DOP 42: Is Your CTO Always Going to Be Your CTO?

Posted on Wednesday, Feb 12, 2020

Show Notes

#42: As a company grows, it’s not unexpected to see executive leadership change. However, those personnel changes mean different things to different people, both internal and external. We discuss the far reaching implications of those changes.


Darin Pope

Darin Pope

Darin Pope is a developer advocate for CloudBees.

Viktor Farcic

Viktor Farcic

Viktor Farcic is a member of the Google Developer Experts and Docker Captains groups, and published author.

His big passions are DevOps, Containers, Kubernetes, Microservices, Continuous Integration, Delivery and Deployment (CI/CD) and Test-Driven Development (TDD).

He often speaks at community gatherings and conferences (latest can be found here).

He has published The DevOps Toolkit Series, DevOps Paradox and Test-Driven Java Development.

His random thoughts and tutorials can be found in his blog

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Darin Pope 0:00
This is episode number 42 of DevOps Paradox with Darin Pope and Viktor Farcic. I am Darin,

Viktor Farcic 0:07
and I am Viktor.

Darin Pope 0:08
We were discussing today what to talk about. Sometimes we plan on way ahead. Tfoday is not one of those days. But based on some of the recent news XebiaLabs merging with CollabNet, it sort of brought up the idea of sometimes the person that got you to X may not be the same person to get you to Y.

Viktor Farcic 0:36
Oh, yeah. I mean, most of the time it is not really. So let's say when you're a small company, 20 people, 30 people, your main preoccupation is technical, right? How do you manage with such a small team to create a great product. But then when you're a person or when you're a company that has like that wants to have 500 people, then we're already talking about a completely different game. About having more than one product, about having a sales organization, about professional services, about expanding all that. And I do believe that there is it is very unlikely that the person who can get you to 50 people company is not the same person who can get you to, let's say, 500. I'm throwing numbers over here, right. But because it's a completely different skill set. We are talking about transitioning from something that is mostly technical, to something that is more business oriented. From a single product, small team to many people. From everybody working as one to having multiple organizations within that company, and so on and so forth. So I do believe it is a completely different game. And I'm kind of very skeptical when I see that the initial CTO or CEO of a company, when it was tiny, is the same CTO or CEO that tries to bring the company to the next level. I'm always skeptical because then I start asking myself, okay, is that the right person? Can he really, if he can do the work of a tiny company, can he really do that same work on a much larger scale? Again, not something against a person, any specific person, but about different skill set. And to me, a great example is Solomon Hykes. He's the CTO, and I think he was the CTO, of Docker. Amazing guy. I think he's brilliant. Really, truly amazing. The only problem I have with Solomon is that he didn't step down from Docker sooner. So I love the guy. I admire his skills and the same time I'm disappointed that he didn't step down sooner. Which is kind of contradictory isn't it? You want the person you like not to step down. That's what our instinct tells us. But I think is the other way around. And I'm using now Solomon...this is not the episode where I want to pick on Docker. I just used him as an example. The first name that popped into my mind and it applies to many different other areas or companies.

Darin Pope 3:45
But there are some that have been able to go there. Jeff Bezos, Elon Musk, Richard Branson.

Viktor Farcic 3:55

Darin Pope 3:57
And I think those are the outliers though.

Viktor Farcic 3:59
That's more exceptions. So I do think, I mean we can probably put Steve Jobs into the same, same bucket. Right? I'm not saying that there are no people like that. I'm just saying that it requires a different skill set. And it is highly unlikely that the person will be able to do equally well both types of jobs, even though it's the same title. I'm not saying that there are no exceptions. There are exceptions definitely.

Darin Pope 4:32
Okay, so let's play the those names that we just threw out. We'll leave Steve Jobs in there for just a minute. Each one of those men that we just listed out have been the high performing typically CEO of each of those companies. I don't have an MBA, I don't say that I am. But here's the thing that's interesting about all of those, other than Steve Jobs getting fired and then coming back. They were all running multiple companies at the same time. Look at Branson, right? All the Virgin properties. You had Steve Jobs, although he got fired from Apple, that gave him the ability to to create Next, which then got re-acquired by Apple. And this little film studio no one's ever heard of called Pixar. You look at...who's the other guy we hadn't list? Oh, Elon Musk. How many companies is he actively in right now? And even Bezos right? Everything sort of under that Amazon brand but between the Amazon Studios and Amazon or AWS. He's still the head of all those things.

