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Social Impact Authors: Why & How Author Frank Calderoni Is Helping To Change Our World

An Interview With Edward Sylvan

The stories in my book that are most meaningful to me are stories from Anaplan employees who feel like they found a place they could belong when they didn’t think it was possible from an employer. I included a story of one employee who transitioned to his true gender identity with complete support from his colleagues. He said, “I felt safe coming out as transgender to my colleagues and talking about my transition at work. I feel supported. I’m still just as good at my job. Now I can be my true self.”

As part of my series about “authors who are making an important social impact”, I had the pleasure of interviewing Frank Calderoni.

Frank A. Calderoni is the author of Upstanding: How Company Character Catalyzes Loyalty, Agility, and Hypergrowth. He is the Chairman and Chief Executive Officer of Anaplan, a cloud-native SaaS company that helps enterprises orchestrate business performance. A technology industry veteran with over 30 years of leadership experience, Calderoni has helped to guide organizations through disruptive change and incredible growth. Before joining Anaplan, Calderoni served as the Executive Vice President of Operations and CFO of Red Hat. He also spent more than a decade at Cisco, during which he was named one of the best CFOs of 2012, 2013 and 2014 by Institutional Investor and CFO of the Year by the San Francisco Business Times in 2015. Prior to Cisco, Calderoni held senior leadership roles at QLogic Corporation and SanDisk Corporation. Earlier in his career, he spent 21 years at IBM. Calderoni previously served on the board of Palo Alto Networks and currently serves on the board of Adobe Systems, Inc.

Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

My father immigrated to the United States from Italy through Ellis Island when he was just five years old and settled in a small, rural town in New York State with his mother, father, and brother.

My father went to college, but he left before he received his degree to provide for our family. He had a strong work ethic and used his job as a tradesman to give us a good life. My mother stayed home to take care of me and my two brothers, Bob and Rick, and later developed a career as a computer technician after we left home.

We lived comfortable lives. We weren’t affluent by any means, but we didn’t lack for anything.

I think my father always regretted not getting his degree, so he impressed on my brothers and me from an early age that we would definitely be going to college. I started working when I was 12, delivering newspapers, and my brothers started working at a young age too. The expectation our father set for us was that the money we made would be put into savings for college. The main focus, however, was on studying and doing well in school.

When you were younger, was there a book that you read that inspired you to take action or changed your life? Can you share a story about that?

This might be a bit different, but a memory I always have is when my parents bought us an encyclopedia set. They were those beautiful brown leather books with gold detailing, and I remember spending hours just going through them throughout my childhood. It helped spark in me a lifelong love of learning and wanting to explore and understand things outside of my own experience. I feel so grateful to them for that gift.

Can you share the funniest or most interesting mistake that occurred to you in the course of your career? What lesson or take away did you learn from that?

The most interesting mistake I made was when I made a decision on something that I didn’t think people would care about. I was completely wrong. As any good organization, we were always looking for ways to reduce costs and be environmentally conscious, so I made the decision to replace all paper towels in restrooms with hand dryers. The reaction was fierce, fast, and direct. Employees were very upset that they were not consulted about this decision as the majority preferred paper towels. I learned right there and then — always be collaborative, open, and transparent. Ideally, with decisions that affect all employees, consulting with them in advance will foster a better solution every time.

Can you describe how you aim to make a significant social impact with your book?

I hope that leaders can use this book as a framework to think about how their values should rise above all else when it comes to their employees, customers, communities, and investors. This is not about one specific cause, so much as it is about rebuilding the business world into a far more diverse, equitable and inclusive way.

As leaders, we need to redefine the best talent with more inclusive hiring practices. We need to create environments within our company culture where people feel safe and supported to do their best work while also recognizing how valuable their time and activities are outside of their contribution to the company. We need to speak out on the ethical and moral issues facing the world today to help rebuild the entire system. This may seem aspirational and I recognize that there is only so much any individual or company can do but if we can all start thinking about things in a different way — we can collectively move that dial.

Can you share with us the most interesting story that you shared in your book?

There are so many to choose from but two that will always stick with me about how company character and the bottom line aren’t targets to choose between but mutually beneficial goals.

The first is when we were on a roadshow ahead of our IPO. One investor group we were speaking with was asking question after question about our culture. When I asked why, they responded “What we have found is that, when you have a strong culture that starts from the leadership and works down through the entire organization, you’re going to have a much better return. We’ve proven that out.”

The second is when an executive at one of our customers confided why he was interested in Anaplan in the first place. He said “I went to an event and several of your people were there. They were so energized and so enthusiastic about what they were doing that I felt like I would be missing out if I didn’t get to know more about what was going on. It piqued my curiosity because of the people and how they were carrying themselves, and the enthusiasm they had for their company. I wanted to be part of it.”

Business today needs to be about doing the right things the right way, and leaving the world and our communities better than we found them.

What was the “aha moment” or series of events that made you decide to bring your message to the greater world? Can you share a story about that?

It really was the last 18 months from the start of the pandemic that also saw a recession, social justice movements and political upheaval in several countries. I have learned more during this time than in my entire 35 years in business and it brought home to me how important it is for business leaders to be able to navigate daily change to support their employees, customers and communities.

