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Why smart leaders fail

Understanding and stopping behaviors that can derail your career

Pamela Rucker

Leadership is a journey filled with excitement, inspiration, and imagination. But more often than we’d like to admit, leadership also includes failure. Every day, bright and capable people fall victim to various levels of embarrassment and misfortune that can define their career. Sometimes their failure is obvious to everyone; other times it’s more private, eating away at their confidence and self-assurance. So what should you do when failure inevitably happens to you? It's an important question since the way you manage failure can determine how high you go in your organization, how wide your reach is across departments, and how strong your influence is over the people you work with.

Join leadership expert Pamela Rucker to learn what causes business leaders to fail, how to recognize the characteristics that precede failure, and how to stage a comeback if you have fallen victim to it. By the end of this practical hands-on course, you'll be able to create a personal process to manage the cycle of failure and use it to draw powerful lessons from failure to boost your expertise and define your resiliency as a leader.

What you'll learn-and how you can apply it

By the end of this live online course, you’ll understand:

  • Why leadership failure is so common
  • What causes business leaders to fail
  • How to accurately define and identify the different types of failure
  • How to learn from your mistakes and the mistakes of others
  • How to use failure as a stepping stone for success

And you’ll be able to:

  • Diagnose your own tendencies when working with others
  • Recognize the signs of impending failure so you can get ahead of trouble
  • Turn your failure experience into a useful part of your leadership narrative
  • Write a failure résumé that demonstrates that you know how to succeed
  • Follow a failure model that helps you recover and reclaim your personal brand

This training course is for you because...

  • You're a new manager who needs to understand how to anticipate and manage leadership failure.
  • You're an experienced leader who wants to communicate your broad view of the business by discussing both the successes and struggles that have impacted you and your organization.
  • You work in a competitive business environment, and you're looking for ways to redefine your image after struggling with setbacks in initiatives you've been identified with.


  • Experience working with teams or within groups (recommended)

Assignments to be completed prior to the course:

Recommended preparation:

About your instructor

  • Pamela Rucker is a featured speaker at CIO events in the United States, Canada and Europe. She has used her practical experience to provide executive education for numerous Fortune 500 firms, and has coached leaders at some of the world’s most recognizable brands and leading academic institutions, including Microsoft, NBC, Kaiser, Federal Reserve, Cisco and Chevron. Pamela chairs the Technology Advisory Council for St. Jude Children’s Research Hospital, serves as a CIO Advisor for the CIO Executive Council, and teaches a professional development course at Harvard University entitled Leading Through Digital Disruption. She runs an advisory services practice that focuses on executive leadership, digital leadership, and corporate reinvention. Pamela has a bachelor’s degree from the University of Richmond, a master’s degree from Harvard University, and has completed professional programs at Rice and Columbia.


The timeframes are only estimates and may vary according to how the class is progressing

Introduction (5 minutes)

  • Lecture: The reasons that leadership failure occurs; the types of failure you've experienced; the Failure Spectrum, which plots failure types on a praise-to-blame continuum

Understanding what causes leaders to struggle (25 minutes)

  • Lecture: The ROLE model—how you handle responsibilities, how you operate in their position, how you lead people and programs, and how you handle your emotions; how to use a leadership failure analysis to highlight personal challenges, so you can create a plan for addressing them
  • Hands-on exercise and group discussion: Complete part 1 of "Leadership failure analysis" worksheet, focusing on situations that are causing you to struggle in your role and how that impacts your delivery

Understanding the characteristics of leaders that are failing (25 minutes)

  • Lecture: Extending the ROLE model to look at the characteristics that leaders start to exhibit when they fail; ways that leaders can choose the wrong behaviors when dealing with others, which weakens their presence and erodes trust in their capabilities and decision making
  • Hands-on exercise and group discussion: Complete part 2 of "Leadership failure analysis" worksheet, focusing on behaviors that show up once you are struggling in your role and how that impacts your interactions with others

Break (10 minutes)

Staging a comeback (25 minutes)

  • Lecture: Ways that leaders can turn things around after experiencing a failure with their teams or stakeholders; profile and state awareness; how to be yourself (but be better at it); how to anticipate and recognize situations that can end in failure; ways to learn from your mistakes and how to use those mistakes as stepping stones for success
  • Hands-on exercise and group discussion: Complete part 1 of "Creating your comeback plan" worksheet, using the personal analysis created earlier in the program to create a plan of action to address the challenges that arise from failure

Telling your story (25 minutes)

  • Lecture: How to identify your own crucibles of leadership; how to build a failure résumé and a comeback narrative; how to use a storytelling model to personalize your account and demonstrate redeeming qualities in a negative situation
  • Hands-on exercise and group discussion: Complete part 2 of "Creating your comeback plan" worksheet, writing a failure résumé and finalizing your comeback story in a way that creates empathy from others

Call to action: Wrap-up and Q&A (5 minutes)

  • Hands-on exercise: Identify what you will start, stop, and continue doing in order to be successful; create a plan for communicating your failure experience