Diedre L. Windsor


Awards & Accolades

USA Today and Wall Street Journal Best-selling Author


Diedre L. Windsor is the founder of Windsor Group LLC, a professional services company based in Chevy Chase, Maryland.

Ms. Windsor, a native of Detroit, Michigan, enlisted in the US Army in October 1986. Upon completion of initial training she served in Germany and later at Fort Bragg, North Carolina as a paratrooper with the elite 82nd Airborne Division. In 1992 Diedre was awarded an Army Green to Gold Scholarship resulting in her transition from the enlisted to officer ranks. Diedre was commissioned a Regular Army Air Defense Artillery (PATRIOT Missile) Officer and later transitioned to the Adjutant General Corps (Personnel). As a military officer, Diedre’s assignments spanned from Kunsan, South Korea to Riyadh, Saudi Arabia and back to Fort Bragg, North Carolina where she served in a myriad of leadership roles until she retired from active service in September 2009 as a Major.

Upon retiring from the Military, Diedre continued along her public service path by joining the federal government. She assumed roles at the U.S. Department of Education first as Chief of Staff to the Federal Student Aid Chief Information Officer and Technology Office and later as Executive Officer and Director of Resources for the Officer for Civil Rights. After five years at Education, Diedre joined the career Senior Executive Service (SES) with the Department of Justice (DOJ), U.S. Trustee Program (USTP) as the Deputy Director for Management.

Diedre left the federal government in late 2016 to pursue entrepreneurship full time. Her company, Windsor Group, LLC, provides a host of professional services and business solutions to public and private sectors. The company’s core services include, Staffing, Training, IT Support and Program and Project Management.

Diedre graduated from Methodist University in 1994 with a Bachelor of Science in Political Science and from Webster University in 2011with a Master’s Degree in Human Resource Management.

In 2015 Ms. Windsor authored her first book, Leadership begins with Hello! Practical Principles of Leadership ~ A Hip-pocket Guide which focuses on practical principles of leadership.
Ms. Windsor resides in Chevy Chase, Maryland with her family.

Published Book

Business Success Secrets: Entrepreneurial Thinking That Works

Now a USA Today and Wall Street Journal best-seller!

BEYOND THE HIGHLIGHT REEL: AN HONEST, RAW AND REAL LOOK AT SOME OF THE BEST KEPT ENTREPRENEURIAL SECRETS! Buried beneath the impressive awards and accolades of each successful entrepreneur lies the hard-knocks story of the grit, determination, and resourcefulness it took to mount the summit of a dream. What you don’t know is just how much they learned along the way…. Business Success Secrets is a book written for entrepreneurs by entrepreneurs. Forget the flashing banners, false promises of overnight success, and the phony internet gurus – this is business insight straight from the source. Laying it all on the line, each author in the anthology has come together for one singular purpose: to bring you the undiluted truth of what it takes to make your business dream a reality.

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