Cheryl Roberts, former Virginia Medicaid director, shares how investing in career staff and building leadership capacity can strengthen teams, sustain institutional knowledge, and drive lasting change.

When Cheryl Roberts got her first management job, her boss gave her a simple directive she’s carried ever since: make your bosses happy and manage your people. Most leaders, she’ll tell you, are reasonably good at the first part, even in Medicaid where “bosses” range from the governor to CMS to the state legislature and beyond. The second part, managing your people, is where the rubber really meets the road.

“The biggest return on investment you have,” she says, “is investing in your people.”

Roberts had worked in commercial insurance in New York before moving to Virginia where she joined the Department of Medicaid Assistance Services (DMAS), the state Medicaid agency, eventually holding the role of Deputy of Program and Operations. She spent years learning the program from the inside out and progressing to higher levels of leadership. Fifteen years later, she stepped into the Medicaid director role. Her experience first as a career staff member and later as a political appointee gave her a unique perspective on how organizational priorities, leadership decisions, and day-to-day operations intersect. Seeing the agency through both lenses helped clarify where she could have the greatest impact, particularly in strengthening staff development, building leadership capacity, and creating the organizational conditions needed for teams to succeed and drive lasting change.

For new executive leaders navigating governor mandates alongside a seemingly never-ending list of priorities, it can be tempting to focus almost entirely on the policy agenda. That’s understandable — the stakes are real. But Roberts is clear that this is where leaders leave the most value on the table. “The average Medicaid director only lasts 18 months,” she notes. “You’re not going to outlast the career staff. The question is whether they’re going to work with you or wait you out.”

The value of getting those relationships right shows up everywhere: the quality of information that reaches the director’s desk, whether people step up or step back in a crisis, and whether the agency is a place where talented people want to stay and grow. Roberts learned through both careful planning and a stark wake-up call that this investment has to be deliberate, and it has to reach further than most leaders expect.

Focus on the Executive Leadership Team

When she became Virginia’s Medicaid director, Roberts’ first priority was building more alignment across the executive leadership team (ELT). Before she could focus on broader organizational development priorities, she needed the ELT to strengthen their communication and work better across silos. To create more alignment, she employed a deceptively simple strategy:On Monday mornings, each ELT member received a text message listing five things, including key priorities for the week, issues to watch, and the critical meetings in the week ahead. “At first they thought it was crazy,” she said. “Then they told their peers it was a best practice — and they hated when I missed a week.”

The underlying logic of the “Monday Morning Text” was practical. It gave ELT members a shared orientation for the week, helped them prepare, and made it clear what mattered most to the director. One ELT member told Roberts it helped him know which days he needed to wear a suit. Another said it helped her plan who she needed to connect with before the week got too busy.

Roberts also worked hard to break down silos at the executive level by explicitly sharing the reasons behind requests and priorities. “The biggest thing leaders don’t do is make time for the ‘why’,” she said. “If you tell someone you need a specific report, but you don’t explain that the governor’s chief of staff is presenting on the issue, they don’t have the full picture.”

She made a practice of bringing the ELT together around shared work like the governor’s fiscal forecast, cross-cutting policy questions, and issues that required a whole-agency perspective, not the de facto coalition of independent functions. The goal was more ambitious than team building. It was to give people enough context and structured engagement so that the whole of the ELT was greater than the sum of its parts.

An Unexpected Gap

Even with a well-functioning ELT, Roberts experienced a moment that stopped her cold. A manager several levels below ELT members made a startling statement, “You don’t care about us at all.” Roberts was taken aback. She had been investing heavily in the ELT members by keeping them informed and building their capacity. The team was communicating, working more in alignment, and doing great work together. However, they passed along only what they thought was essential, and the context Roberts had worked to build wasn’t flowing down.

“Okay, I’ve got a problem,” she thought to herself. She reflected on her own growth within the agency and realized that while career staff are the agency’s institutional memory, relationship holders, and operational backbone, they often receive too little attention from shorter-tenured executive leaders. Roberts recalled her experience as a career staff person: “We used to say we were the B team, as in we’ll ‘be’ here after you’re gone.”

She responded by creating a monthly meeting specifically for division directors, around 30 people, structured around the top 10 biggest issues in the agency that month, both good and bad. The goal was to give them the same picture the ELT had, and to empower and encourage them to provide that same context to their teams.

Investing in Career Staff Development

Roberts also launched a formal eight‑month leadership and technical development program for division directors, partnering with the Center for Health Care Strategies’ National Medicaid Leadership Centerto design two parallel tracks: one on Medicaid fundamentals across program areas, and one on leadership and team effectiveness. Context and cross-functional awareness weren’t just important for the ELT; it needed to flow through the agency to all levels. And the division directors were key to that. As Roberts put it, “You need to understand the whole program, not just your piece.”

She expected resistance and got it. The program took time away from already full workloads. But she held firm. “I’m trying to build a Ferrari,” she said. “It only works if everyone understands the whole car, not just their tire.”

But despite the initial skepticism, it paid off. Division directors became more interested in what was happening beyond their own areas and stepped in to help when cross agency problems arose without waiting to be asked. “Action follows interest,” Roberts noted. Team tenures increased, and the agency built a reputation for strong teams and people development.

Prioritizing Individual Attention

The work didn’t stop at team development. Roberts was clear that investing in people requires both genuine care and strategic thinking. In addition to establishing the division directors’ meeting, she met individually with each of them. “Thirty-two individual meetings. It took ages, but I did it. I’ve learned that people need to feel validated and seen. And I listened and I wrote notes and I remembered.”  She made a point of understanding what mattered to each person, not just professionally, but personally.

Then she took action based on that knowledge. She set aside a budget for each of them to attend a conference of their choosing annually. This could be something meaningful to them, not just one that was required for their specific role. “It sounds funny, but it gave me currency,” she said. “Because I heard them. I saw them. And they knew it.”

She kept an eye out for where each person’s interests aligned with the agency’s direction and was creative about how to foster it. That could look like flagging an AI conference for someone interested in data or carving out time for an operations manager to work on a population health issue that they were personally passionate about. These investments kept people engaged and paid off when those capabilities and cross-cutting knowledge were needed.

More broadly, she invested in DMAS’ Public Service Recognition Week, with individual and team recognition across the department. Not only did this give employees at all levels something to put on their resumes, but it also reinforced that they were seen and valued.

Today, her message is consistent when advising new Medicaid leaders: you have to earn the trust of career staff, who are asking whether you’re worth their time. “But it’s worth the energy,” she said. “Every time.”

Key Leadership Takeaways

1. Orient the Executive Team Early and Often: Alignment starts with making sure the team knows what matters and why. A consistent weekly rhythm gives people a shared read on priorities. When leaders also explain the reasoning behind their asks, people can act on their own judgment instead of waiting to be told.
   
   
2. Build Whole Agency Awareness: Information doesn’t flow down automatically, even from a high-functioning executive team. Building institutional knowledge across the broader organization requires a dedicated structure and investment of time and resources.
   
   
3. Invest in Individual Attention: Understanding what each person cares about and where they want to grow is not separate from running a strong agency. It’s a critical piece of the puzzle. When people feel empowered, they are more likely to stay and to give their best to the work.