Secrets to Succeed as a Fractional CTO!

Hey, in today's video, you can expect to watch a lightning lesson that we did together with Sergio Vizzinoni last year. You learn all about what exactly is a fractional CTO, how to become one, and what fractional CTOs do on a daily basis. Let's get straight into it. Oh, hey, hey everyone. We still have, uh, people joining. Um, people will still be joining in a couple of minutes more, but I have, I have disabled now the waiting room, so Everyone can join directly. But yeah, welcome, welcome everyone to this lightning lesson. It's called How Fractional CTOs Make a Huge Impact in 30% of Time. I'm really excited to also have Sergio, Sergio Vicinoni, with us as well, co-hosting this, this lightning lesson. Before we get into more details, let me ask you, all of you guys, from which country you guys are calling. You can enter your country in the chat. And also, you know, this kind of events are always great for networking purposes. And, you know, if you want to share your LinkedIn, if you want to share your Twitter or your X profile, make sure to share it in the chat as well because, you know, we meet like-minded people in such events and we can connect with each other and we will be in contact even after lesson ends. So don't only connect with us, with me and Sergio, but, you know, connect also with each other. So make sure to share your LinkedIn profiles, X, whatever you like to share on the chat as well. I see a lot of people from, um, from Europe. Awesome. I see also United States, the Netherlands. Um, yeah, it's a big day for United States today because we have election, I believe, today. I was contemplating a little bit, should we keep this this lightning lesson for today or not because it's an election day, but decided to still keep it on this day. Awesome. All right, before we go into specific details of what we are going to talk about, I just want to do a brief introduction about myself. My name is Gregor Ojstersek. I am a CTO and also I'm an author of Engineering Leadership Newsletter. I have over 10 years of experience in the engineering industry, and I also post daily on LinkedIn. And with me today is Sergio. Sergio, would you say a few words about yourself?

Absolutely. Thanks, Gregor Ojstersek, for the invite, and happy to see you all here. My name is actually Sergio because I'm Italian, even though I live in Spain. But, you know, I've been moving around, no worries about that. I'm used to my name being called in different ways. I have about 20 years of experience in the tech industry, and most of them, like, 10+ years I've been in engineering leadership. I also write a newsletter which is called Pseudo Make Me a CTO. I do post a bit less regularly than Gregor Ojstersek on LinkedIn, and among the things I do these days is, you know, different contract work including some Fractional CTO gigs. That's why we're here to talk about this.

Awesome. I have also pasted Sergio's newsletter, Make Me a CTO. It's a great read, so make sure to subscribe to his newsletter. Okay, so let's get into the agenda. What are we going to talk about today? So we're going to talk about first, obviously we already did the intro, what is a fractional CTO and how do you become one? That's, that's going to be the first agenda topic. And then we're going to talk about the key skills needed to thrive in the role. And also we're going to talk about tips on how you can learn and practice the key skills needed. And also make sure to, you know, we're gonna have some time for Q&A at the end of the session. And also if there's gonna be any specific questions, we could potentially pick up some question as well from the chat. So if you have any questions, just put it in the chat and you can also upvote the specific questions that, you know, you feel that are very relevant and that would give us like more, you know, more feedback that it's a really good question that a lot of people are interested in. So yeah, this session is like meant to be very interactive. So we might pick up some questions in the middle of the session, but you will also have some time at the end of the session. Okay, so, but also I want to mention as well that, you know, we will pick one question from you guys and there's gonna be a giveaway. It's gonna be a free t-shirt for one of the questions. So, you know, more questions, the better. And one of you guys will receive a free t-shirt from us. Okay, let's go straight to our first question. And, you know, we're gonna, we're gonna do, we're gonna separate this into two, two-part questions. So the first one is, what actually is a fractional CTO? So, Sergio, what is, what is a fractional CTO?

That's a very difficult question, right? So there's a lot of talks about fractional CTOs these days, and sometimes I have the feeling that it's used as a label for No, part-time CTO, just a fancy way to call a part-time CTO in my view. And I think that there's not an absolute definition in the industry, right? But the way I see it is a way for companies who can't afford to pay for a very experienced CTO full-time to access to that experience, but actually compromising on the time availability, right? Instead of compromising on experience, quality, expertise, they want to have that expertise, but they're happy to have it only part-time. And then of course, you need to come up with arrangements to deal with what happens when the fractional CTO is not actually on the engagement. So that's the way I think about it.

Yeah, yeah, well, very, very good description. I would say you get a very experienced person. Normally a fractional CTO is someone that has done a lot of stuff, has been in a lot of projects, have been in a lot of different things, and, you know, has experience in various different things as well. And you need maybe help in a certain specific thing. You maybe need help in specific direction. And you may need help in specific, you know, challenge and fractional CTO is a great person to have. And, you know, startups and scale-ups, it's mostly like a good fit for a fractional CTO. And the reason is what Sergio mentioned, right? You get a very good experienced person and, you know, it's hard to actually, companies would, it's hard for companies to afford such an experienced person full-time. And you know, you need experience if you want to have a product that is going to be successful in the market. What about, what are your recommendations for, let's say, a specific, let's say, engineer or engineering leader on how could they become a fractional CTO?

