In short
The Thoughtful Entrepreneur: Episode 2213 Summary
Episode Title: How to Turn Your Business Blunders into Laughs and Lessons with William Holsten Host: Josh Elledge Guest: William Holsten, Author of *UH-OH! Avoid Unintentional Blunders That Derail Entrepreneurial Success and Goof-Proof Your Business*
Overview In this episode, Josh Elledge interviews William Holsten, a seasoned innovation leader with extensive experience in avoiding common entrepreneurial mistakes. Holsten shares actionable strategies to help entrepreneurs recognize, prevent, and learn from costly errors that can derail their ventures.
Key Concepts and Strategies
- Importance of Systems in Preventing Mistakes
- Pre-mortem Technique: Imagining a project has failed and working backward to identify potential mistakes. This helps teams anticipate failure and proactively address risks.
- Checklists: Utilizing structured checklists borrowed from high-reliability fields (like aviation) to ensure all critical steps are completed, enhancing decision-making under pressure.
- Kissa Kongo - A Safety Technique
- This method, adapted from Japanese railway safety, involves physically pointing and verbally confirming critical tasks or data. This practice helps reduce mental fatigue and enhances attentiveness during high-stress situations.
- Cultivating Self-Awareness
- Holsten emphasizes the need for entrepreneurs to regularly assess their decisions and implement feedback loops to avoid repeating mistakes. Tools like scenario planning and post-mortems can foster a culture of continuous improvement.
Episode Highlights
- Mistakes: Inevitable vs. Preventable: While some mistakes are part of the growth process, others are completely avoidable with the right systems.
- Learning from Others: Holsten underscores the significance of observing and learning from the mistakes of others to mitigate risks in one’s own business.
- Building Resilience: Implementing strategies to maintain focus and avoid burnout, especially during high-pressure situations.
William Holsten's Background
- Holsten has over three decades of experience in innovation leadership, focusing on helping entrepreneurs identify and circumvent avoidable mistakes. His book, *UH-OH!*, serves as a resource for founders to develop resilient business practices.
Resources Mentioned
- [William Holsten’s Website](https://www.williamholsten.com/)
- [William Holsten on LinkedIn](https://www.linkedin.com/in/william-holsten)
- Book: *UH-OH!* - Available in various formats (paperback, hardcover, Kindle)
Conclusion The episode emphasizes that while mistakes are a natural part of business, many can be avoided with proactive strategies and self-awareness. William Holsten's insights equip entrepreneurs to "goof-proof" their businesses, fostering a culture of continuous learning and resilience.
Final Thoughts Listeners are encouraged to adopt Holsten's methodologies to enhance their decision-making and minimize errors, thus paving the way for greater success and sustainability in their entrepreneurial journeys.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:05Hey there, thoughtful listener. Are you looking for introductions to partners, investors, influencers, influencers, influencers, and clients? Well, I've had private conversations with over 2 ,000 leaders asking them where their best business comes from. I've got a free video you can watch with no opt-in required where I'll share the exact steps necessary to be 100 % inbound in your industry over the next six to eight months with no spam, no ads, and no sales. What I teach has worked for me for over 15 years and has helped me create eight figures in revenue for my own companies. Just head to upmyinfluence.com and watch my free class on how to create endless high ticket sales appointments.
0:51Also, don't forget, the thoughtful entrepreneur is always looking for great guests. Go to upmyinfluence.com and click on podcast. I'd love to have you.
1:05With us right now, it's Bill Holston. Bill, you are an author. You're a speaker. You're a workshopper. You're found on the web at williamholston.com. Your new book is called, uh-oh, Avoid Unintentional Blunders that Derail Entrepreneurial Success and Goof-Proof Your Business. By the way, thank you so much for your volunteerism with SCORE as a mentor. Love the organization. So grateful for organizations like SCORE. But, Bill, it's great to have you. I'm really, really glad to meet you and glad to be here. Thank you, John. Yeah, yeah. Well, listen, before we kind of get going and talking about uh-ohing through the world, what are you doing when you're not working?
1:45Like for fun? What are you into lately? I don't know if you're watching anything in particular or just anything you're kind of geeking out on. Three things. My wife and I, we love to travel and we'll be in France to visit the new Notre Dame and visit Normandy on 4th of July this year. we enjoy movies together when there's the blockbusters out there and mission impossible is coming out looking forward to that and obviously to relax at the end of the day we're watching just the the cop and hospital dramas on tv just it's a relaxing time you know are you watching the pit no i haven't started the pit yet okay we we've we record the network ones and watch all those until the exhaust this month is the end of the season for what we watch then will get into the pit and the ones who've been waiting to get started on.
