Speaker 1: Welcome back to the CTOX podcast.
Speaker 1: When a CEO says they want a player coach, what they usually mean is I want leadership and implementation,
Speaker 1: but I don't wanna pay for it.
Speaker 1: Today, we're unpacking a common but deeply flawed idea in start ups and growing companies. The belief that executives and in our context, of course, fractional CTOs
Speaker 1: should both do the work and lead the work.
Speaker 1: We're gonna explain why this thinking breaks teams, burns out leaders, and ultimately prevents
Speaker 1: real scale.
Speaker 1: Lior, you know I am excited for this conversation.
Speaker 2: Yeah. It's probably yeah. I would say it's the number one reason of burnout
Speaker 2: for executives.
Speaker 2: Right? Pretty much across the board, not just with CTOs.
Speaker 1: You and I have each had seasons in our lives and careers where we've been called a player coach.
Speaker 1: What do CEOs
Speaker 1: usually mean when they say they want a player coach?
Speaker 2: They mean that you can do the actual work,
Speaker 2: but that you also
Speaker 2: do the actual work.
Speaker 2: So it's not just the capability.
Speaker 2: It's the practical application.
Speaker 2: And the reality is they
Speaker 2: want to,
Speaker 2: pay you more or less and get, two for one.
Speaker 2: It's usually what that means.
Speaker 1: Agreed. No.
Speaker 1: That's my label. That's my label today, but I know that doesn't apply to everybody. But why does this expectation show up so often in, in leaders who are hiring for fractional
Speaker 1: roles?
Speaker 1: Fractional roles?
Speaker 1: I think
Speaker 2: I mean, to be fair, I think it shows up often period.
Speaker 2: I think it shows up in full time. I think it shows up in fractional. There's something about technology professionals in particular because,
Speaker 2: there's just so many
Speaker 2: there's so many technology startups. Right? You're not gonna say I have a philosophical store startup.
Speaker 2: Right? Even though in practice, you might actually have. It's like a baby store. You don't know how it's gonna grow. If it's gonna grow, it might close it might shut down, but you're not looking at it like that.
Speaker 2: And the reality is in I was a start up entrepreneur
Speaker 2: as as a young guy,
Speaker 2: and and the business card says CTO.
Speaker 2: Right? Like, on the business cards, there's a CEO, the CTO. We're only a two person startup.
Speaker 2: I've had meetings where we we changed the business card. Like, I I was the CEO for that meeting. He was the CTO
Speaker 2: for that meeting.
Speaker 2: And the reality is in a small team, you do the work.
Speaker 2: You make it up and you make it real and you make it recur, and it's that core team.
Speaker 2: And it's that philosophy because a lot of CTOs come in
Speaker 2: from that doer. That's how they grew. Right?
Speaker 2: It's rare to see somebody that's leading technology that doesn't that had not done technology. So you see it sometime, but had not built
Speaker 2: technology. So it's very,
Speaker 2: it's very common for builders
Speaker 2: to
Speaker 2: be stuck in an environment where they have to build. And it's also very common for CEOs to think, well, I need to build something, so I'm gonna hire a builder
Speaker 2: to build it. But the reality is being accountable for the system while you're stuck in it
Speaker 2: is not a good idea. It actually
Speaker 2: rarely
Speaker 2: works. Now if you're a startup, by the way, if you're a two, three person startup, I don't recommend you hire a functional CTO. Because really what you're looking for, you're looking for a developer.
Speaker 2: You can give them the CTO title on your slide deck.
Speaker 2: That's completely fine. But the reality is you're looking for somebody to actually write code or build product.
Speaker 2: And that context of leadership is irrelevant
Speaker 2: because they're not leading anything.
Speaker 2: They're not leading a team.
Speaker 2: They're not leading a mission. They're doing
Speaker 2: the thing. They're doing they're making the vision,
Speaker 2: real just like in a larger organization. The actual people with their hands on the wheel are gonna drive the car.
Speaker 1: Right. And, of course, I get the appeal here. It's a great deal financially
Speaker 1: to operate with a team of player coaches.
Speaker 1: What actually breaks, though, when leaders are expected to both execute and lead?
Speaker 2: The problem is getting pulled into tactics.
