When you look back on your life, it's the struggles which have made you who you are today. For one thing, having the grit to persevere through challenges makes a person stronger. Here's what more than a dozen executives say they learned from the obstacles they encountered on their career paths.
1. Turn fear into an advantage.
"As a marketing executive, presentations and public speaking come with the territory, but that doesn't mean it's something I was always comfortable doing. I knew in order to succeed though, that I'd not only have to overcome this fear, but turn it into an advantage. And it all had to do with confidence. I began to use several tactics to help myself feel more confident speaking publicly, and I still use them each time I have to present. I over-prepare, rehearsing my presentation again and again. I don't always get an audience for practicing, but when I do I always take it--nothing beats third-party feedback. The practice breeds confidence, and when I feel mastery, presentations turn into simple conversations. Second, I'm a big believer that physical confidence connects to mental confidence. I've found getting into power poses, standing tall, taking deep breaths, and thinking positively makes for a better, more captivating presentation."
--Scott Holden, CMO of ThoughtSpot, recently named a Visionary in the Gartner Magic Quadrant for analytics and business intelligence
2. Don't get defensive and emotional with aggressive people at work.
"As a female leader, especially in the technology industry, there comes a point in your career where you are constantly dealing with overly aggressive and dominant, male leaders. Instead of getting defensive when I hear statements I don't agree with from these leaders, I have learned to slow down, ask questions and stay focused. When facing a conflict, I ask the CEO I'm working with to tell me more. In one instance, I quickly deflated a CEO's frustration by pointing out what he was specifically upset about: wanting to see more photographs and less color in a presentation. Typically, you'll find that it is probably one small thing that sets them off. Instead of getting defensive and emotional, it's more beneficial to find common ground with challenging people you work with and move forward. It creates a more cohesive work environment for everyone."
--Jen Grant, CMO of data analytics company Looker which has received $180 million in funding from Google Capital G, Redpoint, First Round Capital and Kleiner
3. Show empathy even when you have to make tough decisions.
"As a young and inexperienced executive... I was running a 60-person bootstrapped, digital agency that had never taken any outside money. We had a phenomenal run in the late '90s and hit the proverbial brick wall when the dot com implosion happened in the early 2000s. Practically overnight we lost 40 percent of our revenue and our only chance for survival was to do steep headcount cuts. At the time I was a 31-year old first-time executive with zero experience dealing with this type of crisis and I had to navigate through financial peril along with the agonizing decision to let go of 40 people... all at once. Ultimately, I made the cuts and although I was terrified of going through the process, I sucked it up and worked hard to be transparent, open and honest. I made sure I personally met with every single person to deliver the news and explain why we had to make this tough choice to let them go. Through this process I learned the importance of making tough decisions and the importance of treating people with dignity, respect and honesty even when you have to deliver bad news. By and large the folks that were let go, while sad, were appreciative of the way in which we conducted the process. On the positive side, the company rebounded and we were eventually acquired."
--Toby Gabriner, CEO of AdRoll Group, a growth platform company helping businesses compete online to grow revenue, with over 500 employees in six offices around the world
4. Rely on others instead of trying to do everything yourself.
"This is especially true as a venture investor. For example, when I sit on a board of directors, I have no actual control over the decisions the company makes. The best I can do is try to influence a CEO and other executives to consider the advice I give. This is a transition most professionals have to make as they move from being an individual contributor to a manager and eventually to an executive. The shift can be particularly challenging because self-reliant behavior is often richly rewarded early on in one's career, while leaning on others is not. However, I've found as one becomes more senior, those who are most successful find a way to think outside of themselves and gain leverage by acting not only on their own but also via teams. A nice benefit to this approach is that it's much more rewarding to work with others rather than feeling that you have to do everything yourself."
