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470: CTO Excellence in 100 Days with Etienne de Bruin · Giant Robots Smashing Into Other Giant Robots

• VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Etienne de Bruin, Founder of 7CTOs and Author of CTO Excellence in 100 Days. Etienne, thank you for joining me. ETIENNE: My pleasure, Victoria. Thanks for having me. VICTORIA: You're welcome. I'm excited to talk with you today. I hear that you recently published your book. Is it today actually the day it came out? ETIENNE: Today is the day. The book was finished about; I would say, three months ago. So I have had great anticipation now for many, many months. And you caught me on the day, so I feel like today is my birthday. VICTORIA: [laughs] Well, I feel honored that you chose us as your first stop [laughs] in your marketing push for your book. So tell me, what in your experience led you to begin writing this? ETIENNE: Well, as you mentioned, I founded 7CTOs. I think it's about ten years ago now. I myself am a CTO type. I've had a career of basically being born to code in South Africa, which took me to Stellenbosch University in South Africa. I then joined a startup that took me to Germany and then landed in the U.S. in San Diego. And my whole journey has been a progression from individual contributor and really having great coding skills through the messiness and the intricacies of building startups, contributing to startups, and ultimately being in the role of CTO in startups. And what led me to founding 7CTOs was just a realization that I didn't have the support I needed. I felt like I was going to many meetups, which was mostly oriented towards coding and sort of different new technology stacks and frameworks, or I was going to cocktail hours with vendors who were trying to sell you something. And I really felt the need to just be with my people so that I could, in a safe, and consistent, and accountable way, share the challenges that I was experiencing. It was really from this place of founding 7CTOs, talking to hundreds of...I've probably spoken to thousands of CTOs by now. I've also placed people. I've connected people. I've seen people join companies because of connections I've made. And one of the things I saw that really bothered me was finding a great company in search of a CTO reaching out to me, talking to me about the role, me finding or through my network connecting them with a great CTO, only to find that a few months later either the relationship fizzles or even worse, the person did not succeed at the new company. And I just felt like you can have two people, a great founder, and great CTO, individually wonderful people, ostensibly well-suited to work with each other, but then make some basic mistakes that then lead towards not the desired outcome. And so I was really torn whether I should put some thoughts into a book or into some blog posts about what I think the first 100 days should look like in a fledgling relationship. And that's ultimately how the book was born. So long, long, long, long answer, Victoria. But that's where it all started. VICTORIA: No, that's great. I try to ask deep questions that get full answers back. [laughs] ETIENNE: You nailed it. VICTORIA: So I appreciate that context, yeah. So you talk about how to be successful in those first 100 days, which is critical to joining a new leadership team. What are some common mistakes that you mention that a CTO might make? And on the reverse side, what are some wins you could do early on to build trust? ETIENNE: I think a common mistake that I see is a bit of an identity issue. The CTO joins an organization and is eager to deliver value, and I think that that value is oftentimes misplaced. And what I mean by that is you hit the ground running thinking that there's all this stuff that you have to deliver in order to prove that you can make an impact, to prove that you were the right choice. And I think there's an innate desire to impress your new employer, which I don't think is limited to the role of CTO. But I think for the CTO, this looks like some technical achievements and impact, problem-solving. And I think what I like to see is the first 100 days being used to slow down a little bit, to listen, to be curious, to be open to building relationships, to have a longer view on what exactly is the system that you're joining. And I think to a fault; sometimes people will ignore the system they're joining and just start delivering value. And I think that that can often be misinterpreted or misunderstood. And then, if that is misunderstood in the first few months, then that really sets a tone for the rest of the tenure that I think puts the CTO on the back foot to deliver at a pace that maybe is unsustainable, so... VICTORIA: I love that you said staying curious because I think what you can see is a tendency for, I don't know, what I've seen; maybe you've seen this too. [chuckle] But some people have a problem that they solved in a past situation, and they think that that is now the solution to every problem that they come into in a new organization, and maybe it is. But I think dealing in complex systems, having curiosity as to why decisions were made in a certain way can lead you to a better understanding of the business if that resonates