2:30Yeah. Yeah. In terms of hospital dramas, that one's pretty good because it's, it's kind of like, it's a little bit, if you've seen the bear, like in the kitchen, you're just super, I mean, it's not as intense like that, but I think that they really strove to just be, this is as real as possible of like what it can be in a very high stress ER situation. Folks don't scream and swear at each other as much as they do in the bear, but it still kind of has that vibe of like, you feel like you're embedded with them a little bit. So yeah, pretty cool stuff. All right. Well, Bill, let's talk about the work that you do in the world.
3:06So, you know, obviously you're an author. Tell me about your work today. And I know you have a long and storied past with Bayer Healthcare as a senior director, but talk about your work today, please. Okay. In 20 seconds, in four seconds, I was a marketer that an innovator with a global multinational company. And while I was doing that, I was having my side gig of inventing and marketing carnival games. And in that 10, 12 years, we screwed up so many times with making dumb mistakes. I said, I have to do something about this. In my day job, I was a workshopper coming up with problem solving and new product ideas for consumer health products.
3:47And those skills got translated in how to not make mistakes. That's what the book's about. But what I'm doing now and why I'm talking to you now is my mission is to help entrepreneurs succeed by talking about the dangers of dumb mistakes because nobody talks about them and providing simple risk reducing tools to help avoid making them. So the book is out at some point. I'm just beginning my company. I'm looking to speak and be hired for workshops to help people use those tools to reduce the risk to their small businesses. Yeah. Well, okay. So let's balance this whole idea of being afraid of making mistakes, making mistakes.
4:34Are making mistakes good? Are making mistakes bad? Can you address that? Because I think there's a lot of voices on all sides of that topic. Oh, yeah, yeah. Making mistakes and having a culture that embraces mistakes and a learning culture is absolutely the fantastic way to go. It inspires people to do their best without worrying about screwing up. What I'm talking about is ways to protect by avoiding the ones you could avoid. So instead of allowing mistakes and forgiving them and learning from them, yes, that's important. There are some mistakes that you can absolutely avoid in the beginning.
5:19And it comes from the realization of where mistakes come from. James Reason, Cambridge professor, wrote a book about human error. And behind that is a lot about slips and lapses that are caused when you are under stress, exhausted, distracted. There are ways you can focus better so that you won't make mistakes. The tools that are usable help you learn more about yourself. What are the patterns? so you can be aware of your own patterns, about your customers so you don't make mistakes in dealing with them by learning more about their experiences, about your company so you can use imaginary exercises like a pre-mortem to imagine your business has failed and then figure out what did happen imaginatively and then come back and fix those things before they happen.
6:17And a fourth set of tools is looking at others' mistakes. Warren Buffett said, it's good to learn from mistakes, but it's better to learn from others' mistakes. I've translated that into tools in the book that tell you how to do that. But when you see in the news that somebody dropped a Super Bowl trophy or they make dumb mistakes that are in the news, there are tools you can use to observe and understand those and then think and apply what does that mean for your business. The most dramatic one I wrote about was a skydiver in Pennsylvania years ago who was hired to film another pair of skydivers coming out the plane after him.
7:02They agreed on it. He bought himself a new camera, strapped it on. He jumped out of the plane first, and they gave each other thumbs up. The couple jumped out, the instructor and the student, and they opened their parachute. They pulled their ripcords, opened the parachute, and it was a beautiful shot. This guy, Ivan McGuire, went to reach for his parachute, ripcord, and only then realized he'd forgotten it. And he actually fell to his death. It's dramatic and tragic and makes you say, ah. But the lesson for a small business is think about your business. What one thing, if you ever forgot it, could be very damaging to you.
7:38I think of the urban one-store retailer who at night leaves his business and forgets to lock the door. and has a lot of theft overnight, or a chef who left the pilot light on and the restaurant burns down. These are dumb mistakes. If you think smartly and be more aware, you can avoid many of them. I'm sure it's no guarantee, but if you put them to use, you can get there. You know, I love the analogy of the pilot that has the pre-flight checklist. And a lot, I mean, everything on that list is just it could be at the subconscious level for them if they've been flying for any length of time right they could do it in their sleep they could do it their eyes closed they could do it unsedated right they they've got the muscle memory but yet you know it's i think it's it's pretty well known that you know when you've got a pre-flight checklist you you very oh was it in japan i don't know if you know this story too i think it was the the subway did this story sound familiar so it was the subway trainers famously have a check uh you know and and then double check every single process on that and because i'm gonna have to find this story because it was remarkable and i heard it in a book not too late not too long ago But just this value, you know, the value of having checklists.
