Influential Women Profiles Lyndsey Olson: From Public Service and Crisis Leadership to Strategic Advisory

SAINT PAUL , MN, UNITED STATES, August 25, 2026 /EINPresswire.com/ — Former Saint Paul City Attorney and retired U.S. Army Colonel brings decades of experience leading through crisis, institutional change, public-safety reform, and complex decision-making to Grey Matter Strategic Partners

Lyndsey Olson has spent much of her career working in places where the stakes are high, the facts are complicated, and there is rarely a perfect answer.

As a military lawyer, municipal executive, City Attorney, and now Co-Founder and Partner of Grey Matter Strategic Partners, Olson has advised leaders through war, civil unrest, institutional reform, litigation, public scrutiny, organizational change, and some of the most difficult decisions government executives are called upon to make.

That experience now shapes her work at Grey Matter Strategic Partners, where she advises mayors, CEOs, boards, executive teams, nonprofits, government agencies, and other leaders confronting complexity, risk, crisis, governance challenges, and major strategic inflection points.

Her approach is grounded less in abstract theory than in something developed over decades of practice: judgment.

“Organizations often know they have a problem,” Olson says. “The harder question is what to do when there are competing risks, incomplete information, multiple stakeholders, and no obvious path forward. That is where experience and judgment really matter.”

Building Systems, Not Just Solving Problems

Olson’s eight years as City Attorney for the City of Saint Paul provide some of the clearest examples of that philosophy.

As Saint Paul’s chief legal officer, she led an office of more than 100 employees, including approximately 55 attorneys, while advising the mayor, city council, departments, and senior city leaders on litigation, governance, public safety, employment, development, policy, and institutional risk.

But some of her most consequential work extended well beyond the traditional boundaries of a government law office.

Under Olson’s leadership, the City Attorney’s Office developed ETHOS, an innovative pre-charge diversion and restorative-justice program designed to provide meaningful accountability while addressing the underlying reasons people enter the criminal legal system. Rather than relying reflexively on prosecution, the program used restorative practices and community-based interventions to reduce future involvement in the justice system.

The results were significant. Participants in ETHOS experienced substantially lower rates of recidivism than traditional prosecution populations, demonstrating that public safety and accountability do not always require more punitive responses.

For Olson, the lesson was broader than the program itself.

“Good leadership asks whether the system is actually producing the result we say we want,” she says. “If it isn’t, you have to be willing to rethink the system rather than just keep doing more of the same.”

That willingness to redesign systems became a hallmark of her tenure.

Leading Through the Aftermath of George Floyd’s Murder

Few periods tested that philosophy more severely than the civil unrest that followed the murder of George Floyd in Minneapolis in May 2020.

Saint Paul experienced hundreds of demonstrations during a period of extraordinary national anger, grief, public scrutiny, and distrust of government and law enforcement. Olson worked closely with Saint Paul Police Department leadership and operational commanders to develop a protest-response model grounded in procedural justice, de-escalation, constitutional policing, clear rules for police intervention, protection of First Amendment activity, and disciplined decision-making around arrests and use of force.

The objective was not simply to reduce the City’s legal exposure. It was to build legitimacy into the City’s operational response.

That distinction mattered.

Over more than a year of sustained protest activity, Saint Paul experienced overwhelmingly peaceful demonstrations, comparatively low arrest numbers, limited use of force, and no civil-rights claims arising from the City’s protest interactions.

For Olson, the experience reinforced an idea she now brings to organizations outside government: legal risk, operational effectiveness, and public trust should not be treated as competing objectives.

“When lawyers are brought in only to tell an organization what it cannot do, we are leaving enormous value on the table,” she says. “The better question is how legal strategy, operational strategy, leadership, and organizational values can work together to produce a better outcome.”

That approach also helped fundamentally change Saint Paul’s litigation posture. During Olson’s tenure, the City reached its lowest number of pending lawsuits in several decades, reflecting an increased emphasis on early risk identification, preventative legal counsel, settlement strategy, and resolving problems before they became entrenched litigation.

Building a New Approach to Public Safety

Olson was also asked by Saint Paul Mayor Melvin Carter to help build one of the City’s most ambitious public-safety reforms.

The Office of Neighborhood Safety, initially established within the City Attorney’s Office, was designed to broaden the City’s response to violence beyond the traditional criminal-justice system. Olson helped build the organizational and legal infrastructure for the new office and recruited Brooke Blakey to serve as its first director.

The work ultimately included Project PEACE, an intensive community violence intervention strategy focused on individuals at the highest risk of shooting or being shot. The initiative paired community-based intervention and individualized support with focused law-enforcement efforts and coordinated city resources.

Rather than viewing violence solely as a policing problem, the strategy treated it as a complex system requiring prevention, intervention, accountability, relationships, data, and coordination across institutions.

By 2025, Saint Paul had experienced an approximately 70 percent reduction in gun violence from peak levels, one of the most significant public-safety improvements of Olson’s tenure.

The experience remains central to how she approaches organizational transformation today.

“You can have a great policy and still fail,” Olson says. “Implementation is where strategy collides with culture, personalities, incentives, budgets, politics, operations, and reality. Real transformation requires somebody to stay with the work long enough to translate an idea into a functioning system.”

That belief eventually became part of the foundation of Grey Matter Strategic Partners.

From Public Office to Grey Matter Strategic Partners

Olson co-founded Grey Matter Strategic Partners after leaving the City Attorney’s Office, bringing together expertise in law, public safety, leadership, organizational change, crisis management, strategy, and implementation.

The firm’s work reflects a simple premise: leaders facing consequential problems often need more than a consultant who produces recommendations. They need experienced people who can help them think clearly, challenge assumptions, identify risk, navigate stakeholders, and help turn decisions into action.

