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Posted By Keara McGraw


Since 2000, Dr. Loretta Caldwell Thompson has served as Chief Executive Officer of Caldwell Management Solutions (CMS). CMS is an innovative, dynamic, forward-thinking company designed to help organizations take a hard look at themselves from the inside out. Known as “The Management Dr.,” she brings a fresh perspective to board trainings, strategic planning, and program evaluation processes. Her humor adds a spark to any meaningful conversation. Previously, Caldwell served for more than 18 years as Executive Director of a nonprofit organization working with female offenders and their children. She expanded its capacity from a daily community residential living site of 18 female offenders to more than 100 female offenders serving in several residential facilities and in community programs. She worked with local politicians, judges, zoning officials and community associations to establish these capacities.

Years in St. Pete


Organizations involved in

I serve as 2nd VPp of St Petersburg Chapter of Delta Sigma Theta sorority; President of the Pinellas County Urban League Guild; Member of the Board of Directors and Secretary for the Daystar Life Center; and a member of Leadership St. Pete Alumni Association.

What gets you out of bed every day?

The sun: there’s something about the sunlight that motivates me. I love the sun and water. I moved to the Sunshine State so that I could experience the sun more often.

Why St. Pete?

Honestly, the sun and the water. Additionally, its left-leaning political philosophies, southern hospitality, and progressive avenues of growth are of great interest to me. Plus St. Pete reminds me of a mini-Washington, DC.

What is one habit that you keep?

I give reverence to God every day … Thanking him for my blessings and covering and the angels He has sent to watch over me.

Who are some people that influence you?

Ancestors, like my grandparents and parents as well as my late husband and brother have influenced me. I truly remember things that they have said or done that has impacted my life, my thoughts, and my actions. Politically: President Obama and VP Kamala Harris before they had those titles. Obama for his community advocacy work and Harris on her advocacy for people impacted by the predatory home leading practices. Professionally: I have been influenced by leadership gurus like John Maxwell (various leadership styles), Jim Collins (Good is the enemy of great), and Oprah Winfrey (lack of the fear to fail). Businesswise: I am influenced by Ursula Burns, past CEO of Xerox; Cheryl Polote-Williamson (multiple streams of income and collaboration).
Spiritually: God’s teachings and spiritual leaders of megachurches like Dr. Jamal Harrison Bryant, Bishop T.D. Jakes, Joel Osteen, Rick Warren, and my DC Home Pastor, Bishop Michael V Kelsey Sr. Socially and Emotionally: I have a great group of friends, male and female, that keep me grounded. They speak the truth to me and are quite supportive in my times of ups and downs.

What is one piece of insight - a book, methodology, practice - that you would share with our readers?

Always plan or plan to fail! Be prepared for the opportunity, and do not wait until the opportunity comes to get prepared!

What is one thing you wish you knew about your work 3 years ago?

The transition of moving from the North to the South and its impact on my business. Understanding the culture; understanding the norms of the people that I would be associating with; and the ability to collaborate more where all can win!

What’s next?

I am rediscovering my passion in a number of ways. Personally: I am intentionally working on my physical health to be in alignment with my mental wellness. I feel good. Things are happening. I am appreciating life even more and the activities and people that I am involved in. Therefore, I want to ensure that my physical health is in a good place. Professionally: Perfecting my teaching skills to include other areas to add value to others and businesses, such as mental health first aide certification. The pandemic has allowed me to attend more seminars and webinars to learn, develop, and grow! And I love it all. Businesswise: I will always be working to increase my company’s capacity; staying true to my core values in helping and assisting organizations to grow through mentoring, coaching, and training; networking and growing my circles of new and interesting people and groups; working collaboratively with other businesses and professionals.

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