Trade-offs exist between timing of grassland habitat management activities (e.g., weed and brush control) while also ensuring other conservation objectives (e.g., grassland bird reproductive success) are met. On land set aside for grassland conservation (e.g., lands enrolled in the U.S. Department of Agriculture Conservation Reserve Program and some state and federal wildlife management areas), federal and state agencies set time frames for land management based on avoiding disturbance of grassland bird nests. However, recent calls for considering the needs of dependent fledglings in conservation plans imply a need to evaluate whether current time frames are adequate. We used initiation and end dates for 3,257 nests of 8 obligate grassland bird species in Illinois and Wisconsin and a simulation approach for fledgling survival to estimate the potential proportion of active nests at risk when management (e.g., mowing, fire) occurred on the 1st and 15th day of May, June, July, and August during the breeding season. Management during June had the potential to impact 24–61% of nests, depending on the species. Management during July had the potential to impact 4–52% of nests, depending on the species. If disturbance occurred during August, proportionately few active nests were at risk for any species (0–9% of nests on 1 August, 0–<0.5% on 15 August). Potential proportions of fledglings at risk from management were greatest in July for 7 of the 8 species (7–18%). Our study suggests that on lands where a primary conservation objective is to increase or ensure survival of grassland birds, delaying management activities until August could be beneficial for protecting both grassland bird nests and fledglings.