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The ERP Organizational Change Journal

Episode 41 

Taking Smart Risks: How Sharp Leaders Win when Stakes are High

by | Sep 15, 2021

by Dr. Jack G. Nestell | The ERP Organizational Change Journal Podcast

About this Episode

In this episode, we discuss our guest’s book, “Taking Smart Risks: How Sharp Leaders Win When Stakes Are High“ with  Mr. Doug Sundheim.

We examine how Mr. Sundheim helps organizations by breaking through organizational obstacles that prevent effective organizational execution and performance.  Mr. Sundheim will share with us how organizational leaders and teams can change the way they think, reflect,  interact, and collaborate to get things done. We will discuss why leaders should be vulnerable, leading with love, storytelling, rewarding for failure, creating a “smart risk culture”  and more. 

We are pleased to have Doug join us to share his book, experience, and work. 

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Doug Sundheim

Doug Sundheim

Doug Sundheim – Advisor and coach to CEOs, senior leaders, and teams | Author of Taking Smart Risks | HBR & Forbes contributor

Doug Sundheim is an executive advisor, consultant, and coach with over 20 years of experience in growing businesses and helping others do the same. He works with leaders and teams of Fortune 500 companies and entrepreneurial firms to help them maximize their effectiveness.

More About Doug


Doug started a 100-person catering company in his early 20’s, followed by several years in the marketing consulting field where his clients included Sony, M&M/Mars, Mattel, and Motorola among others. In 2000, Doug co-founded The Sundheim Group to help leaders and their teams break through the barriers that stifle performance in themselves and their organizations.

Doug draws on his experience as a leader and entrepreneur to help clients find practical solutions in complex situations. He co-creates each of his engagements with his clients to ensure alignment with organizational goals. Common areas of focus include leading effectively, driving change, and delivering measurable impact.

A frequent speaker on a variety of business topics including leadership, organizational culture, & strategy, he has delivered talks at Columbia University, New York University, The Society for Human Resources, and The World Research Group conference. In 2005, Doug co-authored The 25 Best Time Management Tools and Techniques, which has been translated into 5 languages and continues to be a bestseller. His latest book, Taking Smart Risks, was published by McGraw-Hill in January 2013.

Doug’s clients include American Express, Citigroup, Morgan Stanley, Apollo Management, Swiss Re, Chubb, Spectrum, University of Chicago, Harvard Management Company, Weill Cornell Medicine, Publicis Group, and the United States Federal Reserve System among others.

Doug holds a BS in Environmental Psychology from Cornell University and an MA in Adult Learning & Leadership from Columbia



Taking Smart Risks: How Sharp Leaders Win When Stakes Are High

Episode Resources and Links


The Sundheim Group

Get the Book “Taking Smart Risks: How Sharp Leaders Win When Stakes Are High

Doug on Substack

Connect with Doug

  • Phone number – 212-931-8554
  • email address –


Episode Highlights & More about this Episode


06:06 What should leaders be vulnerable to? Isn’t that a leadership weakness? What can you share with our listeners on this point?

08:01 You state on your website that one of your core principles is “You need to hold people’s feet to the fire. Do it with compassion. Do it with love. Do it with respect. But don’t let people off the hook, including yourself.” Please tell us more.

11:36 You mention on your site that one of your core principles to remember for leadership is that “People need stories. Who are we? Why are we here? Where are we going? How will we get there? Leaders can’t bury the answers to these questions in strategy documents. They have to tell the stories—often. That’s what makes people care.” Can you share more about this idea of storytelling?

16:05 What inspired you to write your book “Taking Smart Risks: How Sharp Leaders Win When Stakes Are High”?

18:15 In your book, “Taking Smart Risks” you discuss how “Smart risk-taking involves passion, planning, active learning, communication, and the ability to embrace and reward the inevitable small failures along the way.” Are you suggesting that we reward organizations for failure? Why?

21:35 Smart risk taking can be easier said than done. I know this is a large and loaded question, but from a high level, what are some general tactics and practices to encourage smart risk-taking?

25:04 Your book teaches how to “build learning into everything”. Can you share more with our listeners and maybe some examples on how to do that exactly?

27:51 In sharing the purpose of your book on your website you state that “Accept that you have to live with failure—since it is an inevitable by-product of taking risks, even smart risks. Failing smart is the best way to learn”. And one way to do this is by creating a “smart risk culture”. High-level, but can you provide some pointers to create a “Smart Risk Culture”?

31:34 As fellow practitioners, we absolutely benefit from learning from our colleagues and friends, both “boots on the ground” as well as researchers. How would you summarize this conversation? That is if you had to distill your work into 3 or 4 sentences, what would you say to ERP organizational change practitioners?


Sundheim, D. (2020). When crisis strikes, lead with humanity. Harvard Business Manager.

Sundheim, D. (2020), We Need Leaders Who Have The Courage To Love

Denning, S. (2005). The leader’s guide to storytelling: Mastering the art and discipline of business narrative (Vol. 269). John Wiley & Sons.

Sundheim, D. (2013). Taking Smart Risks: How Sharp Leaders Win When Stakes are High: How Sharp Leaders Win When Stakes are High (EBOOK). McGraw Hill Professional.

Palmer, P. J. (2017). The courage to teach: Exploring the inner landscape of a teacher’s life. John Wiley & Sons.

More Related Episodes from TheERPocj 
  • Episode 3: Transformative Leader – Mr. Ron J. West

  • Episode 10: Leadership: Myths, Behaviors, and Practice – Mr. Gary A. DePaul

  • Episode 9: Team Performance and Organizational Development – Dr. Timo Sandritter 

  • Episode 24: Slow Down to Speed Up and Thrive in a 24/7 World – Dr. Liz Bywater

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