Predicting Personality

Chapter Twenty-SixBECOMING AN EMPATHY-DRIVEN LEADER

Working with a team (or interacting with your family) is difficult enough, with all of the intertwined relationships, competing incentives, and random situations that life throws at each person. However, it's an entirely different ballgame when you're responsible for the group as a whole, and that requires a special skill set.

There are, of course, many aspects to effective leadership. Most of these general lessons are well-researched, thoroughly explored for hundreds of years, and assembled into clean, organized handbooks that are available with one click. However, most leaders still struggle and many fail to retain their team members (the phrase “Employees don't quit their job, they quit their boss” comes to mind). It's because groups of people are endlessly complex, and boilerplate advice is not enough. Truly great leaders are able to absorb the broad, tried-and-true bits of management wisdom and apply them to the unique dynamics of their team.

Personality differences often drive these dynamics. In high-pressure environments, those differences can create rifts, misalignment, and unpredictability. To navigate successfully, a leader must be first aware of the strengths, blind spots, and motivations of each person on their team—starting with themselves.

Brian Halligan and Dharmesh Shah, the founders of HubSpot who serve as the company's CEO and CTO, respectively, have built a business with over 56,000 customers, 2,000 employees, ...