Yeah, so I don't pretend to give you a recipe like these are the 5 steps to take to become a fractional CTO because I don't think that exists. So I'd rather give you two things. One is how not to become a fractional CTO. And then I can tell you how I became a fractional CTO, which I think is a more honest way to approach the problem. Now, how not to become a fractional CTO. Don't try to become a fractional CTO if you've never been a CTO before. Right. So making it a way, an easy way to kind of skip steps is not going to be a success because as we said before, companies typically look for experience, ability to solve problems that the person has seen before. And, you know, if you're trying to just brand yourself a fractional CTO without the experience, you might not be very successful, right? Maybe you are, you know, if you're lucky, but I don't think that's the best way to do it. And then when it comes to my, my journey, you know, as I said before, I've been 20 years in the industry. I've been covering a lot of leadership roles in technology. I've been CTO of small teams. I've been VP of engineering, but with CTOs reporting to me in different countries. So I've been both in the startup scale-up and corporate. Environments, and I spent a lot of time there. I lost all my hairs in those different realities, and that, that gave me a lot of perspective, right? I've seen now what works in small environments, what works and doesn't work in big environments. I've seen a lot of things. And then, you know, literally at the end of last year, I took an important decision about my life. I wanted to kind of get out of the traditional 9-to-5, uh, work setup. And I thought, you know, with the experience that I've been accumulating, I believe there is a market for me to promote my services and sell my services individually. And that's what I've been doing since January. I currently have one fractional CTO engagement plus other more like consultancy advisory type of roles. And I also believe, by the way, that it's probably very difficult to have more than one, maximum two fractional CTO engagements going on at the same time. Because even though that's only part-time, there's a lot of context required for you to understand the company. And if you have to jump between different companies, being able to zoom in and zoom out at that level, it might be too much cognitive load. So I think, you know, probably from my side, one is fantastic and then I combine that with other activities.

Yeah, yeah, really good point. That is one of the advantages of being a fractional CTO. You're never just a fractional CTO, right? Companies need a lot of other things, like maybe they need just advising and maybe they don't even need a fractional CTO. Maybe they need just some direction, you know, maybe they just need a specific consultancy on specific thing. Maybe it's a buy versus build decision, maybe it's a, you know, team decision, maybe it's, you know, either specific management decision or maybe they need a full-time CTO. A lot of times we are consultants and advisors and we need to find what is the best for the company, you know. It could be potentially, you know, in the best intentions that it's not always the best thing to do if, you know, if someone approaches you and says, okay, I need a fractional CTO and then you You immediately, you know, you become a fractional CTO. You need to find out what actually is a pain point for that company, right? And yeah, you mentioned really a good point about how to become a fractional CTO. You wanna become a full-time CTO first. You wanna build that experience. I'm not saying you need to be a CTO first, but you can be like a VP of engineering. You can be also like a director, but I would recommend at least to have some startup experience because fractional CTOs are a lot on startups and scale-ups. Those are the main two, you know, main two, how do I say, companies, main two specific size of companies they're looking for such roles. So you need experience in this particular field. If you're just gonna be in big tech, a manager in big tech, it's gonna be harder for you to actually like try and, you know, provide your best opinions and also help the companies. As much as possible because, you know, big tech and startups is a different way of working. I wrote an article not so long ago about how to become a CTO. I will be pasting this in the chat, and there are 6 different ways on, you know, the way that you can become a CTO. There's, for example, you can start your own company, you can become a founding engineer, you can go to the management path, you go to the architecture path. Go through the IC path as well, and you can become like a CTO through other roles as well, mostly product. So definitely read this article if you're interested about becoming a CTO. And then my recommendation is, you know, you get experience and after some time you can decide if you want to become a fractional CTO.

If I may, Gregor, because this is very interesting, a couple of comments here quickly. Sure. One is I never made my goal to become a fractional CTO. I don't care about being a fractional CTO. I care about solving problems that can be solved with my expertise, right? And it happens that right now some companies are looking for fractional CTOs, you know, but I don't necessarily advertise myself as a fractional CTO. I advertise myself as an expert, and I have like broad set of experience. I don't care only about technology, I care a lot about business, product, etc. And this touches the second element that I want to share, which is I agree with you that being— having been a CTO might be too hard of a requirement. But there's an important element here though, that is having experience being in an executive team is for me fundamental to be successful in this type of role. Because, for instance, in the, in the fractional CTO role I'm having right now, I spend a lot of time with the CEO and I advise the CEO on topics that go way beyond technology, right? And we discuss a lot about like company strategy, business strategies, how to deal with strategic partners and whatnot. And if you've never done that before, you might just try to, you know, stay in the comfort zone of technology, and then you would lose out on actually one of the big advantages of having an experienced CTO, which is, you know, they can go beyond technology. They are actually business leaders who understand technology.

