How $100,000 Questions Can Revolutionize Your Leadership
In this solo episode of the Mastermind Mastery podcast, host Tina Corner Stolz explains the concept of “$100,000 questions” – powerful, thought‑provoking questions that generate aha moments, increase vulnerability, and improve decision‑making in Peer Advisory Councils (PACs) and other leadership groups. She shares personal stories – a 1998 negotiation where her coach asked, “Are you prepared to lose your job?”; a pivotal move to Florida prompted by a simple question from a friend; and a member’s ESOP dilemma solved by a well‑timed question. Stolz contrasts these high‑impact questions with “dollar questions,” which are shallow and produce mediocre answers. She outlines why great questions matter, citing thought leaders like Elon Musk, Peter Drucker, and Oprah Winfrey. The episode then provides a practical framework for cultivating $100,000 questions: listen fully, suspend solution‑forming, stay curious, and ask at the right moment. Specific techniques include flipping questions back (“What if you did know?”), asking “What has to be true…?” and using the question to surface blind spots. She warns of mis‑applied high‑stakes questions (e.g., Sam Bankman‑Fried’s scaling‑impact query) and stresses the need for moderators to model and teach this skill to their members. The episode ends with a challenge to adopt these questions, a call for topic suggestions, and pointers to resources on lxcouncil.com and her books.
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Welcome everyone to another episode of Mastermind Mastery. This is the podcast for you if you are wanting to create or already running peer groups. It's what we call PACs, Peer Advisory Councils. They might be known as mastermind groups, CEO peer groups, all the same. But this is the podcast if you want to run better PACs, that you want to be better at being a moderator, you want to up your game, learn advanced techniques, hear from myself as well as guests, what works, new concepts, trends, techniques. Also learn content, things you could take back to your meetings, different ways to do different things to solve problems that we all have when we're running groups. It will increase your retention, reduce your attrition, get you more members, make you more money. This is the podcast for you. I'm Tina Corner Stolz. The host. I've been doing this since 2005. I built a territory of 10+ groups, sold for a multiple, started Ellis Council, Leader Exchange Council, in 2012. We are a licensing model. We are the leading educator in the peer advisory council space. We have the podcast. I have a licensing program with certification. I've written 2 books. So today, when you hear this episode, each and every week it's a new podcast where we dive deep into a topic for 15, 20 minutes. One week it's me doing a deep dive on all the experience and insights from not only today with our entire licensed partner community or the past, what I've learned along the way, but we also have guests that are out there doing groups today that share their insights and new concepts. So let's get started with today's episode. Hello everyone, and welcome to another episode of Mastermind Mastery. I am your host, Tina Corner Stolz. And today, a couple of things. First of all, I'm coming to you with a big black eye. So I am counting that many of you don't even look at the podcast. You just listen to the podcast because I look like I am ready for Halloween. I accidentally ran into a doorway over the weekend. So it's, it's, it's pretty black. But here we go. With that said, today's episode is the power of questioning. This is really for those of you, first and foremost, that are running groups, because asking really profound, thought-provoking, game-changing questions is a moderator skill. And I'm going to do two series of this. One is about The $100,000 Question. It's a speech I did at our conference last year, Live Exchange 2023. And as a moderator, it is a skill to continuously develop. And I'm going to do a separate episode about the power of being curious and how important having curiosity is in running your group. So second, this is for you if you're not running groups yet. Because it will serve you well in your life regardless. And asking powerful, thought-provoking questions can be game-changing. And this has happened throughout my entire life. And there are definite moments where they were profound and changed the course of my life, um, for obviously the better. And just even one was when I was younger in my career in telecom, and this was in 1998. And my executive coach, Jean Stafford, and I were on the phone early one morning at 7:00 AM because I was in the middle of negotiating my basically promotion package, and it was significantly lower than what I believed was fair and what I knew the person was making prior to leaving of the role I was being promoted into. It was significantly more responsibility, but very parallel to what I was doing. And they were offering me less than a third of what he made. So I was at a crossroads about what to do. And Jean asked me that $100,000 question at the time, which was, Tina, are you prepared to lose your job? Now, I did not expect that from her. I thought she was going to coach me in a different way, but the point was profound in what I needed to consider, and it would create the next steps I needed to take if I so choose to. As a result of many days of silence that I never answered her, I did come back and said, yes, I am, because I decided to go for what I believed I deserved in salary. And I will tell you that that question that she asked me prompted me to stand up for what I believed in in a very professional way and get what I believed I deserved, which was way more than a deficit of $100,000. So it made a significant difference in how I was perceived in the company aside from the bottom line financially. Now, Jean was trained in these types of questions, and hence why she was such a great executive coach. And anyone can ask what I would call dollar questions. And dollar questions are really mediocre questions. They don't really promote momentum. They're kind of, huh. And, you know, dollar questions are even simple things like, well, how are you? Good morning, right? How, how are you? Well, that's, you know, a very kind, in a way, greeting. But what could it be, even be a better question that could present even a more meaningful answer? And that's what $100,000 questions do. They create aha moments. All of us who run peer groups are always looking to drive more aha moments with our members, and aha moments create change. They create a different perspective, they create better decisions, they