Having leadership skills (LS) may increase an individual’s chances of ascending to a higher rank in hierarchical social structures, which can, in turn, provide the resources needed to support a partner and/or a child. Nevertheless, research on the association between LS and family formation processes (marriage, fertility) is scarce. We explore the prospective association between LS and marriage/completed fertility for 650941 Swedish males. Poisson regression and linear probability models are applied, including sibling fixed effects models. Our findings demonstrate a positive association between men’s LS, as measured at the age of assignment to military service (17–20 years), and their probability of marrying by age 39 or older (depending on the birth cohort). Furthermore, among the men in our sample, we find that LS are positively linked with the number of children, and are negatively linked with the probability of remaining childless. These associations are only partially explained by education and income.