C-suite career advice: Evan Kaplan, InfluxData – IDG Connect

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IDG Connect |
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Name: Evan Kaplan
Company: InfluxData
Job Title: CEO
Location: Los Altos, CA
Evan Kaplan is a passionate entrepreneur and technology leader with nearly twenty-five years of experience in the CEO role. Kaplan’s career spans from creating startups in his own garage to leading NASDAQ-listed companies generating nearly $200m in annual revenue. Prior to InfluxData, Kaplan served as Executive in Residence at Trinity Ventures, and President and CEO at iPass Corporation (the leader in Global Wi-Fi connectivity), and Founder, Chairman, and CEO at Aventail Corporation (the pioneer of SSL VPNs, now part of the Dell Corporation).
What was the most valuable piece of career advice that you received? That as a CEO, I always will be selling something. I like to think of it more as “enrolling” as people don’t want to be sold – they want to be enrolled. But at some basic level, it is in fact selling – selling your ideas, your vision, your opportunity, and your perspective.
CEOs have multiple bosses – their stakeholders, their customers, their investors and their employees. So I’m always selling to one of these groups. I used to think I would never get a job in traditional sales, but now selling is actually what I do for a good portion of my day.  
I try to approach the process by cultivating empathy for where others are coming from, trying to understand what they’re doing in order to engage with them and enroll them in whatever it is that makes sense. This is a constant process; it never stops. It’s all a part of the job, and as a CEO, if you’re not tired of the sound of your own voice saying the same things over and over again, you’re probably doing something wrong.
What was the worst piece of business advice that you received? I feel the argument against micromanagers isn’t nuanced enough. People tell you not to micromanage, so a common piece of advice is to not become a micromanager. My counter to that – and why I think outright dismissing micromanaging is bad advice – is as CEO, you need to jump into the details and identify the changes you expect.
I tell my teams that I reserve the right to micromanage any piece of the business that has significant leverage. I don’t feel the need to do this very often, but I do reserve that right. I wouldn’t consider myself a micromanager, but I tell every employee who works for me that I’ll get involved in projects that have high leverage for the business.
What advice would you give to someone starting their career in IT/tech? Indulge your curiosity and lean into things that are fundamentally interesting for you. It doesn’t have to last forever, but you can explore it as you go deeper and deeper in tech. I’ve found that when you indulge your curiosity and follow it, that’s where you’ll be the most creative and have the most energy. It’s also where you are likely to be most fulfilled.
Did you always want to work in IT/tech? No, but it became pretty natural to me. My undergrad degree is in environmental science – I really enjoy teaching, and I am a very curious person by nature. That curiosity brought me to technology since I love the space and I like trying to understand highly technical concepts. One thing that has turned out to serve me well is that I’m more of a conceptual understander of things, rather than a craftsman. On the other hand, our Founder and CTO Paul Dix is a craftsman and I have a strong appreciation for that skill set so he and I work well together. He’s one of many people in our industry who has gone deep into coding and software architecture and understands how to do this work well while taking an aesthetic view of it. I really admire people with that ability. I’m much more of a conceptual thinker, but that balance between Paul and myself has served us well.
What was your first job in IT/tech? My first job was in aerospace – I worked as a program manager for flight computers at an aerospace electronics firm. I was passionate about it and I really liked it since it allowed me to work on very different and interesting things, including the V-22 tiltrotor helicopter, the F-117, and the Boeing 747-400. My background isn’t technical, but it introduced me to highly technical concepts and allowed me to develop a passion for them. And because a lot of this work was project-oriented, every couple of years I had the opportunity to take time off and go on different climbing expeditions around the world. 
What are some common misconceptions about working in IT/tech? There’s a misconception that you need to come to it with a programming or coding background, or even a deeply technical electrical engineering background. Most of the things in IT and tech are conceptually understandable and explainable, in essence, a broad overview of how systems work. That means you can teach yourself almost everything that’s required. Most may think you need a technical degree to be in these fields, but in many cases, you don’t – but you do, however, need to be interested in learning.
At InfluxData, we don’t require our hires to have a Bachelor’s degree. I don’t think it should be a requirement; having strong experience should be the requirement. Having a degree helps as a qualifier for people coming out of school, and it’s certainly a point of credibility, but there are a lot of other ways to gain experience without a formal college degree. We’ve hired people out of coding school, and we’ve hired people without technical degrees. I’ve also hired people right out of high school.
What tips would you give to someone aiming for a c-level position? Leading with empathy is so important, and it’s a growing trend we’re discussing more amid the pandemic. For example, new parents who need to take care of their newborns while also balancing work. Or working parents who have had a ton to balance and figure out during the pandemic.
I will say I haven’t always been the best at leading in empathy. Earlier in my career, I didn’t have a family. I was single, and I had 11 people working out of my house. We were working intense hours, but killing it. It was incredibly rewarding work, but it was a very different chapter of my life. As I’ve gotten older and been in multiple leadership roles, I’ve realised that leading with empathy should start to come naturally if you’re paying attention.
