I recently went one on one with Anaplan CEO Frank Calderoni. Frank is also the author of the new book Upstanding: How Company Character Catalyzes Loyalty, Agility, and Hypergrowth.

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? 

Frank: I’ve held several leadership roles, which together add up to more than 30 years of experience. Before joining Anaplan as CEO for the past four and a half years, I served as CFO leading Finance, Operations and IT at Red Hat, an open-source software company. Before that, I was CFO for Cisco Systems. I was also the CFO at both QLogic and SanDisk, and I spent the first two decades of my career at IBM. 

Adam: What experiences, failures, setbacks or challenges have been most instrumental to your growth? 

Frank: What I brought to Anaplan was a culmination of my experiences, particularly in the areas of culture and leadership.

IBM has an amazing 109-year history, and you can’t help but be humbled by its perseverance and commitment to customers. Its culture, which is built on a foundation of respect and inclusion for its employees, has been institutionalized through messaging, leadership development, and recognition programs.

When I served as CFO at Cisco, I saw firsthand the role of a CEO and an executive team in a company’s culture.  John Chambers and my peers were the stewards, cheerleaders, and most importantly, role models for Cisco’s culture. We all felt ownership and took it very seriously. 

And at Red Hat, which is an open-source product developed with a community of users, I saw how transparency and raw feedback generate passion and loyalty among employees.

Altogether, I used my experiences and what I’ve learned from others, many of which are quoted in this book, to grow as a leader. 

Adam: What do you hope readers take away from your new book?

Frank: The book, Upstanding, was released on June 9. What I hope readers take away is that now more than ever, all stakeholders, including your employees, potential employees, customers, prospects, investors, partners, and vendors, are paying attention to a company’s character. 

For example, a company’s position on Environmental, Social, and Governance (ESG) topics is becoming a non-financial factor for investment decisions on Wall Street. 

Customers are also giving closer examination of their suppliers. It used to be labor practices, conflict minerals, carbon footprint, and corporate giving. Now it’s expanded to the company’s position on social issues.  

Finally, for employees, engagement is a function of how they feel about the company. Is it more than just a job? If not, chances are they won’t perform to their best potential, and worse, they will leave for a company that does not demonstrate character. 

As a result, it’s imperative that companies don’t sit on the sidelines when it comes to demonstrating their character. 

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

Frank: The key to growing and scaling your business is having a culture that enables you to respond to change quickly. I’ve seen companies stall or fail because they can’t reinvent themselves quickly enough to handle growth. That’s why I often use Peter Drucker’s quote, “Culture eats strategy for breakfast,” because in growing companies, it’s true.

If you’ve built a strong character-led culture, ideally one that empowers employees and builds trust, it gives employees the freedom to make decisions. This freedom eliminates the need for heavy controls and approvals, which can hinder change. The result is a company that’s able to adapt and evolve quickly, which is critical to achieving and sustaining growth. In addition, culture can help to attract and retain talent. That’s why we treat culture as a business strategy at Anaplan.

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

Frank: I believe everyone has something to offer, but not everyone does it the same way. It’s important to understand and appreciate differences, especially at the executive leadership level. Not only does it create a more inclusive culture, but it also creates an environment where people can do their best work. And at the end of the day, that’s what matters most.

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

Frank: Character is the overarching quality, particularly in today’s world. And a quality that contributes to character, in my opinion, is empathy. This means taking the time to stop, understand, listen, and most importantly, respect someone else’s point of view—even if you don’t feel the same way. 

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

Frank: The most important skills for leaders at all stages of their career are listening and learning. It’s a myth leaders have all the answers. The reality is the best leaders are the ones able to take in new information and adapt accordingly.

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

Frank: We’re in a time where character matters. I encourage all leaders, regardless of industry, company size, or sector, to spend the time and work on their company’s culture. 

• Specifically, understand your company’s purpose. If you don’t know it or don’t have one, create it, suggest it, get one started. Use your desired customer experience as your North Star.

• Spend time figuring out the right values—what best supports your company’s purpose and unlocks discretionary effort. Make sure your employees are involved in this process. 

• Finally, and most importantly, character is reflected through behaviors and decisions. Strive to be a role model for the character-led culture you want to create. 

Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them? 

Frank: The most important technology is Machine Learning (ML), which is redefining every industry. With ML, computers can learn the best outcome without human intervention. In SaaS companies, where data is stored in the Cloud, computers are making predictive decisions in real-time, often understanding the customer’s needs better than they do. In other industries like healthcare, computers will determine patient treatments based on vitals, their DNA, and the outcomes of millions of cases and cures and adjust treatments based on the latest data. This is in stark contrast to today’s medicine, where doctors can be a single point of failure. What companies need to understand is how they can use ML to reinvent what they deliver to their customers. It’s a challenge though, because industries, particularly established ones, tend to resist change until it’s too late.

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

Frank: The best tip for all three functions is to have a clear and common understanding of the customer. From there, create a compelling story about how you produce outcomes that matter to the customer. Finally, keep your messaging consistent across all three functions. It sounds simple, but it’s so hard to do, even when all three functions are in the same organization.

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

Frank: The best advice came from my father, who always told me never to give up. And it’s this persistence and a commitment to excellence that drives me to do (and be) my very best.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also 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. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, 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. 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.

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