Truth Telling From The Trenches With Event & Conference Strategist Caroline Kay
There’s nothing I love more than transforming a three-ring circus into an event machine that engages guests, runs like clockwork, and delivers ROI. I’ve been creating, planning, and running corporate conferences and events for more than 20 years, as part of consulting firms in the U.K. and U.S. and as founder of my event management firm, C.KAY International. In the middle of all that, I served as COO for a U.S.-based leadership development consulting firm.
Over the years, I’ve created and produced thousands of events and conferences all over the globe, working with amazing clients and event management colleagues. I attended university in Southampton, United Kingdom.
Where is your business located?
C.KAY InternationalI'm based in Seattle, Washington, but I travel the world to produce events for clients. The world is my "office."
Where did the idea for your business come from?
I've always wanted to own my business. (I would say "be in control of my own destiny," but that's a tall order as an entrepreneur who provides a service that's all about client needs that are constantly changing.)
I'm inspired and motivated by the female entrepreneurs I've known and have studied. I felt that having my own business would enable me to do what I ultimately want to do: do great work, have fun, and travel.
The event management business is a natural for me—it’s all about organizing, developing connections, running a mile a minute, and making clients happy with “wow” experiences that engage their guests.
What is the first thing you do in the morning?
I get up at 5 am to get a head start on my day when it's quiet, especially when I'm on site running an event. I start the day by skimming email to see if anything urgent has popped up. I deal with time zones all around the world, so emails come in 24/7.
What does your work day look like and how do you maximize your productivity?
I keep a running, prioritized "To Do" list covering everything in my life, from errands and birthday reminders to client meetings and event production deadlines. Then I turn to Excel, which I live in—tracking event production schedules and client budgets incessantly.
I spend a lot of time researching and brainstorming. I'm always on the hunt for the latest event technology, event design, cool venue, hot destination etc.
I try to step away from the computer and get out for lunch (if I'm not knee-deep in running an event). I connect with a client or vendor over a meal or get out for a walk. I also make sure I have phone time with real people every day to get my head out of all my apps and technology.
I call 2 or 3 friends, family, clients, or vendors around the world to touch base.
How do you bring your great business ideas to the world to serve your clients?
I showcase ideas by taking clients to events and venues where I think the approaches will work for them. I send clips from magazines or online sources to clients, explaining how I think we could incorporate the concept into their event.
What is one trend in business that excites you?
The possibilities and capabilities of technology excite and amaze me. I travel all the time, as do my clients, and we need to stay connected.
What is one strategy that helped you grow your business?
My key strategy: developing and maintaining strong, genuine connections.
My industry is all about connections with clients, colleagues, and vendors. So I work hard to keep those connections alive. I treat everyone like how I would like to be treated—I take the time to connect with each individual in a personal way. I work to remember the little things, like their birthday, and send a personal message rather making a Facebook post.
What is one failure you had as an entrepreneur, and how did you overcome it?
Like a lot of entrepreneurs, I tried to provide all the services I knew would be of benefit to clients and I stretched myself too thin. It’s hard to hold yourself back from pursuing all the exciting opportunities!
A wise advisor suggested that I focus on my niche and my strengths; that I don't try to be a jack-of-all-trades. So I narrowed my focus to doing what I truly love and where I think I offer the most value: planning and running events.
What is one business idea you’re willing to give away to this community?
It’s more a guiding principle than an idea, but LISTEN. I come across so many people who don’t listen, really listen. Take the time to make sure you have clarity on what’s being communicated and where you and your clients are headed. Then over-communicate! Ensure your clients are clear on the direction too.
Direction can change—will often change, in fact—but it’s critical to make sure everyone is on the same page.
What is the best $100 you have recently spent? on What? Why?
A mini get-away with my god-daughter (though it did cost more $100). I give experiences to my god-kiddos or nephews instead of presents. For my god-daughter, we were two princesses for the night in a hotel in downtown Seattle!
What is one piece of software or app that helps you be productive? How do you use it?
Microsoft OneNote and Excel. I live in this these tools. Also, my "rolodex" — having experts in various specialized event management disciplines to call upon all over the world is critical.
What is the best business book you have read? Why?
Finding My Virginity by Richard Branson. I’ve read it 4 or 5 times.
The book, and Branson, inspire me – the innovative way he set up Virgin and his various businesses and the ways in which he gives back. In reading the book, I always find a new nugget to take away into my own life and business.
What is your favorite quote?
“If you're not having fun, you're doing something wrong.”
- Groucho Marx
I’m not sure who originally said this, but I love it:
“The older you get, the more you realize that no one has a F***ing clue what they’re doing. Everyone’s just winging it.” - Unknown
Who inspires you in business and why?
Richard Branson is always my-go to for inspiration.
I’ve admired him from the start—his work ethic, his values, and his “don’t take no bull” approach. I also admire The Rock (Dwayne Johnson). I love his get-up-and-go attitude. He’s respectful, honest. He gives back. He never forgets where he came from nothing.
I’ve also been following some online influencers lately: Lewis Howes, Brendan Fallis, Brendon Burchard.
What are your thoughts on work-life balance?
It’s taken me a while, but I’ve learned to take care of myself.
Event management is a tough physical and mental job—long hours, little sleep, eating on the run, and a million moving pieces to manage. I work to keep myself physically and mentally fresh with exercise, staying in contact with friends and family.
I get on Facetime every day with my family back home in the UK, even if it's just a 5-minute hello as I'm running between meetings. That conversation grounds and connects me.
What are the 3 business lessons you’ve learned so far?
I’ve learned how essential clear, thorough communications are—communications that make no assumptions, that don’t expect that everyone is on the same track as I am.
I’ve learned to go through every detail again and again...and again.
No detail or possibility is too small to be considered.
I’ve also learned it's crucial to maintain confidence in your own voice and your own choices; to push through the doubt that creeps in when you're in new territory; to trust in yourself and the processes you’ve set up.
I'm a risk-taker by nature and I'm always happiest and most successful when I trust my internal risk-taker voice.
What is your workspace like?
I’m always on the go with clients and events, so I work from a lot of different spots: my office, coffee shops, hotel lobbies, event venues, etc. In my office, I like to be neat and tidy, know where things are.
My dad always used to say: “Everything has a place. Once you’re done with it—put it back.” That rule works for me.
Last thing you do at the end of your work day?
I update my “To Do” list and plan for what's on the next day. Then it's off to hang out with friends, explore a new restaurant, or tuck up in bed with a good book.
What is the one thing you can't leave home without?
My Swell Mug for the voluminous amounts of tea I drink. I love the Swell brand and it helps save the planet one plastic cup at a time.
What superpower would you love to have to use for good?
To FLY. To be able to get around the world faster. And when I have a delayed truck with event assets on it, I’d love to be able to put it in the palm of my hand and whiz to the next location!
Number of unread emails right now?
Anything else you want to add?
How can other entrepreneurs connect with you?
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