Yeah, well said about experience in, you know, in leadership teams. That's very important. You shouldn't be— you should treat your team not like your engineering team, but the team is actually your C-suite, that that is your team. And you should know and understand to speak business language. Not only technical language and, you know, engineering language that you all, you know, love to speak about, but, you know, you need to speak in a way that resonates with non-technical people. Awesome, really great, great point, Sergio. Let's go to the next one, which is we're going to talk about your priorities as a fractional CTO and, you know, how do you actually can structure your percentages of time, you know, what are your top 3 weekly priorities as a fractional CTO?

Yeah, so as always with this, those percentages are approximate. That's why I put 20 to 40%, because depending on the stage you're in, you might focus more on one area than others. And it can be that you're actually spending 40% time on each one of them, meaning that you might have bursts of activity that go beyond 100%, right? Typically, ideally not, but there are those exceptions. But in a way, you know, I think about these 3 buckets Everything around strategic planning and alignment, which is a lot of working, you know, horizontally with your peers and with the CEO to understand and refine business priorities. So I worked with Gregor Ojstersek, working together, iterating on what we want to achieve, how can we get there, alternative ways to get there, different ways to kind of maybe do it easier or more easily or less expensive, which is directly connected with architecture and system designs, which is basically kind of the consequence of once you are clear business strategy, then you start thinking about the tech strategy and how you translate that into the systems and the, that you're going to build. And then very important, figuring out sequencing, right? Not at the micro level, but really at macro level. What are the key things we need to get first in order to be able to build on top of them? So priorities and trade-offs. How do we sacrifice some important things in the short term to be able to, to have better results in the long term? The second pillar is more around execution, right? So you can think strategy and, and then tactics, or, you know, execution if you prefer. How do you then translate the long-term plans into actionable plans for short-term horizon, be it, you know, iterations, sprints, whatever you call it. But like those short-term horizons, 1, 2 weeks, and maybe even 3, 4 weeks, always looking ahead a bit. Tracking and communicating upward, downwards, and sideways on progress is very important, you know, making— make sure that everybody's aware of what is going on and especially the, the progress that is being made and what they can expect next. And then all low-level technical decisions, PR reviews, and other types of hands-on work. By this, I'm not saying that I, as a fractional CTO, I'm responsible for all of them directly. I am responsible for them to happen, right? Which means that there is a lot of delegation. There is a lot of trusting other people, but also like being on top of what we decide and kind of weighing in with my opinions when I believe it's right moment to do so. And ultimately, and it's not like in order of priority, it's more like, you know, the way I think about it mentally. There is the part around team management and development, making sure that everyone is set up for success. This is like typical job of any manager, every engineering manager, making space for individual conversation to surface employees' needs and desires for growth, right? All those one-to-one conversations, understand where they want to go and finding ways to get there while catering for the company needs. And then finally, teaming up with team members on specific needs, right? Doing pair programming sessions or actually sitting down to do some design together, depending on the support they need and the priorities in the company, right? This is kind of where you get more hands-on with the work. But typically also, you know, as a fractional CTO, hands-on work is probably the part that you have the least time for, because hands-on work is what you can delegate to others. All the other pieces you probably shouldn't, because if you do, then you're probably getting a bad result.

Yeah, you mentioned quite a lot of things, and yeah, it's, it's, it's important to know, right, what is the most impactful thing for specific, you know, either week or specific month. And you mentioned that, you know, hands-on work is something that typically as a fractional CTO you try to delegate. But how do you actually like find out what is the biggest impact that you can deliver like as a fractional CTO to the specific week, the specific month? Do you check in with specific business challenges? Do you check OKRs? Are OKRs across the company? How do you find out what is the impact radar that you develop over the years?

Yeah, so I like this term impact radar. I'm gonna steal it, by the way. I never used it before, but I really like it. So it really depends on the company, right? Because typically as a fractional CTO, you're joining a company that exists already, right? Meaning that, you know, there are things in place and you need to pick your fights, right? If you are a full-time CTO, you probably have a lot of bandwidth to actually try to change the way my company works. When you're a fractional CTO, you have less bandwidth for that. So you need to be able to figure out, okay, there are certain things that probably could be better, but I really want to focus on what I can influence most with my limited time. And here I think, no, definitely working very closely with CEO and the chief product officer, if there's such a role. Sometimes the CEO is also the CPO, depends, right? To create strong alignment on where we want to go, right? Making sure that that is very clear and asking those difficult questions to force prioritization and trade-offs. Because of course, if you ask someone what you want, the typical answer is, I want everything, right? But they didn't understand that they can't get everything, or they need to understand what is the cost if they want everything. But so having those conversations, being open, not, not defensive, but actually constructive in those conversations, to me is like one of the highest leverage type of activities for me. Because then if I'm successful at doing that, I'm increasing the chances of the entire team being successful, because they have a very clear scope, it's a manageable scope, and there are low chances that those priorities will change just because someone changed their mind, because we really spend the time to clarify what should be those priorities. And also we agree that, you know, if you want to change those priorities, we should go through a lightweight process, but still should be a process where we, you know, surface why we need to change them and how we approach that. And then some companies use OKRs, some other companies don't use OKRs. With one, the company I'm working with at the moment, we don't use an OKR because we actually building a new product and we have a hard deadline. So this is typical case of fixed date and variable scope. So there the goal is actually we need to get live at a certain date with something that works. And almost weekly we need to have those conversations about how we adjust the scope based on what we're learning to make sure that we're always focusing on the most important things and that we're always pushing down the priority list, those that, you know, will be good to have but we can live without them. And then, you know, this is very important. And again, making sure that all those conversations are shared in a way that makes it easier for the rest of the team to digest them without having to spend too much time going through the same conversation, right? So summarizing and giving updates that are clear, that are spot on, and then making sure that all the relevant tools are aligned in terms of documentation, in terms of issue tracking, etc., etc., so that people— that we reduce chances of people working on the wrong thing. Because especially in these stages of a company being early stage, trying to get to product-market fit, every minute counts because you're basically burning money, right? And, you know, where the zero interest rate policy is over, so burning money in these days is actually very expensive, not as it used to be 3 years ago. So it is, for me, it's like probably one of the most important things is finding this balance of ROI based on where the business would like to go and based on what we can actually achieve with the resources we have available.

