2213 - How to Turn Your Business Blunders into Laughs and Lessons with William Holsten

The Thoughtful Entrepreneur

Goof-Proofing Your Business: In-Depth Strategies to Avoid Entrepreneurial Blunders

In this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with William Holsten, author of UH-OH! Avoid Unintentional Blunders That Derail Entrepreneurial Success and Goof-Proof Your Business. William brings decades of innovation leadership and entrepreneurial experience to the table, helping founders avoid the kinds of costly mistakes that derail even the most promising ventures. This episode is packed with actionable strategies that help entrepreneurs build self-awareness, minimize risk, and create resilient systems that catch problems before they happen.

Build Systems That Prevent Mistakes Before They Happen

William explains that while some mistakes are inevitable in business, many are completely preventable with the right systems in place. One of his most powerful tools, the pre-mortem, helps teams anticipate failure by imagining a project has already collapsed—then working backward to uncover what went wrong. Combined with the use of checklists—borrowed from high-reliability fields like aviation—this method equips business leaders to stay focused during high-stakes decision-making.

He also introduces Kissa Kongo, a physical and verbal confirmation technique adapted from Japanese railway safety protocols. By pointing and speaking aloud during critical tasks—such as verifying data or completing checklists—entrepreneurs can reduce mental fatigue and prevent errors that happen under stress. It’s a simple but powerful way to build consistency and attentiveness into everyday operations.

William’s broader philosophy centers on cultivating self-awareness and strategic reflection. He encourages entrepreneurs to pause regularly, assess their decisions, and implement feedback loops to avoid repeating mistakes. With supporting tools like scenario planning, progress tracking, and post-mortems, William empowers founders to build systems that anticipate, prevent, and learn from failure—without stifling innovation.

About William Holsten:

William Holsten is a seasoned innovation executive, author, and speaker with over three decades of experience leading transformative business initiatives. His book UH-OH! distills hard-earned wisdom into practical tools that help entrepreneurs identify and avoid costly, preventable errors. William's work is dedicated to empowering leaders to goof-proof their businesses and thrive under pressure.

About WilliamHolsten.com:

WilliamHolsten.com is the online home of the UH-OH! framework and a resource hub for entrepreneurs seeking to minimize avoidable mistakes. From free tools and downloads to speaking engagements and workshops, William helps founders and teams build resilience, improve clarity, and lead with intention.

Links Mentioned in this Episode:

• William Holsten’s Website
• William Holsten on LinkedIn
• Get the Book: UH-OH!

Episode Highlights:

• Why some mistakes are essential for growth—and others are entirely avoidable
• How to use pre-mortems and checklists to strengthen your decision-making
• The surprising business power of “Kissa Kongo” verbal confirmation
• Strategies for building team accountability without micromanagement
• William’s tips for staying sharp under pressure and avoiding burnout

Conclusion:

In a high-speed business world where founders juggle constant demands, William Holsten’s insights serve as a crucial reminder that awareness, systems, and a few simple tools can prevent the blunders that tank startups. From stress-proofing your leadership to training your team for clarity and consistency, goof-proofing isn’t just possible—it’s essential.

Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guest

More from UpMyInfluence:

We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.

Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.

What is your #1 Lead Generation BLOCKER? Take my free quiz here.

Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!