of that, that you’re not gonna. Intentionally set aside a bunch of time to work on career related things during the break. However, I encouraged him, leave room for the opportunity for your subconscious to serve up some, awareness.

[00:07:23] And if you do have this sense of clarity about something, like, don’t be afraid to just grab the journal, write that down. Or, or give yourself a cup of coffee in 30 minutes to think about your career as if somehow you’ve ruined. Your break, you know, let, your mind play a little and be open to that because I’ve seen too, a lot of times you know, it’s like the shower, you’re in the shower, you have brilliant idea.

[00:07:47] that’s a real thing. The subconscious kind of working on an idea and then poof, you have it. And if you try to suppress that, like I can’t let that happen, you might miss something really valuable. So passive reflection. I’m going to use that phrase now. Do I have your permission? Can I start talking about passive reflection?

[00:08:04] I really like it. Amazing. Well, why don’t you set the stage? We already addressed where you are today. An incredible opportunity, a job that so many engineering leaders in tech would love to get to in their career. But why don’t you give us the 60 second condensed, uh, career ladder of Omar. Where did it all begin?

[00:08:24] Um, and walk through your experiences briefly. I may interrupt you at a couple of points, but I just wanted to get the full picture of your career journey from start to today. So give us the compressed walkthroughs. What have you done? 

[00:08:38] Omar Halabieh: Absolutely. Absolutely. So, my background’s in computer science, so I have both a bachelor and a master’s in computer science, both from universities and in Canada.

[00:08:48] Um, and then I started out as an IT analyst or. software developer equivalent role with an energy company. I did a two year rotational program, so I get to do a lot of different roles. It was a super helpful experience in terms of gaining that breadth, and really understanding how technology enables various aspects of business.

[00:09:11] So I worked in corporate systems. I worked in risk management and trading systems and energy systems. So a lot of different exposure in terms of application of technology. And then progress my way there with that company to my first management role, leading, leading basically a team. and then about 7 or 8 years into that, journey with this energy company, I got an opportunity to move to Amazon.

[00:09:36] So this was about almost 9 years ago. at the time, Amazon obviously wasn’t as large as it was, as it is today. and while it was recognized as a technology company, it was still in that, major ramp up phase, let’s say. 

[00:09:50] Zach White: What year are we like put us in context when you got that first 

[00:09:54] Omar Halabieh: Amazon role?

[00:09:55] in the mid. 2010, so it was around 2014, 2015 there. And so I was doing really well in my company. I had grown essentially through the ranks. I had really good relationship with all the senior leaders in the organization. So as much as it may sound like a trivial decision now. looking back, I think at the time it was one of the hardest career decisions that I’ve made, because of the fact again, that I felt like I was in a good trajectory where I am, and I wasn’t sure to me that uprooting from the time I was based in Houston to move to Seattle to work for Amazon, was necessarily the right thing to do at the time.

[00:10:34] and so I, I ironically applied, uh, Jeff Bezos regret minimization framework, uh, and that I knew that if I didn’t take that opportunity. fast forward, 10, 15, 20 years from now, I’d probably look back and always say that, Hey, what if I took that opportunity?

[00:10:50] What would have happened? And so I talked to a mentor of mine at the time, and I decided to sort of take the plunge and make the move. And, uh, it’s been a, it’s been a fantastic journey, uh, well beyond anything that I’ve expected. So I started out actually as a, Senior technical program manager with Amazon and then quickly transitioned back into into management because I, I knew that while I could do IC work, I really enjoyed and thought I was a lot more effective as a manager or leader as I was an IC and then progress from, you know, manager software development to senior manager and about 5 years ago, an opportunity came up to lead the team Payments technology organization on the back of an acquisition that actually Amazon had made in the Middle East region.

[00:11:38] And so the opportunity came up in Dubai to come and lead the team. And it was a very appealing opportunity for me, both from a professional perspective, in terms of moving at the time I was working and supply chain optimization. So it was an extremely mature Very advanced in terms of like how long Amazon’s been running it.

