With the eyes of the world on Italy for the 25th edition of the Winter Olympics, which events are you looking forward to? In the spirit of previous leadership series here on my blog, I've asked a dozen leadership and marketing experts to respond to five questions with the hope that both the questions and answers lead you to think about leadership, personal branding, and the Olympics in new and interesting ways.
For today's post, I'd like to introduce Rebecca Herold. Based in Des Moines, Iowa, and with over 30 years of IT, security, and privacy experience, Rebecca is the founder of The Privacy Professor Consultancy (2004) and of Privacy & Security Brainiacs SaaS services (2021). She has authored 22 published books so far, and co-authored NIST catalogs NISTIR 7628, NISTIR 8259, SP 800-213, NISTIR 8425 and TN 2066. She has served as an expert witness for cases covering HIPAA, criminals using IoT devices, social engineering, stolen personal data of retirement housing residents, and tracking app users with Meta Pixels. Rebecca hosts Data Security & Privacy with the Privacy Professor, and since early 2018, she has hosted the Voice America podcast/radio show, Data Security & Privacy with the Privacy Professor.
SHARE THIS: The Olympic Games have the power to unite us because we can all find something inspirational or something we can relate to in each athlete’s story, whether it’s a story of success or of disappointment. –Tatjana Schoenmaker (South Africa’s most decorated Olympian) #OlympicsLeadershipSeries2026 #DebbieLaskeysBlog
QUESTION: What is your favorite WINTER Olympics sport, and why?
REBECCA HEROLD: My favorite sports usually change with each Olympics. I tend to follow individual athletes and their personal stories and struggles, and their dedication to their sport, their goals, and overcoming personal challenges, and then tune-in to watch them. Then secondarily, there are sports I like that I also like to generally watch without knowing about any of the athletes involved. I enjoy watching the men’s and women’s hockey teams play. And I also enjoy watching ski jumping, thanks in large part to seeing the “thrill of victory” intro on ABC’s "Wide World of Sports" from the time I was a young girl. I also love speed skating (reasons coming up in my response to a different question). Each of these sports have such razor-thin margins for errors. The athletes must be completely focused, and have practiced thousands of times to reach their goals. Otherwise, disaster, and possibly career-ending injuries will occur. But just one unknown or unexpected variable introduced during the Olympic competitions can destroy their longtime practicing and dash their Olympic dreams.
[Note: link to ABC's "Wide World of Sports" intro is shared at the end.]
QUESTION: What WINTER Olympics sport most “visually” demonstrates teamwork, and why?
REBECCA HEROLD: Hockey plays and tactics visually demonstrate the need for teams to have practiced over and over again, to have each team member know their role for each play, and to carry through. If one team member fails to perform their actions as practiced, it is seen in real-time by viewers around the world.
QUESTION: According to Suzanne Robb, COO of Alloy, “Define what victory means to you, and keep that vision in mind. You’re the one who gets to determine when you’re making progress, what success means, and what your focus should be. When you get a win, take time to celebrate. In business as if life, you’ve got to run your own race.” With this quote in mind, which Winter Olympics event or result stands out in your memory, and why?
REBECCA HEROLD: Victory means different things based upon the context of each situation. I’ve been super competitive in sports and games all my life. Victory in a basketball, backgammon, running, Monopoly, or any other competition ultimately means, on a game-by-game situation, winning. But business is not a point-in-time competition. It is an ongoing process, filled with responsibilities to many different stakeholders; employees, Board of Directors, customers, patients, and often the general public. The person at the helm of business must be aware of the industry, and of the competition and what they are doing. Also, while one person is at the helm, all who support that leader’s goals and visions must be aligned with doing work that supports success.
With this in mind, here’s my answer. A competitive event in the short track speed skating competition that I happened to see is actually what made me a devoted fan of that sport in the 2002 Olympics. The gold medalist, Steven Bradbury from Australia (also the Olympics host location that year) won by taking a calculated risk regarding what his competitors would do. Reportedly (at the time), he had studied his competitors closely. He knew that several of them had faster times than his fastest time to that date in history. Bradbury purposefully stayed at the back of the pack for most of the race. In the final lap of the final race, the four leading skaters all crashed into each other, and Bradbury zoomed by the resulting pile-up and crossed the finish line first and won a gold medal! You see, he also reportedly knew that his speedier competitors were aggressive competitors, and very physical. So he took a risk, expecting a slow-down at the end, based on the history of those speedier than him, and that risk paid off, based on knowing his competitors’ strengths and weaknesses during competitions. And he surely did celebrate at the end of the race!
