# How a CTO at Microsoft leads and builds teams + more insider insights

## Метаданные

- **Канал:** IGotAnOffer: Engineering
- **YouTube:** https://www.youtube.com/watch?v=-V6YHgrjQBI
- **Дата:** 30.04.2026
- **Длительность:** 1:01:13
- **Просмотры:** 312
- **Источник:** https://ekstraktznaniy.ru/video/49998

## Описание

Art Akerman is a former CTO at Microsoft. During his time, he built teams of solution architects, program managers, and consultants to support Microsoft’s largest enterprise clients. We interviewed him for insights on what it's really like at the C-suite in one of the world's biggest tech companies.

Book a session with Art here: https://igotanoffer.com/en/coach/art?utm_source=ENG&utm_campaign=art-akerman-career-arc-microsoft-cto&utm_id=youtube

CHAPTERS:
00:00 Introduction 
01:18 1. Opportunity 
03:12 2. History with Microsoft & transition to CTO
08:03 3. On building teams and client relationships
10:23 4. Earning trust and managing expectations
15:20 5. Day-to-day life as Microsoft CTO
20:18 6. Getting involved in the sales process
21:02 7. Learning about sales
24:38 8. What he loved about the role: building strategy
27:24 9. The mission
28:54 10. Innovating with AI and technology
32:30 11. Building teams
37:13 12. Microsoft’s culture and learning environment
42:34 13. Transparency a

## Транскрипт

### Introduction []

I was just never worried [snorts] that I'll fail. This is Al Talkington. Al used to be a CTO at Microsoft. I interviewed him about what it takes to succeed as a CTO. I can't be CTO and only be a technology expert or technology leader. I have to support the business. What he looks for when hiring people. You can be an expert in your field and tomorrow you may be asked to do something totally different. Microsoft's surprising performance criteria. Microsoft has this great performance management model which consists of three circles of impact and one of those circles of impact is how much you've done to help others. And the dilemmas you face in this kind of role. Those types of executive roles are very demanding and if you decide to take one of them, you really do need to kind of think hard about are you in the right place in your life where you're willing to dedicate most of your time to doing that. Today, Al is a coach on IGO Launchpad. If you enjoyed this conversation and need support with your career, you can grab some time with him on the platform. Now, here's the full episode.

### 1. Opportunity [1:18]

So, I guess here where I wanted to start was — [snorts] — the time you spent at Microsoft. So, I think you spent around 10 years there. So, can you tell us how you got started there? You were working at Capital One before. So, how was that transition from Capital One to Microsoft? Yeah, it's a great question. It was quite a transition, I have to say. The reason that Microsoft reached out to me was that at the time they were looking for people who not just understood technology, but also understood the mindset of enterprise customers who were buying this technology. There were a lot of people at Microsoft who knew that platform, knew that tools really well and could talk about all the technical capabilities and features. But not as many people who understood what the enterprise buyers are actually looking for. And who could talk to them, talk to them in their language and really become those trusted advisors to the enterprise customers at the largest companies in the world. And that's why they reached out to me. I was a director at Microsoft. I was one of those buyers. I frequently had conversations with vendors including Microsoft about various products and uh they reached out Microsoft reached out and wanted to see if I'd be interested in coming on board in the role of a strategic advisor. So, this was my first experience actually going from an FTE kind of internal IT leader to a consultant advisor role. And I thought it was a great opportunity to expand my horizons and work for one of the top companies in the world. So, and the rest is history. So, you went from client