Yeah, you mentioned a really good point about, you know, having a fixed deadline and variable scope. I'm a big fan, big fan of that because it really shifts our mindset to not to perfect but actually remove unnecessary clutter and try to simplify as much as possible. And that worked quite well for me in a lot of cases, especially in freelance projects, freelance opportunities that I work with. It worked tremendously whenever, you know, a client, a business, they need a certain deadline, they need a certain time when they can expect something to be finished. But they don't expect perfection. And also the customer is not expecting perfection. And also the user is not expecting that it's going to be perfect. It's in the, you know, especially the first delivery of a product, it needs to be good enough in order to showcase the value. And it should not be like the full-fledged product that you see, for example, right now, like Spotify. Spotify built this product over the years. They didn't start with all the features that they have right now. So Yeah, good points about prioritizing.

By the way, I would say just one last thing on this, like part of that work is also making very explicit what are the assumptions we want to validate with the first product, right? Because sometimes, sometimes there's still this idea that we can get to perfection in the first iteration. We know that's untrue or very unlikely. You might be very lucky, but I don't want to bet on luck. I prefer to bet on like systems that work. So for me, it's very important to say now what we want to do, what we want to learn with this launch, and let's make sure that we prioritize those learnings, even though it might mean that the product is not getting the traction that we ideally want, but we want to get confirmation or discard certain hypotheses and then we can actually build on top of those.

Yeah, and you know what I say, if you're not at least slightly embarrassed by the MVP, you have launched too late, right? And you learn from the things that you try, you don't learn from the things that you don't try, right? You miss out the opportunities if you actually don't try. You don't know if you don't ever actually put it out. You don't know what is the feedback going to be. That's the reality. You want to fail fast and learn from it fast and make a next iteration. Awesome. By the way, everyone, make sure to, if you have any questions, put it in the chat. There's going to be one question who is going to get also a t-shirt at the end of the session. So make sure to add any questions you guys have in the chat. Let's continue with the skills, top skills that help you, Sergio, in your role as a fractional CTO. Could you share like what are your top skills that, you know, that you need to develop in order to be successful in your role?

And again, I'm relating to my own experience, so I don't believe these skills are absolute, right? Because there are different nuances in the industry, but what has helped is definitely on the first pillar is the ability to understand and speak the business language, right? In the past, I've been spending a lot of time in executive teams. I've also been part of a board of directors for one company for about a year. So I learned a lot to actually immerse myself in those conversations, speak the same language, and become curious about it because then you learn a lot about what you should focus on as a CTO. And then the ability to make trade-offs, right? Sacrificing good things for great outcomes. Now, we all would like to have everything, right now, but because everything is good, right? But what is great, right? Focus on what is great, and that forces you to sacrifice something that is good or just push it for later. And it's painful, but you need to learn how to do that. Otherwise, you will never be able to be an effective decision maker. On the execution side, I think attention to detail. So this ability, mentioned also later, like to zoom in, getting into the details without micromanaging on every single piece. But when there are important details, you need to be able to actually zoom in and use all your technical knowledge to be able to understand them. Communicating, repeating, right? You should learn to repeat things multiple times over until they sink in, because, you know, attention span these days is just declining continually. So it's very, very important that you keep repeating the things that are important, especially in a remote environment. Exactly, in a remote environment even more, because, you know, written communication has less bandwidth or intensity of information as opposed to oral communication. And I, as I said, I said, zooming out, zooming in, meaning that, you know, this ability to go very high level, think big picture, but then zooming into a specific detail and understand how they connect with each other is super important. And then when it comes to team management and development, there's the casting piece. So being able to select the right profiles, because as a fractional CTO, you know, you need to delegate even more than a full-time CTO, right? So you need to be able to have— I, I believe that at least what's working for me is that having a higher seniority density in my team is what works better because then I can delegate certain aspects to other people. Active listening, as usual, very important to be able to understand what is going on and asking those insightful questions to surface potential hidden fires. And then coaching and mentoring, right? Coaching and mentoring are two different things. We put them together, but basically mentoring is more about teaching people how to do things based on your experience and coaching is actually helping them figure out solutions even if you don't really necessarily know yourself what the solution should be. I think these are the kind of skills that have been helpful for me. The list could be 10 times bigger, right? But again, sacrificing good things for great outcomes, these are the ones that have been great in my case.