9:08I remember, you know, even for something like going running when I was training for my marathon, you know, if you're going to be running long distances, there are just some things you have to, you just have to plan in advance. You got to make sure, gentlemen, your Band-Aids are on your nips. Otherwise, you're going to have a rough time. You're just making your shoes all kind of squared away. You've got your goo. You've got your water. You've got your electrolyte. You've got everything there. The things that you might not be thinking about now, but an hour into your run, you're going to be very grateful you didn't forget that.
9:43But I literally, for something so simple as going for a run, I literally printed something out just so I could visually process that before I went out. And my research told me that making good checklists is an art and a science. You mentioned the airline industry. Yes, there's a pre-flight checklist. There's when something goes wrong checklist. The other big place where they happen are operating rooms. A book I read talked about operating rooms. if they don't do the checklist beforehand, that's how you get, and afterwards, that's how you get the scissor or the tape left inside of the patient, or they did something dumb.
10:20The art of a good checklist, and this is one of the tools in my book, is making it simple and making it usable by, if it's not just yourself, your team, to list only the essential things that if you forgot them, it's terrible. Because if a list is four pages long and in single space, nobody's going to pay attention to it. So it has to be actionable. You know, a lot of this too, I think for any of us who have been in business for any length of time, regularly, or at least I hope we do regularly update our SWOT analysis. And we do SWOTs on, you know, various aspects of our business. And the one that I always pay most attention to is the T-box.
11:05You know, it's like, what could possibly go wrong here. It's not that I'm forecasting doom and gloom. It's just, you know, to me, if I plan in advance, and you'll see this a lot in public relations for those who do crisis comms, crisis communications. And so a good crisis communications professional, they will spend their time thinking about every possible thing that could go wrong and make with the executive team, make decisions on what will we do if this happens. And I've had some friends with some pretty big organizations and have heard some stories. But it's nice to make those decisions in advance.
11:51When you have a clear mind, you can think objectively. And quite frankly, you can prepare. You can build the dam a little bit better. Absolutely. It's scenario planning. And the premortem tool in the book synthesizes some of the learning I read about pulling it together and imagining what could happen and then prioritizing which of these are most likely to happen with the biggest impact. And you focus on those things in advance so you can be creative to keep them from happening in the first place. um and to is there a point where you know our safety is a bit too much like how do we how do we know when we might be a little bit too conservative or a little bit too much of a worry warrant here to being uh analysis a paralysis by analysis right exactly exactly so we're not taking any action the the the pre-mortem one has you say okay you'll think of probably a hundred things, which two are the most important for your patients to, because they're most likely to happen or the most likelihood is to really impact you.
13:00If, if those things happen, it's, it's prioritization that helps you get around that. The story that I was talking about earlier, but the Japanese practice, it's known as Shisa Kanko and it's translated as pointing and calling. That's right. So now that, okay. So, so this is, it's, so I'm just reading a little bit here. I got from AI here. It's a powerful checklist like safety ritual used extensively in Japanese railway systems. This method involves workers physically pointing at important indicators like signals, speedometers and platform edges and verbally confirming their status out loud. This process is intentionally redundant.
13:36Even if the worker is certain, the act of pointing and calling reinforces attention and helps prevent errors. Any thoughts on that? That makes so much sense because I have not been to Japan yet, but I've read that the subways and the passenger railways are so crowded, they've got pushers that before the doors close, they push you in. So any steps they can take to avoid moving forward when somebody's still in the door, I mean, the obvious things that could be problems is really important. And I bet the pointing and shouting or the point out thing is a good translation of checklists. If they're all doing it all the time, it reduces their risk.
14:16Yeah. Yeah. Well, the book, I want to make sure that folks grab the book. It's got some stellar reviews. It's called, uh-oh, Avoid Unintentional Blunders that Derail Entrepreneurial Success and Goof Proof Your Business. Bill, what would you hope, so someone reads the book, what would you hope that they would do about what they just learned in the 30 days following reading your book, aside from grabbing some time with you? Yeah, yeah. My hope is that every person, the entrepreneur, the business owner who's just starting or somebody who's been doing it for years will be 10 % more aware of themselves and their own blunder making tendencies.
