In many closely-held enterprises, a forceful, clearly focused demonstration of executive authority is not only appropriate but also sorely needed. The assertive decision-making entrepreneur is one who points a closely-held enterprise in a specific direction and gets the organization moving. Heifetz describes this approach to executive functioning when he writes of people who tend to mobilize others to tackle tough problems. Entrepreneurship, in this mode, is not just a stance or perspective. It is an activity. Assertive entrepreneurs are seen as hard working and as people who also encourage others to work hard.
Specifically, their job is to identify the gap(s) that exist between the current and desired conditions of the closely-held enterprise. The current condition is often articulated or clarified by the thoughtful entrepreneur (discussed in later essay), whereas the state in which members of the enterprise would like the organization to be is often articulated or clarified, as we will see, by the inspiring entrepreneur. The assertive entrepreneur then tries to fill the gap between this real and ideal state. Alternatively, she tries to change the organization’s appraisal of its current condition (often discounting the contributions to be made by the thoughtful entrepreneur) or commitment to its desired state (often discounting the contributions to be made by the inspiring entrepreneur). In the first instance, the assertive entrepreneur would suggest that if we can’t get from where we are to where we want to be, then perhaps we should find somewhere else to go. In the second instance, he suggests that we either rethink where we are now, or ignore the information that we have so that we don’t get bogged down in despair or pessimism.