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ColumnsLeadership & ManagementSecurity Leadership and ManagementSecurity Education & Training

Leadership & Management

Going Down with the Ship

Three security executives offer insights from their own turbulent voyages.

By Michael Gips
Going Down with the Ship
mikkelwilliam / E+ via Getty Images
October 17, 2025

As the “unsinkable” vessel sank, the eight hired musicians on the Titanic famously played on to calm the passengers. Although they had no obligation to do so — they were not part of the crew — the octet went down with the ship.

Security leaders sometimes find themselves in a similar position, not in icy waters but within faltering organizations. Do they fulfill their duty as the vessel takes on water due to defunding, bankruptcy, liquidation, or political sabotage? Or do they leap into a lifeboat and let someone else secure the last deck?

Three security executives offer insights from their own turbulent voyages. One tried to repel the “pirates” of the Department of Government Efficiency (DOGE) but was overrun and cast off. Another was forced into a lifeboat while the vessel was still listing. The third fought off mutineers and external raiders until the hull finally gave way.

On January 20, 2025, U.S. Executive Order 14169, Reevaluating and Realigning United States Foreign Aid paused all U.S. foreign development assistance programs for 90 days. Secretary of State Marco Rubio expanded this suspension to encompass nearly all USAID operations, triggering a cascade of destabilization for non-governmental organizations (NGOs). At the National Democratic Institute (NDI), the news prompted Lisa Oliveri, then director of Director of Global Risk Management, Security, and Operations, to shift priorities.

“In early February, when the funding was still frozen and the trajectory looked like significant reductions in force across the NGO sector, I began planning out certain contingencies,” she explains. “I started thinking we were headed for a major drawdown.”

Colin O’Brien, then CSO of the U.S. Institute of Peace (USIP), picked up warning signs around the same time. In mid-February, the administration publicly referenced reducing “government inefficiency” and mentioned his agency by name. On March 14, after the board was fired and DOGE operatives arrived at headquarters, he knew the end was near.

“From that point on, it was just a question of how fast,” he says.

Meanwhile, Kirsten Meskill had been brought on to Bed Bath & Beyond in October 2021 to add security and business continuity to the existing loss prevention function. But, despite investments in long-term growth, the retailer started to falter. While Meskill expected security to be among the last functions standing, the unraveling came quickly and with little transparency. Executive departures, a CFO’s suicide, and the targeting of the company by an activist investor all compounded the pressure and contributed to the collapse.

“I never thought the function would go away,” she says. “Security is the one that closes the door and throws away the key.”

As collapse became inevitable, each leader locked in on what mattered most. Oliveri focused on the safe and rapid closure of more than 40 international offices across five continents.

“We had to balance security management with crisis response,” she says. “There were programmatic, legal, and funding factors in play, but we did what we could to support our headquarters and country teams.”

O’Brien’s role pivoted sharply to defense. He was directed to protect the USIP building, preserve critical systems, and buy time for legal remedies. After discovering that DOGE operatives attempted to flip his contracted guard force, he fired the entire team mid-crisis. With no guards remaining, he relied on physical lockdown protocols and shut down USIP’s computer network.

“Security generally relies on rules,” he reflects. “But when you're playing chess and they are playing hand grenades, that doesn’t work.”

Meskill managed a dwindling team amid growing threats and incidents, including ransomware, insider theft, stalking, and organized retail crime. “We were investigating allegations of employees ‘compensating themselves,’” she notes. At the same time, vendors closed in, demanding payment. Even security partners were not being paid. “People lost their will to protect,” Meskill laments. At one point, a senior executive from a security vendor showed up at corporate headquarters on a Friday at 3:00 p.m., demanding a check. “Some of the most significant challenges I’ve faced came in those final days,” she says.

For all three leaders, guiding a team through a shutdown required more than strategy. It called for clarity, empathy, and emotional stamina.

Sometimes, the most honorable thing a leader can do is stay at the helm as the ship founders, securing passengers and closing hatches.

Oliveri took a direct, candid approach. “There was no real precedent for this at this scale,” she says. “I encouraged the team to share their thoughts and concerns. We processed what was happening together.”

As layoffs unfolded, she wrote thank-you cards to every team member and remained present to support those still working.

Meskill’s leadership focused on helping staff reposition themselves. With her team cut from 70 to 10, she helped loss prevention professionals reframe their experience for broader security roles.

“I told them, you’re security leaders — just reword your resume,” she says.

At USIP, O’Brien had little time for coaching.

“I was fighting a five-alarm fire with a Super Soaker,” he says.

Yet even amid the chaos, he kept his team aligned on mission. Field offices received instructions to cease operations and shelter in place. The goal was to protect people and preserve the legacy, even as DOGE coerced internal IT staff to provide network access and stormed the building. On March 21, O’Brien was officially fired.

Though their organizations did not survive intact (only NDI remains afloat), all three leaders left with reputational credibility and hard-earned wisdom.

“I don’t have regrets about the way I finished,” Oliveri says. “The systems we built helped NDI navigate a serious crisis and the staff rose to the challenge. Focusing on mission and my teams got me through.”

When offered the chance to exit immediately after being informed of her layoff, she chose to stay and see things through, including a proper handover to the teammates who remained.

“I earned respect by being public about what happened,” notes O’Brien. “Elon Musk even said USIP was the most resistant agency to DOGE. I think I helped other agencies get smarter and more resilient.”

Meskill finds that her experience now sets her apart.

“I can talk about real-life crises that companies worry about but haven’t been through,” she says. “I bring a calm head to crisis and security leadership, and that’s a direct result of what I endured.”

When asked what advice they would offer to others facing a similar situation, the three leaders echo one another in values if not in tactics.

“Stay mission-focused,” Oliveri advises. “It’s not about one position. It’s about continuity. Create redundancies. Empower your staff. Support your team.”

“Prepare to lose,” O’Brien says. “But lose in a way that protects your people, your data, and your legacy. Back everything up. Prepay healthcare. Lawyer up early.”

“Let go of control,” Meskill suggests. “Your risks will shift. You’ll have to pivot from predictive to reactive. And you’ll need to think about external threats, angry vendors, and reputation management. Help your people move forward.”

Sometimes, the most honorable thing a leader can do is stay at the helm as the ship founders, securing passengers and closing hatches. Playing on, like the musicians of the Titanic, may not save the vessel. But it can make the end a little less chaotic, and the memory a little more dignified.

KEYWORDS: corporate culture security career security leaders security leadership skills

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Michael Gips is a Principal at Global Insights in Professional Security, LLC. He was previously an executive at ASIS International. Columnist image courtesy of Gips

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