Speaker 2: Right? When you're leading,
Speaker 2: that's why in our discovery call, we say, what do you wanna we have this, template. We tell them to ask the CEOs, what do you wanna do and why do you wanna do it? You you wanna jump into the why because you wanna be able to change your plans all the time. Leadership requires
Speaker 2: distance and perspective.
Speaker 2: If you're in the code, if you're pushing,
Speaker 2: if you're looking at the service status, whatever it is, your ability
Speaker 2: to actually argue
Speaker 2: that we need to do a different what for this why is very limited.
Speaker 2: Because you're just looking three feet ahead, and the more tasks you have, that's what's on your mind. That's what's on your mind set.
Speaker 2: So as a leader, you want the ability to keep the vision
Speaker 2: right in front of you and then figure out, well, how can we get this vision closer? How can we make this vision bigger? How can I get there sooner?
Speaker 2: And if you're drowned with tasks,
Speaker 2: you're able to just stand up, take a fresh breath there, and just see, oh, we were completely off is extremely limited. So your value
Speaker 2: of bringing in your decades of experience and judgment and nuance and intuition
Speaker 2: is severely diminished.
Speaker 2: And certainly, they're overpaying. If somebody is hiring Lior
Speaker 2: to write code,
Speaker 2: I'm not a bad coder.
Speaker 2: I know incredible coders. I'm certainly not in the best coders I know. Google is not gonna hire me to figure out the next algorithm,
Speaker 2: you know, for their search.
Speaker 2: I'm probably gonna be somewhere up, but not in the top 2%. If you hire but if you hire Liora to be a coder, I'm gonna do something, and it's gonna be a complete and utter waste
Speaker 2: of talent, other waste of impact because my impact is gonna come on the strategy side, the leadership side. They're making the right decisions so we get bigger visions, so we get them sooner.
Speaker 2: And the fact that I'm pushing code
Speaker 2: is useless, and it's a waste of energy.
Speaker 1: I think about you know what I'm thinking about is we tell our members of the CTOX Accelerator early on, like, you're selling leadership.
Speaker 1: And
Speaker 1: I in my mind's eye, I can see them glitching, some of them anyway Yeah. Because it's like, well, what is my value? What is my what is my value proposition? What am I selling? And we're like leadership.
Speaker 1: What is the real value there of a fractional,
Speaker 1: CTO who is there to
Speaker 2: lead? It's
Speaker 2: the
Speaker 2: discernment
Speaker 2: and the decision making
Speaker 2: that's
Speaker 2: based on decades
Speaker 2: of experience.
Speaker 2: Right? Like, what's better? To write beautiful code or to make a decision? We don't even need this code.
Speaker 2: It's way better to not do something and realize that you don't even need to execute on something. Or what is better? To build something beautiful and polish or realize, oh, some
Speaker 2: I I Googled it, and we can buy a product for $5,000
Speaker 2: that does it, and we get the result today.
Speaker 2: That mindset
Speaker 2: of even looking at the problem and saying, do we need to build? Can we buy? Do we need to even do?
Speaker 2: What is this problem even a problem? Those are leadership qualities.
Speaker 2: And especially for certainly for smaller companies and but in a competitive marketplace,
Speaker 2: you want the ability to know what should you even work on.
Speaker 2: And with that, do it for the best budget, you know, the shortest amount of time, and so on and so forth. So what you're selling is that discernment,
Speaker 2: and you're selling your ability to make it happen by rallying resources.
Speaker 2: And maybe it's getting vendors,
Speaker 2: maybe it's getting employees.
Speaker 2: But the point is you're trying to,
Speaker 2: you're trying to make the vision real,
Speaker 2: and you're trying to make the vision real in the least amount of money in the least amount of time. If you're focused too much on the how, we have entire workshops about this, in the accelerator,
Speaker 2: you're gonna miss the boat and the value is not gonna be created.
Speaker 2: And maybe a company and maybe you're super proud. You know, like, well, we got this done for $600,000
Speaker 2: instead of a million 2, and it took us six months instead of a year. But if the answer was, well, you could have bought something off the shelf for 60,000 and got the value right now, then you actually
Speaker 2: created damages worth of $600,000.