with you at all. ETIENNE: Yeah, I love that you said that. I'm a huge fan and student of complex systems. And so you just spoke my love language. VICTORIA: [laughs] ETIENNE: But that's exactly what happens. And I think that sometimes the debilitater of powerful and impactful people is the problem that you observe is maybe tainted by what you saw in the past. It might be a similar challenge, a similar problem. But what you solved in the past was part of a completely different system, different entities, different relationships. And I think that by nature because the CTO is used to solving thousands and thousands of problems, there may be a bit of complacency around what is it exactly that I'm observing is the challenge here? Why exactly was I hired? What exactly does success look like for them, for the people that hired me, for the system that I've come into? And I think the tendency is to ignore all of those questions and focus on how do I feed my own need to feel valued and start solving problems in sort of a whack-a-mole style? And I have found, even in my own experience, that there are some seriously unintended consequences that can arise from solving people's problems for them in ways that they are not used to, or they don't understand, or in some places just fully disagree with. And I think if you are not patient and take sort of 100 full days to just chill out and really enjoy learning about the system that you're joining, I think you're setting yourself up to fail or to at least be very unhappy. VICTORIA: Right, setting yourself up for some fun conflicts [laughs] to solve if you come out right out the gate. And I think maybe, too, the first 100 days the chilling out and learning, you also have time to build empathy and build trust with people so that when you do bring up suggestions, they're maybe a little more willing to listen, right? ETIENNE: Yes. And I think it's not uncommon to say, "Oh, well, I'm going to onboard myself. It's going to take some time before I show value." And I think there is a general sense that when the executive joins a company that, it's going to take some time. But I think that the temptation to jump into fiery situations is great, great in a bad way. It's a great temptation. And my book and my approach suggests that you take a step back and focus on a completely different area of the company, which is its people and its systems, and what success looks like for those people before you start jumping in and asserting your way of doing things. VICTORIA: And you mentioned a question that I was going to ask, like, what does success look like? Or say you're a CEO, and you're trying to hire a CTO; what does success look like? What kind of value do you think people should expect from someone in a CTO role? ETIENNE: Fundamentally, I think I might not be swimming in the mainstream on this topic. I don't believe that the CTO is a technical role first. I believe that the CTO is the Chief Technology Officer but is primarily a business role. And by that, I mean being a member of the C-suite, you are tasked, just like all the other members of the C-suite, to grow a company in a sustainable way. And whatever that middle letter is, is your domain and your expertise, and that's cool. But that T is surrounded by a C and an O, which in most cases has a fiduciary responsibility to the organization. But also, first and foremost, you are a first-class member of the C-suite. And so my book talks about this, but you are there to join in with the executive leadership team and to help that team towards success. And so what that looks like for me is you are wrestling on what the targets are for the company. You participate fully in that. You then allocate a budget. In other words, you allocate cost towards how you can achieve those revenue goals. And then, with that budget as CTO, you then are budgeting towards a team that you believe can get the technology implemented that will ultimately produce the revenue. So think about revenue target, technology budget, technology people. Now, these are all in the C-suite. These are just entries on a P&L. These are entries on the balance sheet. These are things that ultimately are abstracted towards company growth and company success. So with that, the CTO then turns into someone who wrestles with the tech teams, like, what are we going to implement? What ideas are consistent with our company principles and our vision? What does innovation look like? How do we inspire people to join our organization to do so? That, to me, is a fundamental role for the CTO, to inspire people to join the organization but also to be someone who implements and ideates on that journey. So I think a CTO succeeds when there is revenue growth, and that is due to budget being spent in an effective way to attract amazing people to ultimately build technology that is sustainable that then feeds into tech revenue that ultimately helps the company achieve its goals. VICTORIA: That's great. Yeah, I like that you said sustainable and the importance of people and how that relates to keeping your technology sustainable. And I'm curious if you could share more about what practices a CTO could bring to a new organization to facilitate that inspiration and to really motivate technology teams and people to work together and