--Kevin Spain, general partner of Emergence Capital, which was recently named National Venture Capital Association's "Venture Capital Firm of the Year"
5. Commit to regular self-check-ins to track progress and course correct.
"My greatest professional challenge was making the leap from an accountant to chief information security officer (CISO). In all, it was a 20-year journey that required a consistent approach to nurturing my passions and investing in myself. In addition to constant reading, I gained the relevant experience I needed by building personal server farms, writing code, learning to think like a hacker, obtaining certifications, and developing a passion for data science. To make sure I was heading in the right direction, I took stock of my personal and professional achievements every six months. This allowed me to focus my plan for the next six months and how I would overcome the obstacles or challenges. I discovered through this process that it wasn't the table-stakes skillsets required of most CISOs today that drove my success, but inquisitiveness, dedication, and a passion for learning that ultimately got me here."
--Grant Bourzikas, CISO and VP of Labs Operations at cybersecurity company McAfee which has more than 92,650 corporate customers worldwide and monitors 400 million consumer endpoints
6. Confront your limitations and figure out how to rise above them.
"I was just starting out at a company when I was faced with a potential third-party breach that no one could ever plan for. While I am normally quite calculated in my day-to-day, there was no time for second guessing even though the stakes were extremely high. I also needed to confront my own limitations in this situation, which re-enforced how critical leadership is during high-pressure situations. Teamwork, communication and trust played a critical role in getting us through."
--Tom Pageler, chief revenue office and chief information security officer at Neustar (a neutral provider of real-time information services and security solutions), who also served as a special agent within the U.S. Secret Service where he established the San Francisco Electronic Crimes Task Force
7. Small details can have a big impact on long-term financials.
"Before joining Mya Systems, I was a founding team member for a behavioral analytics platform provider that catered to small to medium financial institutions. For all of its successes, the platform initially lacked features required to deploy customers at scale. Growth surged thanks to regulation that advocated our fraud prevention approach. However, the strain on our delivery teams resulted in a revenue backlog that impacted cash and customer satisfaction. After right-sizing the professional services and customer support teams, I shifted my attention to platform enhancements that would improve deployment speed. In partnership with product management, engineering and professional services we were able to eliminate large segments of the backlog and accelerate our time to revenue while maintaining a flat headcount within services. I learned several lessons but two stood out. First, teams that deploy your solutions should be considered first-order actors as it pertains to achieving your revenue goals. Next, small technical design details can have a dramatic impact on long-term financials. I now make it a point to form strong collaborative partnerships with product management and engineering so that we can design and implement platform features that allow delivery at scale while still providing world-class customer service."
--Jay Murphy, VP of customer success for Mya Systems, creator of conversational AI-recruiter, Mya, and recently named to CB Insight's AI 100
8. Focus on understanding the details.
"The greatest professional challenge I have experienced took place during a transitional time for FastSpring, as I led the company through the process of private equity funding. It was important to me that I honored the legacy of the company while also preparing it for a new era of innovation and growth. To do so, I had to focus on observing and learning the details of the culture and business that had been built over the past ten years. Having a deep understanding of both, prior to making any major strategic changes, was critical to my success."
--Chris Lueck, CEO of FastSpring, a SaaS company that powers the digital economy for thousands of businesses around the world
9. Transcend the boxes others place you in.
"One of my greatest professional challenges has consistently been to break out of the boxes people naturally want to place you in. As an example, everyone wants to put you in a box in terms of the type of marketer you are--you're either consumer or enterprise--but I've found these skills to be complementary. At the end of the day we are all human and using empathy and great storytelling in marketing is universal regardless of who you are selling to. Ultimately to make the transition from consumer marketing to enterprise marketing, I used my consumer expertise as an asset, particularly in crafting a story that resonates more broadly and deeply. And to ensure my transition would be successful, I surrounded myself early on with a trusted circle of veteran enterprise marketers to ensure I had the appropriate context and understanding of the uniqueness in selling to the enterprise. A part of your challenge as an executive is to define who you are to the market and use the unique skills you bring to bear as assets, versus having someone else put a label on you."