Viktor Farcic 5:51
Yes. So let me rephrase what I was saying. I think that I was referring more to CTO role because all those people, I'm not sure what were their official roles but they were all very, very business oriented. I was more referring now from technical aspects, CTO role, and I'm sure that if you Google now we will find examples of that happening as well.

Darin Pope 6:21
That would probably be rare though. Okay. I agree with you. I just thought I had some good stories there but okay, whatever.

Viktor Farcic 6:29
Yeah. So see unfortunately business is not my thing. I don't really know how that works. And amazing those all those people you mentioned are amazing but CTO I think different. Because let's say that you're a small company. What are you trying to do as a small company in today's world? In most cases, that is you want to you live from investors money and you want to attract as many users as possible, right? You want to convince the world that your product is amazing, most likely giving it for free. And then some time passes and you need to grow. And then suddenly, it's not about convincing people anymore. It's about convincing people to give you money. And that's not necessarily the same product, as you were saying, go over and over again. The problem is people want to use and product people are going to pay money for is not necessarily the same thing. And the portfolio you are planning to build is quite different, and so on and so forth. At least that's my theory. I might be wrong, though.

Darin Pope 7:51
Well, I think that's still partially true for today. I think as in the next five to 10 years as the next big generation, the millennial generation, starts to take control of the CFO, the purse strings, as more of those people come in, their buying habits may be different. Now in super large companies, maybe not right, because those things are just institutions. But for medium sized, I'm going to define medium sized as 1000 to 5000 people, person company. I think the buying habits could become very different and I wonder if the free or freemium model is going to continue on.

Viktor Farcic 8:45
I do think that the trend of people in companies adopting stuff that they like is going to continue and it's only going to increase, I believe. Now, at one moment comes the point where company wants to decide to make it official kind of Okay, so, oh, look at this. One third of my people are using Docker or one third of my people are using Jenkins or one third of my people are using whatever else. Why don't we make a deal with the company behind that product, give them money and get something in exchange so that we are more secure in our investment and when I say investment I don't mean investment only in money but mostly investment in time. So we want to now take this more seriously. So we want some enterprise product support whatever it is on top of that. Now, where it becomes kind of tricky is that when it gets to that point, then the requirements of that same product change like when I'm adopting Docker Enterprise, after my engineers already adopted Docker, then my requirements are not necessarily the same as those that made my engineers like the product, or for example Jenkins Enterprise, right? It's different set of requirements that are asked for on top of the same product, only for the fact that now we are paying for it. Because I believe because those people making this people adopting something and people making decisions to make it used officially in a company are having different criteria about what matters.

Darin Pope 10:44
Yeah, I mean, one of the things that sort of a subtext I heard there and you may not have meant it this way, but let's say a company does invest into let's say a client company invests into a vendor company because they're wanting a feature. So they're willing to pony up the money to pay for a feature. That feature, if properly vetted, could help, not just that company, but the larger community as a whole. Custom coding, right? I came back from years ago. One of the companies I worked for, we sold a packaged piece of software. Then we would customize it customize an implementation for each client. But a lot of the time, there were new feature requests that came in that were actually got baked back into the core product that everybody got to take advantage of.

Viktor Farcic 11:44

Darin Pope 11:47
I think that's where external, I'm going to air quote, investment. Not necessarily for's basically pay to play let's just boil it down. Right? It's like I'm paying you. I would like this feature. Make it so. Knowing that everybody's going to get it. It's not just for me, it's just everybody. And it's just helping things get there faster.

Viktor Farcic 12:11
Yeah, but you know, when when you're deciding when you're the person who initiates that process, okay, so I need this feature. Instead of waiting for somebody else request that feature, then you're more in control of how that feature will be. Which is basically the reason why I believe big companies are contributing to open source. I don't think that Red Hat and Microsoft and Google and so on and so forth, are contributing and investing heavily in open source because of the goodness of their hearts. They're investing in it because they want their needs to enter that project instead of needs of somebody else. And what you're mentioning I believe it's very similar, except that instead of me investing my engineering effort into that, and molding it to my needs, I'm paying for that. Right? So that's when request to vendor comes, I need this enterprise feature, that's, that's the same thing except the way how to accomplish it is different.

Darin Pope 13:27
Either you have the time, I can commit resources to code, or I have cash because I don't have the skill set to commit people.