[00:11:59] It’s a core competency, et cetera. systems running obviously at super high scale, et cetera. And then be able to move to an area of the company, which literally is a startup that has just been acquired. Handful of people and looking to essentially significantly scale that business. So I felt it was a new challenge for me in terms of organization building, elevating, the engineering bar.

[00:12:21] So lots of good elements of experience to add to my profile and then. Personally, I’m originally from the Middle East, so being in Dubai brings me closer to family and home. So, made the move, to Dubai. And it’s been now a little bit over a year and a half since then that I’ve been promoted to director of software development.

[00:12:41] So that’s the journey in a nutshell. Sorry, more than 60 seconds, but 

[00:12:45] Zach White: no, it’s really good though. Then why don’t we. First, go back to that decision to join Amazon because everybody faces that decision at some point in their career journey. you know, in my perspective, the 35 year one company career path and retiring with the gold watch is no longer a thing, and so we’re going to face these points of decision and especially for a top performer.

[00:13:13] Achievement minded engineering leader, it’s very normal to have an upward trajectory in your current company at the time that an opportunity comes onto your plate. how do you approach those kinds of decisions yourself?

[00:13:28] Or maybe if you were coaching me, what would you encourage me to think about those moments? 

[00:13:33] Omar Halabieh: It’s never an easy decision, as you said, especially for high performance, because you’re generally in an environment where you’re doing well. You’re you’re appreciated. you have the momentum going for you and you feel like you’re taking a risk.

[00:13:46] Right? So again, I think a few things help not necessarily just 1 thing and specific regret minimization framework is definitely a big fan there. And it really helps. I think seeking guidance from mentors. To really act as a, let’s say, a mirror or reflection board in terms of like, here are the inputs I’m considering.

[00:14:06] Here’s how I’m thinking about my decision to really bring in that objective mindset and have somebody to talk to to be able to reflect. Ultimately, you’re making the decision. and so your mentor is not making a decision for you, but I think that conversation, really helps.

[00:14:22] And then the 3rd piece. is really looking at the potential. And what I mean by that is not necessarily thinking about the immediate job that you’re getting. because that’s in some sense, one step, I think it’s to really think that in my current company, besides the role that I’m currently in.

[00:14:41] So don’t compare like what you’re in right now versus the role that you’re going to just in terms of like, for like, but look at the potential. It’s like, where can this role take me? 2 years from now, 3 years from now, 5 years from now, and then what about versus the other opportunity and where can that take me?

[00:14:58] Because that potential is a lot more important than where you are right now and I would say coupled with that and a big part of that is also. The, the quality of the people that you will work with, because I’m a big believer that in some sense, you rise to the level of the people that you work with.

[00:15:21] And I think for me, one of the biggest. Let’s say benefits of working with Amazon has been really working with, top notch, engineering talent that really helps, inspect my work, helped me get better. and I think that for me is like, I always want to be, in an environment where I’m definitely not the smartest person in the room so that I can learn from others that are, that are smarter than I am.

[00:15:44] So I think the combination of. considering these various elements, I think is really, really helpful. Uh, in that respect, 

[00:15:53] Zach White: the piece about potential I heard in an entrepreneurial context, something that really connected for me. And it’s the same in your career, but for whatever reason. I feel like career professionals don’t think this way as much as entrepreneurs do.

[00:16:11] And it was related to this classic conundrum of, do I push or do I pivot? do I keep battling with the company that I’m in or the company that I’m building? If I’m a startup and we have an idea and you don’t know if you’re. six inches from diamonds, so to speak, or that you’re that close.

[00:16:28] And if you walk away from it, you missed it by that much, but there’s a shiny object over here. And should we start this other opportunity or change the company direction? And the framework I heard from this amazing entrepreneurial coach was if the vehicle that you’re in at its maximum can get you where you want to go.

[00:16:50] If it aligns with the vision, if, if this thing that you’re could theoretically at its max. Hit the dream or the vision of what you want to create for your business, then you better have a really, really compelling reason to leave it because you’re going to go back to the beginning and have to rebuild in your new company, he said.