### 2. History with Microsoft & transition to CTO [3:12]

from a Microsoft client, right? To working internally. So, what was the your first role title at Microsoft and how many times did you change role before becoming CTO? Yeah, quite a few times. Um Well, I changed my roles at Microsoft quite a bit just in general. So, in 10 years I probably had five, six different roles. I started as an individual contributor. I started as a consultant advisor. Then I was promoted to lead a team of advisors and then from there I was working for a CTO and I can tell a story about how that transition happened, but from there I became a CTO. You were working directly for a CTO and then you made that transition. So, how did that happen? Yeah. I was. So, I was working for a CTO and and I should just clarify that CTO roles are different in different companies. So, there are I I've worked for other CTOs that were very operationally focused or delivery focused. This particular CTO that I worked for was focused on strategy, innovation and we were part of a field organization. So, in Microsoft there there's engineering, basically people who sit and write man and build products and then there is a field which is all the people working with customers. So, so the most part of my career at Microsoft I was part of the field. I did have a few years in engineering, but in the field it was all about serving the customer and making sure that customers get the most value out of their investment in Microsoft technology. So, the CTO that I worked for the mission their mission was to serve enterprise customers in the eastern region for the US and as you can imagine there's a like some of the largest banks and pharmaceutical companies and others. A lot of global customers. So, even though it was a US team, but we worked with customers all over the world. And so that was the group that I was part of part of. And when I joined the group, I was actually one of the first managers there. And the group was still developing. It was a new function at Microsoft. As I mentioned, kind of the new type of capability that Microsoft was building to be able to engage with enterprise customers at a very senior executive level. So, I was one of the first managers and I actually was helping very actively my boss to build a team. So, I was part of all the interviews. I helped him make a lot of hiring decisions. We were hiring leaders and we were building the team at the same time. So, in fact for a few months I was actually managing couple of teams because we didn't have leaders there. So, I was flying back and forth to New York every week to meet with people there and uh kind of reassure them that leadership was there, was looking after them even though they didn't have a formal manager at the time yet. So, as we were building this team and as we were making a lot of decisions about talent and how we were going to operate and about the strategy and plans, I kind of became the right hand for the CTO. So, we performed many of the critical decisions and topics frequently. So, when he had this opportunity to go and work in a worldwide team to take on a big global scope, it was basically a no-brainer decision for him to tell his boss that I should take over, right? Because I already was in many ways functioning in that capacity. So, so that's the story. You know, everybody has a different path to get to the CTO role and my path was just being part of that whole building the team and building that new organization. Okay. So, did you have to interview for it or did you just happen naturally? I did have an interview for that. I was first put in the role as an acting and then there was a lot of that expressed interest and I had to interview for the role, but like I said, I've always been sort of that uh position as a default choice. So, it helped me for the interview process. That makes sense.

### 3. On building teams and client relationships [8:03]

And so, earlier you talked a little bit about um you know, having to work with large clients and executives and so on. So, what was your typical client like? Who was uh who was across the table from you? Were you talking to CTOs from other companies or head of engineering? Like yeah. CTOs, CIOs, head of engineering, head of infrastructure, sometimes CISOs. Um And the teams you were building. So, you mentioned building several teams. How was it organized? Was it by industry or client size or how did that work? — We were organized geographically initially. It's actually changed. So, initially we were organized by geography. But then Microsoft actually went through transformation to become a lot more industry aligned and we started to realign our teams to be focused on financial services versus pharmaceutical versus film other major industries. And who was in these teams? Was it Yeah, what type of roles was in these teams? Yeah, so it was actually really interesting because people that worked on those teams were themselves top leaders in their past lives. Most of them were. Some of them came through the ranks at Microsoft, but a lot of people were brought from the outside, people like me. So, they were directors, they were VPs in past lives. They were leading big teams themselves. So, it was an interesting experience of leading the type of team where many of the members had a lot more experience than I had. So. So, was it so it was teams mostly of the consultants, solution architects, that type of role, sales engineers? That's right. And then we also had some teams that were responsible for working with Microsoft engineering teams to build offerings that we would take to our clients. Um People who actually worked with clients on implementations, pilots, and prototypes. Um so to kind of build momentum for larger transformation programs. Uh so we had uh various sub-teams in the organization as well. Okay. Okay, so you were essentially building these teams with your boss

### 4. Earning trust and managing expectations [10:23]

boss and potentially stepping up, right? And so when he got his promotion, you essentially took over. Um When you look back now, like I guess what's What do you think made it work? Is it that's uh you had been proactive and s- essentially doing your manager's job? Is that what's kind of like helped you uh make that step up? And then I guess just a little bit of luck from him getting that opportunity. Yeah, I think all of it. As I reflect back, I think ability to just jump in and take on whatever challenge was presented. Um This is the first time I was doing this. Uh building that type of team, first time I was even in consulting space myself. So, um I never said no to any challenge. Of course, you know, I had to be conscious of my bandwidth and and everything else, but um I was just never worried that I'll fail. You know, I kind of can-do attitude, and I think it was uh a bit contagious cuz I tried to also build that culture within the team. So, um so that was that was a big part of it. Um I learned a lot from my manager, so um I think that also made the transition easier for me, and I felt more comfortable because I always felt very supportive. Um Right away we kind of clicked, and uh um once he saw what I can do and results I could deliver, he had trust in me. And um that trust was also kind of driving me forward um because I didn't want to let you down. Um I didn't want the organization uh to let the organization down. So, that confidence in me also gave me confidence to just take on whatever was needed to be done. Yeah, when I talk about uh promotions with people, the word trust comes back a lot, right? Uh earning trust, building trust with people. Um — [snorts] — You know, how did you go about that? Was it just, you know, uh doing what you said you would do, like showing up consistently, that sort of thing? Or was there any anything different to the way you um you went about earning and building trust with your manager? I think that that's definitely a huge part of it. Um and when I have I usually have this conversation with every new direct that joins the team, and I always say that this is the number one expectation that I have. If you said that you're going to do something, I expect you to do it or tell me you can't, right? Uh but there is more. I think genuinely caring about helping others and um approach everything from that perspective, every relationship from perspective of uh what I can do to help, support, to help others grow, to help others uh meet the objectives. Um that definitely accelerates that trust-building um by very by a lot. Um so, being curious, um asking a lot of questions, uh being humble, not coming across as a know-it-all. Um so, yeah. So, can you can you explain on that a little bit? Like so, how does like helping others help you build trust with the person you're reporting to? I think what happens is they just see that um you're there to support them, um and they would give you opportunities to um to show what uh what you can do to support them. And as long as you deliver, uh you know, uh can meet those objectives, um you know, you you build trust. A lot of that, especially at the higher level, uh depends on your ability to deal with ambiguity and uncertainty um because they would not give you uh every direction, every step um that you need to take. They would give you high-level objective, and then they'll expect you to ask questions and to come back to them with if something's not clear. Um So, I think com- combination of showing what you can do, being willing to um help them in do that, and also ability to deal with ambiguity, those three things um build trust really quickly at the executive level. Okay, so thinking back to, you know, you got, you know, you got the role. Um