15:01So that on any given day, they might pause before they make a choice or leave at night or whatever might be the problem. um entrepreneurs are so busy with managing cash flow watching customers dealing with employees all of those things it's over excuse me bless you it's a yawn uh it's overwhelming and in those stressed fatigued uh situations especially when times are really tight that for many people and I know it for me it's the most likely time I'll make a mistake when they're aware of those things when I'm aware of my own tendencies, I'll slow down. I'll take a breath. I'll ask a friend. I'll ask my wife what might go on here.
15:51So I hope that they would personally have a mindset that slightly changed, that they're more aware of themselves so they can be watching for these things to shout out, to call out whatever the Japanese situation was by themselves. Mm hmm. Bill, are you tell me about the workshop work that you do? So to our friend that's listening right now, they might be researching you right now. And so they're listening to our conversation and they're considering engaging with you aside, obviously, from hearing you speak or reading your book. How do you work with folks? I'll be honest with you, Josh. I'm just starting because the book is just out and I'm looking later this year to build it out and there'll be a page on my website describing it.
16:34But the intent would be there are 10 tools in the book, looking at yourself, your customers, your business, and the world out there. How might we apply those 10 tools to insulate, to risk reduce your business? I would imagine in two or three hours with a small team, your leadership team, we can go customize it for your company and come out after a morning or an afternoon with a checklist, a set of plans of your areas of biggest risk as a group and what you might do about it. My work in my big company was all about facilitating. I'm not going to tell you what to do. I'm going to help you discover it by applying these tools in a workshop.
17:18I love it. The book is, uh-oh, avoid unintentional blunders that derail entrepreneurial success and goof-proof your business. It's available paperback, hardcover, and Kindle. Again, your website, Bill, is williamholston.com. We have the spelling for that to our friend that's listening to us right now. Just click around in your show notes and you'll find the direct link, Bill, to your website. Any parting thoughts? Yeah, there's a freebie in there when you go to my website. It's actually chapter one of the book, but I retitled it as a downloadable PDF. It's titled Why the F Did I Do That? It's the tool in the book.
17:59It's called Look in the Mirror. It's the one you use to self-define, self-diagnose your own dumb mistakes, blunder making tendencies. You look at your last year's worth of mistakes. You do this by yourself when you're honest by yourself, write them down. And then you compare that with a list of about a dozen likely causes and you circle them so you can see patterns and recognize how it was when I was most stressed or it was when I was working at 4 a.m. So what steps, it helps you think, what steps can I take to avoid that in the next time to keep it in mind? That's free. I love it. Why the F did I do that is available to everybody.
18:40So when I go to your website, how do I find that? When you go to the landing page on williamholston.com, the first thing that comes up is a page that's got the book on the left and this why the F. Oh, there it is. Yeah, the why the F on the right. Big red and yellow image, Joshua. Here it is. Yep, free and it's 10 minute self-assessment. Awesome. Great. Well, Bill Holston, thank you so much for joining us. Again, great conversation. Josh, I was really pleased to be here. Thank you very much for having me. Take care.
19:14Thanks for listening to the Thoughtful Entrepreneur Show. If you are a thoughtful business owner or professional who would like to be on this daily program, please visit upmyinfluence.com and click on podcast. We believe that every person has a message that can positively impact the world. We love our community who listens and shares our program every day. Together, we are empowering one another as thoughtful leaders. And as I mentioned at the beginning of this program, if you're looking for introductions to partners, investors, influencers, and clients, I have had private conversations with over 2 ,000 leaders asking them where their best business comes from.
19:56I've got a free video that you can watch right now with no opt-in or email required where I'm going to share the exact steps necessary to be 100 % inbound in your industry over the next six to eight months with no spam, no ads, and no sales. What I teach has worked for me for more than 15 years and has helped me create eight figures in revenue for my own companies. Just head to upmyinfluence.com and watch my free class on how to create endless high-ticket sales appointments. Make sure to hit subscribe so that tomorrow morning, that's right, seven days a week, you are going to be inspired and motivated to succeed.
20:38I promise to bring positivity and inspiration to you for around 15 minutes every single day. Thanks for listening and thank you for being a part of the Thoughtful Entrepreneur Movement.
From the publisher
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:
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...