[00:17:10] But if the vehicle you’re in. You can see, doesn’t have the potential to get you where you want to go. Yeah. Then it’s time to pivot anyway, like go ahead and take the opportunity. Cause you’re, you’re never going to get there. If you can see already that it won’t, that to me is so useful as one of the many inputs simply to say, what’s the ultimate vision for my career?

[00:17:30] Where do I really want to get to? What kind of work do I want to be doing? What kind of team do I want to be a part of? Where do I want to live? All these different pieces. And is the vehicle or the company that I’m a part of. Able to get me to that vision, if it is, then the new opportunity better be really, really juicy and it needs to be an obvious.

[00:17:50] Yes, totally. Totally. So I think that’s super helpful to push that framework. It’s not common to think beyond where I’m at versus the first day one opportunity of where I’m going. And looking at that comparison. So I really appreciate 

[00:18:04] Omar Halabieh: that. Yeah, and, and I think a lot of it, what I learned, at least in terms of how to think about this, Zach, is primarily taken like from the, let’s say the financial world.

[00:18:14] I always think, about investing, thinking long term, you know, big fan of, Warren Buffet thinking. you have a stock and it’s like, are you trading a stock, that may be priced at a similar price point as it is today? But it’s really your belief in the future potential of the thing that you’re holding.

[00:18:30] And I think that if you approach it from that mindset, a lot of what you talked about definitely connects even in terms of like risk reward, right? For the amount of risk that you’re taking by moving and starting fresh and building those relationships, whatever else. It’s the reward that’s there still worth it.

[00:18:46] And a lot of times people think reward, they immediately just think about dollar compensation. And while that’s definitely an important piece of it, I think there’s also the element of, growth and, how much skill building is happening as well. Yeah. 

[00:19:00] Zach White: So Omar, you not only lead one of.

[00:19:03] arguably most critical teams within Amazon, which is awesome, but you’re also really passionate about mentoring and coaching and helping other engineering leaders to create the success they want in their career. And so what I’d like to spend time on is this overlap of those two passions, your own success and how you’ve helped others specifically when it comes to breaking Yeah, I’m sure there’s a ton you could offer on the IC side as well, but what I see, that’s such a tough place for many engineering leaders to break out of is they’re in that manager or senior manager level, and they want to get to the director or executive , season of their career, they aspire to high levels of leadership of teams and technology.

[00:19:48] there’s something about that middle band. It’s really tough. You tend to bring some bad habits of your IC life and how you became successful there into those roles and mitigate through some, band aids maybe more than true development. And then it gets very competitive. These director positions, especially at a company like Amazon.

[00:20:07] And how do you stand out? How do you make your. Ability known and the network, it’s just a lot of pieces there. So tell us for you, if you think about what it takes to not just be successful and avoid burnout as an engineering manager, which is hard enough. But to actually get yourself prepared and ready to make that director role a possibility and then a success, where do we need to begin on that journey?

[00:20:36] Omar Halabieh: the first thing I would say is there’s famous book by Marshall Goldsmith, like what got you here won’t get you there. I think the first part is acknowledging that to get to that next level, as you exactly mentioned, you need to. Think and do differently than than you have done in the past.

[00:20:55] And as you said, like, while it sounds simple, it’s not easy and practice to do that. But I think you have to start there because in some sense, acknowledging that if you just keep doing what you’re doing. You may do very well at the current role that you’re in, but it’s going to be difficult for you to kind of ascend to the next level.

[00:21:16] Once you kind of establish that, I think the next step is really finding out as much as you can about, well, what does it really take to To, um, to get to that level and to operate at that level, and I think that’s where, you know, engaging with and interacting with a lot of the folks that are at that level, I think becomes important, whether it’s to learn how they think, whether it’s to have them critique some of the work that you’re doing, uh, or providing you with with inputs, whether in terms of getting mentors at the next level, et cetera.

[00:21:50] But I think you really need to it. Start, engaging with because until you see people operating at that level, the concept remains maybe a bit fuzzy, maybe a bit theoretical, in terms of what it is. And it really it’s a humbling experience because you look at these people and you’re like, wow. I mean, they’re, they’re just like at a whole other level, right?