### 5. Day-to-day life as Microsoft CTO [15:20]

Um — [snorts] — I guess you know, what was the day-to-day like? Walk us through a typical day for you. Yeah, uh I get this question a lot, uh especially from people who want to become a CTO or into the executive roles. Uh and I always have a really tough time answering this because uh there was really no typical day um as a CTO. That the role was so multi-dimensional. Some days I would be traveling and meeting customers, and that um I should mention is a huge part of being CTO. Not just um in the field, but just in general. Um there is this external focus that most of CTOs have, not just on what's happening in the company, but also uh how you are an evangelist for what your company does. Mhm. Uh so I did a lot of that. Um and of course, when you travel and meeting with customers, your days are just gone, right? And then you have to take care of uh other things at the hotel at night and things. Um when I was in the office, um because as I mentioned, uh we had organization that was global. Uh My days often would start very early and very late. Uh I worked with Europe, I worked with uh APAC, Asia. So, I have you know, sometimes get up at 5:00 in the morning to actually to have a uh call with a peer in uh you know, Singapore and things. So, so that was um um also very frequent. Um But the days were spent in either discussions with my customers, with my peers, with my team, with with the leadership. Um in some focused work uh when I had to block my calendar for a couple of hours and work on a strategy or um play with a new technology because as a CTO, I was still expected to be uh fairly deep in technologies. So, I had to dedicate time to that. It was quite varied in terms of the day. Interesting. And so, yeah, I would just say it's a demanding role. So, how did you go about, you know, managing your time and, you know, not burning out, right? Cuz you mentioned like very early calls, very late calls. There's probably a thousand things to do, but you can only do like 50 or 100, so. That's right. And um I wish I could tell you that I uh did a great job with that. I didn't. Um especially in the first 6 months, I had no life. Uh I lived and worked. And um my wife was very unhappy with — Um I did learn to set some boundaries, so um a lot of that, being able to manage my time better and carve out time for personal life, came down to saying no to things. Uh came down to focusing more on building leadership capability within the team, uh elevating leaders, other leaders who I could trust with key initiatives, and um um like if I couldn't go to meet the customer, I had some people on the team who I would send in my place, and I would not worry that they would do something there that I don't you know, that I then I would have to um unwind. So, so that's what Once I um started to focus more on those things, then my life became a little bit more bearable, but um those types of executive roles are very demanding, and um if you decide to take one of them, you really do need to kind of think hard about are you in the right place in your life where you're willing to dedicate most of your time to doing that. Right. Yeah, so is this [snorts] is this the right time to do it? And then when you look at the people around you in the team, like is there other ways you can build leverage to uh to decrease the load on yourself, right? Can you spread the load in your team? — Exactly. And sometimes it takes time, right? You um you start with a team who where you may not have the talent to do that, and you have to hire them, you have to train them, uh you have to invest in maybe some people on team. So, you may just need to say for the next 6 months I'm going to have to double down and do more myself, but there is a light at the end of the tunnel and I have a plan for how gradually I'm going to upskill skilled more throughout this. And so I guess when you came into the role, you had certain expectations, right? Like you probably thought it was going to be a certain way.