Speaker 2: Because if you compared it to some big enterprise build and you were like, no. I was scrappy. I'm like, well, did you even need to do it? Right? And that's what leadership is. When if,
Speaker 2: for some of you that have been leaders of different levels,
Speaker 2: directors,
Speaker 2: VPs,
Speaker 2: chiefs, if you think about
Speaker 2: your activity inventory, like the time to do think about like a time study
Speaker 2: of of a normal month in your job, and you realize how much time did you actually code, did you actually build, it's gonna be very minimal.
Speaker 2: Very, very minimal.
Speaker 2: So in the context of selling fractional leadership, you're just selling the leadership hours,
Speaker 2: the leadership insight, the leadership
Speaker 2: value, and you completely disregard all those meetings that you were just there
Speaker 2: staring at the paint dry, listening to people coordinate between themselves. You're not making strategic decisions,
Speaker 2: and you didn't actually create value. With this kind of work, you can consistently only sell the things that move the needle,
Speaker 2: really move the needle. So that's why
Speaker 2: you're selling discernment. You're selling your judgment,
Speaker 2: prioritization,
Speaker 2: your orchestration of everything, and not delivery. Just like a conductor
Speaker 2: is probably a good musician,
Speaker 2: but there are better musician in the orchestra right now. And none of them can do their job without the conductor
Speaker 2: with their back to the audience,
Speaker 2: coordinating and telling them what to do when because he understands everything. He's not as good as the first year violinist.
Speaker 2: He's not as good as the pianist, but he understands all of their job, and all of them trust him to make sure they can create a beautiful symphony together.
Speaker 1: You're selling discernment. You're selling judgment.
Speaker 1: And
Speaker 1: I love this. And what's tricky is that discernment often gets undervalued because the traditional workplace
Speaker 1: doesn't always operate that way. It's the roles and the description.
Speaker 1: What language is helpful for fractional CTOs to use when they're speaking with prospects and these CEOs who may be used to working in that environment and not really used to hearing a fractional CTO pitch?
Speaker 2: For us, we focus it about outcome. That's why in our discovery call, we say ask what and why.
Speaker 2: And one of our positioning for the fractional space is saying, I can give you a 100% of this outcome for a fraction of the price
Speaker 2: because we want the conversation to be about what are you trying to do. And good news, you can get it for cheaper, but rather good news, you can get it for less effort. We don't want you to think about effort. We want you to think about outcome. We want you to think about vision. We want you to think about efficiency.
Speaker 2: Right? That's where the cost
Speaker 2: kinda comes in.
Speaker 2: And as long as they can
Speaker 2: notice themselves that if they talk to a prospect
Speaker 2: or if you're a CEO and you're listening to this and you're talking to a CTO, if you're noticing the conversation suddenly,
Speaker 2: revolves around the how and the hours
Speaker 2: and the resources, you're missing the boat.
Speaker 2: You're missing the boat. You really wanna clarify. That that that's completely fine after you clarify the vision,
Speaker 2: after you clarify the impact. The best advice I can give for fractional CTO once they're in those conversations,
Speaker 2: don't mistakenly
Speaker 2: say stuff like, I can do it.
Speaker 2: I've done it, you know, 50 times. Because then you're actually positioning yourself as the bottleneck,
Speaker 2: and you're positioning your your future
Speaker 2: engagement as they're gonna be in a meeting, and they expect you to do it.
Speaker 2: And when you create the road map, they expect your name to be on the initiative,
Speaker 2: on the task. As a you wanna talk in we.
Speaker 2: What do we wanna do? What is the organization wanna do? What is the impact we're trying to create? What is the value we're trying to create? So So make sure to talk about the future. Talk about us. Come talk about impact. Talk collectively,
Speaker 2: not personally.
Speaker 2: And then when you eventually do get the job, you'll be able to continue delivering in that same modality. Look at what we're doing.
Speaker 2: Look at the impact we're creating.
Speaker 2: And we're hiring all these people to do the work because both of us, you and me, CEO,
Speaker 2: we're getting this done. Just like the CEO
Speaker 2: is not doing any of
Speaker 2: the actual tasks, metabolizing the actual tasks in the business, again, I'm putting in a slash from, like, two person startups. Right?