[00:22:10] Then it’s like, am I ever going to get there? Is it achievable stuff like that? But I think though. Yeah. You have to put yourself in that uncomfortable situation because in my mind, that’s where growth really starts. So I think that’s more around sort of the mechanics, if you will, in terms of how you, how you set this up.

[00:22:30] But I would say, you know, there’s a couple of fundamental pieces that really help differentiate between. Sort of the manager, senior manager, and then above role. I think the first one is definitely around organization building, and this has come up a few times already in our conversation where at that level, one of your primary responsibilities is building an organization, building a high performing organization that’s sustainable.

[00:22:58] And by sustainable, what I mean here is I always like to use the term is like the team is better off having you. But they don’t need you to function going back to the conversation around vacation and whatever else. 

[00:23:10] Zach White: So let’s repeat that. That’s a really nice thing. The team is better off having you, but they don’t require your presence.

[00:23:22] Yeah, that’s a really beautiful way to frame up this dance between you creating value and your role matters. You are a multiplier to the effectiveness and the productivity of the team and the results, but it’s not a dependency. Super. Nice way to sum that up. I’ve never heard it said that way, but I love that.

[00:23:44] Omar Halabieh: Yeah. I mean, building, the right culture. Both in terms of how we do things, performance driving high performance. that, element is so important. And it’s not just from a sort of a tactical perspective in terms of like, let’s hire some talent.

[00:24:00] Let’s manage some talent. But it’s really about the time horizon. Also, that you’re thinking through, you’re thinking about things like, For example, what roles do I need to have in the organization 2 to 3 years from now basis the business demands that that we have you worry about things like, hey, how am I going to increase diversity of thought and leadership into my team?

[00:24:23] what sites do I leverage to build my team and how do I diversify any kind of risk that you may have, whether in terms of, hiring for specialized skill sets or senior skill sets or whatnot. So you’re really thinking about, that element of developing the organization.

[00:24:39] Not just from a tactical standpoint, but also from a strategic perspective, because ultimately, this is your team. And so you need to build as solid of an organization as you can. And you’re the steward of both the culture that is there in the team and also the performance bar. Because ultimately, team will rise to the performance that you tolerate, if you will, in that respect, so it’s your job to not only set a high bar, but to continue to push that bar higher and higher with every cycle to help grow the team and your mark of success here is really the amount of leaders, both on the IC side, as well as the manager side that you’re able to generate under, under your leadership.

[00:25:24] that is definitely one key pillar, of success and move to the, to the next level. 

[00:25:30] Zach White: what is the key? To, getting ready for that first real experience. how could I ever, as a manager who has, a single line of six or eight or whatever engineers working for me. Demonstrate to a hiring vice president that I’m ready now to build out an entire organization when I’ve never done it before, what’s the ways to get some experience or practice or readiness?

[00:26:02] If you don’t have the job, the old catch 22, you know, we did it once as a manager, I’ve never led people. How do you get that first manager job? This is to me, that corollary, it’s like you’ve never built an organization and you need to go show somebody that you’re ready to do that. How do you. 

[00:26:19] Omar Halabieh: a couple of pieces that, that play into that, and this may be obvious is that you need to deliver, uh, and you need to deliver results in a big way, because in some sense for you to have the, let’s say the platform to even have a meaningful conversation around scope, I think definitely you need to be.

[00:26:39] Not only delivering, but I would say knocking it out of the park in terms of results and what you’re able to achieve with the current team that you have. and 2nd is that the way you also deliver results matters a lot. Um, and so, for example, how are you leveraging your team?

[00:26:58] How are you scaling through your team? How are you working with your peers? How are you influencing without authority and getting things done? Because these are all indicators that other senior leaders would be looking at to say, do we believe this person can scale? Because obviously, there’s an element of Like taking that leap of faith or taking that, let’s call it a risk to give you more responsibilities.