SHARE THIS: While one person is at the helm, all who support that leader’s goals and visions must be aligned with doing work that supports success. ~Rebecca Herold #OlympicsLeadershipSeries2026 #DebbieLaskeysBlog
QUESTION: During the 2024 Summer Olympics in Paris, entertainer and businessman Snoop Dogg used the hashtag #FollowTheDogg and shared his Olympic experiences on social media. My favorite story and related photos were when he and friend Martha Stewart dressed in equestrian clothing and attended the dressage competition. According to reports, Snoop’s involvement was intended to attract a new audience to the Olympics. If you were in charge of the Winter Olympics, who would you invite to attract a new audience, and why?
REBECCA HEROLD: I’m a huge, life-long Kansas City Chiefs fan. And while I could sit here and try to think of someone else, the first person who popped into my mind was Taylor Swift. The impact she has had on NFL viewership, and increasing the fanbase of the Chiefs and for football in general, goes far beyond the central Midwest, and has been tracked and reported on often. After her fiance, Travis Kelce, (in my opinion one of the very best tight ends in the history of the sport) retires, and she is no longer fitting in attending Chiefs’ games with her concert tour appearances...maybe in the next year or two?...I think she would still be the perfect celebrity and role model to attract a wide range of new audiences to the Olympics. She is a great role model and also demonstrably cares about her fans.
QUESTION: The 2026 Winter Olympics will be the first Olympic Games under the leadership of International Olympic Committee (IOC) President Kirsty Coventry. She is a former Zimbabwean politician, sports administrator, and former Olympic swimmer and world record holder. She is also the first woman, first Zimbabwean, and the first African to serve as IOC President. According to Reuters, “Kirsty Coventry smashed through the IOC’s glass ceiling in March 2025 to become the organization’s first female President in its 130-year history.” What are your thoughts about this development for the world’s biggest multi-sport organization – and its future?
REBECCA HEROLD: I think it is great to see a former athlete, world record holder, and demonstrably successful leader in multiple facets of her life, to have been elected as IOC President. Her election win demonstrates substantial international support for her leadership capabilities. As with all elections, there will always be others who question her performance and ties to the Zimbabwean government. However, given, from my amateur sports-viewing perspective, and knowing nothing meaningful about most of the government politics in other parts of the world beyond the U.S., this seems to show that those electing her did so based on her history as an athlete, an Olympic champion, and likely her other demonstrated leadership skills throughout her life.
I find her election to be a refreshing outcome in a world that disappointingly and sadly seems to be going backward in progress for inclusion for consideration of women and other historically marginalized communities in such roles. Hopefully the Olympics leadership can continue making decisions to provide a type of role model to other governments and businesses throughout the world. Of course, such recognition requires an appetite for such changes, so in the short-term, the countries that most need to recognize such enlightened moves will be the ones who will more than likely denigrate and nitpick Coventry’s work, no matter how successful she is in this role.
A final reminder, as you watch the competitions, make a note on your calendar to swing by #DebbieLaskeysBlog each day through February 22nd for leadership and marketing inspiration. A small interruption to the series will take place on February 20th to celebrate "National Leadership Day," then the Olympics series returns on February 21st. A series recap will be featured on February 22nd. Enjoy the Olympics!
Image Credit: Olympics.
Read Rebecca's previous appearance here on my blog:
SPRING LEADERSHIP SERIES 2025 – Featuring Rebecca Herold (June 2, 2025)
https://www.debbielaskeysblog.com/2025/06/spring-leadership-series-2025-featuring.html
Meet Rebecca at this link:
https://www.privacyguidance.com/
Watch the 1976 opening to ABC's "Wide World of Sports" that Rebecca referenced in her first response:
https://youtu.be/SnakqX0pTUk?si=7ikfjfJH_AinYLAh