### 6. Getting involved in the sales process [20:18]

So, how was How was being a CTO different to what you actually expected when you got started? Yeah, and I was working with my CTO boss, right? So, I thought that I had pretty good insight into what was going on, but there were some things that surprised me and I'll One thing that I didn't anticipate was how much I needed to be involved with the non-technical aspects of the role and in the business. So, um in a field organization, um in a customer-facing organization, it's all about making the customer happy and also growing the business. So, um I was very involved in the sales

### 7. Learning about sales [21:02]

process. Um so, probably more involved than I wanted to be. — Right. Um and that was a surprise and um I took it as a challenge. something that gives me an opportunity to learn. Uh and I definitely realized that I can't be CTO and only be a technology expert or technology leader. I have to support the business. I have to make the business successful and that was part of making the business successful. How much of your role was external and selling versus executing? If you had to put a number on it. Probably about 50/50. Okay. Yeah, and I wasn't really selling necessarily. I was Right. more just kind of evangelizing and uh helping customers understand the art of possible uh as part of that broader sales strategy and to, you know, eventually um helping them — And did you essentially learn that yourself or how did you go about like ramping up in that area? — I was watching others. I was I was surrounded by very talented and capable sales leaders and um consulting leaders. Um so, I learned a lot from them. And my mistakes, too, and people around me who were very gracious in sharing with me uh feedback, right? So, um I was always very appreciative to that, although at times it hurt, but uh it was — So, what's one or two things you've learned as a you know, as a technical person, as an engineer that about sales that surprised you? What one or two things you remember from learning at that time? About sales, um one is uh the sales cycle that I learned, uh which is basically end of the quarter, end of the year is absolutely crazy. It's all hands up on deck. Um I also learned that good sellers were not aggressive or um kind of pestering their customers. Good sellers were genuinely trying to help, find value and sometimes were not afraid to even go against um their company um if that was not the right decision for the customer. So, um it was a bit surprising for me to see um that in sales, um sometimes you have to say no even to your own team because that's not the best interest of the customer. So, taking your client's interests really at heart, basically. Yeah, and it pays dividends, obviously, in the future. — long run, right? Yeah. In the long run. Um it was also interesting because when I was involved in sales, my role was to become that trusted advisor to the customer, but at the same time I could not come across as somebody who's just trying to sell them stuff. So, I had to do that pushing back probably even more so than some of the sellers. Um so, because it was important for the customer to see me as their advocate uh versus somebody who's just wants to sell. And so, what was it that you enjoyed most about this role when you

### 8. What he loved about the role: building strategy [24:38]

think about it? What was, you know, the one thing that you really loved? I loved building the strategy for the organization. Um it was really um exciting to think about what's next. It was exciting to see the strategy become real uh with execution, but um yeah, that was probably one of the most exciting things and I was lucky because the team was still evolving, the business was evolving, so we were learning how to do this and so, there was a lot of need to set the goals, set the direction and re-envision the work. And so, how did you go about that? setting a strategy? Was it like setting a vision then setting some uh milestones or like, you know, Yeah, you know, so um first of all, I like to work collaboratively. Uh so, I never went into the corner and come just thought for a while and then come back and say, "Here's what we're going to do. " So, uh all the uh discussions, all the work that revolved around building strategy was were um very collaborative with my peers, with the key stakeholders in sales and delivery and engineering um with my leadership. So, so the first step was always just get people in a room and uh get the input on what are we trying to achieve, how does it link to broader organizational objectives, Okay. — what capabilities we have to um um to achieve this vision, where we have gaps, kind of doing SWOT analysis and things like that. Um and then coming out of those discussions with a clear articulation of the vision for the team, for the organization, the mission, um and some high-level roadmap um you know, um show people the milestones, the key milestones in getting to that vision. Uh so, making it real for them by saying, "Like here's the North Star, this is what where we want to be year and here's some uh specific milestones, specific results that we're looking to achieve in the 6 months or that. " And so, what was the high-level like strategy direction? For that Yeah. vision, um Well, we

### 9. The mission [27:24]

our mission was to become um the trusted advisors for our enterprise customers on how to get value out of the investments in technology in general and in Microsoft technology uh specifically. So, that was the broader mission. The vision was that we would have our um advisors, our consultants embedded in every top customer, top Microsoft customer in the world. And uh embedded um in a way that they could help the customers with their technology strategies and roadmaps um as well as um you know, helping Microsoft achieve um achieve its goals. So, so that was the overall vision and um at the time we were just starting to build AI capabilities uh so, um Azure was still Microsoft Cloud was still uh an underdog and was still trying to catch up with AWS. So, um a lot of that vision was also grounded in what the company was trying to do, moving the customers to the cloud, um exploring some early AI use cases. So, Yeah. So, you actually launched like uh