Viktor Farcic 13:38
Exactly. It's I think that most companies would rather commit people than pay cash or to improve something that they really need. But more often than not that they don't have that skill set. Like how many companies can seriously contribute to, let's say, Kubernetes? Not many.

Darin Pope 14:04
Not many.

Viktor Farcic 14:06
So it's not only I prefer cash, but it's also very often that's my only option. I would actually even go as far as saying that, though, that's tiny, tiny, tiny percentage of companies who can do that they tend to not tend to even buy enterprise products because they know that they can add the things that they're missing to, to the project itself, open source project itself, and they have the skill set. So why would they buy a feature when I can develop it and contribute it back, or not, depending on my strategy,

Darin Pope 14:46
All of this, let's let's play out this scenario here, CTO X has been in place. He was the person that was able to get them from bare metal to virtualization. However, this CTO X is failing at getting it from virtualization to containerization.

Viktor Farcic 15:09
In a simplified way, yes.

Darin Pope 15:10
Right. Highly simplified. So when does sometimes the CTOs can't see the forest for the trees? Some of them are wise like, Okay, this is this is beyond my skill set I need to step out. But sometimes not. Sometimes it's like, oh, we're just going to keep or the exact opposite. We're going virtualization. They're getting pressure from their board of directors. It's like, Look, we're falling behind more and more every day. We've got to get to this Kubernetes thing, because I read it in a newspaper article. It was in Financial Times. Kubernetes is the hotness. Why aren't you doing Kubernetes? Well, we don't need to. We just need to stay with virtualization. That CTO is not long for that place.

Viktor Farcic 15:58
And it's hard. I'm not sure whether I would be able to do it. I've been thinking about it. And if I would be a CTO of a highly successful small company, but highly successful, and everybody would be saying, Viktor, you did a great job, look how successful you made us. I'm not sure that I would be able to see it for myself that Okay, now it's time to step down. I honestly don't think that I would be able to do that. Because you just did something great and you're going to step down? Really? It's more that very few people have that capability. I'm pretty sure that I wouldn't. So it's more that company needs to force that change, maybe.

Darin Pope 16:56
Maybe not force, but rethink,

Viktor Farcic 17:02
Yeah, kind of I'm not gonna kill you, I'm gonna push you down the stairs. Potato, potato.

Darin Pope 17:12
Okay, so let's, let's play this out. Let's say what we got for CTO X got us from 50 to...let's just call it 200. A more reasonable number. And the CTO was able to say, okay, we did all this. This is good. It's been a couple years this has grown, this company has grown to more than what I want to be. My story and I'm not a C level, but most of the companies I've worked for, except for one, have been under 100 people or less in general. So I tend to thrive in smaller organizations. When I'm just a number in the faceless thousands. I still perform well, I think I perform well, at least in my head I do but I don't feel like I'm contributing as much. And that could be the same level, the CTO, CTO, some CTOs love the startup, think about a bell curve. You get CTOs that are in the first 20% of the bell curve. And then you have CTOs that work in that 20 to 50 to 60%. And then you have the CTOs that are the maintenance people. Right? They come in after everything sort of stabilized now we'll get a long term person.

Viktor Farcic 18:32
Look at it this way. If you're 20, 30, 50 people company right CTO you're most likely coding significant percentage of your time, right?

Darin Pope 18:41

Viktor Farcic 18:43
If you're 500, would you be coding? Probably not.

Darin Pope 18:47
Doubtful. Doubtful. You're doing you're doing frontline you're helping your frontline you're probably having to deal with board members. You've just got stuff even in privately held you're still gonna have those kinds of political business things.

Viktor Farcic 19:00
Exactly. So for example, let's say that if I would be a CTO of a tiny company, that would be kind of okay. Because I will still be able to be a techie and do my stuff. And I most likely wouldn't stop doing techie stuff when we grow.

Darin Pope 19:18
I would hesitate to say even you may have the title of CTO in that size of company, but really you're an architect/lead developer.

Viktor Farcic 19:28
Exactly. But then that's, that's stepping down in a way.

Darin Pope 19:36
To some people, yes, Yeah.

Viktor Farcic 19:38
But then, you know, if you have a CTO that becomes effectively, not necessarily in title, effectively becomes a lead developer, how would that reflect on company workforce? You know, there is a person who was Alpha and Omega and now, there is a new Alpha and Omega in our company. And that person that we admire is now under him. He's, he's a tech leader, or architect, whatever would be the title, right? And that might not be a good idea simply of the perception of the people working in that company.

