I recently went one-on-one with Chris Caren, CEO of Turnitin.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?

Chris: As a kid, my dad was an early computer hobbyist, so I became interested in programming before personal computers existed. I loved science and engineering in school, which paved the way to college and internships. That is where I discovered I wanted to be in business, working with people (versus pure science) - because making a difference in the human experience matters as much as the technology. From there, I fell in love with the power of software - quickly transforming ideas into beneficial and transformative products, and if you get it right, you can make a global impact in ways that advance humanity.

I’ve made more mistakes of judgment and focus than I could list, but with mistakes comes wisdom and learned resilience. These experiences have made me better and wiser because I focused and reflected on the learnings from these failures. As a leader, I make it a point to share these stories with my teams so they can learn from them and realize it’s okay to admit mistakes. Learning and growth can be a gift.

If I were to summarize the most consistent theme of my career mistakes as a leader, it would be: ‘not objectively focusing on product-market fit enough.’ 

It’s easy to be blinded into a bubble of optimism around early successes. The gratification of scaling all parts of a business can distract a leader from the maniacal focus they need to have on building a great product that, first and foremost, fits the market need deeply as a ‘must have’. Constantly tracking and measuring your ‘must have’ value prop will bring customers today and secure them long-term, and the ‘nice to haves’ help ensure customer loyalty.

Adam: In your experience, what are the key steps to growing and scaling your business?

Chris: Define clearly where your ‘right to win’ is by constantly reassessing your short and long-term market strategies – and stay focused there. So many companies have early success and then extend into areas where their right to win is much diminished ... and that rarely goes well. It is essential to maximize product-market fit continually. You must also have an economic model that is profitable at the customer level and then scale up so that you can self-fund growth as soon as possible. A good principle [often attributed to Warren Buffet] is to be patient for revenues but hungry for profitability.

Leaders must be clear on strategy and priorities:

• Avoid getting entangled in day-to-day operations when scaling; count on capable managers to do this. 

• CEO failure often results from becoming too mired in operating and losing sight of the big picture – their market and new dynamics.

A CEO should seek to surround themselves with leaders who are a super strong cultural fit and who can each scale to a job scope 2x where they are now. I need to emphasize the importance of cultural fit because from my experience, this is even more important than raw talent level.

As you scale up, internal senior-level promotions are great when it’s clear that person is ready … but if it is not apparent, you need to weigh the pros and cons of external hiring vs. internal development. Many leaders fail when promoted to jobs beyond their current abilities. If the leader is truly coachable with 2x potential, and you can make the investments in coaching and development, internal development is a viable route. If not, you need to go outside.

It is also essential with scaling to keep the bar for who you bring in. If you are lucky enough to have a top leadership team of all "A’s," work hard not to hire "B-players." I've rarely seen a "B" manager hire "A-players." If you start lowering the bar, you will soon see your company's grade point average drop quickly, and that is a one-way door.

The actual test of leadership comes into play when navigating the unknowns and unplanned and responding thoughtfully. It's much better for a CEO or top leader to make few, very impactful or high-quality decisions daily. I plan and focus my time to plan for high-level thinking, and know the importance of managing my energy when I am out of gas. I build slack into my calendar – having free hours held in advance – to handle the unexpected without sacrificing quality of decision-making or work-life balance. You can't be your best leader if you aren't at your best.

• Senior leaders cannot afford to hit a wall; strategic planning of your time and energy is crucial.

• Planning calendars for both expected and unexpected issues become more critical as one moves up the hierarchy.

• As an example – the CEO of J.P. Morgan, Jamie Dimon, said he spends about 50-60 percent of his time learning [reading and thinking]. I 100 percent agree with that for CEO success criteria.

• Increasing role responsibility requires meticulous planning to avoid burnout and maintain energy levels. 

• Know when to say no with your time. Protect an hour at the end of each week to reflect on where you spent your time. Was it the best use at the right altitude? Were you in the weeds or contemplating your five-year strategic plan and competitive landscape? Use this to adjust where your time and energy goes the following week.

Finally, and very importantly, focus on a culture where the company feels as small as possible -- flat in hierarchy, high in empowerment and accountability, and always trying to improve internal communications. High team engagement, paired with rewarding work, are essential to success.

