Taught to Succeed – Not How to Fail

This did not work. That worked. Understanding how to fail is to understand how to pick yourself and your team up and be stronger for it.


Nothing is perfect.  Every decision is a lesson that opens perspective on the next.  All great leaders make bad decisions (yes, you’re included in here).  It could be as simple as choosing the wrong lane in heavy traffic only to come to a complete stop, while the lane on the right continues to steadily roll along.  It could be designing a team structure that didn’t work and hurt communication.  It could be forming a team for an important challenge, only to realize the team was comprised of the wrong individuals. It could be many things.


Why are we afraid of failure? What we don’t see when someone fails is they are closer to success.  Their idea might be years ahead of it’s time.  The environment might not be ready.  Or it could just be a bad idea.  The nugget to remember here is that eliminating what doesn’t work, brings to focus what does or what can work. There is a pattern here.  The most insightful and brilliant minds, have failed and failed BIG. How do you compare? What have you done that has been a total flop?

  • “Akio Morita – Morita co-founded Sony, a multi-billion dollar company. But the company’s beginnings were not so rosy. Their first product was a rice cooker, but it burned the rice. However, this didn’t stop them from moving on to building bigger and better things.


  • Evan Williams – Before co-founding the social media giant Twitter, he founded a company called Odeo, a podcasting platform. Soon after, Apple announced that the iTunes store would include a podcasting platform, making Odeo obsolete.


  • Fred Smith – While studying at Yale University, Fred Smith presented a business idea to his business management class that received a nearly failing grade. The idea was for a parcel service that could deliver packages overnight. Smith ignored the grade and founded FedEx.


  • Richard Branson – Even the fifth richest person in the U.K. didn’t get to where he is now without a few failures along the way. Along with his famous Virgin Records and Virgin Airlines, he also developed Virgin Cola and Virgin Vodka. The fact that you don’t recognize them says it all.


  • Soichiro Honda – Honda initially applied for a job at Toyota as an engineer, but was turned down. Being jobless, he started making scooters at home, which he sold to neighbors. With the support of his family, he founded Honda, the world’s largest motorcycle manufacturer and one of the most profitable automakers.


  • Walt Disney – Disney was fired by an editor because, “he lacked imagination and had no original ideas.” His first animation company went bankrupt and it’s said that he was turned down hundreds of times when he sought financing for Disney World. The Walt Disney Company makes average revenue of U.S. $30 billion annually.” (6)


If you are not afraid to fail and remove all negative fear, what is left? What is left is the possibility you may in fact succeed.

There are 1,000’s of book and articles on why leaders fail.  Ok, great–this can help identify some signs that are correlated to potential failures.  But what when you do fail.  You made a bad call.  How do those books help now?  You already identified the bad call and need an immediate approach to get back up and charge forward.   You lost confidence.  Your organization lost confidence. What book is there now to help?


Campbell et al. in the 2009 Harvard Business Review article “Why Good leaders make Bad Decisions, captures this well, “The reality is that important decisions made by intelligent, responsible people with the best information and intentions are sometimes hopelessly flawed (4).”  The most successful leaders and visionaries are not afraid to fail–they are afraid of not trying.


Executive leaders are accepting new roles and broader responsibility.  The ability to acknowledge a bad decision and call yourself on it, is the definition of an authentic leader.


5 Steps When You Fail

  1. Accept the Current Situation– Denial does not empower. Take ownership for your role and the larger your role the more ownership for the failure you must take (legit or not).


  1. Hold Yourself Accountable– Teams are uncertain, organizations feed off information from leadership. State the facts: a mistake was made, I own it, and we’ll together make a plan to correct this. State the reason for the issue (facts), don’t mentioned the excuses.  At this point no one cares.


  1. Safeguard Against Your Biases– We all have stereotypes, ideals and beliefs that impact our judgement, that’s normal. Recognize this and make a decisions cognizant of your prior experience to ensure it doesn’t create blind spots on your next decision.


  1. Communicate– Reach out to those involved and acknowledge that a new approach is coming and that feedback is welcomed to formulate the go-forward plan. Triage and determine the criticality: stop, adjust or restart fresh (2).


  1. Identify a Plan Owner– Establish a single person accountable for the plan, and provide several named supporting resources to ensure the plan comes together and has support (3).


Every decision brings success closer. Trust your gut and move your organization forward decision by decision.  The difference between a mediocre team and an amazing team is the sequence of wise decisions which leaders make.





  1. Hyacinth, B. (2014). Leadership Lesson: The Wisdom of Failure | Brigette Hyacinth | LinkedIn. Retrieved from https://www.linkedin.com/pulse/leadership-lesson-wisdom-failure-brigette-hyacinth


  1. Llopis, G. (2012). 5 Things Failure Teaches You About Leadership. Retrieved from http://www.forbes.com/sites/glennllopis/2012/08/20/5-things-failure-teaches-you-about-leadership/


  1. Mckeown, L. (2013). What to Do When You Fear Your Leadership Is Failing. Retrieved from http://www.inc.com/les-mckeown/what-to-do-when-you-fear-leadership.html


  1. Campbell, A., Whitehead, J., & Finkelstein, S. (2009). Why Good Leaders Make Bad Decisions – HBR. Retrieved March 29, 2015, from https://hbr.org/2009/02/why-good-leaders-make-bad-decisions/ar/1


  1. (2012). How Close Are You? Image, retrieved from http://www.thegreatnessmind.com/2012/11/04/how-close-are-you-the-dont-quit-poem/


  1. Truong, L. (2015). 13 Business Leaders Who Failed Before They Succeeded. Retrieved from https://www.americanexpress.com/us/small-business/openforum/articles/13-business-leaders-who-failed-before-they-succeeded/




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Peter is a healthcare business and technology executive, recognized for Digital Innovation by CIO 100, MIT Sloan, Computerworld, and the Project Management Institute. As Managing Director at OROCA Innovations, Peter leads the CXO advisory services practice driving digital strategies. Peter was honored as an MIT Sloan CIO Leadership Award Finalist in 2015 and is a regular contributor to CIO.com on innovation. As Head of Information Technology, Peter was responsible for Connecticut’s Health Insurance Exchange’s (HIX) industry-leading digital platform transforming consumerism and retail oriented services for the health insurance industry. Peter championed the Connecticut marketplace digital implementation with a transformational cloud-based SaaS platform and mobile application recognized as a 2014 PMI Project of the Year Award finalist, CIO 100, and awards for best digital services, API, and platform. He also received a lifetime achievement award for leadership and digital transformation, honored as a 2016 Computerworld Premier 100 IT Leader. Peter is the author of Learning Intelligence: Expand Thinking. Absorb Alternative. Unlock Possibilities (2017), which Marshall Goldsmith, author of the New York Times No. 1 bestseller Triggers, calls "a must-read for any leader wanting to compete in the innovation-powered landscape of today." Peter also authored The Power of Blockchain for Healthcare: How Blockchain Will Ignite The Future of Healthcare (2017), the first book to explore the vast opportunities for blockchain to transform the patient experience. Peter has a B.S. in C.I.S from Bentley University and an MBA from Quinnipiac University, where he graduated Summa Cum Laude. He earned his PMP® in 2001 and is a certified Six Sigma Master Black Belt, Masters in Business Relationship Management (MBRM) and Certified Scrum Master. As a Commercial Rated Aviation Pilot and Master Scuba Diver, Peter understands first hand, how to anticipate change and lead boldly.