[00:27:24] But those are elements there. the other ones I would say are around bringing up opportunities and that thought leadership. Sometimes again, these opportunities may come to you. But then at times you may need to go and say, Hey, there’s this area right that we believe there’s an opportunity and and maybe you’ve done some some pre work.

[00:27:47] And I have to, you know, 2 different examples here. 1 where opportunity came up this way, where you would literally go advocate to your leaders that. Hey, we’ve identified an opportunity where we can, enhance the system in this way, or we can create a service to do X and it can serve Y teams and, elevate decision making stuff like that.

[00:28:07] And of course, there are times where it’s more reactive in the sense, for example, like a manager of a sister team, for example, transitioned out and then you are close enough in that area. You’re performing really well, you may get that opportunity without too much you going and asking for it in that respect.

[00:28:26] But I think it’s you need to do both because you don’t know where the opportunities may come from. But I think those are, in some sense, the, the building blocks, but. Really building that trust with your leaders, because ultimately for your leaders to give you more responsibilities, they need to trust you and trust again is not like they trust me as a, as an individual or as a person, but they really trust my leadership, my judgment, my ability to deliver, et cetera.

[00:28:54] And more importantly, again, through the team, because if they see that, yes, you’re delivering. But then you’re having to go all out to be able to do that, they would really worry about adding more things on your plate and everything coming down in that respect. 

[00:29:10] Zach White: That’s a huge point to make clear, you know, knocking it out of the park while essential to prepare yourself for this next level, it doesn’t mean on the back of your nights and weekends and brute forcing it through your own strength.

[00:29:25] You know, one of the things I look for is that manager, senior manager who. Knocks it out of the park and makes it look easy because they are leveraging the team. They’ve done the work to establish the systems, the processes, and the, they trust their teams. They have a high performing team and in a way you can go home at five o’clock and relax.

[00:29:46] And still delivering credible results. That’s the kind of evidence of the 

[00:29:51] Omar Halabieh: absolutely. And it’s reflected also in the growth of the team. So one of the things that, you know, senior leaders will look at is like, what leaders are you also generating in the process of delivering those results? Because if you’re truly delivering through the team.

[00:30:04] Then this should also be reflected in growth in terms of the engineers you have, the managers you have, et cetera. So they’re looking at your track record of developing, promoting these folks, et cetera, as an indication of, scaling through the team. Cause that’s essentially, beyond a certain point, it’s like, if you’re not scaling beyond the team, then your capacity just maxes out.

[00:30:27] Zach White: So good. All right. Building block one. Get yourself into the place where you’re ready and excited to tackle organizational design and development and building a team. What are the other building blocks to breaking through to director and 

[00:30:42] Omar Halabieh: above? So I would say definitely the second one is obviously where we’re a tech organization after all.

[00:30:49] So I think that the technology strategy aspect of it becomes foundational, first level management is a lot about execution where the path is more or less chartered. for you in that respect, right? So there are projects in the pipeline and we’re just going ahead and turning them.

[00:31:08] Not that that’s easy. Not that it doesn’t have its own complexities and whatever else. I don’t want to demean that by any means. But I think the other part is to say, where do we need to go? there’s obviously a difference in level while it’s important for the senior manager role.

[00:31:23] Typically at senior manager, you’re thinking about it more from maybe a one year or two year dimension at the director level. It’s even further than that. You’re looking at three year trajectory, five year trajectory, and this really then embodies both not just your technical acumen in terms of understanding the technologies that we have and how they should evolve.

[00:31:44] But a huge amount of business acumen because you need to understand where is our business going? What do our customers want? What is it that we’re trying to do? You know that we need to do 2 years from now that I need to start building today so that by the time it’s needed the foundation or the infrastructure for it is already done so that technology strategy again.

[00:32:07] It’s not like you’re doing this 1 in isolation. It’s a collective effort. But again, you’re the. Shepard Stewart and ultimate owner of that technology strategy as the tech leader for that space. your effectiveness in that respect is judged by how much your technology is really enabling the business.