The murder of George Floyd led to an overdue awakening for me and fundamentally changed me as a person and a leader. I realized how much work I had to do and that it was my responsibility to use the privilege and power I had as a business leader to help dismantle systemic racism.

I learned how important it is to speak up, immediately. Silence is deafening when people are waiting for you to show up and call out wrongdoing and check on their wellbeing. Always ask those affected what they need, do not assume you know the answer. There’s a delicate balance in this to avoid putting further burden on the marginalized group, so do your homework and come into the conversation with a selection of what you can offer but never assume you know what someone else is feeling or needs. And finally, your values should always rise about politics.

I think about these lessons every day as I approach my job, knowing that I have far wider-reaching responsibilities than just looking after the bottom line.

Without sharing specific names, can you tell us a story about a particular individual who was impacted or helped by your cause?

The stories in my book that are most meaningful to me are stories from Anaplan employees who feel like they found a place they could belong when they didn’t think it was possible from an employer. I included a story of one employee who transitioned to his true gender identity with complete support from his colleagues. He said, “I felt safe coming out as transgender to my colleagues and talking about my transition at work. I feel supported. I’m still just as good at my job. Now I can be my true self.”

I shared another example of an employee who has Asperger’s who said his previous jobs made him feel like a cog in a machine. Job hunting was difficult because his condition can make 1–1 interviews uncomfortable given the demand to make eye contact and speak confidently about himself. He started with us as a contractor and was quickly made full-time. He said at Anaplan, he feels like he’s valued for all the parts of himself.

Another employee came to Anaplan having faced so many rejections that he took to the Minneapolis Skyway with 100 copies of his resume and a cardboard sign that read: “On a mission: launch career, take a resume.” An Anaplan manager was impressed with his creativity and tenacity and he started his career with us as a product support analyst. He’s now a Master Anaplanner, working at one of our partners.

Focusing on company character creates space to find amazing talent that could otherwise go overlooked and helps people find their place.

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

Since my book is written for business leaders, I will target this advice at them, and you’ll have to excuse me for including four. When I think about Upstanding Company Character — there are really four key things leaders need to do to create it. They are:

  1. Operate with a larger purpose,
  2. Be values-led,
  3. Follow through on convictions, and
  4. Answer the call in challenging times.

Business leaders who focus on these four things in addition to the bottom line will be far more successful than those who adopt a win-at-all-costs mentality. With a character as a guiding star, you become an organization that people want to work for, buy from and invest in. It really is a rising tide situation. Consumers and employees are looking at companies for how they are making the world a better, more inclusive place.

How do you define “Leadership”? Can you explain what you mean or give an example?

In a very broad sense, leadership is accountability. It is taking risks and owning your mistakes but giving your team credit for accomplishments. It is putting the needs of your organization and your community before your own ego.

In the business context, executive leadership used to be all about driving performance, getting results, executing, and delivering for shareholders. The new modern leadership mandate goes beyond solely managing operational and financial results. Its expanded purpose is to serve all stakeholders.

One example I like to use of this is when I interviewed a business leader in my book about when Cisco came out against a California initiative called Proposition 8 that sought to ban same-sex marriage. This was back in 2008 when supporting same-sex marriage could have been seen as controversial or political. Instead of staying out of it or coming out in support of something that had long been an acceptable political viewpoint — the leadership team at Cisco took the risk of publicly supporting same-sex marriage simply because it was the right thing to do. I am proud of the fact that we were on the right side of history in that debate.

What are your “5 things I wish someone told me when I first started” and why.

  1. Seek out a mentor. Find someone that cares about your trajectory and has walked a path that interests you. You get to learn from their mistakes and get honest guidance from someone outside of your immediate circle of family and friends.
  2. Take more risks. The fear of failure is so very real and so very limiting that it often prevents people from taking the risks that will launch their success. Failure is just an opportunity to learn.
  3. Take jobs others don’t want. Find the things that take a steep learning curve that others are put off by. It will give you skills that most others didn’t want to take the time to learn and make you invaluable to your organization.
  4. Volunteer for the big projects. The big projects won’t just get handed to you, you need to back yourself and go for them.
  5. Be more appreciative of feedback. This is such a big one and feedback puts so many of us instantly on the defense. No one likes giving negative feedback so if they are, it’s because they care enough about you to help you get better. Once you see that, you can take the gift for what it is and grow.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

In that old tradition, I start each chapter of my book with a quote that’s meant something to me over the years. One that I come back to again and again is from Lao Tzu: “Watch your character, it becomes your destiny.”

It’s so simple, yet so profound and is my guiding star each day. Am I doing the right thing? Will I be proud of myself for this action later? Am I trying to do right by all those involved? How can I do better?

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

Jane Goodall has always been a hero of mine. I remember growing up watching her on nature documentaries. She didn’t just focus on understanding and saving a species of animal, she broadened the concept of conservation to include the needs of the local people and the environment. I bet she would have fascinating stories to tell, and I’d love to sit down with her one day.

How can our readers further follow your work online?

Learn more about Upstanding at XX and You can also follow me on LinkedIn.

This was very meaningful, thank you so much. We wish you only continued success on your great work!



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Edward Sylvan, CEO of Sycamore Entertainment Group

Edward Sylvan, CEO of Sycamore Entertainment Group

Specializing in acquiring, producing and distributing films about equality, diversity and other thought provoking subjects