### 10. Innovating with AI and technology [28:54]

uh a 20 million AI business, right? Like inside Microsoft before like before AI was a thing, right? — Yeah, that was actually a different role. Uh yeah, that happened after I left. Um I got I myself got an opportunity to go and work in a worldwide world worldwide organization and um I was part of the group um that was working with early adopters, um the customers that were also very large, but also but were willing to invest in something that was less proven. And what we did is we created a partnership between Microsoft engineering teams and those customers where the customers would get early beta versions of our products and uh um my team would help them uh uh, with those prototypes and pilots and even some of the early production implementations. So, um, in that innovation incubation capacity, um, we were driving some of the early AI use cases and at the time it was called conversational AI, uh, which later became, uh, GenAI, but uh, we were Microsoft built some, uh, um, early versions of, uh, chatbots, um, and some and some uh, platforms for the companies to build their own, uh, kind of conversational AI capabilities. So, that was the genesis of this new business is to work with large customers and instead of them just taking something off the shelf, like Siri or something else and trying to integrate them that into their enterprise solutions, helping them build their own, uh, kind of Siri-like or Cart- Cortana-like, uh, solutions. Interesting. Okay. And, um, I know as well that you're a Microsoft Gold Club winner, right? Mhm. So, can you explain what that is? Yeah, so Microsoft has this, um, award program. Um, so every year, uh, top, I don't remember from what's percentage, maybe 1 or 2%, um, get this those awards, um, and uh, one of the awards is this gold club and, uh, there are two ways that you can be nominated and get this award. One is based on your revenue impact. Uh, so, you actually, like, most of those awards go to sales teams, uh, for, uh, driving large deals. And then, few other awards go to people who are not part of the sales organization, but they're more like performance-based awards where, uh, the company recognizes, uh, an outstanding achievement. And that was the type of award that I received, um, and that actually was about the same time that I got promoted to the CTO role because, uh, as I was helping my boss build that team, my own team actually delivered one of the best results within the sub around, um, kind of, um, creating that um, digital advisor capability and and embedding that in, uh, um, in the top customers, uh, so, we had the best scores in the business. So, that was Okay. And I also helped a few other, uh, teams uh, mature that capabilities. So, that's how I got recognized. And so, you seem to have had a lot of success, you know, building teams

### 11. Building teams [32:30]

right? Mhm. So, how do you go about that? Like, you know, what type of people do you look for? You know, what culture do you try to set? What type of leader be, you know? Can you share more about how you go about building a team? Mhm. Yeah. So, the first quality that I look in people is their ability to learn and grow. Um, because technology changes all the time, business and um, I you can be an expert in your field and tomorrow you may be asked to do something completely different. Okay. And so, how do you evaluate that, right? someone's going to, you know, uh, growing? Yeah, yeah. I ask them about the experience, uh, Okay. from to walk me through a scenario where they had to pick up a new skill, technology, um, or just, um, start in a new role that they haven't done before. And, um, I look for an approach that is mature, that is, uh, very aggressive and, um, and not just hey, I read some books, I um, watched some YouTube videos and but like people that do that well have a system, kind of comprehensive system for how they, um, approach something new. Um, and, um, I look for ev- evidence that somebody has done it and also has a system to do this repeatedly and successfully. Okay. So, people who are able to grow, what are the traits that you look for? I look for people who are competent, for sure. Um, I look for good foundation. Uh, it doesn't necessarily mean that they have all the skills, but I want to make sure that they have enough skills for them to, um, be able to build on top. Um, I look for people who are collaborative and, uh, genuinely supportive of others. Um, Microsoft has this great performance management model, which consists of three circles of impact and one of those circles of impact is how much you've done to help others. And, um, so, I always look for um, examples and I ask questions that help me understand how they they've helped others, how they engage with others. Uh, if I hear somebody who just talks about I did this, I did this and I, you know, I'm the best thing since sliced bread, I'm always very, uh, skeptical and and, uh, um, not not, yeah, about those types of people. So, um, yeah. Interesting. What are the two other circles? Just out of curiosity. Uh, helping to help others and, yeah. So, the other two circles were, uh, your individual impact Okay. and the third one was, uh, leveraging work of others. So, um, what you've done yourself, what you've done to help others and what you leverage from others. So, kind of you didn't reinvent the wheel all the time. Interesting. Mhm. And was the the kind of like interviewing and hiring you were doing was it aligned along these three circles or not necessarily? Yeah, it was. Yeah, and in fact, we often had conversations when we were done interviewing and we were making a decision, we had conversations about people who seemed to be super capable, like, you know, we had no doubt that as individual, they would have a great impact, but we didn't see any evidence that either they helped others or that they've, um, leveraged — leveraged leveraged, uh, work of others and was a hard choice for us to say no to somebody who would be an expert, but we just didn't think that it fit well in the team and even in that organizational culture. Yeah, I'm surprised you have the three all like they're not about you, right? They're about how you use other people's work and how you help others. That's a big, you know, two out of three is a big percentage. It is a big percentage and look, um, not everybody always honored that, uh, when I say, through promotions or hiring or, um, any kind of performance management conversations. Actually, people gravitate to what did that person do? What was their impact? Um, so, I would say that usually that would make up about 60 some percent — Okay. of Okay. Makes sense. Yeah. But that's the actual weight. Of the actual weight, but somebody who did zero in those other two dimensions, um, would not be highly rewarded or respected for that matter. — Okay. Is that you think one of the things that sets, uh, Microsoft's culture apart from