[00:32:26] To hit its long term trajectory in terms of, customers, in terms of their level of satisfaction, engagement, growth of the services that you’re having. 

[00:32:36] Zach White: Omar, how do you break down your typical, maybe we can look at it in a week context. Maybe it’s important to look at a longer time horizon to really answer the question.

[00:32:47] But what I’m curious about is how you invest time and energy into staying up to date. With technology trends and how the, the tech is developing sort of at a level of execution, even to, you know, how, how are these new languages being deployed, which ones do we use? What, what should we be using in the future with the building blocks of this tech and maybe somebody who’s in a more mechanical world and aerospace or automotive might have a different lens than thinking about full stack and architecture, but still it’s the same idea, the modern director.

[00:33:22] needs a level of technical acumen that seems to be maybe higher than in the past to keep up with the pace of the change. So how do you accomplish that successfully in your own role? Are you looking at this every day? Is it something you block lots of time for? Do you use conferences or, you know, how do 

[00:33:39] Omar Halabieh: you do it?

[00:33:40] It’s a very multi pronged approach. I’m privileged to be working for a tech organization that has a lot of internal resources. So that helps a lot. But then again, the challenge is like, how do you make time and know sort of where to tackle? But I think maybe it starts with Zach in terms of, I look at it in two ways.

[00:34:00] I think one is your understanding of Your business and your industry become very important because these act as anchors to help you understand where should I go look or where should I pay more attention to, than perhaps because without those indicators, you would literally get lost in the sea of yes.

[00:34:19] Things that are happening out there. So, I think that helps bring the focus there. using the 80, 20 analogy, like the 20 percent of pure exploration where, you know, you’re looking at technologies that are emerging that even right now may not have any.

[00:34:35] Direct intersection with, with the business or the industry that you’re specifically in at the moment, but it’s more to understand, like, where things could potentially had, uh, and more so to just satisfy your own personal curiosity and that, that respect, but I also feel that, with technology.

[00:34:53] there’s a lot of fundamentals that also don’t change. taking a look at what do we really need? what problems are we trying to solve? It’s so easy to get distracted with the new shiny object syndrome as well. So part of my role as well is how do we really bring that aspect of engineering, but really in support of it.

[00:35:14] What’s useful and helpful for customers today, tomorrow, the next year, et cetera, because again, it’s so easy to get distracted in that regard, but definitely super important. And we do this at multiple levels. Obviously, there’s a strategic level where we look at this more from a 3 year horizon.

[00:35:31] And there we’re looking at trends. both internal and external, but then you take a narrower view of, we doing next year? What are we doing next quarter? And there things tend to get more tactical, more decisioning around specific choices and whatnot. But this is something that one needs to stay as close to as possible because it really helps shape the overall thinking.

[00:35:55] So it’s something that I get involved in pretty hands on. Capability and something that I enjoy doing just being a techie. 

[00:36:01] Zach White: I think that’s something great executives that I’ve met have in common is the ability to quickly discern a disruptive technology change or a trend that has meaningful impact on the business direction and strategy versus something that’s getting a lot of hype or is exciting to talk about, or maybe even really fun to read and learn about, but it’s just an incremental change or a new approach to accomplish the same fundamental things that we already do.

[00:36:31] And it’s nice to pay attention to it. And maybe we should invest in that tool, or we, we would be wise to put some energy behind it because we’ll need to adopt it, but it’s not a fundamental shift in what we’re doing. And they could kind of. Pick those points where they really need to focus depth versus just awareness.

[00:36:49] Like, okay, here’s a, something we’ll probably need to bring in at some point. No big deal. I don’t know the answer on how you become great at that, but it’s a useful lens to ask, like, is this a fundamental strategic shift that we’re talking about here? Or is it just a 5 percent improvement on your speed to deliver X?

[00:37:08] Yes, let’s do it. Put it in the pipeline next topic. Right. And move on. 

[00:37:11] Omar Halabieh: it takes years to develop that judgment or you call that a radar or whatever intuition, but definitely like once you have it, it’s more about like, how do you consume the inputs that then help you, make that, discernation and, look, you, you don’t always get it a hundred percent, right.

