Unveiling Insights with Reagan Cannon: Keynote Speaker for the Horse Racing Women's Summit 2023

Events / Travel
Horse Racing Women's Summit, Santa Anita Park
A panel participates in a question and answer session at the 2022 Horse Racing Women's Summit (Horse Racing Women's Summit)

The second annual Horse Racing Women's Summit will feature Reagan Cannon as the event's keynote speaker. An international leadership speaker and coach, Cannon brings more than 20 years of experience from Fortune 15 companies like Amazon and AT&T.

Passionate about women's advancement, she's the author of “The Cure for Career Quicksand” and presented a TEDx talk titled, “The Real Reason Women Aren't Promoted.” The following Q&A details Cannon’s insights on advancing in male-dominated industries and how her career knowledge lends itself to the world of horse racing.

In addition to Cannon’s keynote address, the summit will showcase a variety of speakers and panelists, detailed here. You can now purchase tickets to attend the 2023 Horse Racing Women's Summit from Sept. 27-29 at Santa Anita Park at www.womeninracingsummit.com.

Q: With over 20 years of experience in executive leadership positions, you've amassed a wealth of insights. Could you highlight one particular experience or challenge that significantly shaped your perspective on leadership and personal growth?

Reagan Cannon (Courtesy of Reagan Cannon)

It’s not faster just to do it yourself. I mean it’s true in the short term, but eventually, doing your job and the job of someone else does not make you faster. It makes you exhausted. Learning how to effectively delegate has been a game changer for me. As women, we naturally “feel bad” for asking others to do things so we are vague on our ask and unclear on our expectations. But over time, I have learned that people thank me for being clear on outlining the guardrails for what I do and do not want. Once I set clear expectations, they can then be empowered to deliver.

Q: With a TEDx talk, workshops, and keynotes under your belt, you've impacted thousands of individuals. Could you recount a particularly memorable success story of someone who applied your teachings to overcome obstacles and achieve their career goals?

After a speaking event, a woman approached me for a coaching engagement. She had enjoyed her job for four years but knew in her heart she had outgrown her current role and felt lost on how to transition into anything different. We started by using my Career Bullseye Framework – a tool to measure her energy-giving and -draining activities. We met over a few months and by the end she had a short “elevator pitch” on what she wanted to do with her career. She loved sales, but knew she wanted a role where she could combine her career ambition with a role where she was giving back. We armed her to start the necessary networking meetings to alert her network on exactly what she wanted next. I was elated when she called me and told me she found the perfect role – a development role for a nonprofit where she could combine her love for sales and her love for giving back. This is EXACTLY why I do what I do, to help unlock leaders’ potential and achieve more than they ever thought possible.

Q: In the context of the unique challenges within the horse racing world, could you share a pivotal leadership lesson that women in this industry might find valuable as they navigate their careers?

In male-dominated industries like horse racing, I can’t tell you how many times I have heard women say, “I had an idea in a meeting, but I didn’t say anything.” The reasons are varied, “I wasn’t 100% sure I had the right answer,” “I didn’t want to slow the meeting down,” and “No one wants to hear what I have to say.” However, the leaders who are successful at advancing know how to bring their unique perspectives and insights to the table. To speak up and challenge, I encourage women to become expert question-askers. We always worry about, “Saying the right thing” but I say, “obsess over asking the right question.” People think YOU are brilliant when THEY are talking. So, use questions to challenge the situation in a way that preserves and promotes the other person.

Q: Drawing from your experience coaching leaders globally, could you provide an example of how cultural diversity and inclusion can be leveraged to enhance collaboration and innovation within the horse racing community?

My secret weapon for being an inclusive global leader – curiosity. I learned that asking questions, particularly from others who were different from me, was a fantastic way to improve my thinking and actions as a leader. I remember landing in India, China, Germany, or [fill in the blank country] and having all the natural instincts of my upbringing in America. I quieted those voices and instead learned to immerse myself in the differences of the culture I was in. I heard new ideas. I experienced new culture. I ate amazing new food! The more questions I asked, the smarter I got. We learn nothing when we are talking. If you want the best place to start your journey of diversity and inclusion. Ask a question. And then listen. Really listen. And allow the answers to influence your thinking and enlighten you to new and interesting possibilities.