### 12. Microsoft’s culture and learning environment [37:13]

what you've seen at other places? I think that's part of it. Um, I think learning, uh, culture is also something that sets Microsoft apart. Um, Satya always says, like, don't be know know-it-all, be learn-it-all. So, that's really, um, embedded in the culture and in day-to-day operations. So, I've been in other cultures where people were very, um, kind of just focused on what they know and that's what they respected for, but not necessarily open they are for learning new things or even learning from others, uh, and uh, listening to others. So, I think that is also a big part of success for Microsoft. Okay. So, learning. Okay. — [snorts] — And is that So, within your team, is that kind of like the culture you were trying to set as well? Um, It is. Um, and on in addition, since we already talked quite a bit about that, um, I would always try to make sure that um, the team has this psychological safety, uh, so, which is really important, especially when uh, you go through a crisis, uh, and all the kind of bad behaviors tend to uh, show up and manifest themselves both on the leadership side and on the, uh, performer side. So, thinking about this ahead of time, uh, preempting that those types of situations and building an environment — give us an example of that? I mean, we don't have to name names, right? Or anything, but like, an example of crisis where you were able to actually, like, you know, uh, implement psychological safety cuz that's a concept we hear about a lot, but, um, yeah, how does it really work in practice when it's successfully implemented? So, let me think of a best example, um, I uh, it wasn't Microsoft, uh, it was another company. Uh, we had a very important initiative, um, which was basically make or break initiative for the business. If we weren't successful, we would put business in jeopardy and expose business to, uh, huge risk. We had a deadline, which, um, was, um, immovable and at the same time very aggressive and, um and we knew that there's a high likelihood that we wouldn't be able to deliver. Okay. on that timeline. So, the team was stressed. Um I was putting a lot of pressure on the team uh too. I was getting pressure from my leadership, so I was um Yeah. communicating that sense of urgency to the team. Um and they were working long hours. Um and um so it was stressful environment. Um and people were complaining. Um people were um questioning decisions that um each other kind of that that others made. Um and what I tried to do um and I wouldn't say that I was successful 100% of the time, but what I tried to do is to be as open as possible with the team about um the situation and um about the rationale for my decisions. Uh even when those decisions were hard. Um I actually had to let go a leader in the middle of this project um because they were just not um being accountable and and not um kind of pulling their weight. Uh so when I did that, I had a very frank conversation with the team. And I told them exactly what happened. Uh I didn't try to make it like all this leaders looking for another opportunity or had a bad opportunity. I told them what it was. And not because I wanted to scare them, but share with them, being open with them about how I thought about the situation and also acknowledge that um I was part of the problem too, because as I was. Uh so showing that vulnerability goes a long way. Um And at the same time, I think I was fair with the team when I said that what they what doing, I wasn't questioning. Um I was very confident in their ability to deliver. Um I was not confident in this leader's ability to deliver and this is why they're gone. Um so kind of reassuring the team that they still have my trust um at the same time as being vulnerable and just being open about um my thought process. So, and it did have an effect. Uh it did put people at some ease. Um and even prompted some people to start mimicking that, to start being more open about the decisions they're making and why they were making it. So, um I always believe in leading by example. So, you can't expect from the team something that you're not willing to do yourself.