build these systems. ETIENNE: I think that speaks to my earlier answer, which is the investment in people and investment in understanding the systems that exist. So whether you are a CTO, that is the first time a company ever scales and grows into having that role being created, which, you know, most tech startups these days will have the role of CTO allocated and available. The important thing to understand for you as someone stepping into that role is that your teams have a construct. They have an impression. They have an image, either of your predecessor at that company or their experiences with leadership and technology at their previous companies. And I think it's extremely important to understand how you're being seen as a leader in the company and as CTO and that that vision of what people have of you is not necessarily based on your actions, your reputation, your good mornings in the mornings and your good evenings in the evenings. It really is based on people's constructs about what their experience has been of a CTO in their career, or like I said, the previous CTO, your predecessor. And so I think that it's critical as you step into this role that you take the time to bring that change to show people your ways, to show people what is important to you in a way that's not a bull in a china shop. But when you break stuff, and you come in, and you announce your presence, and you assert the new way of doing things, I think that that is met with suspicion and concern most of the time. And so I think if you can show people in the little things that you care about them, you're listening to them, you're curious about the system they're operating inside of, I think that that sets you up to then come in with the big ideas later on. But again, the emphasis being later on, past the 100 days. I talk about this in the book where introducing your tech strategy, introducing your way of doing things really comes a lot later in the 100 days than is maybe the preconceived notion. VICTORIA: And you also mentioned a few times what the CTO should be doing and a lot of great questions that you ask, like, what does success look like? How do we build this together? And finding ways to maybe generate more ideas than just what you would come up with with your team, you're more powerful. ETIENNE: Yes. And I think tag teaming on to that is a lot of times...and this is actually really a confounding thing that I've come across, which is the C-suite won't always understand what the role of CTO actually is. And teams won't always fully understand what the role of CTO is. When you talk about a CMO, or a CRO, or a CFO, I think you can generally understand what they're supposed to be doing. That isn't always clear for the CTO. And it's amazing how many times I have gotten the question, well, we knew we needed someone to help us with the tech, but we don't really know what it is that you do, or what you should be doing, or what success looks like. I think not making the assumption that people know what you're there to do is a form of showing some respect and humility. And this is why always when I'm in executive meetings, when I'm in stand-ups, or I'm in some sort of an architecture meeting, I will almost without fail I will say, "As the role of CTO, this is what I bring to the meeting," or "This is what the role of CTO would be looking for as an outcome of this conversation." Or "As the role of CTO, it is my job to ensure that our development capacity increases," to just never assume that people know what it is that you're there to do but to show them, I think, the respect and the courtesy that the role of CTO has a certain place in whatever meeting or brainstorm session is going on. VICTORIA: I think that makes sense, too, because I could see, you know, especially you mentioned with people who maybe have had past experiences with CTOs that are not the most positive. If you bring up an idea in a meeting, everyone thinks, well, that's the solution. That's what the CTO wants. And it might not. Everyone might not feel comfortable, like, without you caveating; this is why I'm bringing this up. You know, we're here to brainstorm and not for me to just tell you what to do. [laughs] ETIENNE: Yes, yes. And that's why I will often...honestly, this might be a real tip for people listening. But I will actively divorce who I am from the role that I'm in. And it enables me to have difficult conversations. It enables me to assert leadership without dominance. And that is to just say, "Hey, Sandra, in my role as CTO, this is what I am looking for in your growth or in your career path." Versus, "Hey, Sandra, I want you to..." or "I need you to..." And I think the subtle difference there is to just assure someone that you're operating in a capacity that the company expects from you versus somehow having your identity wrapped in the outcome of a conversation. And that really has been a very powerful tool for me as I integrate into new companies or as I need to navigate tricky conversations. VICTORIA: I appreciate you sharing that. I think hopefully that will be a great point for someone who's maybe struggling with something similar at this time. And maybe there are other common questions or themes that come up when you're talking to all these CTOs in organizations that you