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#1 Wall Street Journal Best-Seller

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The pit of success​

How Leaders Adapt, Succeed, & Repeat


“Insightful and relevant…The Pit of Success gives leaders—and all people—the ability to reinvent, reimagine, and transform their future success. The engaging stories and useful tools make The Pit of Success helpful for day-to-day actions. Backed by theory, grounded in research, and drawing on experience, this is a must-use set of ideas.”


Dave Ulrich, #1 Most Influential Global HR Leader and New York Times Best-selling author

What you need is Learnable

When you face a challenge bigger than your experience, you often feel doubt and confusion. In these moments, everyone wonders, “Am I good enough?”

Our research shows that this struggle is normal for people at all levels. Fortunately, you are not in your job because you have all the answers. You are in your job because you have what it takes to find answers. The Pit of Success provides you a path to learn faster and climb to the next level.

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praise for the pit of success

“Powerful and practical…The Pit of Success is a must read for today’s leaders. I highly recommend it! You will never have to worry about plateauing as a leader or an organization if you apply these principles. Jennings and Leishman give the mindset, skillset, and toolset every leader needs to accelerate their learning curve and grow their business.”

Sean Covey, President, FranklinCovey Education and

New York Times Best-Selling Author


“Relatable and applicable for everyone…no matter what stage you are in life or in your career. The Pit of Success takes the concept of the innovator’s dilemma to a personal level and helps leaders to let go of what got them here and learn to lead for the new marketplace. This is going to be so helpful for so many people.”

Andrea Leszek, Executive Vice President and Chief Operations Officer, Technology, Salesforce


“Highly recommend! The Pit of Success highlights, and helps anyone overcome, a critical dilemma: that your core skills and expertise can become a roadblock to overcoming your next challenge. The principles shared here will help you become a life-long learner who can overcome each new challenge.”  

Jeff Dyer, Best-Selling Author, The Innovator’s DNA


“Learning to learn is truly the master skill we all need. Jennings and Leishman’s offer powerful and practical tools to help us move through the pit of success with mastery and develop the mental strength we need to tackle the next set of challenges.”

Liz Wiseman, Best-selling Author of Multipliers and Rookie Smarts

“Real personal growth requires leaving behind the very things that got you the success you’ve enjoyed so far, demanding that you take on unfamiliar tasks and roles that can feel scary and unrewarding.  Jennings and Leishman’s delightful new book helps you realize that everybody faces the same challenges and feelings – not just you  – and offers straightforward practices to help you navigate.” 

Rita McGrath, Best-selling author of Seeing Around Corners: How to Spot Inflection Points in Business Before they Happen.

“The Pit of Success gives leaders and their teams what they need to grow faster. I have personally experienced how the tools and concepts push teams through their pit of success to become more aligned and strategic.”

Garry Wiseman, Chief Digital Officer, Nautilus


“Compelling and enlightening...the kind of book that stays with you over time. I have found as much benefit in both my personal and work life as any book I have read. I wish I would have understood this at the start of my career but fortunately I can apply it to my next pit of success.” 

Bernie Tobin, General Manager, Natera--Precision Medicine

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Dave Jennings

Dave Jennings accelerates leadership results. In the trenches with executives and managers implementing global and local change initiatives, he understands the risks, stresses, and opportunities. 

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Amy Leishman

 With a background in Organizational Psychology and Strategy, Amy Leishman combines a research background with consulting experience to help leaders accelerate their learning. 

Ways to Embrace the Pit Of success


Customizable Pit of Success Keynotes for your conference, retreat, luncheon, or meeting. 

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Virtual webinars available with state-of-the art LightBoard Studio.

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The Pit of Success workshops are designed to accelerate your career and results. We provde Individual contributors, manager, and executive programs.


Individual coaching is available to help you and your business through the pit of success.. .




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