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Building the courage to take risks

How to step up, stand out, and speak truth to power

Topic: Management/Business
Pamela Rucker

We’ve all worked long and hard to build our leadership brand, and we go to great lengths to protect it. Sometimes, though, the best way to solidify your trademark brand is not to protect what you’ve built but to promote new things that you can do—which requires the courage to take risks. The way you approach risk can dramatically impact the perception of you as a leader and when managed well, can open up doors of opportunity to broader roles.

In this practical, interactive, and results-oriented course, Pamela Rucker teaches you the dangers of playing it safe, how to use risk strategically to advance your career, and how to speak up in a confident way when situations require transparency and candor. You'll leave prepared to create a personal process to manage risk and use it to build influence in your organization.

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

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

  • Why risk is an important part of the leadership growth process
  • The intersection between risk and fear
  • How to accurately plan risk so that it works in your favor
  • How to use risk to stand out from your competition
  • How to speak truth in ways that create value

And you’ll be able to:

  • Evaluate your work environment and identify elements of risk
  • Recognize when you are being hindered by a lack of risk taking
  • Use a repeatable framework to build the courage needed to embrace risk
  • Diagram risky conversations so you are on the right radars of the right people for the right reasons
  • Develop the courage to take risks in a variety of situations

This training course is for you because...

  • You're a new manager with less than three years of leadership experience, and you need to understand the value of risk and overcome your fear of it.
  • You have five or more years of leadership experience, and you want to communicate your leadership agility by discussing the ways you've used risk strategically to successfully help your organization.
  • You work in a competitive business environment, and you're looking for ways to step up to new opportunities and stand out from your competition.


  • Experience working with teams or within groups (useful but not required)

Recommended preparation:

Recommended follow-up:

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 concept of risk and why we all care so much about it; the value of risk taking; why sometimes the best ideas and the best solutions are treasures only found through the odyssey of risk

Stepping up (35 minutes)

  • Lecture: The reasons we're normally afraid to take risks; the dangers of playing it safe; why doing risky things means that you'll fail many times; why you need individual and group risk taking in organizations
  • Hands-on exercise: Identify the issues you're afraid of at work; complete the “Playing It Safe” assessment, highlighting the repercussions of avoiding risk in your environment
  • Group discussion: Concerns about stepping up; the value of stepping out of the shadows
  • Break (5 minutes)

Standing out (35 minutes)

  • Lecture: Why you need courage to take risks around innovation and growth; how to measure risk through a risk framework; how to start using risk to your advantage to give you an edge over your competition
  • Hands-on exercise: Use the risk framework to assess your current risk opportunities and identify ways you can use risk to your advantage right now
  • Group discussion: Concerns about standing out from their peers at work; what smart risk looks like when it’s used to show leadership agility

Speaking truth to power (35 minutes)

  • Lecture: The times you must take the risk to speak up, even when you feel pressure not to do so; how to recognize when you need to deliver an unpleasant message; how to frame the conversation; how to speak in ways that create value and help you feel safe
  • Hands-on exercise: Using the “Speak Truth to Power” framework, create a plan of action to identify who you need to have conversations with, specify what you should be talking about, and note how you will change the way you approach challenging conversations
  • Group discussion: Concerns about speaking up about issues at work; how to approach critical conversations with leaders and peers.

Wrap-up and Q&A (5 minutes)