can share. ETIENNE: By the way, if your name is Sandra and you're listening to this conversation, I totally made up the name Sandra, so I'm not referring to you, Sandra. VICTORIA: [laughs] ETIENNE: Okay. I think an interesting thing that I've noticed is given the stage of my company, have I addressed all the things that I need to by now? And I think that is such an indication of the times that we live in. Technology is always changing. Expectations are always changing. Clearly, if you're in a technology innovation company, things are rapidly changing. It's funny because some things just stay the same, i.e., people problems and all that. But as far as technology landscape goes, I think that there is a little bit of a daunting feeling that, hey, I'm CTO in this company, but I don't know if I am where I need to be at compared to what other successful companies let's say, for instance, a series A company is doing. And as CTO, am I applying, am I showing up in the way that great CTOs of other series A companies are showing up? And so I would say that's problem number one is, am I operating at the level that I should be that my company is expecting of me? That's a real challenge that CTOs have. And I think level-setting expectations communicating where we should be at is a skill that I think is missing from a lot of people who are in that role. And I think it's because we get to the roles of CTO by being people who rapidly solve problems or speedily deliver on technology. And we start associating speed with being good at our jobs, and I really think that that is wrong; that is just wrong. When you're in an executive role, patience and spending the extra day or the extra week fighting for the extra month, I think, is actually a very important role that the CTO plays in the C-suite. And so if you have an underdeveloped sense of your own leadership style, an underdeveloped sense of your being and your essence and what it is you actually bring to the table, I think you end up just being sort of a knee-jerk tech person that just implements what other people want you to so that you could be valued for what it is that you do. Versus having that solid executive presence inside of a company that really influences and can shape the vision of the organization. VICTORIA: Yeah, I think that's super interesting how common that question is. And I wonder if it gets to sometimes creating a shared understanding between the executive team about the technology and why certain things are important or not important. I wonder if you could talk about any maybe major trends that you see executive teams trying to take advantage of that are either positive or negative. ETIENNE: The thing I've seen the most, which has had the greatest impact on, I think, executive teams, at least from my vantage point, is the desire to adopt some sort of business playbook or a business operating system. I think one of the most popular ones is the EOS model, Entrepreneurs Operating System. Gino Wickman, I think, wrote the book "Traction." And so it's caused a big trend with companies to try and streamline their operations by following the EOS model. And I do think that that might be the wrong solution to the right problem for many companies. What I mean by that is, again, we're talking about blueprints. What works for one company isn't necessarily going to work for the next company. The way you set goals, the way you set your so-called rocks, or the way you set your quarterly goals, or even working by quarter if you think about a quarter, it's such an interesting...it's really a Wall Street concept. It's three months. It's really so arbitrary. And I think that I see C-suites trying to adopt a business operating system that other companies are doing without really the necessary work being done as to, hey, what compels us through our culture, who we are, how we like to do things, what it is that works for us? And I will see some C-suites sort of spin their wheels a little bit on trying to adopt other systems when really all it takes is for them to do their own work to see what is the value stream? What does it look like inside of their company? I actually encourage, and I think I talk about this in this book; in days 60 to 70, I talk about learning to improvise. And I think this is where I look to the CTO to use their spidey senses and their logical deduction skills, their deconstruction skills to observe what is actually happening inside of the C-suite and to facilitate conversations around what is it that people need? How do we improvise on systems that we already have? Or how do we deal with missed expectations? And I do think that the CTO can play a wonderful role inside of the C-suite to facilitate those conversations. But I see inside of C-suites, the role of CTO being relegated to the IT person or just the tech person. And I think that victimization goes both ways. But the C-suite, where the CTO is actually facilitating hard conversations and able to do the decomposition of a complex system or the deconstruction of an often repeated problem or challenge that the company is experiencing, could really push the C-suite into a different track of thinking that could be super beneficial to unblocking some stodgy issues they've been facing. VICTORIA: That makes sense. And it reminds