Darin Pope 20:22
I'll use an example, a friend of mine, and I worked for him at a startup and I followed his career. We've known each other now for going on 20 years and stepping back and trying to be objective because he's like a brother to me. Being objective, looking at his career, where he's excelled, is helping people get from being stuck in the past, to getting them into the present and moving towards the future. That's his that is his amazing ability. Not everybody can do that. But if I was to take him and drop him in to be the CTO of Salesforce, it wouldn't be the same thing because that's not where he shines.

Viktor Farcic 21:15
Does anybody shine in Salesforce?

Darin Pope 21:20
I'm not gonna say any...Salesforce is Salesforce. Well, okay, so let's talk about Marc Benioff for a second. And I'm not gonna slam him because alright so you might want to slam Salesforce. That's another large company that has been successful.

Viktor Farcic 21:38
Yes, definitely.

Darin Pope 21:40
And they tend...from the outside. Again, whether you love Salesforce or you hate Salesforce, it doesn't matter. But they've been able to help breathe life into ecosystems that you probably wouldn't think about. There's a couple of small companies that were acquired by Salesforce that has now been able to keep companies alive because of the acquisition. Another one all that this probably isn't that same story with when Salesforce bought Heroku. That was a great thing. I mean, everybody knows my love for Heroku from a prototyping and actually operational perspective. It's those kinds of things that Salesforce. But did the CTO even have any real say in that? Probably not. Because those were all business plays. Most of them were business plays at least.

Viktor Farcic 22:36
I don't know the internal situation of Salesforce so I cannot really say for sure but those are the types of purchases and decisions that actually CTO is making...should be making

Darin Pope 22:47
should be yes

Viktor Farcic 22:49
Exactly. And that's why that there is the difference between CTO of small companies CTO of big company because we are now making. You're a Chief Technology, whatever, that is not actually figuring out how to build a new, what would be the great new feature? You're trying to figure out which which company to buy for many millions of dollars.

Darin Pope 23:17
Right. Alright, so let me let me ask this question, because this is rumbling in my head. A smaller company CTO, or let me make the statement and then tell me, if I'm even ballpark or not. A smaller company CTO tends to be more tactical, whereas a larger mid to larger company tends to be more strategic.

Viktor Farcic 23:38
What was the first you said technical or

Darin Pope 23:40
tactical, tactical, more. So they're not even though they may be thinking some big picture, really, they're just trying to get things shipped and keeping it stable so they can get to the freemium model to start paying to get to paying models, versus a CTO at a larger or institutional company. They're just trying to keep the pieces moving and looking at acquisitions.

Viktor Farcic 24:04
Exactly. And looking at the much, so it's about the level looking at the much bigger picture. You know, when what you're looking is a feature is different than when what you're looking is, is an application, then what when you're looking into a whole ecosystem, and then you're buying, you're acquiring companies because you need a product or because you want to kill the product. Those are highly complex decisions that are not really that technical.

Darin Pope 24:36
Can we go up? We've already been on a lot of limbs today, but can we go on a limb? That really a CTO position at a super large company, institutional size companies, is really just a waste of time. It's a waste of a role.

Viktor Farcic 24:51
I wouldn't say a waste of time. You need somebody technical to make those decisions.

Darin Pope 24:56
How many CTOs though at large institutionals do you know that are actually technical?

Viktor Farcic 25:01
I don't. Some. I mean, most of CTOs I know are terribly bad at their job, which is probably for a different episode. I mean, it is technical role, but is the same thing like difference between a developer and a good not majority, but a good architect, right. Both are very technical, but looking at different level of complexities and implementation and so on and so forth. Same thing with CTO I think. It should be technical. It must be technical. That's where many companies are failing. But that is only a part. You need to combine with the business decision with corporate decisions. We need to need to align many many different things that are not really any more about was this function nicely written then it doesn't introduce any technical debt? That type of technical is out of the picture. But technical as if we're going to go to cloud not because we want to be in cloud but because we are going we need the distributed system that will combine all that XYZ. That's still a technical decision. We are going to acquire Heroku. Now there is a possibility because we want to kill it, which is probably not likely in Salesforce. But we're going to acquire Heroku because we need this huge capability being tiny part of our machine. Right? So I'm making a decision to add something that is bigger than what most CTOs do or manage. And yet that huge thing is a tiny piece, tiny element, almost insignificant by itself.