Q: Your book, “The Cure for Career Quicksand,” offers valuable principles. Can you highlight a specific “Reagan’s Rule” that could particularly resonate with and guide women striving to make their mark in the traditionally male-dominated realm of horse racing?

One of my Reagan’s Rules is, “In your career you will face disappointment. How you handle it will determine your career.” As women, we are experts at “shoulding” ourselves. We say something wrong in a meeting – should have said something else. We make a mistake on a report – should have quadruple checked it. We even “should have” ourselves for things we could not have predicted – I got a question off topic in a meeting but I should have known everything about everything in the world and answered it on the spot. We beat ourselves up all night long, losing sleep and feeling terrible about ourselves. What is everyone else in the meeting thinking about that night? Anything other than you! But, we magnify our disappointments and often become paralyzed. Or worse, we overcompensate and feel like we have to be perfect and relentlessly work to never make a mistake ever again. How do we fix this? 1) Acknowledge the disappointment. It sucks. 2) Realize that your obsession with your problem is probably isolated to yourself and actually pretty prideful that you think others are worried about you – they are worrying about themselves. 3) Forgive yourself. You will never be perfect, and neither is anyone else. 4) Create space to reflect and learn. Making a mistake once is tuition to learn a lesson. Making it over and over again is the real mistake.

Q: The Thoroughbred industry is known for its intensity. How can women apply your insights to manage pressure, navigate setbacks, and stay resilient in such a high-stakes environment?

Horse Racing Women's Summit, Santa Anita Park
The 2022 Horse Racing Women's Summit (Courtesy of Horse Racing Women's Summit)

Some of the best medicine I can give myself at work is laughter. I find other driven women and make a point to carve out space for us to connect and laugh. Sometimes over coffee. Sometimes over wine. There are all kinds of studies that support having a friend at work and its positive benefits to productivity. I can’t underscore the sanity that has been restored by a friend who I vent to, strategize with, and most importantly, laugh my head off with. I share the embarrassing stories and inner dialogue that happens in meetings. Have I ever had someone double cross me when I trusted them – absolutely. But on the whole, we cannot do this intense work without someone we have a genuine relationship with and can traverse the ups and downs of our professional life.

Q: Could you suggest a practical strategy or approach that women in the Thoroughbred industry might adopt to create a more supportive and empowering network?

We can often be the only woman at the table. We enter a meeting and, once again, we are the only woman, or we are vastly outnumbered. So, it is natural we would have a scarcity mindset that if I get ahead, I can’t make time or space for you. But we cannot advance without helping each other. Men will naturally help other men they connect with. They went to the same school. They golf at the same club. They share a hobby or interest. But for women, we can feel isolated and on the outside. We turn this tide when we look out for one another. We call each other when an opportunity comes up. We say positive things about our women colleagues. We advocate for them when it comes to promotions. We lean into the fact that we know from first-hand knowledge that when women get involved in projects, we are catalysts for change and that is worth fighting for.

Q: As the keynote speaker for the Horse Racing Women's Summit, what key message or insight do you hope to convey to young women aspiring to excel in the Thoroughbred industry?

“Confidence is an emotion. Courage is an action.” If you wait until you feel confident, you will miss out on so many opportunities in your career. We must practice courage in situations and move forward even when we are still afraid. These are not wild and irresponsible actions, but thoughtful risks we take to dismantle the narrative we inherit as little girls to “be good.” From my nationwide research, I found that it was not intelligence, education, or performance that held women from advancing to senior leadership – it was these limiting beliefs that manifest in the way we interact with others. In my talk, I want women to leave with tangible tools and frameworks that will allow them to advance to new heights in their careers.

You can now purchase tickets to attend the 2023 Horse Racing Women's Summit from September 27-29 at Santa Anita Park at www.womeninracingsummit.com.

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