[00:37:29] But that’s where, having a diverse team and being part of a larger organization. You also get signals from others and at times you may need to correct your signal in terms of maybe you’re over indexing on it or maybe you’re under indexing on it, et cetera. And that’s where a lot of, professional forums, even like LinkedIn and other means, I think are great platforms to, exchange ideas, see what’s happening, learn about what the latest is.

[00:37:55] But I think it’s really about going behind the buzzwords. I think it’s probably the most important thing. Otherwise, if the conversation stays at that level, it’s not very productive. 

[00:38:05] Zach White: Yeah, love it. If there was one more building block to how we break through to director and above from that middle management band, what would it be?

[00:38:15] Omar Halabieh: I would say that the third one is, is really around like how you engage the broader organization. I think clearly to make things happen at that level. You really need to be able to, influence lean on. Engage in ways that sometimes could be difficult, challenging, having difficult conversations, et cetera, with others.

[00:38:38] let’s call them interpersonal skills. really need to take a step up, and that respect is the people that you’re working with and dealing with in that regards become higher. That also includes aspect, like, how do you make your team’s work and efforts visible? Not just from a, like a recognition perspective, but also to understand that could they be working on things that could be beneficial to you?

[00:39:01] Could they benefit from things that are that you’re working on and broaden the idea and expand it even further? that whole angle of, like, how do you engage with the external world, especially working in a very large organization, it becomes really essential because in some ways. relatively speaking, the rest of your team is very focused on the specific, business, customer segment, et cetera, that you’re serving today.

[00:39:25] Yeah, but you’re the one that’s playing the role of looking out and looking at things that either, you want to import, you want to export. things of that nature. that part is definitely important. And something that takes intention, takes effort sometimes could even be uncomfortable, but it’s absolutely necessary to drive things forward.

[00:39:44] Zach White: What’s interesting about this sort of cross functional relationships and influence and even acumen, like the skill sets and understanding what is. The sales team thinking, what are they doing? What are their strategies? How do they operate? What is the marketing team doing? What’s, supply chain doing what’s internal it up to versus things that are extra, like all of that.

[00:40:05] what’s tough is the bigger the organization, the less likely you’re going to have natural organic interaction with those organizations, because there’s more layers to the hierarchy. There’s just more. Incidental silos, even if it’s unintentional or undesirable, because we have work to do in our space and there’s just so many people, but that’s when it’s even more important to build the relationship.

[00:40:30] that’s where you need it the most, a small company, like your staff meeting by director level, you’re already in a room with all the other, the sales director, the marketing director, like so everybody’s there and it happens a bit more organically. At a company like Meta or Apple or Google or Amazon, these huge, you know, take it into like General Motors or Lockheed Martin, these big companies, you could be a director.

[00:40:53] And very rarely be in the same room as a sales director, if ever, you know, maybe it’s once a year and a big planning kind of conversation, because there’s just so much more happening, but it’s really, really important. So How do you make time? What’s, what’s your specific strategy at Amazon?

[00:41:09] did you have to just schedule these meetings yourself or their forms you could tap into? What are the tactics, if you will, to accelerate that cross functional? 

[00:41:17] Omar Halabieh: Skill set. Yeah. there’s a couple of points to it, Zach. I think the first one is you yourself over time developing, let’s say, the acumen because for you to be able to go and have a meaningful conversation, let’s say, with, your director in finance or your director in sales.

[00:41:34] You also need to be able to speak the language, if you will. so that, that I think is, is one part of it. And yes, there are definitely forums where teams present, whether on their goals or objectives or their achievements, et cetera, that you can tap into. So it’s not a, let’s say a point to point conversation and that, in that respect, and then similarly, you establish forums and you invite them over to have these conversations and then one on ones.

[00:41:59] there’s definitely. no substitute for doing 1 on 1 conversations, but that’s also where you need to start, to think of your internal network. I like to think of it as a series of, concentric circles, right? Where you have, like, these 1st degree connections, which are people that Their role is heavily interlinked with what you’re doing, and you need to make sure that you’re having, a very high level of engagement intentionally with them, et cetera.