Adam: What do you believe are the defining qualities of an effective leader?

Chris: Effective leaders have clarity of goals, the strategy to get there, and can clearly explain the thinking behind them. I also feel strongly that leaders need to role model optimism and resilience. Everyone is looking at you to form their view of the company's outlook.

Being transparent and authentic is crucial; it extends trust and inspires your team. Anything else shortens runways and brews uninspired, mistrusting teams and confusion. Admitting mistakes and learnings as a CEO is also a powerful way to foster trust with your teams.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

Chris: Learn from osmosis. Far and away, the best way to advance leadership skills is to work for and with people with better leadership and management skills than you have. From there, push your boundaries and take on new challenges to accelerate your leadership growth. If you are not taking risks in your comfort zone, you are not maximizing your growth potential. I have asked many retired CEOs about risk-taking, and almost all wish they had taken more risks in their career.

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

Chris: 

• Focus most of your time on the short list of high-impact decisions and projections -- 2x more than you think.

• Scale your impact by hiring great leaders who strongly fit your desired culture. Don’t settle for even B+ players to close a painful gap quickly.  

• Find enough time each week to step away from operations and think at a high, strategic level -- about your market, customers, and trends. I’ve seen many CEOs fail over time for losing sight of the big picture.

Adam: What is your best advice on building, leading, and managing teams?

Chris: Leadership is not about one or two career-defining acts. It's about keeping your team focused on a goal and motivated to do their best, especially when the stakes are high and the consequences matter.

On building - be incredibly selective on your top leadership hires; don't compromise. If cultural fit is a question mark, move on. Break down the obstacles and bureaucracy that drag down a high-performing team. Let them innovate and disrupt. We can figure out how to roll out the plan once the ideas are on the table.   

On leading - leave your ego at the door. The team is not about the leader, rather it is about the synergy the team generates above and beyond the sum of the individuals. By focusing on the diversity of strengths in the team, you empower them to collaborate, create, and innovate efficiently.

Emphasize the positive attribute of admitting mistakes publicly to signal to others it's okay to be transparent about missteps, and the importance of taking ownership:

• Stress the significance of naming mistakes rather than glossing over them, detaching oneself from personal ego;

• Encourage retrospectives often on events (e.g. product launches) and performance to plan (e.g. customer retention vs. target) – to build a culture of using data for continuous improvement.

The importance of resilience: 

• Cultivate a culture where individuals can admit burnout, but must also underscore the need to pick themselves back up;

• Employees in the company shouldn't depend on others for their resilience; instead, they should aim to inspire and promote self-resilience across teams.

• Use stories as powerful tools to empower others to bounce back. 

• My story is about not reaching my full potential until later in life. I took school for granted as a teenager and was not accepted into my dream university out of high school. This was a major wake-up call to strive to focus on doing my best. I went to another college for a couple of semesters, hitting the grindstone to get good grades to eventually transfer into Stanford – suitable lessons in grit and resilience at a young age before it materially impacted my life. I also played a lot of competitive sports, and learning to get back on the field after getting creamed the day before is another powerful life lesson for careers.

Adam: What are your best tips on the topics of sales, marketing, and branding?

Chris: The best businesses focus on their ‘must have’ value propositions over ‘nice to have’ – meaning they address urgent and critical customer problems versus bonuses over the long term. Double down on the value you give your customers with a solution that takes that immediate pain off their hands. For example, every day, we focus on helping deter student misconduct, preserve integrity, and protect the value of college degrees around the globe (must-haves), while also saving teachers’ time grading student work as a bonus (nice-to-haves). Both are important, but your focus needs to be on the ‘must have’ value prop to gain traction, and the ‘nice to have’ will naturally follow and build loyalty.

Adam: What is the single best piece of advice you have ever received?

Chris: The best career advice I received was from my dad: always plan your career looking two steps ahead, and make sure you are working at a place where the mission of the work resonates strongly with your purpose.

Adam: Is there anything else you would like to share? 

Chris: Life is short. Do your best to find companies and jobs that are enjoyable and meaningful to you. Achieving compatibility among your job, career, and overarching life goals is essential. Living the wrong version of yourself doesn’t lead to happiness or success.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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