The Leader’s Dilemma: Asking Tough Questions (Before Someone Else Does)


Powerful organizational and industrial forces can keep any senior leader from asking (or hearing) uncomfortable questions, creating an answer-centric environment at his or her own peril. They lose sight of the big picture of how things really are, ultimately missing opportunities for innovation and increasing the risk of disruption. This blind spot of what “we don’t know what we don’t know” rests at the core of what Hal Gregersen, Executive Director of the MIT Leadership Center, calls “The Leader’s Dilemma.” Gregersen says reconnecting with your organization begins with asking—and encouraging others to ask—tough questions. By becoming better questioners, leaders unlock new solutions, innovations and processes, ultimately creating greater business value.
This session is designed to help you identify the process and environment in which leaders are most able to expose catalytic questions—the questions that break down barriers and encourage transformational change. Learn ways to create a more question-centric environment in service of the leader and the business. Informed by interviews with hundreds of the world’s most innovative business leaders, it will help you:

  • Recognize and change the conditions in which you or others may habitually find yourselves that are limiting your success
  • Seek out the uncomfortable, risky and challenging in search of a line of inquiry that will lead to innovative products and process
  • Surface your own catalytic questions in real time by applying key questioning tools designed to disrupt the status quo and discover new sources of business innovation.

Keynote Presenter

Hal Gregersen

Executive Director of MIT Leadership Center, MIT