By Allen Haynes • August 18, 2025

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Lane Jones (00:02):
Welcome to the Andy Stanley Leadership Podcast, a conversation designed to help leaders go further faster. On today’s podcast, we’ll explore a question that can revolutionize how you make decisions. Andy, today’s podcast is a little different than usual because our topic has application in personal leadership and organizational leadership.

Andy Stanley (00:22):
Yeah, you’re right. I think a lot of the things that we talk about land both with personal application and professional application, but today’s in particular, it really does.

Lane Jones (00:29):
Well, I really am excited about today’s content because it comes from a great book you’ve written called Ask It, and what I love is the subtitles, the question that will revolutionize how you Make Decisions. Well, we’re going to get to the question in just a minute, but first, where did the idea of the book come from?

Andy Stanley (00:45):
Actually, this is something that I’ve been talking about really for 30 something years. When I first began speaking publicly, this was a topic for me that really, again, boiled down to a simple question. I’ve taught my children to ask this question. I’ve asked this question all my life, and every time I teach this material, or every time I share this question, people come up and say, wow, I wish I had heard that years ago, which is their subtle way of saying, if I’d heard that years ago and ask that question, I would have a lot fewer regrets in my life. And this is one of those big, broad questions that applies to every area of life that really will reduce regret. I’m absolutely convinced of that.

Lane Jones (01:24):
Well, you make the point in the book that a lot of the regret is associated with a lot of planning.

Andy Stanley (01:30):
Yeah, that’s true. And what’s so strange lane is there are a lot of bad decisions that actually require a lot of planning and time. I mean, all of us can think of bad decisions we made in the moment, or bad decisions we made because of temptation or because we had too much to drink or because we were with the wrong person. But there are some big bad decisions people make that require, as you said, a lot of time and a lot of planning. In fact, the meeting I was in right before this one, I was meeting with a couple, and this won’t be an unfamiliar scenario for some of our listeners, they lived in a condo, found a house they loved. So what did they do? They bought the house before they sold the condo thinking, oh, it’s a condo. Everybody wants to buy a condo. So now they’re in a situation where they’ve lost the house and they’ve moved back into the condo. This question would have kept them from making that decision.

(02:18):
And here’s my point, bringing it up. Buying a house is not a casual endeavor. I mean, that’s not a spur of the moment thing. Getting a condo ready to sell is time consuming. So here’s a couple, well-meaning couple trying to get on in life and prepare for family who made a really big, complicated, time consuming bad decision. And this question is the kind of question that addresses those kinds of big time consuming bad decisions.

Lane Jones (02:45):
And yeah, I’ve heard you say that. Well, nobody plans to mess up their life, but the problem is few of us plan not to.

Andy Stanley (02:52):
Yeah, that’s exactly right. Nobody wants to make mistakes on purpose and nobody wants to have regret. The other thing that comes to mind, a few years ago, a friend of mine insisted that I sit down and talk to a couple that was developing a freestanding coffee shop in our community. And the person that introduced me to the couple was excited about this business. And so I met with the couple, and I’m not a business person, but honestly, lane, this sounded like a terrible idea. And they were so excited. I mean, they were so emotionally engaged with how it was going to look and the location. And I later drove by the location, and it was a house that had ended up on the edge of a business district. So it was in a transitional area from residential to business, which wasn’t too bad. But in terms of the rest of the community, I thought this is a terrible decision. So then eventually I was invited to come see the coffee shop, and again, I went in and it was cute. And again, there’s so much passion and so much energy. I’m thinking there’s no way that this is going to work. And sure enough, less than a year later, I’m driving to the office and I drive by and it’s empty, and that property is for lease again and again, I thought, you know what? This is the question that if they had paused, because this question is a question that peels off emotion.

(04:02):
It peels back the relational complexities, and it really is a question that brings in some cases instant clarity. In fact, one of the reasons we’re going to discover in a few minutes people don’t like the question is it brings painful clarity because again, I want to talk myself into things. It’s emotional, it’s relational, it’s financial, it’s the future. But this is a question that brings extraordinary clarity. And in those two instances I just described, I think if either of these couples, both personal as we talked about and professional had asked the question and been honest with the answer, they would’ve avoided not just regret, but time consuming, expensive regret.

