character navigating a path to becoming a CEO

When I was a little girl, I played “business” at my grandmother’s house. She gave a box of blank payroll checks from a defunct business and heels and fancy clip-on earrings that she wore to work. I stuffed a bunch of blank checks into a purse and strutted down the hall to the back bedroom (y’know, the official boss’s office), where I’d wave my hands around telling everyone to get to work. I was awesome at imaginary business, and I knew I’d make it to the corner office one day, bossing around real, live employees!

Imagine my delight when I recently got the chance to ask real C-suite execs at Atlassian how they climbed the ladder, achieved the success I’ve always dreamed of, and made their way to the highest position available in their field. I was determined to get the secrets for myself, and of course, share ’em with readers as well. Surely, these people carefully crafted every decision, every move, every project, to claw their way to the top.

Spoiler alert: Not a single one of them sought to get to the C-suite. And not a single one actually thinks you should plan to arrive in the C-suite. In fact, most feel uncomfortable with the term… it evokes that same sense of bossy entitlement I showed as an eight year old. So if they didn’t plan to become a CEO, what was the journey like?

“Focus on improving yourself and doing your best work. Focus on the outcome you want to achieve, be mission-driven, not title-driven.” – Sri Viswanath, CTO

Discover what drives you

“As long as I felt like I was building something, I felt like I was moving forward.” – Robert Chatwani, CMO

Atlassian’s Chief Marketing Officer Robert Chatwani laughs remembering how he started selling temporary tattoos to his schoolmates at eight years old. When the principal finally shut him down, he started selling the tattoos on the bus. Building was the path that propelled him. “That’s the one thread that carried me through and lead to a lot of growth opportunities.”

“It was so interesting to see the inside of whatever they were working on.” – Archana Rao, CIO

Understanding the entire system drives Chief Information Officer Archana Rao. When she was young, her dad and her uncle would take apart broken electronics to find the issue and fix it. She sat at the table watching them tinker, fascinated by how all the parts worked together. “They rarely fixed the electronics, we always had to take them to the store afterwards because they’d be missing a screw… but it was so interesting to see the inside of whatever they were working on.”

“I knew I wanted to be ‘successful’, but I didn’t really figure out what that meant until I went to university and discovered this whole world of careers and roles.” – Helen Russell, CPO

Helen Russell, our Chief People Officer, was always looking for the next thing. “I grew up in a really sporty, competitive family, so I was always trying to win. I’d race my brothers in the backyard, or try to shout out the first answer to the trivia game shows. Even on the merry-go-round at the fair, I was running from horse to horse with each rotation, I couldn’t stand still waving at my mom! Where I grew up, if you were sporty and smart, you became a physical education teacher, so I always thought I’d become a teacher. I knew I wanted to be ‘successful’, but I didn’t really figure out what that meant until I went to university and discovered this whole world of careers and roles.”

Define what success looks like for you

“When you’re thinking about your career, you have to understand what you want, how you work, and what you’re good at.” – Sri Viswanath, CTO

“When I first became a manager, it was really hard, especially coming from engineering. I used to spend all day building a product, and now I’m in all these meetings. I’d get home and think, ‘What the heck did I do all day?’ And once you’re leading an organization, things like bringing new people in and helping your employees grow are much more important than individually contributing to the build-out of a feature,” Sri says as we walk around our Mountain View campus. He also talks about knowing what kind of leader you are. “Some people are meant to take the company from 0 to 1, which means they’re great in early-stage start-ups and building something from scratch. But they might not be the right leader to help the scale.”

How to use your impostor syndrome as an asset

“We all feel like we have imposter syndrome and that we’re under-equipped to take on something new.” – Jay Simons, President

Jay finds it energizing to grow and develop the people in his organization. “When I’ve been stretched into a bigger roles, I’ve always had someone saying, ‘You might not be quite ready for this, but we’re going to partner with you to help you succeed.’ I get to pay that forward now, and I love how we succeed as a team.”

“Don’t start with the opportunities in front of you or the expectations other have of you. Start with you.” – Robert Chatwani, CMO

Go where you can make the most difference

“Find the gaps and fill them, whether it’s your job or not. That’s how you create success.” – Archana Rao, CIO

“I didn’t want the easy stuff, I wanted to move mountains. I don’t care what you call me, I want to give and get more value, have more impact, and continually grow. I realized that if I’m not learning, I’m doing something wrong.” Archana tells me that she had a light bulb moment after 19 years at Cisco. She’d changed roles and teams many times over her tenure, but she’d underestimated the value of changing companies. “Cisco was good to me, and I did a lot of great things there, but I realized that I was comfortable. I knew that I needed a big change to keep thriving and keep my skills sharp.” Archana had one of the most intense years of her career when she made the leap to her next role at Symantec: standing up all of IT when the company decided to separate a business unit into its own organization. “Everyone said it was impossible, but I’m a naturally optimistic person. It took all of my energy to corral this skeptical team, but some things are doable when you think they’re not. That project made me feel free to do anything.”