me of trying to adopt agile right when it was first becoming popular and committing so hard to a framework that you don't look at what works for your team [laughs] and works for the specific technology and tools that you have. So it makes sense to me that the CTO could bring an experience like that into applying frameworks to how the business operates. ETIENNE: Absolutely. And I think that's really when dogmatism could be your enemy. And, again, CTO joins a company, knows a certain set of skills in order to accomplish things, dogmatically tries to apply that because they are the so-called expert. And then they fail, or they're unhappy, or there's misunderstanding because we had these high expectations for you. Your interviewing was brilliant, and you said all the right things. But then, when you walked into the organization, your desire for acceptance and delivering value trumps your opportunity to be the new person and be curious about what is actually happening and what is actually going on. This should be so obvious, but when you walk into a C-suite, there are obviously existing relationships between all the different members of the C-suite. And I advocate for being a student of those relationships. Understand the history that exists between the CEO and the CFO. And these could be very great newbie conversations to have with these various members of the C-suite. "Hey, so when did you join the company? Hey, why did you join the company? Hey, wait, which company did you come from? What drew you to this company? Where did you used to live? Why did you move?" I think these are such incredible nodes in a complex relational hierarchy that can give you some very sound ideas as to, oh, well, why does the CEO constantly challenge what the COO is saying? Or why does the COO seem surpassed all the time? You, as CTO you, would do very well. I mean, as any C-suite member, any leader would do well to seek some insight and perception into what is going on for people. VICTORIA: That makes sense, right? If you're going to have influence, you have to kind of understand what are all the connections and energy that's going around in the team? ETIENNE: Absolutely. Mid-Roll Ad: As life moves online, bricks-and-mortar businesses are having to adapt to survive. With over 18 years of experience building reliable web products and services, thoughtbot is the technology partner you can trust. We provide the technical expertise to enable your business to adapt and thrive in a changing environment. We start by understanding what’s important to your customers to help you transition to intuitive digital services your customers will trust. We take the time to understand what makes your business great and work fast yet thoroughly to build, test, and validate ideas, helping you discover new customers. Take your business online with design‑driven digital acceleration. Find out more at tbot.io/acceleration or click the link in the show notes for this episode. VICTORIA: And maybe you can tell me more about 7CTOs and what that community can mean for someone who's growing in this role. ETIENNE: 7CTOs, like I said earlier, I founded it...I almost said 100 days ago. I founded it ten years ago. And it was as I mentioned, the genesis of the story, which is important, is I co-founded a company with two people. I wrote the first lines of code for our product. In fact, I wrote the whole version 1 myself. And as the company grew and as the company grew beyond what it was that the three of us were comfortable with, I noticed that my CEO joined an organization a peer group organization. My COO joined a peer group organization. And I just saw this transformation in them that I really admired. I was actually really envious when they were able to start taking what they've learned from their peer groups and bring them into our company to start operating more efficiently. And so, it was just natural that I would look for something for CTOs, and I couldn't find anything. I actually tried to join sort of more generic business leadership groups like Vestige or EO even. And I found that I wasn't really with my people. I wanted to feel like I was with the geeks who could talk all day about tech and development and probably watch the same movies and read the same books or inspired or laugh at the same jokes. I wanted to find my people who were facing the same problems and challenges that I was, i.e., scaling companies beyond the things that we knew, beyond the things that we were comfortable with. And I wanted to have deep conversations with those people. So I wanted to be able to share my insecurities or the politics that I was facing, or the anger that I was feeling, or not feeling seen or heard. I wanted to have deep, meaningful conversations with my true peers in a regular meeting setup that was confidential and fun. And I couldn't find that. So I decided to host a few meetups. My first meetup was actually in Old Town, San Diego, at my buddy's restaurant. And I hosted the first 10 or 12 CTOs and realized that people had a real need for that kind of interaction. And I then ended up hosting 30 different meetings in three different cities. And everywhere I went, there was the same expression that people wanted what I wanted. And then I tried to host a few more meaningful, smaller