### 13. Transparency as a leader [42:34]

yourself. Okay. So, is is transparency one of your leadership values, yeah? It is. And sometimes you can't be transparent about everything, but I would say kind of transparency to the degree that you can. Okay. What [snorts] else do you what else characterizes you as a leader, do you think? I um I think I'm a leader who's very supportive. Um who thinks about people before the business, the results, all this other stuff that I have to deal with. Um People say that I'm very calm as a leader. Which is kind of interesting because that's not what's going on inside of me. Right, right. I'm actually uh like when I'm calm, a lot of times inside it's like fire and then everything's boiling. But I do try to project that calm and confident. Um for some So, um I don't get my anxieties and my worries to um you know, infect everything else around me. Okay. I'm laughing because I've been told that a few times as well that you know, I'm calm in stressful situations, but it's definitely not what's happening inside, so. Right, right. That that's the skill, right? To be able to control it and not show it. Okay. And so you mentioned being supportive. So, how do you support your people? How do you go about for instance, let's say you have like a first-time manager in your team, they've never done this. Like how do you go about supporting them? Yeah, and um the first step is just to learn more about them, to learn about where they at, uh what's going on inside. And um how they feel about being in that role and their capabilities and their strengths that they bring to the role, but also where they see potential risks and challenges. Uh so those starts with being curious about uh the person. And not making assumptions, not trying to judge before you actually have that conversation and have a chance to uh dig in and learn more. And I have a lot of conversations with my clients now about that exact thing. Uh how we tell we form the stories about people, about events before um we had a chance to get curious and actually try to find out what what's really going on. Um I think the second thing for me is um especially in this type of transition from IC to manager, I always remember what I went through. And I transition was very painful. Um I was uh an engineer for over 10 years, first 10 years of my career. And I loved it. And um when I became a manager for the first time, I was still trying to be an engineer and also do all this other things on the side. So, I think uh my ability to empathize with others going through this transition is rooted in my own experience and I always tell them that look, I know exactly where you at and I've been there. And look, I was able to make this transition and be successful and so will you. So, giving people that confidence and um but also being transparent again, come back to that transparency about all the challenges that they might expect. Um they need to learn how to delegate, let go, they need to learn how to get themselves out of the tactical day-to-day and um be forward thinker. They need to learn how to protect their time, how to not get sucked into meetings that you know, it seems like every promotion you get, that number of meetings goes up exponentially, right? So, how do you get control over your calendar and how do you start again focusing more on getting things done through others versus always jumping in and doing it yourself. So, I help I support people by helping them build a system where not only they know that they need to do all those things, but it's embedded into their work. So, it sort of becomes their second nature. Um Okay, [snorts] so you kind of like listen to them, be transparent about what it is they have to achieve and help them build a system to get there, right? That's right. And then I uh give them feedback as they navigate this process. Um sometimes uh hard messages if uh if they are not um making the right progress and uh but always with a positive mindset, always with positive intent, which uh goes a long way. So, in your time at Microsoft

### 14. Structuring projects and engaging executives [47:33]

you worked you know, you were part of the field team, so you worked with your fair share of uh of clients, right? So, what did you learn about you know, engaging with clients, engaging with executives and and what did you learn about structuring projects um and setting them up for success? So, there are there are a couple of different parts of this question, so I'll So, let me start with what I learned about the enterprise clients. And um it was interesting because as I mentioned, I was one of them. I was sitting on the other side of the table, but um as I was coming in as part of that technology provider uh as as a vendor, um I learned a lot about um what um they don't want from the client. I thought I knew because it was just me, but um you can never just completely project your experience on the situation, right? So, there are a lot of other things that I've learned that um executives are frustrated why uh when dealing with vendors. Um I've also learned So, what were some of them? I'm curious. You know, what what people are frustrated with? being sold to all the time, right? So, always talking about your product as it's the best and trying to throw competition under the bus. Um always trying to find a way to highlight how your product is superior regardless of what the customer need really is. Um not really understanding the environment and constraints that the customers have. So, for example, um and I know it actually frustrated me even when I was on the other side, the technology vendor always wants you to move fast and always like, "What if you don't take advantage of this, you know, you're going to regret that. This is Right, right. You should launch this project. You should invest in this without realizing that executive is dealing with 10 other top priorities at the same time. And you know, if the only thing that they had on the table was, you know, implementing this particular award you know, dealing with this particular problem, maybe. Yeah, they they would have taken that project and run with it, but they have to fit it in and have to figure that out. So um So, that's what I learned. I learned how to be more understanding how to read the room and read the situation better. Um so, and then think about where can I help? Where can my team help? Where can our technology help? Um and if it can't be um open about that as well. So, today it was all about the the customer. Um I don't know if you want to go on about projects, so Yeah, so in terms of the projects, um I've learned that things always take longer than you think they will. Um I've learned that um you really want to be sure that this is going to work for the customer and become before you try to influence them. And you do that through POCs, pilots, having deep dive conversations with experts. Again, kind of understanding the customer environment and make making sure that your technology is going to fit there. So, I've learned that trying to wow the customer and show them the art of possible could be double-edged sword because they would then expect that future is going to be available uh next month or 6 months from now. So, kind of always structuring the projects in a way that you're gradually building the capabilities versus um targeting a complete revamp and obviously promising that this is going to happen very quickly. Well, this is really interesting. So, kind of like yeah, building it step by step, right? Showing value step by step. That that's actually really good point um because uh like they it helps you um continue to be credible. It also helps your customer to continue showing that the investment that they made, the decision that they made is the right decision. They kind of every time they make a decision to go with a vendor, they stuck their neck uh out there. They put their credibility on the line. So, anything you can do to help them um continue to prove that they made the right decision through delivering incremental value is going to go a long way. Yeah, building momentum. Building momentum, yeah, building support. That's great. Okay. And so, what do you do now? today?

