Lyndsey Olson
Lyndsey Olson is a strategic legal and leadership advisor, co-founder of Grey Matter Strategic Partners, and former City Attorney for the City of St. Paul. With more than 20 years of experience spanning law, military service, and public-sector leadership, she specializes in governance, crisis management, and helping organizations navigate complex, high-stakes decisions. She works with executives, boards, and government leaders to strengthen decision-making, manage risk, and guide organizational change.
Before founding her consulting firm, Olson served for eight years as City Attorney of St. Paul, where she led a team of over 100 professionals and oversaw all legal operations for one of Minnesota’s largest municipalities. Her tenure included managing major public crises, advancing innovative public safety programs, and advising city leadership during periods of significant national scrutiny and reform. Prior to that, she held senior legal roles in the Minnesota National Guard, including General Counsel and Staff Judge Advocate for the 34th Infantry Division, and is a veteran of Operation Iraqi Freedom.
Olson holds degrees in philosophy, law, and strategic studies, including a master’s from the U.S. Army War College. Today, she combines her military, legal, and executive experience to advise organizations through Grey Matter Strategic Partners, focusing on leadership development, crisis response, and strategic execution in complex environments.
• Certified Virtual Facilitator
• Mitchell Hamline School of Law - JD
• Attorney of the Year 2012 (Minnesota Lawyer)
• Attorney of the Year 2025 (Minnesota Lawyer)
• In-House Counsel of the Year 2015
• 40 Under 40 (2013)
• Litigation Counsel of America Fellow
• The Boardroom
• Ramsey County Bar Association
• 34th ID Assn, Commander’s Own Chapter
• Association of the United States Army, Vessey Chapter
• Minnesota State Bar Association Military & Veterans Affairs Section
• National Guard Association of the United States
• Hennepin County Bar Association
• Corrections
• Central Minnesota Legal Services
• EMS US
• Ramsey County
• The Infinity Project
What do you attribute your success to?
My success is built on a strong foundation of education, military service, and a lifelong commitment to helping others. I studied philosophy, attended law school, and earned a master’s degree in strategy, which equipped me with the critical thinking skills I use throughout my career. Over 24 years in the military—including 15 years on active duty and a deployment to Iraq during Operation Iraqi Freedom in 2008–2009—I developed leadership, resilience, and crisis management abilities, with my desire to serve first sparked by a volunteer experience after a tornado in southern Minnesota. As a JAG officer and later a city attorney, I focused on supporting military families and communities during times of need, continuing a family legacy of service rooted in my father’s and grandparents’ military careers. Today, I carry that same purpose forward through my consulting work, coaching, mentoring, and board service.
What advice would you give to young women entering your industry?
My advice to young women entering law is to stay committed to what genuinely interests you and not be discouraged by others, even when they try to steer you away from the profession. Law school and practice can be challenging and very different experiences, but perseverance matters if this is truly your passion. I also encourage avoiding the temptation to pursue roles based solely on money or prestige, because that often leads to burnout and dissatisfaction. Instead, focus on areas of law that align with your values and interests, as that is what leads to a more meaningful and fulfilling career.
What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in my field right now is transitioning from leading a large, established government organization to building a business from the ground up, where I now manage everything from operations and technology to client development with a very small team. Unlike my previous role overseeing more than 100 employees across multiple divisions, entrepreneurship requires wearing many hats and adapting to constant, day-to-day challenges. At the same time, it presents strong opportunities, especially in government contracting and leveraging certifications as a disabled veteran-owned and woman-owned business, which open new doors for growth.
What values are most important to you in your work and personal life?
Service is the most important value in my work and personal life, and it has been shaped by both family legacy and lived experience. With a father who retired as a Lieutenant Colonel and grandparents who served in World War II, I grew up with a strong tradition of military service, but it was a volunteer experience after a tornado in southern Minnesota that truly clarified my purpose and led me toward the National Guard. From there, my work as a JAG officer providing legal support to military families around the time of 9/11, and later as a city attorney, reinforced my commitment to using my skills to make a meaningful difference in people’s lives. Today, I continue that same focus through consulting, coaching, mentoring, and board service, where I remain dedicated to contributing to the community and finding fulfillment through service.