conversations and people...quite frankly, it was a disaster. I don't think it was the right container for people to respect each other and have empathy for each other's decisions. And instead, it just became a pissing contest for who made the right decision about what situation. And that's when I realized I'm not going to be able to create a meaningful conversation without some rules. And those rules I put in place, i.e., you must attend the meetings. You need to have some skin in the game. And that's how 7CTOs was born. And to this day, it is a vetted peer group organization. We know we have some skin in the game. There's a membership fee. There's a time commitment. And there is a commitment to yourself to grow, to have empathy, to show up for your people, to be accountable to your people, to learn the stuff that you like to learn about and to learn the stuff that you don't want to learn about. And that is where we are today. So anybody who's listening to this who has a CTO who feels cold and lonely, come join us. VICTORIA: I appreciate the hustle, that many meetups in that many cities. I would have gotten tired. [laughs] Like, that's too much. But it seems like there was a demand, and it created something that's really meaningful for people. ETIENNE: Yes. And I was surprised. So from San Diego, I went to Austin. And then, I also started investing in Portland. And I was really amazed how we were in different cities, but each tech scene had this group of people called CTOs who they knew how to talk about technology, and they knew how to geek out of trends and all that. But they were lacking solely in team composition, budget management, C-suite executive presence, handling disagreements with the CEO, maybe knowing when to leave, how to find new positions, to carefully consider the arc of their own careers, to just manage your LinkedIn page. I mean, it was really shocking in the early 2010s how much of that was going on. I will say I was reluctant to actually start something. You know, 7CTOs is very much a membership organization filled with people. Not the most intuitive move for me. I thought I would be building more and more and more tech companies, SaaS products. I do that as an interim or a fractional CTO now, but I don't have my own startup right now in the tech space. But I love 7CTOs. We have a new CEO. Her name is Beth Rehberg. We have our head of coaching. Her name is Brittany Cotton. And we have about 200-plus companies that have enrolled their CTOs in our organization. And the journey is remarkable, truly a remarkable journey to see how people are just blossoming into the full essence and the full impact that they can have in other companies. VICTORIA: That's wonderful. And I wonder, if you could go back in time and give yourself some advice back when you started it knowing what you know now, what advice would you tell yourself? ETIENNE: I grossly underestimated how many White guys I would be attracting. I think about three or four years into the organization; it took someone else to bring it to my attention that there were no women. There were no underrepresented minorities in this group. And so I think from day one, I would have made that a key focal point for myself to really invest in the diversity of the group. We've come a very long way. Our numbers are growing pretty quickly in terms of women joining us and people from various communities joining us. I think that's actually becoming a hallmark of 7CTOs. And I'm very proud of it today. But, boy, back in the day, I would have made that a key prime directive. VICTORIA: Well, that's a really honest take, and I appreciate you offering that to us. And I think that's an important thing to focus on always going forward. [laughs] But I like that, and now it's become a focus for you and creating that space that, you know, hindsight is 2020. [laughs] Well, great. Is there anything else that you'd like to leave as a takeaway for our listeners? ETIENNE: No. I think, of course, I would love some book purchases. Apparently, the first couple of weeks are vital for any new book. So please go over to Amazon and get "CTO Excellence." I also have a website: ctoexcellence.com. So really, anybody who has an inclination towards leadership in the tech space, I'm super passionate about those people. The opportunity to influence in a creative and confident way is just limitless. And I want to help unearth that for fledgling leaders, existing leaders, some leaders who might feel stuck. Please reach out to me. I'd love to get you connected, either through 7CTOs or even I do some coaching as well. So I consider it my life's mission to expand this ecosystem because so many people are impacted by the way we show up. And there's a great opportunity as CTOs to be transformational in our organizations. And this is what I exist to do. VICTORIA: Well, thank you so much for joining us today. And I really appreciate you sharing what you did, and I enjoyed our conversation. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thank you for listening. See you next time. ANNOUNCER: This podcast is brought to you by thoughtbot, your expert strategy, design, development, and product management partner. We bring digital products from idea to success and teach you how because we care. Learn more at thoughtbot.com.