Lyndsey Olson turns crisis leadership into strategic advisory work

Former Saint Paul City Attorney and retired Army Colonel Lyndsey Olson is bringing decades of experience in public safety, governance and crisis response to Grey Matter Strategic Partners. Her new work focuses on helping leaders navigate complexity, manage risk and turn decisions into action.

Why it matters: - Olson’s career spans military command, city government, public-safety reform and crisis management. - Grey Matter Strategic Partners is built for leaders who need more than recommendations. It is aimed at organizations facing high-stakes decisions, operational breakdowns, public controversy or major change. - Olson’s background suggests a practical value proposition: legal strategy, leadership judgment and implementation can be combined to improve outcomes in complex situations.

What happened: - Lyndsey Olson is now co-founder and partner at Grey Matter Strategic Partners. - Olson previously served as Saint Paul City Attorney for eight years. - Olson retired as a Colonel after 24 years in the U.S. Army Judge Advocate General’s Corps. - Olson works with mayors, CEOs, boards, executive teams, nonprofits, government agencies and other leaders facing risk and strategic inflection points. - Olson’s profile and consultation details are available through Influential Women and Grey Matter Strategic Partners.

The details: - As Saint Paul’s chief legal officer, Olson led an office of more than 100 employees, including about 55 attorneys. - Olson advised the mayor, city council, departments and senior leaders on litigation, governance, public safety, employment, development, policy and institutional risk. - Olson helped create ETHOS, a pre-charge diversion and restorative-justice program meant to provide accountability while reducing future justice-system involvement. - ETHOS participants had substantially lower recidivism rates than traditional prosecution populations. - During the civil unrest after George Floyd’s murder in May 2020, Olson worked on a protest-response model centered on procedural justice, de-escalation, constitutional policing and protection of First Amendment activity. - Over more than a year of protest activity, Saint Paul saw overwhelmingly peaceful demonstrations, comparatively low arrest numbers, limited use of force and no civil-rights claims from protest interactions. - Olson’s tenure also coincided with Saint Paul reaching its lowest number of pending lawsuits in several decades. - Olson helped build the Office of Neighborhood Safety and recruited Brooke Blakey as its first director. - The office’s work included Project PEACE, a community violence intervention strategy for people at highest risk of shooting or being shot. - By 2025, Saint Paul had seen an approximately 70 percent reduction in gun violence from peak levels. - Olson’s military service included a deployment to Iraq during Operation Iraqi Freedom and senior advisory roles on legal, operational, personnel and strategic issues. - Olson was the first woman to serve as General Counsel for the Minnesota National Guard and Minnesota Department of Military Affairs. - Olson also served as the first female Staff Judge Advocate of the Army’s 34th Infantry Division. - Olson co-chaired a review of the Minnesota National Guard’s sexual-assault prevention and response systems and helped author the findings and recommendations. - Olson earned degrees from Stephens College, Hamline University School of Law, the U.S. Army Judge Advocate General’s Legal Center and School, and the U.S. Army War College. - Olson’s honors include two Minnesota Lawyer Attorney of the Year awards, an In-House Counsel Award and a 40 Under 40 distinction. - Grey Matter Strategic Partners is a woman-owned and disabled veteran-owned business serving government, nonprofit and private-sector clients.

Between the lines: - Olson’s career reflects a consistent theme: solving problems by redesigning systems, not just reacting to symptoms. - Her work suggests that legal risk, public trust, operational effectiveness and policy goals can be aligned instead of treated as trade-offs. - The move from a large public office to a smaller consulting firm also gives Olson direct experience with the operational demands faced by the leaders she advises. - The firm’s name signals its core thesis: many difficult decisions are not black and white, and effective leadership depends on judgment inside ambiguity.

What’s next: - Olson is positioning Grey Matter Strategic Partners as a long-term advisory platform for organizations confronting crisis, governance challenges, leadership transitions and implementation problems. - The firm will continue emphasizing legal analysis, strategic thinking, organizational dynamics and execution support. - Olson’s consulting work is expected to build on her experience in public safety, military leadership and complex institutional change.

The bottom line: - Olson’s story is less a career pivot than a continuation of the same mission: helping institutions make better decisions when the stakes are high and the path forward is unclear.