It Is What It Is: Interview with Kiley Dean

I recently went one on one with Kiley Dean. Kiley is a performer, singer and songwriter who has worked with Britney Spears, Madonna, Demi Lovato, Timbaland, New Kids On The Block, and more top names.

Adam: Thanks again for taking the time to share your story and what you have learned from your journey to date. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your development and success?

Kiley: As cliché as it may sound…never give up. There have been times that I have wanted to give up, and honestly, there have been days when I set out to do so or just stop completely. But my love for music and singing always kept me planted in what I love. The amount of "No"’s I have received and still receive to this day is unreal. But I can tell you, you will hear "no" one million times or more, just to get to that one "yes" that changes your entire life. At times, the setbacks have been unbearable. For instance, walking through massive doors just to have them slam in my face, or having major record executives tell me that I’m "not good enough" or "not skinny enough." Those things stick with you. I still work through those rejections to this day, but I know what God has in store for my life. I have known it since I was a child, so here I am. I am going to keep walking through this journey and do my best to find all the joy along the way. Never giving up.

Adam: In your experience, beyond natural talent, what are the common qualities among those who have been able to enjoy success as performing artists?

Kiley: I look at my peers, I see the ones who have made it to the top, and I think - it’s all about consistency. Granted, it takes a few things like timing, knowing the right people, some may say "luck," etc... but nowadays with social media, it is so easy to be seen. Anyone can put themselves out there. That’s why music is oversaturated at this moment, but it's also how people can continue to show up. During my 20+ years in this industry, I have seen consistency be the key to success. For me, success will be my consistency with writing. I haven’t been as consistent with it as I’d like to be, but that’s a daily choice of mine. One I can change and improve at any time. I'm motivated and inspired by those around me, by artists like Ryan Tedder, who have stayed consistent and earned their place at the top. I watch them. And they are who become the biggest artists of the generation.

Adam: What are the best lessons you have learned through your career that are applicable to those who will never earn a living as a performer?

Kiley: Great question. My answer - Do it because you love it. No matter what "it" is. I have found myself getting paid very well on certain tours that actually brought my spirit down. I was doing what I loved (singing), but I wasn’t happy. Now, looking back, I realize that my surroundings were toxic and I found myself asking, "Do I even want to do this anymore?” Yet, even in those tough times, in the toughest of environments, the answer was - and will always be - "Yes." I want to sing and perform always, for as long as I am able. While I now realize that I have the power - we all do - to only take gigs and jobs that allow my mental and emotional self space to flourish, it took me time to get here and to build myself up. And that's not always a bad thing. You learn a lot along the way about yourself and your art. So I am not saying that you have to love every single performance or boss you work for, but you must always remember WHY you do it. Paid or not. The answer should always be, “Because I love it.” Everything you do should always be rooted in love.

Adam: You've worked with Britney Spears, Madonna, Demi Lovato, and many other big names. What are some of your favorite memories, stories, and lessons learned from your time around America's most successful performers?

Kiley: The women I have been able to sing beside have all, in their own special ways, taught me so much.
Britney and I were just kids when we toured together. We were both 17, bright-eyed and brand new to the game! Britney's tour was my first professional gig. The "Baby One More Time" and "Oops! I Did It Again" tours started the trajectory of my entire career. The memories I have as such a youngster with her are incredible. We shared a tour bus and we were very close during this time. I learned the ins and outs of touring with Britney. I learned how to be a background singer - and that consists of SO much more than just singing in the background. It is the entire way you hold yourself around someone when they are the star. It was humbling, and I learned that from her - not because she asked for it or even knew she needed it - but instead, it was kind of an unspoken thing you learn and abide by. I am so thankful that I learned those lessons of how to show up and carry myself for this kind of position, because Lord knows I needed that nine years down the road when I started working with Madonna!

I eventually left touring with Britney to sign to Interscope Records. I did the solo artist thing for about 10 years. That’s when all other doors started shutting, and brought me to Madonna. Talk about working for the best of the best. The caliber of professionalism blew my mind! She demanded perfection and that is what she got. Watching her work ethic made me want to be a better artist in that way. Till this present day, I have worked for anyone like her. She is on top for a reason. The first tour I did with her was the "Sticky & Sweet" tour in 2008, my first world tour. I remember getting off the tour bus in each city and dropping my bags off in my hotel room and just roaming around whatever incredible city we were in. Those were truly magical times. I do miss it.

I toured with Demi Lovato in between tours with Madonna. Demi was a blast. Her laugh is infectious and I just love the girl. She reminded me of Britney a lot cause she loved to laugh. There were so many fun times with her! I also remember really admiring her for her sobriety. She was so determined to stay healthy. She would do whatever it took, and I still remember how cool I thought that was.

Adam: What is something you have witnessed up-close or experienced that would shock fans?

Kiley: I cannot, and will not, spill dirt on people who have given me such incredible opportunities. But I can share a shocking story! There was this one time a crazed fan came after Madonna at one of our shows. She didn’t even flinch. It was crazy to witness. Her security took care of him, but she is like 5-foot-nothing, so tiny, and she didn’t even flinch! I remember just thinking, "That woman is truly a bad a$$!"

Adam: Who are the best leaders you have been around and what have you learned from them?

Kiley: I have learned over the course of my life that leadership does not always come from a boss. It can, but many “bosses” are not leaders. Many people in power are not actually leaders. Leaders are people who do just that: Lead people. Tour managers do not get the credit they deserve in that aspect. They lead the entire camp on tour. Jason Milner was our tour manager and he did such a great job. I admire him to this day for his work in leading a bunch of musicians and dancers, making sure we got to where we needed to be safely and on time. It takes a lot to do that, so when I think about leadership (keeping it within my touring experience), that defines it for me. A lot of people I know want to be a tour manager, but it is worth sharing that it's not an easy gig. Not at all. No matter how big or small the tour. So it's worth saying then, that no matter how big or how small anyone's role, they can still step up and shine as a leader if they prioritize taking care of those all around them - not just those who are under them in terms of seniority.

Adam: What is the single best piece of advice you have ever received?

Kiley: The single best advice I ever received came from my manager, Kairi Brown: “It is what it is.” Kairi would see me freaking out when something did not go as planned, and to this day, that's something I struggle with. It drives me crazy when things don't go as planned. Especially when you work so hard to build the best-laid plans. Yet, Kairi would look at me and say, “Kiley. It is what it is.” Ultimately, it meant that there is nothing more you can do; accept what you have no power over; accept the things you cannot change. As I write it, it still agitates me...So clearly I’m still working on this phrase as it applies to my life! I think if you embody this advice and its meaning, it will save you time, stress, worries, allowing you to identify what you cannot control, and therefore allowing you to move on faster to bigger and brighter things that are in your control.

Adam: Is there anything else you would like to share?

Kiley: I would love to add this: I am still walking my journey out. I am still at times wondering if I’m supposed to be chasing after this dream. I still get very discouraged, but I keep pushing. It’s all I know and all I want, so I continue. I am not sure if this journey will ever meet its destination. (Does any?) So what I am doing is finding peace and joy in the journey. At times that can be very hard, but I’m down for the ride. Besides...it is what it is.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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