Speaker 2: Then the CTO shouldn't do,
Speaker 2: any of that as well. So if they can keep it more communal, keep it vision oriented, then they can make sure the language is always about impact and then not
Speaker 2: really
Speaker 2: sell hours, which is, the challenge most CTOs come into this space.
Speaker 1: Well yes. And I I wanna stay there for a moment, and let's say you're on the other side. You're working with them now as a client. They're not a prospect anymore because there is a bit of a learning curve when it comes to staying in the leadership lane.
Speaker 1: How do you protect yourself
Speaker 1: from being pulled into the weeds?
Speaker 1: Because that is another moment of danger where you may have successfully enrolled them on the leadership part, but now it's,
Speaker 1: standing up and setting those boundaries when it matters.
Speaker 2: I think to me, the way I do it, if I find and I do this all the time,
Speaker 2: nearly every week. If I find myself in a conversation
Speaker 2: that's very tactical,
Speaker 2: like the CEO has a project they wanna get done or,
Speaker 2: one of the other executives and they pull me in. They're like, well, we wanna do this. We wanna do that.
Speaker 2: I immediately
Speaker 2: put the why conversation,
Speaker 2: as the big awareness of of what we're talking about because it makes sure that they still understand
Speaker 2: that I'm leading and not doing.
Speaker 2: If I'm
Speaker 2: biting
Speaker 2: on whatever they have to show me and I'm like, yes. They said, oh, you're right. Yep. Totally. We can get it done in fourteen days. Yep. I'll talk to three people. If I'm acting that way, I'm instantly in manager mode. I'm instantly in individual contributor mode, and they're getting confidence because I just said, yes, I'll take care of it. Instead of me continuing acting like a leader and questioning,
Speaker 2: you know, this, should this even exist
Speaker 2: and clarifying everybody about the impact. So I'm definitely
Speaker 2: focusing in on why,
Speaker 2: challenging the project,
Speaker 2: clarifying the impact.
Speaker 2: And the last thing I do
Speaker 2: is saying something, I'll take care of it. I'm gonna say, okay. Now that I got it, let me go back to the team and see how we can get this done
Speaker 2: and then go back. And I'm very careful of not suddenly say, I got it. I'll take care of it. Don't worry. We'll it'll be ready in ten days. You'll never hear me say that,
Speaker 2: because I wanna keep that boundary. So I'm not gonna get expected as, like, well, you said you're gonna send me an email in three days with all the solution. Right? You said you're gonna the feature is gonna be released in a couple of days.
Speaker 2: So I always go back to impact
Speaker 2: vision,
Speaker 2: and I say, I'm gonna see how we can do it as a group, as a collective, and then actually go back to my, you know, subordinates resources, whatever it is to to give the report. Ideally, by the way, I don't I I have one of the people I speak to actually send the update and cc me.
Speaker 2: So they know that the tactical updates also don't come from me.
Speaker 2: Because if I train, it's like dog training. If I train them that I talk tactics and I give them tactical updates, then that's what they're gonna just continue doing. It's just gonna snowball. It's gonna be a positive feedback loop, and it's never gonna stop.
Speaker 1: This is important.
Speaker 1: And I imagine
Speaker 1: this gets really tricky when your comfort zone is building and engineering
Speaker 1: and doing. How do you how do you coach folks to self correct that instinct? Because it is
Speaker 1: just I mean, it's a second. It's one line, and you've not pat down into it.
Speaker 2: There's a lot. One of my favorite mental models, you know, like in the military and leadership training, you would say something like, you know, hands in pockets.
Speaker 2: Can't do anything. Hand and pockets.
Speaker 2: I like to say and this is I also say to people under me. Right? Like, as directors or VPs.
Speaker 2: I tell them, imagine you had the same job, same responsibility, same accountability, but you're Stephen Hawking.
Speaker 2: Right? You talk very slow. You have to be super discerning
Speaker 2: about what you're gonna say. And you can't use your hands.
Speaker 2: This is voice commands.
Speaker 2: Right? Like, what do you do? So imagine how you because it forces you into leverage.
Speaker 2: It forces you into leverage. It forces you out of being the actor in the scene.