Lane Jones (04:40):
Well, I can’t think of a better way to lead into the question than that. So why don’t you tell us, or I guess ask us the question?

Andy Stanley (04:47):
Well, the question is simply this, what’s the wise thing to do? What is the wise thing to do when I face a decision, a business or my personal life, to ask the question, what is the wise thing to do? And at this point, I imagine all of our podcast listeners are thinking, oh my gosh, how extraordinary. What is the wise thing to do? I’ve never heard that before, but before you hit the pause button and go onto something bigger and better, I just want you to give us a few minutes as we unpack this question because it really is a clarifying and powerful question.

Lane Jones (05:21):
Well, Andy, you make the point in the book that this question really stands in stark contrast of how we usually make decisions.

Andy Stanley (05:28):
Yeah, a lot of times we make decisions based on the lowest common denominator or the lowest common factor I should say, which is, is there anything wrong with it? Is there anything bad about this? Is this illegal? Will this get me in trouble? Can I get by with this? We often make the assumption that if there’s nothing wrong with something that we’re doing or something we’re planning, then it must be okay. If it’s not illegal, unethical. If it’s not immoral, then it qualifies as a live option. One big example we can all remember and relate to, and perhaps lot of us got burned by was what happened in 2008 as a result of subprime lending, lending practices? That would’ve been unheard of 10, 15 years before, but suddenly it was in vogue. It’s what everybody did. And in fact, laws had been changed and adjusted to allow for people to borrow up to a hundred percent of the value of their home or to borrow money based on future value of their home.

(06:20):
So of course, everybody’s going crazy, borrowing as much money as they can and buying houses they can’t afford. But in the midst of what was a huge national, really international meltdown financially, if anyone at any closing table in any boardroom had stopped and asked the question, wait a minute, it’s not illegal, it’s not immoral. It’s not necessarily unethical if you kind of look the other way and wink wink. But really, is this the wise thing to do? Is it wise for our economy or a big part of our economy to be based upon lending practices that never worked in the past? And then again, if we’re honest, the answer to that question is no. It may not be illegal, it may not be immoral, but this certainly isn’t the wise thing to do. And then if the individuals borrowing that money for homes, ask the question, is it really wise for us to borrow a hundred or a hundred plus percent of the value of a first home? The answer would’ve been no every single time. So that’s the power of this question. Again, it cuts through some of the emotion, the passion, I think it has the potential even to cut through our greed if we’re wise enough to stop and ask the question, what is the wise thing to do?

Lane Jones (07:27):
Andy, one of the points I’ve heard you make before is that the problem with this, is there anything wrong with it approach? Is that it usually leads to the question, well, how close can I get to the line between right and wrong without actually doing something wrong?

Andy Stanley (07:41):
And in some cases, the subprime lending debacle was that it was like, okay, we can’t loan 115%, but how close can we get to lending insanity without actually being insane? I mean, that’s where that question goes back in the realm of personal decisions, every single affair, every single affair begins with an unwise decision. It does not begin with an immoral decision.

(08:05):
It generally doesn’t begin with an unethical decision, but every single affair, and you and I as pastors, we’ve heard every version of every story as it relates to that. I think when you go back and say, let’s start at the beginning, people don’t make immoral decisions upfront. They make unwise decisions. So even when you think about our biggest personal failures when it comes to debt, people end up with too much consumer debt, not because they’re greedy, not because they’re immoral or because they’re unethical or because they broke a law. They begin making unwise decisions. So again, in every realm of life, if we would just hit the pause button and get beyond the emotion and the right and wrong factor and ask the question, what is the wise thing to do? This is a question that brings almost instant clarity.

Lane Jones (08:50):
Andy, in the book, you encourage us to ask this question from three different angles.

Andy Stanley (08:54):
Yeah, what is the wise thing to do is a little bit flat. But this next part of our conversation is so important because it’s asking this question from these three angles we’re going to discuss. That really gives this question traction. And I think especially the third angle we’re going to talk about bring such a strong component of inspiration to this question that I think for some people it can be life changing.

Lane Jones (09:20):
Well, the first of these three is in light of your past experience, what is the wise thing to do?