Darin Pope 27:02
Well, and especially just for the, what we'll call the acquirer, but for the acquiree, it's huge. That could have been the last thing that kept them from shutting down.

Viktor Farcic 27:15

Darin Pope 27:17
And we're back to our beginning. And we're not saying that either one of them would have shut down, but we're back to XebiaLabs and CollabNet merging. There's been, you know, a couple of press release. Actually a lot of press releases about it. We don't have any details, but it's not an abnormal pattern to see. There's always consolidation. And you can guarantee the CTOs were talking to each other during that time.

Viktor Farcic 27:37
Somebody needed to expand their portfolio and expansion is so much easier by acquiring something that is at least partly successful than building your own. Chances are, if you try to build your own second product, you're going to have to build at least 10, until you find out what works.

Darin Pope 28:00
Acquiring, it's it's easier to find out fast. Okay, that's a good place to stop. I think we stayed we I think we stayed in the safe bounds today.

Viktor Farcic 28:11
I didn't swear today.

Darin Pope 28:12
You didn't swear. I don't think we crossed over any lines. I hope we didn't cross any lines. I'm sure we did. But that's if we did we apologize.

Viktor Farcic 28:23
There is always a hidden motivation in what we speak about that we don't mention directly. It's up to people to figure it out.

Darin Pope 28:34
But sometimes that subtext is just a subtext to the larger general population. These are just, you know, that's the XebiaLabs/CollabNet thing just sort of popped up a couple ideas, andit I was like, oh, let's talk about this. But that's okay. Now, if you are listening via Apple podcasts, please go ahead and subscribe and leave a rating and review. All of our contact information, including Twitter and LinkedIn, if you're not following us on Twitter, or you can't say friending on LinkedIn, I don't even know what you say on LinkedIn. Anyway, all of our information can be found at If you'd like to be notified by email when a new episode is released, you can sign up at The signup form is at the top of every page. There are links to the Slack workspace, the Voxer account, and how to leave a review in the description of this episode. And if you don't know what any of those things are, just click on those links and you will find out. Any final words for today? It's mid February when this releases. Unless you're in the southern hemisphere, it's cold. I don't care where you are. It's just plain cold in the Northern Hemisphere anyway. If it's not cold where you are, be thankful.

Viktor Farcic 29:54
It's not cold where I am.

Darin Pope 29:59
Are you now in the...middle of are now where? It's February 12th. Where are you?

Viktor Farcic 30:07
I'm home...Barcelona, but it's like 20 degrees Celsius.

Darin Pope 30:11
I'm not saying today. Okay, see, we're having to break the fourth wall again. We're recording on January 23rd. Today is February 12th. Play along with me here. Come on.

Viktor Farcic 30:28
I know. Time travel confuses me all the time. It's very confusing.

Darin Pope 30:33
Are you saying are you saying that time travel does not exist because it confuses you?

Viktor Farcic 30:40
I'm not sure about that, but it's confusing.

Darin Pope 30:42
Okay. Anyway, Viktor's probably on the road so middle of it when you're listening to this. I think Viktor is on the road every day in February.

Viktor Farcic 30:51
Yes, I'll be somewhere.

Darin Pope 30:54
Not home. Let's put it that way, because you're always somewhere. You're just not home. So if you see Viktor out at any of his...we've got to get an events calendar up on the like, Where's that's like we're in the world is Viktor?

Viktor Farcic 31:08
Where's Waldo?

Darin Pope 31:10
Where's Waldo? Where's Carmen San Diego, all the Where's. You need you need to get a striped shirt like Waldo. We need to come up with a Viktor look. Anyway, we're just rambling here at the end. Do you have anything else? This was sort of a somber episode, right? Not highly technical, but I think we both said our peace about some of the things that we think about the CTO role, as it as somebody moves through the ranks. I like a CTO role. I think it's a wise thing. But when you have a non technical, a completely non technical person end up in the CTO role, that's when things go bad and we didn't really talk about that.

Viktor Farcic 31:53
One of the next episodes, we will.

Darin Pope 31:56
Hopefully we don't have to talk about that. Hopefully that's just plain and simple, but it isn't always for companies. But anyway, that's it?

Viktor Farcic 32:06
That's it.

Darin Pope 32:07
That's it. Alright. Thanks again for listening to episode number 42 of DevOps Paradox.