Yeah, it's— you can see the broadness of specific skills that you need to be successful. You need to be a good generalist. That's what I like to say, that has like experience in a variety of different things. And I think, you know, technology and, you know, details like coding expertise is just like a really, really small percentage. Would you agree with me, Sergio? Like the importance of your role, like understanding the really, really fine details. It's more important that you have experience in high-level details, architecture, system design in general, but not so much like, you know, code-specific, language-specific knowledge.

You don't need— if you need to be an expert on the language, it means that you have a casting issue. That's my view, right? I mean, if you have to do it yourself, it means that, you know, if there is nobody else who can do it, you have a casting issue. It doesn't mean that you should not be able to do it, right? To me, there is a big difference between being able to do something and having to do something, right? I think that as a fractional CTO, if you have to do it, you need to shift your focus on figuring out how to structure your team so that you don't have to do it again.. But then still being able to do it can be helpful in those situations.

Well said. Let's now talk about how can specifically like a person with 5 years, how can they, you know, get better at this specific skill set. We mentioned variety, like a lot of different skills, you know. How can like a person, like an engineering leader with 5 years of experience, how can they progress in the specific skills?

Yeah, so again, looking at those 3 buckets or pillars on the strategy side, I think, you know, learning how to speak the business language is very important. And I speak multiple languages, like actual spoken languages, because I've been traveling around the world. The only way I was able to learn languages was by practicing them, right? I'm very bad at learning languages by just reading a book and try to learn grammars. And I realized that that's how kids learn. And the same goes with business. Don't read business business books only. Well, that's always useful to do it. If you believe you're going to learn it by just reading business books, you're probably going to miss out on 90% of the benefits. So actually speak that language with people who speak that language every day. So speak to your CEO, your CFO, CPO, CMO, depending on the roles you have in the organization. Actively dedicate time to talking with them, not to tell them about technology, but actually to learn about what they're doing and figure out ways you can frame what you're doing in technology in business terms. I remember a fantastic conversation I had in during my role as a CEO, a CTO down in Mexico in 2014, '15, I think it was. I had lunch with the CFO who wanted to understand why it made sense for us to migrate from on-premise to cloud from a financial perspective. Because actually, you know, OPEX wasn't going to grow, CAPEX was going to go down. So from an EBITDA perspective, things didn't look good. But then I was able to explain, no, increase velocity of the team, we reduce cognitive load, we can focus more on developing the business, blah, blah. And he understood that. But if you only look at the numbers and say, no, cloud is good, whatever, they will not understand. You really need to frame it in terms of what are going to be the benefits for the business, not for you or your team or the vendor. Then practice thinking in terms of outcomes for technical investments. That's actually what we just discussed, right? So this is very important. And then documenting trade-offs. And evaluating alternative solutions. We all tend to fall in love with new technologies, new solutions. We all have our favorites, right? Might be a language, might be a framework. Resist the temptation to just push forward your favorite option and actually force yourself to write down the arguments and rationale for why this solution is a good solution to the problem. Therefore, start from the problem first, right? What is the problem you're trying to solve? What are alternative options you can evaluate? What are upside, downside of those options, and then figure out what's the best option for you. Then on the execution pillar, you know, very important to get organized. And especially, you know, I really write, become obsessive with how you use your time and your team's time. It doesn't mean use 24 hours a day for work. Actually, I'm a big believer on limiting, putting a cap of how much time you want to work because that's going to be a lot more effective. There's someone with the microphone open. I don't know who's that. Yeah. Then practice communicating with the written, oral form to people with different backgrounds. It could be different countries, different languages, etc. So learning how you communicate effectively to people that don't necessarily share your same background, and it goes back also to speaking with people in different areas in the company. And then also use writing as a way to clarify your thinking. That is something both you, Gregor Ojstersek, and I probably do a lot, right? And we learned that by doing that, you actually get better thinking because you've, you know, when you write something and then you read it back, it needs to be clear, otherwise it really sounds very bad. So, you know, the more you do that, the more you realize how you can write clearly in short form and very concise. And then on the team management side, spending time with people in your team and really developing a genuine interest in them as a person, not just as employees, right? So really understand, you know, what motivates them, what do they like to do, what are their passions. Build that rapport because that rapport is going to be the base for trust, and trust is going to be the base for you to actually have constructive conversations. Also, might sound, sound, uh, counterintuitive, but overcome the fear of being perceived as micromanaging. I've seen leaders fail feeling, uh, because of this fear, and they become too distant, and therefore they're actually not on top of what they should, and they don't know what is going on in their team. As long as you're explaining why you're taking certain decisions and why you believe that you need to take certain decisions, it's perfectly fine to do so. But now the problem is that if you do that 90% of the time, that means you have a problem with delegation, which, which leads us to the next point, which is practicing giving up the driving seat and take the passenger seat, which Trends, you know, learn how to delegate effectively to people in your team. Delegating doesn't mean giving up completely, right? Accountability is still with you. You need to make sure that the person has all the information and that you're, you're giving the right level of information for them to be successful. And then you follow up, you follow up with them, you, you oversee, you supervise, you check if they're doing a good job. And the more that happens, the more you can become disconnected, or like the more you, you can delegate with a specific person, and you the entire thing grow. But this, this again, this has been ways for me to practice important skills, like deliberate practice to become better at my job.

