Although associations of sleep with workplace-related outcomes have been reported, little work has examined correlates of sleep among top business leaders. The present study examined whether business leaders (N = 379) reported a weekend–weeknight discrepancy in sleep duration, whether the discrepancy was reported throughout the age group in this sample, and whether it predicted performance ratings from supervisors or peers. Weekend–weeknight discrepancy ≥1/hr was reported by over half of this sample and did not appear to be age specific. Leaders with greater weekend to weeknight change in sleep duration received lower performance ratings from peers after controlling for age, health (number upper respiratory infections/year, Body Mass Index), stress, general life contentment, hours/week commute, days/year travel, and estimated average hours/week sleep duration. A predicted stronger association of sleep with an emotion-related performance dimension was not found.