create better outcomes. And that's what this whole $100,000 idea is all about, is how is it that as a moderator Not only do you lead by example and ask these great questions, but you teach your members how to do the same. We all have had members, or we were lucky enough to have had members and still have them ideally, that exhibit this naturally and so, so well in the group. Because those members that do that, a few things happen, right? Number 1, it makes your job as a moderator so, so, so much easier. Because that member understands those great questions to pose out there, and all the other members learn from that. So they lead by example, but also they create more aha moments in the group. And if you don't have a member or members that do that, you have to cultivate that. You have to fill that gap as a moderator first while you teach your members to do that, or hopefully bring on a new member who has skills at doing that. Now, understanding the importance of questioning has been around for some time. There's Elon Musk who says a lot of the time the question is harder than the answer. You have Peter Drucker who has said the important and difficult job is never to find the right answers, it's to find the right question. And then of course there's Tom Watson whose ability to ask the right question is more than half the battle of finding the right answer. We also are all aware of Oprah Winfrey, probably the most famous and best interviewer of all time, who says the best interviews are basically because she has come up with the right questions to provoke those answers we all are wanting to hear from who she is interviewing. And even so much so that she believed in the power of the question that she devoted an entire year's worth of the O Magazine in 2018 to a thought-provoking question every single month for 12 months. So I'm here to also illustrate to you that these really thought-provoking, meaningful questions that I call $100,000 questions are worth way more than $100,000. And it started not only with the story that I told you at the beginning of the episode, but it has showed up in my life all throughout. And even to the extent that in 2017, I was sitting at a desk, and a girlfriend of mine who twice have profoundly asked me questions that have changed the trajectory of my life— the first one was, Tina, why don't you write a book? And I'm like, oh, why? I don't know, you know, it's a lot of effort, etc., etc. And through her prompting, not only did I write one book, I wrote two. But it was when I was sitting at a desk trying to decide what I was going to do with the fact that I had sold my house to someone who had knocked on my door and I couldn't find a place to live and move to. So I put my stuff in storage and I was temporarily at my other home at the Lake of the Ozarks in Missouri, and I was unable to continually find a place to move into in Annapolis, Maryland. And she finally said to me, Tina, why don't you move to Florida? And I thought she was absolutely crazy. But it's that simple question at the right moment. That is what I'm talking about as a $100,000 question. And it was through that prompting and basically her insistence that I get down to Florida and take a look if that's not really where I was supposed to live next. As a result, it was the place, and 30 days later I moved and live now in St. Petersburg, Florida. Now, why was that so transformative? From the fact that, number one, I didn't know anyone in St. Petersburg, Tampa Bay, but when I arrived 6 months later, I met my husband, the love of my life. We were married in 2020, but I also met someone that helped me figure out and change my model into a licensing model, which profoundly has changed Alex Council. And third, I got to live in the place that I'd always dreamed of. So just that question from someone who was thoughtfully listening at the moment and being present, my girlfriend Sharon, by saying, Tina, why don't you move? To Florida. Now, where I see this happen in actual peer group meetings is a great example of a member in a group, um, that I was leading back in Baltimore. And Chris was running a company that was an ESOP, employee stock ownership plan. He had bought the company, he was not the founder, and he had a dilemma and that his margins were not where they wanted— he wanted them to be or where he believed they should be. Now, he had two primary clients, the private and the public sector. So government employees that required high-level clearances, and then of course his sales team who was working with the privately held business owners. And the ESOP concept applied to one really and not the other. And as many of you know, ESOPs if you are no longer an employee at the company, you're still part of the ESOP, and that can be problematic if you have too much turnover. And that's where his organization was. It was not a question he was going to pose to be processed that day, but it was because a member was listening and being present said, hey Chris, if you started the company from scratch, what would you do differently to prevent the issue? And it was at that moment, I can recall to this day and seeing it, I know exactly what room we were in. I can see exactly where Chris was sitting that he had the aha moment that changed the trajectory of his firm by splitting it in two divisions underneath a different umbrella company so the ESOP could apply to one part of the organization that it mattered and not to the other, changing his bottom line forever in such a positive way. Again, a profound question that is just very simple. It's not this question that you've never heard of. But it was a question that was the right one to ask at the right time. It was more than a $100,000 question for him. No different than it was more than $100,000 questions for me. Because without $100,000 questions, you get insignificant, shallow answers. Poor decisions are made. There's fuzziness and ambiguity. It's basically the existing mindset prevails, status quo. But when the right question is asked is when you get the aha, you get better decisions, you get clarity and focus. There's progress, it's transformational, there's new thinking, and it's also motivational. And what you will find is it increases vulnerability in your groups. If there is a lack of vulnerability at the level you desire and want for your groups, what will get you there is $100,000 questions, not minor questions. And if you observe your next meeting at the level of questions that exist, you will probably find out what I'm talking about. So as a moderator, it is your job, it is your duty to be excellent at this so that you can illustrate this with your members. Because typically, if