We have all questioned the impact of the past 20-plus months on our team members’ sense of belonging. Recently I had the opportunity to sit down with a leader who is driven by creating meaningful connections with those she serves inside her organization and in her community. Deena Ware has worked as a public servant for several municipalities throughout Polk County. For the past two years, she has served as the CRA & Neighborhood Programs Manager for the City of Winter Haven. Prior to that, Ms. Ware was the Town Manager for the Town of Dundee; the first minority woman to serve as a municipal manager in Polk County. She has a bachelor’s degree in Urban Affairs and a master’s degree in Public Administration from Wright State University in Dayton, Ohio, where she graduated Magna Cum Laude. Ms. Ware is also an adjunct professor at Polk State College, teaching online and hybrid classes on Foundations in Public Administration and Human Resources. She serves on the Central Florida Development Council board of directors and chairs the Community Stakeholders committee. Ms. Ware has three daughters and in her free time enjoys writing poetry, traveling, skating (she’s a self-described “former roller derby wannabe”), and yoga.
What are the most valuable leadership lessons you’ve learned in your first two years as the City of Winter Haven’s Community Redevelopment Agency and Neighborhood Programs Manager?
I’ve learned many leadership lessons in the past two years. The most important lessons are cultivating emotional intelligence, being my authentic self, allowing myself to be vulnerable, and becoming an active listener. Connecting in a genuine way is key to successful outcomes. My role must be to listen actively to each stakeholder, whether that stakeholder is an employee, another agency, or a community leader, and consider their issues with empathy and concern. The relationship is strengthened when I am my authentic self and can be vulnerable as we discuss difficult topics. When we have built a meaningful connection, stakeholders trust me to bring their issues to the correct audience so that progress can be made.
In what ways do you most want to contribute to Winter Haven’s future growth and development?
Winter Haven is fortunate to have outstanding leadership. Our city manager is top-notch and, together with our city commission, is committed to creating effective change and protecting what makes our city great. Our current leadership has set a high standard for collaboration and innovation. We work closely with other groups like Main Street, the Economic Development Council, and the Chamber of Commerce, who are passionate about the future of our city. I want to strengthen and support that engagement while continuing to connect to new groups who share our vision. I want employees and the community to have a sense of belonging. We can accomplish this by continuing along the path of finding new ways to appreciate and celebrate diversity. The desire to connect with others in meaningful ways is hardwired into all of us, and I want to continue building on our progress.
What are the most notable life and work experiences that have shaped you as a leader?
Becoming a mother has had a tremendous impact on my leadership journey. The empathy and humility required, combined with the multiple roles you must play – listener, nurturer, advocate – have contributed greatly to how I show up as a leader. Being adopted into a multiracial family also shaped my leadership style. Even though I didn’t look like others in my family, I always felt loved and supported. I knew people were in my corner cheering for me no matter what happened. My goal as a leader is to provide that kind of support for each team member. I want them to feel connected to something larger than themselves and see how their work makes a difference in the world.
What is one piece of advice you have for women who are navigating a career change?
Don’t second guess yourself. Believe in your abilities and remind yourself that you are capable of more than you think. Women tend to second guess their ability to do more because of their many roles: wife, mother, friend, and daughter. We pour into others, and we neglect ourselves. There’s a time and a place for nurturing and putting energy into relationships, but we also have the capacity to do more, stretch our abilities, and grow into roles we never thought possible.
Before being appointed to my first executive leadership position, I questioned whether I was smart enough or worthy of the role. I let negative thoughts creep in and create doubts about my abilities. I forced myself to work through those feelings and allowed my talents and passion for the job to take over. My success as the first woman of color to serve as a city manager in Polk County led me to my current role with City of Winter Haven.
What sense of purpose guides you in your life and work?
Being a positive role model to my girls guides my life and work. Regardless of the situation, they watch me and observe how I respond. I strive to have the humility to admit when I have made a mistake at work or at home and to be accountable for my actions. I want them to understand that circumstances don’t define success and that anything is possible with dedication and hard work. My girls have seen the ups and downs of my career, moved to different cities to support my various roles in city management, and even cheered me on when I wanted to be a badass and join the roller derby team! I hope that everything they have experienced with my career and our family life has made them feel loved, supported, and capable of accomplishing anything.
Emily Rogers, Founder & CEO of Emily Rogers Consulting + Coaching, is an executive coach, team coach, and keynote speaker. She strategically advises and supports individuals and organizations in growing and realizing their full potential in purposeful and balanced ways. You can connect with her at emilyrogers.com. Want to strengthen your capacity to lead with excellence and grow with purpose? Consider enrolling in Emily’s Leadership Development Programs.