Give us a synopsis of your business and career. What you offer, who you serve, etc.

I’m a CXO and Certified Exit Planning Advisor. I’ve coached and developed over 50 leadership teams and hundreds of leaders throughout my career in both the corporate and SMB space. These experiences introduced me to many wonderful methodologies for scalability and growth. For 15 years I was a Gallup-trained Strengths and Engagement Coach!

My true superpower is being a People Builder! Each person has their own greatness to uncover and leverage, and I help leadership teams collaborate and build the true value of the business. Using a unique blend of EOS® and Exit Planning Institute® strategies, I help companies build their intangible value and capital to ensure success today and at the time of an eventual exit. After all, good exit planning IS good business strategy! In addition to supporting wonderful companies with integrating systems and building a foundation for the future, I also do a lot of public speaking for conferences, mastermind groups, and podcasts, which I love.

What inspired you to pursue your career path?

There is a voice that whispers into my soul and paints vivid pictures of what I am designed to do in this life. I listen, I seek it out, and run toward those visions with relentless determination. If the visions and dreams keep coming, then I will keep running. While I've been fortunate to sit in the leadership seats of small businesses, large international organizations, non-profit boards, and everything in between, I wanted to expand my reach across as many companies and teams as possible! I love that I can have a much broader positive impact as an external coach engaging with a multitude of diverse leadership teams.

Leaning into my core value of Build Others, I found that operating as a Fractional CXO in this environment can help me fast-track and achieve my goal to impact 10,000 leaders in the next 10 years. Like many driven women, the tricky part for me is balancing my values and goals. I won’t compromise on keeping Family Above All, and that's been difficult at times as a business owner, wife, and mother/stepmother of five children in our blended family. My husband has been my anchor and my inspiration on this journey, speaking love and truth into me at every turn. I’m grateful to have an incredible teammate who enables me to stay grounded and present. He has a servant's heart and truly enables me to operate in the highest and best use of my time and talents. Whether it’s making my coffee every morning (there are five ingredients and a blender involved, so it's a whole thing), or acting as my sounding board when I'm grappling with big decisions, he is truly my anchor in all aspects of this beautiful life we've built together over the last ten years.

How do you measure success and how has that changed over time?

It’s amazing how our measures of success change over time. Last year I read nearly 50 books and about 90% of them were business, professional, and personal development oriented. First, I don’t recommend reading that many books consecutively, because it’s virtually impossible to implement and evaluate the utility of that many strategies in a short period of time. However, there were a few that created a paradigm shift in how I truly measure growth. Specifically, The Gap & The Gain by Sullivan/Hardy, The EOS Life by Wickman, Essentialism by McKeown, and The Go-Giver Marriage by John & Ana Mann.

Like many young professionals, I previously gauged success on external factors like promotions, financial gains, and recognition. However, over time I have come to realize that the money, the role, the recognition is “easy come, easy go”. Anyone with a strong work ethic and determination can accomplish those things.

I now appreciate that there are far greater accomplishments in this life beyond the trappings of financial success. I've come to measure success based on my core values- Family Above All, Maximize, Build Others, and Abundance Mindset. These values have provided me with a comprehensive framework to evaluate my achievements and a matrix to make key life decisions. They help me predict and assess, not just the tangible outcomes, but also the impact on my well-being and the fulfillment of my purpose. For me, true success is finding a harmonious blend of achieving my goals while maintaining a balanced and purposeful life.

At the end of my day, I want to leave every person I encounter better than I found them in some big or small way. Anything from complimenting a person’s outfit when I pass them in the grocery store aisle, to helping a leader better support their team, to influencing the success of an entire organization; these are all examples of how I maximize my gifts and leave my fingerprints on the people I touch. Most importantly, I want my children to see how one person is enough to make a big, positive difference in this world.

What has been the most important lesson you've learned as an entrepreneur?

There is no "top of the mountain" for people like me. Every time you think, "This is it! I did it! I arrived!" there is another peak that presents itself for ascension. And I just can't say no to it. If there is a chance to grow another level, I'm going to pursue it. Another truth is that there are going to be big, emotional, complex problems at every level of success. This mindset of "If I just earned this much money, if I could just write one more book, if I just win these accounts and then it will all be good" is a lie. Biggie was right: Mo' money, mo' problems.

But the good news is that I have survived every climb and every problem so far, and I have faith that I will continue to not just survive but thrive through those moments. The Gap & The Gain was a powerful book for expanding my mindset on how I approach, process, and move through all circumstances, the good, the bad, and the ugly. I highly recommend this for literally everyone I meet, regardless of your entrepreneurial inclination. It actually had an unexpected, huge impact on how I parent my children.

At the end of your career, what is the legacy that you hope to leave behind?

The concept of legacy speaks to me at a deep, heartfelt level. One of the methodologies I leverage with my clients is Strengths-based Leadership. My professional background includes training by some of the best coaches at the Gallup organization, who specialize in this type of work. One of my identified natural strengths is Significance, which, for me, means I want to leave my mark on the world. My intention is to use my positive energy to change the world one person at a time. I work with 10-12 companies at a time, but the greatest feedback I receive is that they all feel like I am working only with them. Even as a Fractional executive, they embrace me as part of their team.

What's next? Do you have any exciting ambitions for the future?

I'm currently in the early stages of writing my first book. It's been on my heart for years and the timing finally feels right. That’s more of a personal passion project, but I finally have the time to bring my vision to life.

I’m fortunate to be in an exceptional second marriage, but I’ve been through some dark and difficult times. There are strikingly few resources for divorce apart from counseling and self-help books. I want to write a book that normalizes all the ugly parts and gives women fellowship in the moment and hope for the future. I’ll probably want to do another photo shoot just for that book, likely with some of the incredible women I’ll be interviewing for it!

My Fractional CXO business is on the verge of some interesting expansion. It’s incredible- when you open your mind and energy to it, the opportunities come flooding in! There are some new partnerships on the horizon that could create beautiful growth opportunities for other coaches as well because, frankly, it’s never been about me. It is always about leaving others better and stronger than I found them. I’m ready to unlock my next level of growth, and it’s all going to happen by creating opportunities for others.

Kristyn Drennen is a Fractional CXO, Certified Exit Planning Advisor, and keynote speaker serving small-to-medium businesses across the USA. Learn more at Kristyn Drennen Coaching.

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