Through Grey Matter, Olson works as a strategic advisor, legal strategist, facilitator, executive thought partner, and crisis advisor.

Her clients span sectors, but the underlying challenges are often remarkably similar.

An organization may be facing a leadership transition, governance breakdown, public controversy, litigation threat, cultural problem, operational failure, public-safety challenge, or strategic decision where every available option carries some risk.

Olson’s role is often to help leaders understand the whole system rather than reacting to the most visible problem.

That perspective is reinforced by her training in Human Systems Dynamics, a complexity-based approach to understanding patterns within organizations and helping leaders act effectively when conditions are changing and outcomes cannot be perfectly predicted.

It also reflects lessons learned much earlier in her career.

Twenty-Four Years of Military Leadership

Before becoming Saint Paul City Attorney, Olson spent 24 years in the United States Army Judge Advocate General’s Corps, retiring as a Colonel.

Her service included approximately 15 years on active duty, a deployment to Iraq during Operation Iraqi Freedom, and senior assignments advising military commanders on legal, operational, personnel, organizational, and strategic issues.

She became the first woman to serve as General Counsel for the Minnesota National Guard and Minnesota Department of Military Affairs and also served as the first female Staff Judge Advocate of the Army’s 34th Infantry Division.

Military service placed Olson repeatedly in environments where decisions had to be made quickly, often with incomplete information and significant consequences.

It also taught her that effective leadership depends heavily on trust.

“You learn very quickly that people need to know both that you are competent and that you will tell them the truth,” she says. “Sometimes your job as an advisor is to say what others in the room may not want to say. But you also have to help the leader figure out what comes next.”

Her military work included helping lead a comprehensive review of the Minnesota National Guard’s sexual-assault prevention and response systems. Olson co-chaired the review board and helped author its findings and recommendations, examining not only individual cases but organizational culture, leadership, accountability, reporting systems, and institutional practices.

The work again required looking beyond isolated incidents to understand the system producing them.

A Career Built Around Service

Olson’s path to military service began unexpectedly.

While volunteering after a tornado in southern Minnesota, she found herself drawn to the sense of purpose that came from serving people during a difficult moment. Military service was also familiar within her family: her father served as a Lieutenant Colonel, and her grandparents served during World War II.

But Olson says her own experience ultimately gave service a broader meaning.

Over the course of her career, it has meant helping military families navigate legal problems, advising commanders during deployment, leading lawyers in municipal government, working with police officers during civil unrest, developing alternatives to prosecution, building violence-prevention systems, mentoring professionals, advising boards, and helping executives make difficult decisions.

That continuity matters to her.

“Service isn’t necessarily about where you work,” Olson says. “It is about what you do with the skills and opportunities you have.”

Her education reflects the same combination of law, strategy, and complex problem-solving.

Olson earned her undergraduate degree in Philosophy, Law & Rhetoric from Stephens College and her Juris Doctor from Hamline University School of Law, now Mitchell Hamline School of Law. She later earned an LL.M. in Contract and Fiscal Law from the U.S. Army Judge Advocate General’s Legal Center and School, where her thesis was subsequently published in The Army Lawyer.

In 2020, she graduated from the U.S. Army War College with a Master of Strategic Studies.

Her professional achievements have been recognized through honors including two Minnesota Lawyer Attorney of the Year awards, an In-House Counsel Award, and a 40 Under 40 distinction.

Her own career though has rarely followed a perfectly predictable path.

Moving from military service to municipal leadership and then from running a large government law office to co-founding a small consulting firm required another reinvention.

At Saint Paul, Olson led more than 100 employees across multiple divisions. As an entrepreneur, she suddenly found herself dealing with everything from strategy and client development to technology, contracting, operations, marketing, and the dozens of small tasks required to build a new business.

She embraces the contrast.

Entrepreneurship has given Olson a different view of the challenges faced by the executives and organizations she advises. It has also opened opportunities for Grey Matter Strategic Partners as a woman-owned and disabled veteran-owned business serving government, nonprofit, and private-sector clients.

Helping Leaders Navigate the Grey

The name Grey Matter reflects the kind of work Olson and her partners believe matters most.

Most difficult organizational problems are not black and white.

A board may have competing legal and fiduciary concerns. A public institution may need to balance safety with civil liberties. A leader may face several defensible options but no risk-free one. A strategy that makes perfect sense on paper may fail because the organization is not ready to execute it.

Those are the environments in which Olson has spent much of her career.

Through Grey Matter Strategic Partners, she now helps leaders confront those situations deliberately—bringing together legal analysis, strategic thinking, organizational dynamics, governance, operational experience, and implementation.

The firm’s philosophy emphasizes judgment over rigid methodology, execution alongside strategy, independent thinking, discretion, and recommendations grounded in operational reality.

For Olson, it is the natural continuation of work she has done throughout her career.

From the U.S. Army and Operation Iraqi Freedom to the Minnesota National Guard and Saint Paul City Hall, she has repeatedly worked inside institutions facing consequential decisions and profound change.

The title has changed.

The underlying mission has not.

It is still about helping people make better decisions when the path forward is unclear—and helping organizations emerge stronger on the other side.

Learn More About Lyndsey Olson or schedule a consultation.

Learn more through Lyndsey Olson’s Influential Women profile at:

https://influentialwomen.com/connect/Lyndsey-Olson

Or through Grey Matter Strategic Partners:

https://thegreymsp.com/about/lyndsey-olson

Influential Women

Influential Women provides a platform where women from all backgrounds can connect, share their perspectives, and create content that empowers themselves and others. Through storytelling, thought leadership, and creative expression, Influential Women amplifies voices that inspire change.

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Written By: EIN Presswire