Leading with courage and vulnerability: In conversation with Courtney Stanley

Hi Courtney, as we start I am curious as to where you are connecting from at the moment.

I am based in Detroit, Michigan. I just moved here from Grand Rapids, Michigan a few months ago. So far, I’m loving living in the D!

If you don’t mind sharing, why did you move?

I made the decision to relocate because I wanted a personal life refresh where I would be closer to my niece and enjoy plenty of opportunities to meet new people. The direct flights in and out of Detroit don’t hurt, either!

That’s lovely. I also recently moved to be closer to family. So, onto the topic at hand, I remember reading in one of your interviews that you were actually studying to become a doctor?

Wait, how did you find that? I hardly ever talk about being a pre-med student!

It was quite an old interview and I was really searching for as much material as possible! So, how did that happen? Was someone in your family a doctor and that’s what inspired you to pursue medicine?

No, no one in my immediate family was a doctor, but I have always loved science and really enjoyed studying anatomy and physiology.

So why did you stop pursuing medicine then?

After a few semesters, I realised that I did not see myself staying in school for twelve years or more to become a doctor. I wanted to travel, explore the world and have more life experiences outside of being in school. This is when I started considering changing my degree, but I was not sure what I wanted to do for my career.

Right. I remember you eventually found a degree that introduced you to the events industry.

Yes! I had a short yet life-changing conversation with a student who was studying international tourism at my university. She told me she was going to Ireland that summer to intern as an event planner at a castle, which sounded like a dream experience to me. This friend shared more about the commercial recreation, event management and business hospitality program at Central Michigan University… and I was sold.

Really bold and cool change! Where was your equivalent of the castle-in-Ireland gig? Did you get to do something as magical as that?

Initially I was quite interested in building a career as an event producer of large-scale entertainment events like the Emmys or Grammys, so I did my internship at the Country Music Association in Nashville, Tennessee.

Ah, the land of Dolly Parton.


So if I understand it, you worked in event organising at first and then became a keynote speaker and event emcee? How did that change come about?

I got into public speaking right after I graduated university. I wanted to attend an industry conference to start building my network, but it was expensive, and being a junior employee, I was not selected to attend. However, I quickly learned that if you presented content at these events, your registration and some travel expenses would be covered, so I started submitting speaking proposals to various industry conferences. What I didn’t expect during this process was how much I would fall in love with public speaking! I loved having the opportunity to share knowledge and support and mentor others who were looking to learn. Eventually I began charging for my presentations because I realised that I was offering valuable time, energy and information that should be compensated. During this time of speaking at the beginning of my career journey, I continued to work for various employers as an event professional. I worked full-time and side-hustled for about 8 years before I launched my entrepreneurial venture full-time as a keynote speaker, event emcee, podcaster, and business coach.

Wow you sound so meticulous and determined in actualizing your dream! 8 years of doing it on the side. How did you manage to keep doing both your job and the side hustle with equal commitment?

There were times when it became difficult to invest time and energy into both my full-time job and my side hustle. Actually, when it became so difficult to balance the two, that’s when I realised that I needed to choose which path I wanted to invest all of my energy into, and ultimately, I chose the path that, to me, appeared to have the most growth potential. I will say that what made building a side business easier was the fact that I truly did – and do – love the work. Sharing knowledge, connecting with incredible people, learning from one another and feeling like you’re doing work that aligns with your life’s purpose… all of those things filled my cup and drove me to continue moving forward, no matter what obstacles arose along the way.

Of course, that must be a great motivation just getting to do exactly what you love. Speaking of doing what you love, you’ve also been hosting the podcast on women in leadership “Dare to Interrupt ” for 3 years now. What was the inspiration behind starting the podcast?

Dare to Interrupt was a project that was inspired by personal experiences – my own, as well as other women in the events industry.

I had participated on multiple leadership boards and from my experience of being in those rooms, it was impossible not to notice that there were not as many women sitting with me at the table, even though the events industry consists of 80% women. Additionally, in those conversations around those tables, I often experienced women being spoken over or interrupted while they shared their thoughts and ideas. Over time, the idea came to me to create a space where women could share their perspective and knowledge, uninterrupted. When I pitched the concept to Meetings Today, they were fully on board to build a partnership that would make an impact on our industry.

