How portable are top management skills? Should (and do) firms care about firm manager fit when they hire new managers? How is fit related to managerial “style”? We hypothesize that if firms and managers are matched with each other on the basis of fit on multiple dimensions, then firms that employ the same manager at adjacent points of time should have similar characteristics. We find strong evidence that firms that employ the same manager sort on a number of characteristics. Our empirical design ensures that these results are not explained by managerial style, or by moves among firms of similar size, or within the same industry. We construct a measure for the quality of fit. We find that a worse fit leads to less positive stock price reaction to the announcement of managerial appointments, lower managerial pay, and shorter tenure for the manager, suggesting that management skills do not necessarily transfer from one firm environment to another. We also find evidence that when the firm and the manager do not fit well, managers influence several firm-specific variables, consistent with managerial style.