Speaker 2: You're like, this thing needs to happen, and you're not the actor that's doing the action.
Speaker 2: So it forces you into this mindset, into this mental space of still focusing on the outcome,
Speaker 2: but not shortcutting and saying, oh, I'll take care of it.
Speaker 2: Give me give me the gun. I'll shoot.
Speaker 2: Alright. Give me the rope. I'll tie it in. So I think those are, like, you know, hands and pockets, one of my favorite, you know, mental models, and then Stephen Hawking, one of my more exotic ones. But both of them talk about the same thing. You don't get to use your hands.
Speaker 2: You don't get to get involved.
Speaker 2: You only get to influence.
Speaker 2: And if you focus on the only thing you can do is influence
Speaker 2: and not do, you're way more likely to keep your leadership positioning
Speaker 2: and not suddenly get drowned in tasks.
Speaker 1: On zooming out, this is also what unlocks
Speaker 1: scale as a fractional CTO.
Speaker 1: So there I'd love for you to speak to that a bit because there is that need. You separate the leadership from execution on a one client basis, but it also enables you to fill the portfolio.
Speaker 2: That's exactly right. When people come in,
Speaker 2: first of all, we do a lot of work with them to make sure they don't sell hours. They don't think about hours. They don't create hourly expectations in the conversation, like, to do all that. But and, really, if they
Speaker 2: do, if they act in the way we teach in terms of philosophy,
Speaker 2: right, you're about influence and leverage, you're not about actions and
Speaker 2: and tasks, then, yeah, you actually get to a point. Like, I can I can I can support a $2,030,000
Speaker 2: dollar retainer sometimes within an hour to a week?
Speaker 2: And people are mind boggled by it. But the reason they're mind boggled
Speaker 2: is because they assume they need to be in the standing meeting.
Speaker 2: That's right. They assume they need all the updates
Speaker 2: to come through them. Like, why do you wanna be a bottleneck with all of my clients?
Speaker 2: This is the reality of it. If Leora leaves,
Speaker 2: nothing happens.
Speaker 2: Meaning, they're continuing smooth sale. Right now, if I leave a 100% of my clients,
Speaker 2: they will not miss a beat.
Speaker 2: A beat.
Speaker 2: Now people might say that means you're,
Speaker 2: replaceable.
Speaker 2: I'm like, yeah.
Speaker 2: Absolutely.
Speaker 2: I'm trying to give them scale.
Speaker 2: I'm trying if I'm sick, I don't want the organization to slow down.
Speaker 2: I don't wanna create some kind of a system or a process that if Leor is not available,
Speaker 2: God forbid, the organization
Speaker 2: gets hurt.
Speaker 2: The tasks get hurt. The outcome that they're trying to do. So I'm very pointed on it. I would that that's my point. My point is to create a super resilient process that lives without me, not only without me, by the way, without any single one
Speaker 2: under my team. If the director of product leaves, nobody's missing a beat. Director of engineering leaves, no one missing a beat. If one of the developers leave, nobody's missing a beat. You wanna create that
Speaker 2: resiliency.
Speaker 2: And because
Speaker 2: I do that, my clients love me. They're
Speaker 2: afraid
Speaker 2: as the company grows, the system is suddenly gonna become nonresilient.
Speaker 2: That's why they're keeping me. They're not keeping me because they're enjoying the fact that I'm, quote, unquote, no longer important.
Speaker 2: They're keeping me because they get to enjoy the fact that the way I design the teams and design the processes,
Speaker 2: the organization can keep scaling.
Speaker 2: And when life happens, because life happens,
Speaker 2: people leave, people switch priorities. That's just you can't. That's a constant in business.
Speaker 2: They know that the systems and the technology capability of the company
Speaker 2: doesn't go away.
Speaker 1: Potent.
Speaker 1: If this episode helped you rethink leadership and boundaries,
Speaker 1: share it with a founder or executive who keeps asking for a player coach and doesn't realize
Speaker 1: what they're really asking for.
Speaker 1: Lior, thank you as always for the fabulous, fabulous insights.
Speaker 2: Thank you. And don't forget,
Speaker 2: keep your hands in your pockets.
Speaker 1: See you.