And how do you choose whom to approach for each episode? How do you finalize the right person for an episode?

I choose people who are leading with integrity and courage, and also keep an eye out for women who constantly support, empower and inspire the people around them.

And what about the content of the episode? I remember thinking when listening to the episode you did with Mariska Kesteloo that death is not a commonly broached topic, especially in professional contexts. So what made you choose that?

I draw inspiration through engaging in conversations with people and by observing what our industry is talking about both at conferences and also online. What are their pain points? In which areas do they need support?

Regarding Mariska’s episode, she was the one who inspired me to have the conversation, through her vulnerability and courage in discussing the experience of losing a loved one. Death is a universal experience, yet a taboo topic. Mariska is on a mission to change the conversation, and I wanted to amplify her message.

That’s true and I’m glad you and Mariska got into it. Of course it’s a small part of the episode at the time level but it really goes to show how these things determine the course of our lives.


Going back to the inspiration for the podcast, you mentioned that there were times when you felt women were not listened to at meetings. Do you remember anything in particular?

It’s not only that women are frequently interrupted, but it’s also that oftentimes women are not treated the same way as their male counterparts. I remember a moment when I was sitting in a board meeting and a fellow board member was referring to every woman as “sweetheart” when she would share her ideas. It felt condescending and it felt as though it discredited the woman’s input.

When it comes to being an event host, what parts of you do you feel really get channeled into the work?

I am a highly empathetic and emotionally intelligent person and those skills can really come in handy as a speaker or emcee.

If you can read the room, it is easier to read between the lines and adjust to the audience to best serve their needs. I believe that’s my superpower. I am also really comfortable with public speaking. Even if that sounds like a small thing to mention, that confidence allows me to help others feel that way too. I also just like to have fun and when I run some of my own events, I focus on the vibe and energy I want to create. I want it to be meaningful and allow people to feel something special when we are in a room together. People have consistently told me that I allow them to feel like the only person in the room and that I have a very calming presence. Being able to create a safe, meaningful space for people to connect and share is a sacred part of my work.

You mentioned that you wanted to travel a lot and have different kinds of life experiences. Did you get to do that because of the work you chose?

Absolutely. My work has shaped me into a better person, a different person. The life that I live now has been purposeful and there have been so many experiences where I have been able to learn from different people and cultures around the world – and for that I am so grateful.

That’s affirming to know that you did and moved toward the things you wanted for yourself. Is there something you think that will help events become better in the coming year?

If we are able to lean into tough conversations with empathy, vulnerability and open mindedness, our industry – and our world – will be a better place. We need to design experiences that include speakers who aren’t afraid to spark real conversations as well as intentionally create spaces that encourage people to connect on a deeper level. People want authenticity – and they want it now more than ever before.

And finally, is there something you’d wish to share that my questions didn’t allow?

One thing I would like to speak about are the specific topics I present on. Everything I speak on is somehow rooted in building confidence. Whether it is about leading with empathy, advocating for yourself or understanding your value – it all comes back to building your confidence. This foundation is really important to me because it has been my biggest area of personal growth on my life journey. The tough life lessons I learned became the knowledge that I wanted to teach others as well.

[This interview was conducted and edited by Aayati Sengupta.]


Now I will write something about myself. I like to be with people – but I don’t like it when the atmosphere is tense. That’s why I’ve learned to shorten the distance and make it bearable. Sometimes it’s even friendly. So much so that I host the largest conferences and panel discussions in Poland, and increasingly abroad.

My specialities are technology, environment and business. I am also a legal advisor (but that’s a longer story for another time). I have created dozens of radio and TV programmes, including a talk-show in English. I studied at Appalachian State University in North Carolina. And I love the United States. 

see next post

Wait a second!

Want to receive occasional e-goodies like video courses, newsletters or event industry pieces?
Schedule a free consultation