### 15. Current career path: career coaching [52:40]

What do you do today? So, I I'm a coach. I'm a leadership executive and career coach and I work with tech leaders um to help them scale to help them build those systems that will allow them to either be successful in new roles or transition into new roles um or just take any challenges like um scaling up that come their way. Um I work exclusively with tech leaders because um they find that my combination of being a coach and I am a certified coach through International Coaching Federation, my ability to coach them and use uh all the proven coaching techniques combined with the fact that I do have experience uh — find a new job, but to um develop yourself as a leader within your current role or to look for another job internally within the organization that gets you closer to that uh your future vision. And then when it comes to some of the tactics of how to get there, um building the networks, engaging with leaders, recruiters, um hiring managers, um going through interviews, kind of preparation for interview, mock interviews. So, those are different type of things that I'm helping leaders with. Cool. Why did you choose that path? I mean, there is, you know

### 16. The impact of career coaching [55:39]

10 other things you could have done. That is true. That is true. So, um it started at Microsoft actually. Uh Okay. At one point, Microsoft uh sent all the leaders uh to training on how to be a better coach. Uh they weren't trying to make all the managers into coaches, but um they recognized that coaching is such a integral part of any leader's toolbox that they wanted to learn how to coach. And when I went through this training, which was probably one of the best trainings that I had in my life, I realized that my leadership style was very authoritarian, very directive and I was missing that coaching aspect. Uh listening, asking questions, uh supporting, challenging. Um so, I decided to learn more about it. Um so, I enrolled in coaching training, like went through the official certification program. And initially, I was just thinking I would do this because that would help me be a better leader. And it did. Uh and it had a huge impact on my career, which I can talk about uh as well. But, it also made me realize that I'm good at that and uh people started coming to me informally for coaching. So, um when it came time for me to think about what's next, for me to kind of create my own vision of future me, Okay. I also realized that having those types of discussions with people getting giving me a lot of energy and was really um in many ways the highlight of my day. Um I actually went through this exercise where for 2 weeks I was keeping track of everything I did um and I noticed that uh and I keep track of like my energy level on different meetings and different and I noticed that every time I would engage with somebody in a conversation about their career growth or leadership challenges, my energy level just went up. So, um so, I thought that this would be a great uh next step in my career and uh here I am. And so, it sounds like coaching made a big impact on your own career as well. Like it sort of created a bit of an inflection point. So, how when was that uh training you talked about? When did you have it? Yeah, it was um probably a few years before I left Microsoft. Okay. And was that before you were a CTO or That was um that was after. Okay. And um it was also at the time when I kind of in my career, I went back and forth. I didn't talk about that, but I uh often went back and forth between um a management role like uh leadership organization leadership role and an individual contributor role. So, um I went through this training. I was a manager. Then I wanted to get more in-depth with technology and this is when I um joined that incubation team, that innovation team and to drive the AI um initiatives. So, um and then I uh went back to management and um I landed um with a larger team that I had even when I was a CTO. Um so, I was a consulting practice manager and I had um you know, a large team of consultants and program managers and and delivery managers. And um I had um direct reports who themselves had large teams. So, um I that this is where I realized that um I couldn't scale without um applying some of those coaching skills, without listening, without uh building investing more in building other leaders uh that reported to me rather than trying to jump in and uh and do things myself. So, Okay. And then my next role after I left Microsoft was even bigger. I had 300 plus uh people in a engineering organization and um I probably wouldn't even gotten that role if I uh didn't learn how to coach and how to listen and ask questions because through my entire interview process Right. I had 11 interviews to get this role including the CEO himself and I — was that? Uh it was FICO. FICO, yeah. And I was asking a lot of questions during those interviews. Uh I was being very curious and I think I let the interviewers talk more than I did. And — Right. um they somehow thought that was great and they hired me because uh I think in a large part because they saw the way that I operate.

### 17. Final tips [1:00:23]

Amazing. So, what's the what's one last piece of advice you want to leave listeners with before we end this episode? How to say be bold. Don't be afraid of a challenge. Uh take risks. Um it will pay off if you commit to it and uh if you Yeah, it will pay off. I like that. Shoot your shots. Yes. Great. Thanks Alex. It was uh amazing to have you and uh thanks everyone for listening and see you in the next episode. Thank you for the opportunity, Max. I appreciate it. If you want to get help in your career from someone who's done it at the very top, go to igotanofer. com, choose your coach, and book a session.