Awesome. Um, I'll just, uh, address, uh, two points that, that you mentioned, and then we'll go straight to the Q&A. Uh, we are getting a bit out of time, but we will make sure we also take some time for, for questions as well. Um, so yeah, you mentioned the writing, writing online. It's, uh, you know, it's been so much beneficial ever, ever since, uh, you know, I started writing online, I've been able to communicate a lot more clearly about specific things to my team and also to the leadership and stakeholders. I wouldn't be able to do that if I wouldn't be, you know, being able to put clearly my words into the articles, you know. That's a huge factor, and I recommend everyone, you know, to at least try to write somewhere, either a blog, a newsletter, or something. It will really, you know, help not only with knowledge and, you know, helping with communication, but also with personal brand in general. And the second thing, a lot of this stuff that you mentioned, I wouldn't be able to develop, develop a lot of these skills that you mentioned without freelance work that I did over the years. And I was working freelance at the same time as doing full-time roles, and I specifically worked on projects that, that involves non-technical people. Non-technical clients, and I needed to develop like an application, a website, or something else for them. And if I wouldn't be able to communicate clearly in a way that it resonates with them, they wouldn't be hiring me. If I would be just, okay, we will pick React, I'm gonna do this with this database, this is how long it's gonna take, and I wouldn't be trying to actually, you know, be helpful and actually find the right solution to them. What are the needs? Amazing. I see a lot of really good questions in the chat. We will get straight to them. But first, before we get to them, I just want to mention that I have a course here on Maven. It's called Senior Engineer to Lead: Grow and Thrive in the Role. If you want to learn the skill set in order to grow from engineer to leader, we start on November 12th. And the second option is on January 21st. There's also a 25% discount for all of you guys here. It's code Lightning. You can either scan this QR code or also here is the link to where you can enroll to the course. Okay, let's get straight to the Q&A. I see a lot of really good questions here. I see one question that stands out, and I believe you have also the most, the most of the thumbs ups. So Dinesh, Dinesh Adithan, make sure to send your LinkedIn in the chat. I will contact you after, after this, this session, and I will give you a free t-shirt. Congrats to you. The question is, how do you set boundaries on your time so that company does not expect your availability full time? Sergio, you want to answer this one?

I love this question, Dinesh. I think you really deserve that t-shirt. Well done. I think it's just one notch above what you should normally do as part of your daily job, right? So as part of your daily job, you need to set expectations for your availability, right? Especially when you're working remotely. In my case, you know, I'm being very explicit with the company that I'm working with. For instance, I have like like one full day completely dedicated to them. So, you know, on that day I'm going to be 100% dedicated to working with you, and then I have a few other hours that I spread along the week to check in to make sure that things are working and progressing. That means that we need to work asynchronously, and that means that all the meetings are usually scheduled on the day that I'm available, right? So people know that I'm there synchronously on those days, and they know that, you know, at least once a day I will check in to check on other things. And here what is important is It's a very important concept I understood, I learned recently, which is that clarity trumps availability. I mean that if people know when to expect a follow-up from you, they will have peace of mind. When they don't know, that's when immediate availability becomes very important, right? Typically companies that don't have a structured process tend to favor like on-the-spot communication because, you know, that's the only way to deal with it. So you basically need to establish those processes. There's always an element of negotiation, right? So maybe one company, you know, I'm No, I prefer you to be available 2 half days a week because of reasons, right? And then, you know, you need to get to compromise. Make sure you also educate the company on the cost of context switch. We can have a single lecture only on that topic, but we don't have time for that. But the more you context switch, the less effective you are. So that's why, for instance, in my case, I prefer to like have at least one full day where I can really go deep on a single topic, quote unquote, even though it's multiple topics.

Sergio, I'm here.

And once they know when you're available, you know, you're gonna be set.

