Research has shown that mid-level leaders are vulnerable to both loneliness experiences at work and poor sleep quality at home. Although generally employee emotional experiences at work are connected to their sleep problems at night, few studies have specifically identified the individual characteristics that may trigger lonely individuals to experience more sleep problems. Specifically, from a self-determination perspective, the loneliness experience often includes a sense of helplessness and a perceived lack of control or autonomy. We hypothesized that lonely individuals with a high sense of control would be more at risk of sleep deprivation. Focusing on the often stressful mid-level management contexts, we conducted a three-wave time-lagged survey with 200 mid-level leaders in the United Kingdom. We found that workplace loneliness is positively related to sleep problems. In addition, this positive relationship was amplified when mid-level managers reported a higher need for control. In addition to establishing the loneliness-sleep problems link in work settings, our findings imply both theory and practice to assess high-risk employees and to develop interventions to manage the need for control for improved leader well-being.