Innovation & Insights

Executive Insights with Regena Frieden: Leadership Where It Counts

26 February 2026

Providence Health Plan’s (PHP) Chief Administrative Officer, Regena Frieden sat down with Candace Beeke, president and publisher of the Portland Business Journal, for a conversation about what leadership really looks like when it counts.

With more than 25 years of experience across nonprofit health plans and healthcare technology organizations, Regena oversees cross-functional teams that shape member, provider, and stakeholder experiences, guide organizational strategy, and ensure regulatory readiness. Her perspective offers a candid look at executive leadership grounded in humility, resilience, and human connection.

Living in the “Messy Middle”

As her scope expanded from functional expert to enterprise leader, Regena said her definition of leadership changed dramatically.

“When you’re coming up in your career, you own your expertise,” she explained. “When you get to be an enterprise leader, you step into something much more uncomfortable. It’s not about owning your domain – it’s about living in a messy middle.”

A self-described “recovering perfectionist,” she learned that letting go is part of growth. “You’re going to have to let balls drop, and that’s okay. Sometimes it’s better for someone else to pick it up so they can learn and grow.”

For Regena, what separates good leaders from truly effective ones is “the ability to live in that messy middle and lead when things are tough.”

Decisive, With the Discipline to Pause

Regena describes herself as naturally decisive. “I move really quickly,” she said. But experience has taught her the value of balance.

“You need to balance the facts and the data with urgency. There’s a point where you have to make a decision – but you also have to avoid analysis paralysis.”

At the same time, leaders must be willing to change course. “There’s lots of new information coming at us all the time. You can’t be afraid to stop a project and pivot.”

Inspired by Brené Brown, Regena emphasized the importance of naming change. “Just acknowledging what’s happening and how people are feeling can help bring them along when you have to make tough calls.”

Building Resilience Through Growth

Leading through industry headwinds requires reinforcing resilience daily. Regena believes people are stronger than they realize.

“We can do hard things. We’ve proven that,” she said.

At Providence Health Plan, leaders encourage teams to prioritize personal well-being while also adopting a growth mindset. “Every single thing we do is part of a tool you build in your toolkit. You can take that with you no matter what.”

Rather than focusing on fear, she encourages optimism grounded in purpose. “Isn’t it incredible to be living and working during this time – helping shape the future of healthcare?”

The Power of Being Local

As a regional, nonprofit health plan, Providence Health Plan’s approach is grounded in community connection.

“Healthcare is inherently local,” Regena said. “It’s built on trusted relationships – with your doctor, your hospital, your community.”

That commitment shows up in hands-on leadership. “All of us call members just to check in and ask, ‘How are you feeling? Is there anything we can do to help?’”

 

Those conversations provide insight no research report can replicate. “That direct feedback makes us a better health plan. It’s just part of how we do business.”

Owning Your Leadership

When asked what advice she wishes she had heard earlier in her career, Regena didn’t hesitate: “Own your leadership.”

“Leadership is a choice – not a title,” she said. “Don’t wait for someone to hand you an opportunity. You’d be surprised how many people are willing to open a door – but it’s your job to walk through it.”

And as for the myth that leaders must have all the answers?

“They don’t,” Regena said plainly. “The best leaders are the ones who ask the right questions to get the best outcome.”

Throughout the conversation, one word surfaced repeatedly: courage.

“Courage is important as a leader – especially right now,” Regena said.

In a moment of transformation across healthcare, leadership where it counts means embracing uncertainty, staying grounded in purpose, and never losing sight of the people at the center of the work.

Watch the full conversation on the Portland Business Journal website.