--Kristen Alexander, CMO of Certain, a provider of enterprise event automation software to companies including Microsoft, Oracle, CA Technologies, and Disney
10. Let go.
"When you build a company, it is your baby. And when you're just getting started, you do everything for the company. You shape the vision, build the product, execute on sales and marketing, run financials, build pitch decks, wash dishes--everything. To try to succeed, you attempt to do your best with everything even if it means 100 hours a week. It was very hard for me to let go of attending every important meeting, joining each product meeting. But I overcame the challenge by hiring people who were way smarter and better than me at their piece of the business, and then trusting their expertise and intuition. By letting go of more things and assigning those things to people who were infinitely more capable, I was able to focus on the next big thing and get out of my team's way while they build a sustainable business making everybody faster and more efficient."
--Jeremy Sicklick, cofounder and CEO of HouseCanary, a data analytics real estate platform forecasting home-price valuations and market trends for 3 million residential blocks, 18,000 zip codes, and 381 U.S. metropolitan areas
11. The right people turn challenges into success.
"When I bought NetWitness out of the intelligence community I was faced with the challenge of taking government-created technology and converting it into a commercial success. It's something that is rarely done because of the incompatibility problems and solutions that exist between commercial and government markets. The task was daunting. Fortunately, I had a great team of very committed, bright people and together we were able to create a market that drove the company to success. Ultimately, my biggest challenge paved the way to my biggest professional success."
--Nick Lantuh, CEO of Fidelis Cybersecurity, a provider of automated detection and response, used by dozens of household name enterprises
12. There is no substitute for immediate communication.
"Transitioning from a B2C to B2B company required a level of urgency that I previously had not expected. We were developing a complex product for a key partner on a tight timeline when we hit a snag in development. The partner's PM told me 'if the deadline slips we have to have all the features' while the partner's marketing manager told me 'we can compromise on the features, but we have to make deadline.' I realized we needed to get everyone in the room immediately. I called our partner's VP and I flew down the next day. While in the same room, I communicated the risks and tradeoffs and collectively, we decided to try to hit the deadline and keep the feature set but accept the possibility of failure. The product shipped with zero days to spare. The key was getting on that plane ASAP. At critical moments there's no substitute for meeting face-to-face, and no time for miscommunication."
--Nick Kohut, CEO of Dash Robotics which makes turning legged robots featured in big box retail stores including Target, Toys R Us, Best Buy and Barnes and Noble
13. Surround yourself with believers in the solution, not the technology.
"Naysayers can be just as bad as yes men. Neither provide much value. But rebuffing naysayers is not a one-time challenge--it happens continually. Experience and track records are great, but just because you were right before, doesn't mean you're right now. Measured self-doubt is healthy, but how do you know if you're crazy right or just crazy like the naysayers think? Surround yourself with believers in the solution, not the technology. Not blind zealots, just believers in solving Problem X. This helps maintain energy rather than having to fight naysayers on a daily basis. Educate more believers by painting a picture of the future. Don't assume everyone has perfect foresight or your imagination. Get early wins with validation ASAP. If you're not getting it, adapt quickly. And of course, deliver on promises. Nothing quells naysayers like delivering on your vision."
--Jeff Slosar, cofounder of NextWave Ventures (nextwave.vc), a seed to early stage venture capital firm focused on commercializing university research and advanced technologies with experience growing technology companies from zero revenue to profitable private market exits in under five years
14. Getting personal is crucial to compete in a crowded market.
"Establishing tech21 in the U.S. represented a huge challenge, with the phone case market incredibly crowded... Market understanding had to be at the heart of our plan, and we invested heavily here. Tech21 established two U.S. offices in San Jose and Austin to have subject matter experts across all key functions. Our business intelligence systems track performance, all the way through to store level, and we utilize additional market research to ensure we can identify trends and react to them quickly so our product roadmap is always on point. Most importantly we spend a huge amount of time with our U.S. customers. We have dedicated resources working daily with each retail partner alongside a field training team in stores. I also spend 50 percent of my time travelling to, and across, the U.S. This enables me to maintain a high level of local engagement and a strong personal understanding of the market."
--John Doughty, CEO of tech21, a U.K. company which has grown to become the number two manufacturer of smartphone cases in the U.S.