you're leading a CEO peer group, those CEOs get a little bit lazy as they progress in running their company because they get lazy in that asking great questions takes effort, it takes time, and they are busy and they don't have time and they just want to move forward and get on with it. And they have the answer, so they typically give it instead of doing leadership development and coaching with their teams and asking $100,000 questions. So how much better could their companies be? How much better could the leadership team be? How much better could that CEO be developing their successor, etc., if they also did $100,000 questions within their company? So what are different types of $100,000 questions and when— how do you cultivate them? Well, first of all, let me just tell you a skill set in cultivating this type of question is very, very simple and straightforward. It's, first of all, you gotta listen. Now, listening takes effort. It's also a skill, but you have to listen. And then while you're listening, not formulate the solution in your head while you're listening, because that's part of the other issue, is that a lot of times people are listening, they're already formulating a solution, which then requires that they don't listen, and therefore they miss important points and they don't have enough information to formulate a solution. And you have to be curious, which is why I'm going to talk about that in a whole nother episode next, is about being curious. You have to sincerely want to know more and want to understand more. So types of $100,000 questions is, as you can tell, First of all, they don't have to be just extremely well-written. They can be very simple and straightforward just at the right time. And they can be positive, but they can also get you in trouble. So an example of a $100,000 question that gets into trouble is one from Sam Bankman-Fried. So if you've read anything about him and his book, one of the questions that he was always searching for is how does he impact more people? He always wanted to make more of an impact on more people. And how could he do that? How could he scale that? And that is what got him into trouble. And that's what got him into the business that he was in. He just went the wrong direction with that. Now, there is also something that I love about the opposite of $100,000 question that can be used in an everyday scenario in business, and that is about when you're hiring people or making a decision about something. And a great question to ask is, what has to be true about this in order for it to be successful? So let's say you're going to hire somebody, and you would ask them the question, what has to be true about this new hire that in 90 days they'll be successful? So what has to be true about them that 90 days from now they're going to be successful? And what has to be true about our process for them to be successful? And what you will find when you are asking yourself or your team these questions, that it prompts where your blind spots are, what assumptions you're making that probably aren't accurate, or that you need to be sure, or what else you need to know. Which brings me to one of my most favorite questions that I learned from mentor of mine, is if someone asks You know, I don't know how to blah, blah, blah. How do you incorporate a $100,000 question when somebody is asking you the question? You flip the question back to them and you say, what if you did know? Yes. What if you didn't know? Anyone who knows me knows I talk about this all the time, about if someone comes to you and says, you know what, I don't know how to solve this customer situation, blah, blah, blah, blah, blah. I would say back, but what if you did? And then they're going to say, but if I did, I wouldn't be asking you. And you're going to say, but what if you did know? Just take a moment and think about it. What if you did know? It flips something in the brain to open up a whole new path of thinking that comes with more insight. So what if you did know? It works wonderful on kids, by the way. It really does. So that can be one of your other takeaways. So what I've talked about is anybody, any moderator, anybody running groups can ask just basic questions. I'm asking you guys today as a challenge to step up your game to asking $100,000 questions that drive better results and a more wow experience for your members, and to practice it through curiosity, listening, being present, and not formulating your ideas, but putting it out there to be curious and be truly thinking about what can I ask right now that this person really needs to answer in order for them to make progress on where they need to make progress. So thank you again for listening to another episode of Mastermind Mastery. And if any of you have a topic you would love to be sure is discussed on one of these episodes, please send me an email at TinaCornerStolzl.com. I would love to hear about what you want to hear about, maybe what guests I need to go get that could be an expert in it, etc. But what is it that you haven't heard about me talk about that would be most helpful to you? So until then, go make it happen. And thanks for listening. Thank you everyone for listening to another episode of Mastermind Mastery. And to get access to today's episode, episodes, not only the show notes, but any tools and resources, encourage you to— not only will you find them in the episode show notes, but also you can go to the website www.lxcouncil.com. So, LXCounsel.com, and you will find a plethora of articles and content and tools and resources and worksheets and things like that that can be helpful to you in creating and running successful packs. I want to leave you with one thing that we end and teach to do in every single meeting, and that is the very last thing is to ask, what is your takeaway from today's episode? I encourage you to give that thought. Take advantage of the time you just invested in listening to the episode, and what can you do to move one step closer to the vision that you have and the goals that you're trying to achieve with your groups. So again, take a step back. What's your key takeaways? What can you actually act on? And I leave this with one note, and those of you that have read my book, Your Seat at the Table, you know that I ended the book with a story about my mentor. He always, when he met people, had a pebble in his pocket that he passed to them when there was knowledge shared. And so I ask you today to think about that pebble concept and to pass what you learned today on to someone else, which could be your members, or take it internally to yourself and act on it. So now go do something with those takeaways.
