When a project to roll out diabetic retinopathy cameras landed on Benjamin Dolewski's desk, he kept it. Dolewski, a senior director at Sentara Medical Group in Virginia, had run the same kind of rollout at a previous job and was confident it would work.

In hindsight, he said, it belonged with one of his managers, someone who hadn't yet led a project of that size or quality impact and would have grown by owning it. Keeping it was the comfortable choice. For a director whose job now included building other leaders, it was also the wrong one.

That pull toward familiar work is a common way the move from operations manager to executive stalls. Medical groups tend to promote the people who run things well — the manager who rebuilds the template and settles the upset physician before lunch. The bigger role asks for different work, and organizations rarely spell out what that work is.

Dolewski, who addressed the transition in his session at the 2026 MGMA Annual Conference, described his own move into a director role as arriving without a playbook. As a manager, he had largely been left to work on his own — “let Ben cook,” as he put it. Feedback rarely went beyond “good job.” When he later took an emotional intelligence assessment, his independence score came back high enough to be a problem. He wasn't pulling the right people into decisions or asking for their input.