Okay, we lost you for a second, but you're right back, you're right back with us. Yeah, Dinesh, if you have any sub-questions, feel free to add. Also, please make sure to add your LinkedIn so I can contact you after the event. I will just add here one thing, which is what really helps me, is daily goals and weekly goals. If I know what my daily goal is, if I'm able to achieve that, I would be more than happy, you know, if I fail with a lot of other stuff, if my daily goal is achieved, that is really important. And yeah, boundaries, you need to set up your calendar, you need to make sure that your calendar is very clear on what, when are you available and when you're not available. That's also very important. Make your time, manage your time. If you're a full-time role, if you're in fractional role, You need to, you need to have your, your, your calendar as a way to set boundaries. Um, awesome. Let's go to then to Juan Pablo, uh, Chapa. We've been seeing fractional CTO work requested much more frequently this year. Are you also seeing this? What do you attribute to this uptick? To, um, tell you what, what's your opinion of this?

Yeah, so I haven't been having a lot of conversations myself lately, or mainly because I'm not looking for new engagements, so I'm relatively booked right So I will try to answer the second part of the question. I think that there's been a lot of talks about fractional CTO. You know, there are, there are hype waves in this industry. We know that, right? We've seen, we've seen, you know, who doesn't remember Web 2.0? Who doesn't remember big data, right? There are periods where certain terms and labels become very hype. And I think many companies are trying to explore these new concepts because what often happens in the startup and scale-up industry is that CEOs speak to other CEOs, they discover that they're doing something, they want to try the same thing. So I'm attributing this to that, but that's just my speculation. I don't really know. I didn't do thorough research, so don't quote me on this. It's just the way I think about it.

Yeah, you know, my take on this is a lot of people, especially— I've seen a lot of uptake in non-technical founders, they're starting their startups. And it's becoming very popular to find a fractional CTO which help them to guide them with technical decisions. And then they either is hired offshore team, normally it's an offshore team, like if you were talking United States because a lot of startups are from San Francisco. And because, you know, offshore team is done a lot less costly than if you would hire inside the United States. But normally, you know, a fractional CTO is the one that is going to be handling the overall vision, regarding the technology, but then that person has enough experience that is able to lead a team in order to build the right things. That is, I see a lot of uptake in the recent, let's call it last year, this year, and I think that that's where it comes like a lot of, you know, popularity regarding fractional CTOs. Let's talk about pricing and let's talk about equity. Should Good. So this is Dustin's question. How do you price your services and also should you take equity as a fractional CTO? You wanna answer this one, Sergio?

Yeah. So this is very interesting and there is always an element of magic on the pricing side. The way I do it, the way I've done it has been twofold. On one side, I've been talking to other people, right? Not necessarily fractional CTOs, but I've been talking to people I know coming from similar industries who've been making the move of going from full-time employees to the more advisory type of work, understanding what are the fees that the market seems to be accepting. But that's, that was the first step I took. The second step I took was testing the market myself, right? Before, actually before leaving my full-time job, similar to what Gregor Ojstersek did, I was doing some freelance consulting to see, you know, what is the willingness of companies to pay for my services and how much are they willing to pay. So I've been testing, and basically I've been reaching a certain level where I'm com— that I'm comfortable with. And, you know, over time I will try to test pushing it, right? Uh, you know, trying to see what is the, the pain level for prices that becomes counterproductive. The other thing, you know, it's, it's a bit less relevant for the Fractional CTO, but I also realized that, um, I'm actually now applying different fees depending on if I'm working with companies, so B2B clients, or if I'm doing mentoring and coaching to individuals, because I'm doing that as but it's an important part of my job. There is different ability to pay, right? The spending ability is different when it's a company or an individual. So I'm actually kind of fluctuating my process based on that, and I'm constantly experimenting, trying to figure out things. When it comes to equity, that's a very good discussion because— so sometimes I've seen, mostly from people I've been talking to, didn't happen to me, but I've seen in some cases the approach of trying to offer equity instead of cash or fractional roles. Um, I don't think— I don't know if I like that personally, right? And let me explain why. As a fractional CTO, it, you know, you're already dealing with uncertainty, right? You, you don't have a full-time job. You're not employed 24/7, 5 days a week or whatever. So you're taking a certain level of risk on your And that justifies also why you are, you know, maybe having higher fees than you compare with the normal salary, because there is no job security associated with that. There's less cost for the company in terms of overhead cost. Secondly, a fractional CTO, in my view, is supposed to be a temporary gig, right? You don't want a fractional CTO to be permanent. So I, I see the equity discussion, and I'm having a similar conversation, but I see the equity discussion coming in at a certain second point, if there is a willingness on both sides to make this more of a permanent role, right? Starting with equity as a way to keep costs low, no, I'm not comfortable with, because, you know, I still need to pay, you know, the bills. And again, this is going to be a short-term engagement. Equity comes in the long term. I need to manage my finances. It really depends. Again, if you want to do the fractional role as a way to get in and potentially increase, then, you know, probably discussing an equity component can make sense. But I wouldn't be too stressed about doing it early on. I would try to say, no, let's focus on having a cash component that we are both comfortable with. And you can also play, by the way, and then I'll shut up because I am speaking too much, but you can also play the argument of, if you want me to commit to supporting you, I need to be comfortable with the level of pay, because otherwise, as soon as I get another client find who's willing to pay the fees I want instead of giving me equity, I'll probably jump ship, right? So there's an element of keeping you engaged for at least the duration of the contract, which is very important. It's, it's a way to kind of balance risk on both sides.