Andy Stanley (09:25):
Our past behavior is generally an indicator of our future behavior. We tend to do the same thing the same way every time. So in the midst of a decision-making environment to ask the question in light of my past experience, not everybody else’s past experience, my personal past experience in light of my past experience, what is the wise thing for me to do right now? This angle is what keeps us from comparing ourselves to other people in an inappropriate way because again, my strengths and my weaknesses as indicated by my past behavior should shine a light on my current decision-making environment. So consequently, I have to factor in my past as I think about my future. So to stop and ask it from this angle in light of my past experience, what is the wise thing to do? Now, every parent listening to this, you’re going to totally get this when you take that angle and apply it to your children, because you’ve said to your kids a thousand times, honey, I don’t think you should do this, which is your way of saying, I don’t think this is the wise thing for you to do.

(10:18):
And your kids have told you about what all their friends are doing, and then you’ve tried to say, yeah, but you didn’t pass the last three math tests. You’ve already missed four days in that class. You’ve already, and you pointed back to their past and said, in light of your past experience, honey, here’s what I think you should do in spite of what everybody else is doing. Well, to some degree, both personally and professionally, we have a past that indicates our future. So again, asking the question in light of my past experience, what’s the wise thing for me to do? For example, if your history points to the fact that you have an oversized risk tolerance, I mean, you’re just a risk taker and consequently, three out of four deals don’t work, three out of four decisions you go back and regret. Well, again, if that’s what’s in your past, if that’s been your history, then again, a person who’s on the verge of making a risk oriented decision should say, wait a minute, in light of my past experience, the fact that it’s easy for me to talk myself into these things, to look at a deal with rose colored glasses, really what’s the wise thing for me to do in this situation?

(11:21):
So again, our personal history is personal, but we have to bring our personal history into the present, into our current decision making reality. So that’s why this is a powerful angle. In light of my past experience, what is the wise thing for me to do?

Lane Jones (11:36):
Yeah, Andy, back on really the personal side. I’ve heard you make the point that our past experience really should affect the places we go and the people we interact with.

Andy Stanley (11:44):
I have a friend who’s a partner in a real estate acquisition business, and his travel schedule is pretty intense, but he gets to choose it. He gets to pick and choose.

(11:53):
And so I remember about a year ago him telling me about an opportunity that had come along and he chose not to do it, and it was completely related to the fact that they’d had a really tough run with one of their kids. It was really painful, and he had been on and off the road during that time. Now he’s at a place where things have settled down, things are better than they’ve been in a while. This opportunity comes along and he chose to say, no, I can’t take that on because it meant two or three days a week until the deal was finished. And I remember thinking, there it is. It’s not that you don’t ever do this. It’s not that no one else should do it. It’s in light of my past experience, his past experience as it related to his kids, his family, but again, our personal and professional lives. There’s no hard line between those. So he made a professional decision based on a personal reality, and again, just coming out of this difficult time, he said, this is just not the time for me to take that on. In other words, it’s not the wise thing to do. Again, he didn’t compare himself to other people. He took his most recent pass into consideration, and that’s how this principle works, and that’s why stopping and asking it from this angle, it’s just really powerful.

Lane Jones (13:03):
Andy. The second angle is, in light of my current circumstances, what is the wise thing to do?

Andy Stanley (13:09):
So in light of my past circumstances, in a lot of my current circumstances, again, we have to look around and ask the question, what’s going on right now? Is this the wise thing to do in light of what’s going on right now? Again, every parent, you don’t have to go back too far to realize how important this is. When our kids ask us to do something, they’re looking at the decision. They’re looking at what everybody else is doing. We’re looking at current grades, current emotions, how late it is, all those kinds of things. Well, the same again, is true for us in light of our current circumstances, what’s the wise thing to do? Where I think this is most important has to do with two things financially, current debt. I see people take on what would normally be a good opportunity, but it’s not a good opportunity right now because of current circumstances.

(13:53):
And then the second one is emotions. There are options we should avoid when we are going through very emotional times, and generally this is related to relationships, job upheaval, transition, all those kinds of things. There have been many occasions when I have said to people, Hey, in light of what’s going on right now, is this really the wise thing to do? I mean, it’s not immoral and not illegal, not unethical. But again, when you think about what’s going on in your family right now, when you think about what’s going on in your industry right now, when you think about what’s going on with your personal finances right now, maybe later, maybe at a different season, but is this really the wise thing to do right now? So again, this question pulls us out of the broader context of what’s going on in everybody else’s world.