15. Timing is key.
"Even with the best ideas and with excellent execution, you can be right but just too early, or spot-on but too late. I saw this during my years at Microsoft, I see it at the startups on whose boards I sit, and I see it first-hand at Donuts. Here at Donuts, our challenge is not what to do: we need to innovate to drive more uses for our domains, and we need to market effectively, to drive more awareness. Our challenge is when to do these things, and how much to invest."
--Bruce Jaffe, president and CEO of Donuts Inc., offering digital online identity solutions and recently named number one in the Deloitte Fast 500
16. Keep your eyes on the prize.
"While there is always a lot of excitement when launching a new project or business it's easy get caught up in the moment and forget about the ultimate goal and what lies ahead. Set expectations and don't oversell what's happening because there will be moments when things won't go as planned. This is normal. But as a leader, it's your responsibility to keep your eye on that prize while others might get caught up in the commotion. The road to victory is filled with tons of unexpected detours, and navigating it requires precise focus. "
--Taj Manku, cofounder and CEO of Cognitive Systems (creators of the patented WiFi Motion technology and Aura Home) who also has founded several companies including Sirific Wireless, which merged with Icera and then sold to Nvidia for just under half a billion dollars
17. Build high-performing teams.
"The three major lessons I've learned along the way include: First, put the right people in the right seats. It sounds cliché but I often see people in product marketing with better skill sets for business development, or back-end technical people better suited to work on front-end user interface. Keeping people in the wrong roles lowers their performance and typically job satisfaction. Second, high-performing teams are diverse teams. I fell into the common early manager mistake of hiring people like me and quickly learned that team performance increased as I brought in diverse skill sets and perspectives. And third, attitude matters. Smart, talented employees with bad attitudes always lower team performance. It's often painful to move perceived stars off the team, but I've always regretted not doing it sooner."
--Ashley Still, vice president and general manager for Document Cloud and Creative Cloud for enterprise at Adobe, who helped lead the transition of Adobe's business and products from desktop software to SaaS, driving record-breaking business growth
18. Be honest with yourself and everyone else.
"This advice from my late grandfather has proved invaluable when faced with difficult choices. When I was a product line manager at Macromedia, we were going through a major inflection when, in the mid-90s, the internet was fundamentally changing the market around us. We had a new CEO come in and the first thing he did was ask the product line managers to assess, in two weeks, if we could each build a $100 million-a-year product line in three years. At the time we were at $10 million and the next closest competitor was at $20 million. My engineering lead and I got to work and in two weeks were brought before the executive staff with our entire engineering team in attendance and asked the same simple question. We laid out our analysis of the market and our product plan and the determination that we'd make no more than $25 million at year in three years. I was then asked another simple question, 'If you were me, what would you do?' I simply pointed to the engineering team and suggested that they get deployed to other projects that can meet the goal. I was issued a 'thank you' and the meeting ended. The following week, the company announced that it was going to cut 10 percent of the workforce and I was sure that I was out of a job as I essentially just fired myself. When the actual day of the lay-offs occurred, I was brought into a meeting and asked to join a new business unit focused on the enterprise market to which I accepted readily. It was a sequence of events that ended up changing my life forever in a very positive way. Heeding that advice was the best judgment that I had exercised under duress and I pass it on readily today."
--Rix Kramlich, CEO and director at self-publishing platform Blurb, who has six startup exits to his credit and has held senior management roles in public companies such as Macromedia, i2 Technologies, and ABB
19. Sometimes the tough choices are the best.
"I was running my own consulting company, supporting upwards of twenty clients and happy being my own boss. But Kathryn Petralia, one of my friends, a client and a cofounder of Kabbage, presented a compelling opportunity that would force me to stop building my own company, and instead help build something unique with Kabbage. I was convinced that--even though a difficult choice--foregoing my entrepreneurial pursuit to work again for someone else's company was the right decision. It was a difficult choice, but it has since proven to be a great decision."
--Amy Zimmerman, head of people operations for Kabbage, ranked one of the Best Places to Work by GlassDoor in 2017