What are your career ambitions and have you reached them yet? I don’t think about the world that way. If I’ve achieved something I don’t then think I’ve “arrived”; I think I’m in the constant process of arriving. My view is that I’m either growing or dying, much like any system. If I’m not learning something new and not challenged and not interested, then I lose the threat. But if I’m growing, I don’t think about it as I’ve “arrived” here.
I’ve run a public company. I’ve run private companies. I’ve worked on challenging projects. Each of those experiences was a career ambition of mine, but I don’t necessarily view where I am today as having arrived anywhere. I view myself as a lifelong learner. I want to be constantly challenged. To the degree that ambition plays a role, I would say my ambition is to create situations where I have the privilege to work with high-quality people who teach me new things and challenge me.
Do you have a good work-life balance in your current role? As a CEO, I don’t really believe in the work-life balance concept. I believe in taking care of myself and my family. That’s the priority, so I organise my life in that way. I don’t necessarily think of it as “balance.”
Being CEO means you never put the ball down. You’re always carrying the ball. On weekends, nights, on vacation, you’re always thinking about the business, the quarter, the product, etc. It’s relentless. This is not unique to me – it’s an experience I share with other CEOs and leaders that I talk to.
Overall, I think COVID and being fully remote have given me more time. It’s saved me a couple of hours each day in terms of transitions and commuting, and I’ve made good use of that time. I definitely think I’m working more now, but I also have more free time.
What, if anything, would you change about the route your career path has taken? I don’t have any regrets about the career path I’ve taken. It’s been an amazing journey. I do look back and think about decisions I could have made differently or better, but I wouldn’t trade any of my experiences for something different. I also started my career relatively late — I didn’t get serious about my career until my late 20s. After graduating from college, I spent several years skiing and climbing around the world. Those experiences influenced how I think about and approach work in many ways, and gave me an appreciation for people’s experiences as opposed to their credentials. I really want to understand people’s journeys. I have a deep interest in how people arrived at where they are at this moment and what they want to create in their lives.
Which would you recommend: A coding bootcamp or a computer science degree? If everything were neutral, I recommend the computer science degree because it means you embrace something deeply and you got really into it. I know different life circumstances present different challenges. Getting a CS degree allows you to go so much deeper into the subject matter. I really appreciate people who try to understand the theory of operation and how things around them work, as opposed to learning technical skills. And sometimes coding camps only focus on individual technical skills or concepts at a high level. On the flip side, with a computer science degree, you learn the theory of operation, the way all languages work, the way computers fundamentally work, the way they’re likely to evolve. That broad view can certainly be learned on your own, but a CS degree provides a good framework for it.
How important are specific certifications? It’s not super important to me. In the context of representing an individual’s experience, they’re interesting, but I care more about the real-world experiences and tangible outcomes that people developed in other ways.
Generally speaking, I care much more about a person’s actual experience. For example, just because you’re certified in a specific programming language doesn’t mean you know all of the nuances necessary to be effective in a particular role or position. I do understand their value, but to me, real-world experience tops certifications any day.
What are the three skills or abilities you look for in prospective candidates? First, I look for self-awareness. Do they know who they are in the world? Do they have a firm sense of identity? Do they know what’s important to them and what they are passionate about? Next, I look at their resilience. I try to understand their personal journey to see what they went through in their lives that may have been difficult and get a sense of their perspective and how they worked through it. And finally, I look for sheer competency. Are they productive? Can they show me how they’ve been productive? Can they show me they can work? Looking at candidates through those three lenses can tell you a lot about how they can contribute and lead within your business.
What would put you off a candidate? Lack of humility, arrogance, entitlement and inauthenticity. You can see those traits pretty quickly in candidates. At InfluxData, we have core values that include things such as valuing each other, getting stuff done, believing humility drives learning and embracing failure when things don’t go as planned. If it’s clear a candidate won’t adapt to these values, it’s a safe bet they won’t be a good fit for our team culture.
What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? A significant part of evaluating a candidate involves the questions they ask; in many ways, that’s more revealing than how they answer questions. When you turn the microphone around, what do they want to know? What do they want to dig into? That tells me how their brain works and how they think. If they ask me an open-ended question that forces me to really be reflective, that’s powerful. So the lesson is to prepare a short list of thoughtful questions to ask.
Ironically, one mistake I see sometimes is people not listening well. They’re ready to repeat the things that they need to do to sell themselves, which is normal and understandable. But not listening to how each question is asked or rushing to say something without formulating a thoughtful response can hurt you in an interview.
Do you think it is better to have technical or business skills – or a mix of both? Both are incredibly valuable. And people should feel pigeonholed by one or the other – you can come from either background and transition to the other one if you’re passionate about it. I believe it’s much more important to have curiosity than a technical or business background. One of the things I like to ask people during interviews is, “What do you do to indulge your curiosity? What are your hobbies? How do you explore? How deep do you go?” The answers to these questions can reveal a lot about a person. The more curious a person is, the more likely they will be able to grow their knowledge and technical or business skills over time.
Copyright © 2023 IDG Communications, Inc.

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