[00:42:25] And then you have, then, people further and further away, where it may be that even if you talk to them once a month or once a quarter, it may be enough, sometimes even if you Ran into them and happened to have a conversation. It’s okay. But if not, then in some ways, it’s, it’s no big deal, but I think it becomes so, so important because of the fact that then, what your team can deliver for it to be effective.

[00:42:49] It’s not so much as to it’s enough to just. Generate the technology or the code behind it, right? So that’s where I think as a, in some sense, once you get to that level, like, yes, your functional hat that you’re wearing is one related to say, in this case, technology. But you’re wearing another hat, which is your leader, maybe in a small company to think yourself like, hey, you’re a stakeholder or shareholder in this business that you’re running.

[00:43:16] And so you have a vested interest in both understanding. Um, But also challenging in a constructive way, what everybody else is doing in a similar manner that they challenge you to make sure that we’re ultimately delivering something that will add value to to customers. giving an example, we could ship the best service.

[00:43:35] Technologically, supported product out there, but let’s say we don’t have a good marketing plan for it. It’s not going anywhere in terms of, getting in the hands of customers, customers, knowing about it, et cetera. So that’s where your role becomes so important to make sure that you’re, attending these meetings, you’re bringing that perspective and also vice versa is like the marketing team may need a feature without which it’s difficult for them to say, target the right.

[00:44:01] Customer segment to provide the service to, or something like that. and that’s where, you’re in some sense providing those inputs to your team, but also pushing out those to make sure that ultimately whatever your team delivers ends up having the right impact to customers, to your business, to your organization.

[00:44:19] Zach White: I’m thinking of so many moments in my own career where, this third bullet point was absolutely essential to how. I was able to get things done that seemed really impressive to people who didn’t have those relationships. But for me, it was, a few phone calls. Like I had these pre existing deep connections with cross functional partners and was able to get some things done.

[00:44:42] But this is awesome. Omar, we got, three points. I’m sure we could give ten more, but just entrusting Pareto in these are probably really important ones. Building an organization. Extending the horizon, getting altitude on your, your technological strategy and, and the thinking that you bring around technology, and then being very proactive and intentional to have a broader cross functional organizational engagement, relationships and acumen.

[00:45:12] If engineering managers would tackle these three starting now, I guarantee they’re going to be really happy with their opportunities in the future. So amazing. Let’s land the plane right there. And Omar, if somebody does want to tap in and get more advice, mentorship, and coaching from you, what’s the best way for someone to do that?

[00:45:32] Omar Halabieh: Yeah, just connect with me and send me a connect request on, on LinkedIn. Uh, I do post content on a daily basis about, career development and sort of leadership growth as well, connect with me and we can take the conversation from there. 

[00:45:45] Zach White: Perfect. 

[00:45:46] Omar, I appreciate your time. It’s been amazing.

[00:45:48] Omar Halabieh: you’ve experienced this in your own career success. you know, that the questions we ask really matter because questions lead and answers follow and we all want better answers. So we need to ask better questions.

[00:46:02] Zach White: What would be the question you’d lead the happy engineer with coming out of this conversation today? 

[00:46:07] Omar Halabieh: how do you measure success? Cause I think for me, everything else in terms of what you do and the growth that entails, et cetera, all derives from there.

[00:46:16] So think about how do you measure success for yourself and kind of work backwards from there to say, how do I make that happen? 

[00:46:24] Zach White: How do you. Measure success. 

[00:46:27] Omar Halabieh: the more expansive that definition becomes. Yeah, I think the more both fulfilled and purposeful your career will be.

[00:46:36] beyond just the basics of externally quantifiable things that you can see, 

[00:46:40] Zach White: Broaden that horizon. Look at your whole life. Your career moves up as everything else moves up. So let’s define success in a broad way. Omar, thank you so much.

[00:46:50] This has been tremendous. 

[00:46:52] Omar Halabieh: Thanks again for having me, Zach.