Yeah, awesome, awesome answer to this one. You mentioned basically everything I had in mind. It's a, it's a short-term, it's a temporary role, similar to interim CTO. It's not a long-term, and if, if, unless you have plans to go either to go to a full-time, extend to full-time CTO, then equity is normally not the case. That fractional CTOs would be looking for. Um, yeah, well, real good analytic answer, uh, Sergio. Let's take one more question and then we will need to cut it, uh, we will need to end it. Uh, Sergio, which, which question do you like? Which one, which one should we, should we take?

Uh, I, I picked the question you answered it there. Let's do this. Um, I like this one from Mariana, actually. She got a lot of votes. How How much hours per week do you work as a fractional CTO? How do you keep control of it with the company?

All right, you want to answer this one?

Do you want to try first? Yeah, yeah, of course. The question, you try this.

Oh, okay, got it, got it. Yeah, uh, you know, for me, the good thing about, uh, being, uh, you know, either, either being a fractional CTO, you can do a lot of different stuff. You normally don't do just fractional CTO, as Sergio mentioned. I'm doing a lot of advising, I'm doing a lot of consultancies at the moment, and I'm working with, let's say, 4 to 5 different companies right now, and also with different people coaching and mentoring. And, you know, normally what I do is I try to dedicate at least 10 hours per company at the moment, and if it's less, it doesn't make a lot of sense. But if it's 10 hours per month, it's good enough. You can do a lot in that time. So it really depends how much hours per week would you work. Like for example, like a normal, if there's like just a fractional CTO position for a startup that wants to deliver their first MVP, I would normally go about 30%, 30% of time, 30% per week. That's like 10 to 15 hours per week. And yeah, how do you keep control of it with the company? You know, as Sergio mentioned, you need to provide when do you work, when do you not work, what is your balance, which days are you working, are you online all the time to answer questions. I prefer to be there in case there's any emergencies or any problems, but I'm not always going to jump on a meeting if there's any, if there's like, you know, outside of my working hours. So I try to be as strict as possible with my calendar and ruthlessly prioritize. But yeah, as a good thing is being like a fractional CTO, you can do a lot of different stuff and companies don't need always just a fractional CTO. Being a freelancer for more than 10 years, I work from whole project just to helping on specific things, just doing solution design, working on, you know, system architecture, working on team management, on hiring. I was also hired just for conducting, you know, a hiring process for a certain role and so on. So there's many different things things that you can do in this case. You want to add something, Sergio?

Yeah, I think you covered it very well. And maybe a bit of a nuance on the question from Mariana about how you keep control of it with the company. I think there is an element of trust there, right? Where, no, I do timesheets, but I do them mostly for myself because I want to account for the time I spend with the different companies. Invoice, but then I don't send with the client— to the clients the timesheet. I just send the invoice with a certain amount. And typically when it's a fractional CTO role, which is like a fixed amount of time per month, we just agree on a forfeit payment, right? A certain fee that is for the month. And then I try to gauge my time, right? I sometimes I do more than that, sometimes I do less than that, and I try to always focus on what is most important thing to do with this client. And we generally work well there because there is both transparency but also trust. If they reach out to me, and actually touching a bit on another question, what I'm seeing is that most of my clients are coming from network or referrals, right? So generally the level of trust is already relatively high because they know you from somehow, right? Because they met you, they work with you, or someone recommended you. So you don't start from, you know, I want to make sure that you're actually 'Give me the hours that you're promising.' They are more about, 'I want to make sure that we're getting to the results that I'm hiring you for.' Yeah, well said.

It's a lot, a lot more is important, uh, as I, as I have seen, like the actual word of mouth from, from, uh, happy, happy customers, happy clients. And that's why I like to say reputation is very, very important in this field. And you don't want to like, uh, burn any bridges in this field. And a lot of, a lot of actual work is coming from referrals and it's coming from recurring companies, recurring people. That is the gist of, I would say, any freelancer out there or any person trying to get to becoming a fractional CTO. Develop a good reputation, you know, do good work, and that is going to get you more work. That's normally how I see, and that's normally how it works as well in my case. Awesome, thanks everyone. Thanks also to you, Sergio, for being here us a lot of interesting insights from you. Anthony, there's going to be a recording about for this, for this session. You can find the recording on this, on this landing page where you subscribed, when you signed up for the event. So all of you guys will be able to watch the recording as well. I think, yeah, you will also get an email with the recording. So yeah, you guys will be able to watch this again after. If you guys have any questions or anything, feel free to connect with us on LinkedIn, uh, and let us know, you know, let us know if there's anything you guys are, are thinking about. Uh, we couldn't get into every, every specific question, but really awesome questions from all of you guys, and appreciate all of you joining. And, uh, yeah, I wish you guys all a great rest of the day. And, uh, yeah, let's, uh, let's— let us know if there's anything LinkedIn, contact us. Have a great day.

Bye everyone, thanks for your time.