This paper looks at the timing chosen by CEOs to exercise their stock options and to sell their shares of stock compared to the timing chosen by other top executives in the firm. We first present a model that predicts when CEOs should exercise their options and/or sell their shares, and when other top managers should. Using a tournament approach we find that other top executives should exercise their stock options later than the CEO. We test this model using an unique data set of Canadian companies from 1993 onward. Our results seem to support the theoretical model as non-CEO executives seem to exercise their stock options about a calendar year later than the CEO. Moreover, non-CEO executive a more likely to exercise when a new CEO has been appointed, confirming our tournament model results.