“Instead of leaving the amazing work, I was going to the place where I could make the most impact.” – Robert Chatwani, CMO

The new approach to work life balance

“I had what I thought was the dream job at eBay. I was reporting to the CEO, running the company’s social impact ventures around fundraising and empowering non-profits,” says Robert. I built the team and the strategy, and we were working so well together, making a big impact, and I felt emotionally connected to the work and the people. And suddenly, I was asked to move over to the marketing organization to run part of it and take over this massive shift. I only had a week to make the decision, and I called one of my mentors for advice. I asked, ‘How can I abandon this team that I built? How can I leave this amazing work?’ His reply really hit me. He asked one question: If the organization is asking you for your help, what message would it send if you didn’t take it? That helped re-frame it not as abandoning the team, but going where I was most needed. Instead of leaving the amazing work, I was going to the place where I could make the most impact. That was huge for me, because I wanted to go where I was needed most, and it turned out to be a great choice.”

“It taught me that to be successful, I needed to find the most valuable skill in each discipline and build competency in that area.” – Helen Russell, CPO

Helen talks about the unexpected opportunity to become head of HR. “I was working in recruiting and I was actually hunting for a Head of HR for a company with offices across Europe. It turns out that my client didn’t want any of the final three candidates, they wanted me, specifically because I had broad experience and they knew they wanted to build something different. Labor laws in Europe are unique and complex, and to succeed in HR leadership, you have to be extremely competent in labor and employment law. So I attended every meet-the-attorneys session, every webinar about how things work in Germany or France, read every paper on the latest updates to employment rules in each country. I had to work toward very specific milestones to build my skills and knowledge and credibility when I took on that role.”

Keep learning and questioning

“Yes, you have to go deep in your profession, but that broader perspective is also important.” – Sri Viswanath, CTO

“When I became a manager, I kept asking, ‘How do I become a better manager? How do I work better with teams across the company? What does finance do? How do I partner with the recruiting team?’ I read a lot of books, but getting my MBA helped me make space to learn about the business and broaden my perspective. Yes, you have to go deep in your profession, but that broader perspective is also important. And I was able to make connections across a number of industries and companies, so now I have network to help me with advice and problem-solving,” Sri says.

“I was loosely qualified, but I was willing to work hard and learn.” – Jay Simons, President

Jay’s advice is to keep working hard, and become known as a person who can jump in and learn new things. “I was loosely qualified, but I was willing to work hard and learn. This meant that when I was in the right place at the right time, people were willing to take a chance on me. And I was willing to take the risk when the opportunity came along.”

“I’ve learned what people valued from me and I try to do more of that.” – Archana Rao, CIO

Some learning comes through feedback. “People have a perception of who you are that will never perfectly match what you think of yourself. You’ll be very surprised at what people value you for and what they don’t value you for. It’s hard to get this kind of feedback in a formal performance review, so always ask for feedback after a big project. What worked well, and how did I help you most? How could I have improved my contribution? I’ve learned what people valued from me and I try to do more of that. And what your peers think of you is just as important as what your manager thinks.”

The best careers are discovered, not planned

“Be known as a person who is curious, a good communicator, and a good listener. Build trust and credibility and the opportunities will come.” – Jay Simons, President

Jay reminds me to stay open to new things. “I try to learn and soak up as much as I can. I tell my kids to try a lot of different things. You’ll be great at some things, and you’ll like a lot of things. But you won’t know what you’re best at and what really plucks your strings until you’ve been exposed to many options. ” Jay’s string-plucking analogy is apt, considering he spent his early years as a traveling piano player before he found a leader and a company that inspired him to join the corporate world.

“I started getting all these emails from recruiters about CIO jobs when I was working on a massive IT integration project. That’s when I realized that my background was actually perfect for the CIO role.” – Archana Rao, CIO

Archana remembers the first time she moved out of engineering. “I really wanted to understand how all the parts of the business worked, and there was an opening with the Mergers & Acquisitions team. I’d never done M&A, but I went in and I made my sales pitch to the hiring manager about why I was the best fit. And afterwards I wondered if I knew what I was getting myself into, and of course, I didn’t. But moving to that team gave me exposure into what to look for when buying a company, all the ins and outs of integrating a new team into an existing company, and how you handle bringing two sets of technology together. That knowledge was instrumental in helping me plan and execute standing up an entirely new organization at Symantec a few years later.”

“Get comfortable in the gray. Most people are in such a rush to make everything black and white. But the gray is where the possibilities lie. Learn to live in that space and thrive in that space.” – Archana Rao, CIO

The path is hard and exciting and uncomfortable and victorious. You know, I think I’ll sit back for a bit and enjoy whatever comes next.

The unexpected path to the c-suite...