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7 Questions on Leadership with Caroline Dennis

Name: Caroline Dennis

Title: Founder/Executive Director

Organisation: NuJourney Foundation

Caroline Dennis is an example of leadership driven by purpose. She has devoted herself to creating organizations that embody purpose, passion, and intentional effort. Caroline has recently launched, Coaching with Caroline, and Caroline's Coaching Academy under the Chayil brand. These ventures provide invaluable online courses, empowering individuals to reframe success.

Caroline is also a Financial Service Manager for a financial service firm. As the leader of the NuJourney Foundation, a non-profit organization, she focuses on promoting financial literacy and entrepreneurship in underserved communities. Through her efforts, Caroline empowers individuals and families to achieve financial independence and create a promising future for themselves and their communities. Her mission is to create financially healthy individuals who in turn create financially healthy families with financially healthy businesses in thriving communities.

Caroline's educational background includes an undergraduate degree in Corporate Finance and a graduate degree in Project Management. Her dedication to personal and professional growth is evident through her completion of the Yale School of Management Executive Leadership Program. Furthermore, Caroline holds impressive certifications, including being a Certified Financial Education Instructor, a Certified Practitioner of the Entrepreneurial Mindset Profile through Eckerd College's Leadership Development Institute, and a Master Trainer Financial.

Adding to her list of accomplishments, Caroline recently published her book, "Take the Journey: The Powerful Steps to Owning Your Story." This book serves as a testament to her expertise and provides readers with practical guidance on embracing their journey to success.

Outside of her entrepreneurial pursuits, Caroline actively contributes to her community. She serves as a Program Advisor for the MUMA School of Business, Design Thinking Program at the University of South Florida and as the Chairperson for the Apopka Area Chamber of Commerce's Young Entrepreneurial Committee. Her commitment to leadership excellence and community service has been recognized through various honors, with her most recent being an inductee into the 2023 Marquis Who's Who.

Caroline Dennis exemplifies a leader who leads with purpose, dedication, and commitment to empowering others. In all her endeavors, she strives to uplift individuals, organizations, and communities.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Caroline's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

As a leader, one of the most challenging things I have encountered is finding balance. Carving out time to ensure my professional priorities do not neglect my commitments. However, finding that balance means understanding the challenge of prioritizing tasks, allocating time, and appropriately managing my energy to be fully present wherever I am needed. This balancing act has been both demanding and rewarding. It has taught me the importance of self-awareness and understanding my limits. It has made me realize that taking care of myself is not a selfish act, but rather a prerequisite for effectively leading and showing up for my team.

2. How did you become a leader? Can you please briefly tell the story?

I believe since I was a child, I have always had inherent leadership qualities. Thus, the transition of leadership from my personal to professional endeavors was seamless. I opened a company in my 20’s and from there made the jump into Corporate America, where I found my way into management and leadership roles. I learned to embrace the role of a leader because I understood true leadership involves empathy, integrity, and a deep understanding of the people you lead. Being recognized as a leader is truly an honor, as it signifies that others identify with something within me that inspires them to follow or become part of my journey. I consider this recognition to be a genuine blessing and do not approach it with a nonchalant or cavalier attitude.

3. How do you structure your work days from waking up to going to sleep?

My days always begin and end the same way, in meditation, affirmation, and prayer starting at 6 a.m. It’s the quietness that leaves me with my thoughts to begin or end the day with intention or purpose. Once my quiet time is over, I try to get in some exercise to get my blood pumping for the action-packed day, I undoubtedly will face. Once I have refreshed myself, I turn my focus to the realities of priorities, meetings, and deadlines. No day is the same so from about 8 a.m. to 11 p.m.; I adjust or pivot my schedule to handle and maintain the many tasks that need addressing, this includes the corporate job and personal commitments with family and/or friends. The weekends are reserved for special work projects or DND time as well as much-needed rest, relaxation, and rejuvenation. I will admit once your passion meets your purpose time is an asset and not a liability.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

There are a few lessons that come to mind, but I will choose to share that authenticity is the anchor that grounds the message. People have a sixth sense of detecting the realness of authenticity. How you show up is sometimes just as important as the message delivered when you arrive. So, it is important to be fully present and deliver communication that cultivates a genuine voice, one that reflects your values, beliefs, and experiences. Be willing to show vulnerability, admit mistakes, and acknowledge your growth, if applicable. Authenticity is your superpower and your competitive advantage, embrace all of it, the greatness as well as the imperfections. It took me some time to develop into an authentic leader, but once I embraced the power of me, all of me, I became a better person and thereby a better leader, in my opinion.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Jon Gordon's book, "One Word," while it is not directly focused on leadership, it offers valuable insights for both personal and professional development. This book simplifies setting intentions with one simple word. Initially, I used this to replace resolutions at the start of the new year. I would choose what I wanted to accomplish that year and add the one word that would dictate my actions, attitudes, and endeavors. In past years I have used the words intentional, commitment, consistency, declutter, grace, motivate, etc. Now, not only do I create a new word at the beginning of the year, but I also use this for new projects, new professional relationships, and meetings. This practice sets clear measures, fosters accountability, and helps me maintain focus throughout the year. Moreover, I extend this approach to my teams, urging them to choose their own One Word and then collectively choosing a word for the work we will accomplish together. By doing this not only are they invested, but I am invested in achieving successful outcomes with them.

6. If you could only give one piece of advice to a young leader, what would you say to them?

The best advice I can give is, to learn the power of grace for others and yourself. Grace is a powerful asset. Trust me, you will need it for your leadership journey. When you are able to exert grace in its true form, you become more gracious, inspirational, and aspirational; meaning you can stand in the moment and see beyond the current circumstance to a place of ascension and success. Additionally, I would advise not to be consumed with filling someone else’s shoes, they won't fit. Understand your value and use that as the foundation of your leadership journey!

7. What is one meaningful story that comes to mind from your time as a leader, so far?

Early on in my career, I learned a valuable lesson about the significance of communication within a team. There was a particular team member who had been reassigned from another team, and I was given the responsibility of mentoring them before considering their potential release. I saw this as an opportunity, but first, I knew I had to understand where the disconnect between their performance and the team's expectations lay.

To begin, I sat down with this individual to comprehend their current deficiencies. As I shadowed their work, it became abundantly clear that the directions provided were being interpreted differently. This revelation emphasized the importance of truly understanding someone's perspective before attempting to guide them effectively.

By taking the time to devote some attention to their world and comprehend their viewpoint, I was able to redirect their actions. This experience served as a profound lesson, highlighting that effective communication plays in fostering a successful outcome. Not everyone comprehends messages or instructions in the same manner, even if the communication or training methods seem clear to you.

Consequently, my experience taught me to be intentional in my efforts to establish communication standards. Recognizing that individuals have varied ways of understanding and processing information, thus tailoring the communication approaches accordingly. A one-size-fits-all approach simply won't suffice when it comes to leadership. For some, you may have to verbally convey the message and others may need a visual diagram, the goal is always to set a standard of success for all stakeholders.

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