(14:37):
And again, we’re forced or encouraged to look at a current decision through current circumstances. And again, I think we have to pay attention to what’s going on financially and emotionally. I think those are the two areas where this angle intersects with our reality. Most often, I have a really close friend who’s in the financial services industry, works for a company we’ve all heard of, and about nine or 10 years ago, in fact, Elaine, this guy, he came to me and he had been offered an opportunity that he was the youngest person in the firm history of the firm to ever be offered this opportunity. He would have to move and he would have to travel. He’d been married a few years, they had a baby, they wanted to have other children, and he was so excited. And then I saw sort of his expression change.

(15:21):
He said, yeah, bud. And then he told me about, we have to move. Actually, I think I won’t name the city way up north and there would be a lot of travel. And I said, well, here’s what I think. I think congratulations. You got the offer. Now you can be in an even smaller category of people by being someone who turned it down. And he laughed. I said, but congratulations. I mean, you got the offer. You’re the youngest person to be offered this type of position. There was only about a half a dozen of people in the company that did this, and you don’t have to go. And I sort of saw this look on his face and said, really think about it in light of your current circumstances, your current season with your family, is this really a wise decision? It was a lot more money. And he turned it down. I was shocked, but he turned it down. That was years ago. He’s done very, very well for himself. He’s never regretted that decision, and he was in fact, the youngest person they ever offered it to and the only person at that time in the history of the company that ever turned it down.

(16:21):
So again, over time, within the context of his business world, it was kind of a legendary decision. Oh, you’re the guy who turned it down, but he turned it down based on his current set of circumstances. So again, what is the wise thing to do in light of my current circumstances?

Lane Jones (16:39):
Andy, you write in the book that as a leader, you’ve learned that there is a certain current circumstance that it’s really better for you to do nothing during this circumstance.

Andy Stanley (16:48):
And this is embarrassing, except maybe this is an experience that’s not just common to me. I’ve learned that when I’m mad, it’s just better not to make a decision. When I make a decision, when I’m upset or when I’m mad, or when I’ve just gotten information and I’m ready to fire off an email or call somebody or ask my assistant to, what’s SO’S cell number? I need to call ’em right now. In light of my current circumstances, in light of my current emotional state, what is the wise thing to do? Nothing. Do nothing. I always regret doing something when my emotions are inflamed. That’s the time when I do nothing. Now, again, this is a good illustration because I eventually have to do something. But in light of my current circumstances, what is the wise thing to do? The wise thing to do is nothing.

(17:35):
And probably every leader listening wishes, they could go back and unsend a bunch of emails, wish they could go unha several person one-on-one meetings. I mean, we all wish we could go back and retrieve a lot of words, whether it’s with our kids, our spouses, our people at work. And so in light of my current state, in light of my current emotions, what’s the wise thing to do? Probably nothing. Now I got to do something eventually. But again, in light of my current circumstances, what is the wise thing to do? So again, the angle on this question, the angles on this question are really what give it traction and bring it to life.

Lane Jones (18:12):
Well, the first two angles that you’ve given us so far are in light of your past experience, what is the wise thing to do? And in light of your current circumstance, what is the wise thing to do? That brings us to the last angle that you said earlier that you think could really be the most powerful.

Andy Stanley (18:26):
What is that? Yeah, it’s in light of my future hopes and dreams. What is the wise thing to do in light of my future hopes and dreams, not what everybody else is doing, not what everybody else is dreaming. In light of my future hopes and dreams, what is the wise thing to do? And as leaders, we’re prone or we’re apt to have a mental picture of how we want our futures to look. It could actually be as formal as a personal mission statement or a personal vision statement. The tragedy is we’ve all seen, and perhaps to some extent, we’ve all been guilty of this, of undermining our own success, of undermining our own progress toward our preferred future. By unwise decision. Again, not immoral. I mean, it may lead to immoral, not unethical. It may lead to unethical. But at the beginning of all those decision making sequences that we regret, I guarantee you there was one unwise decision that was the first domino.

(19:18):
And in the end, again, we undermine our own dreams, we undermine our own happiness. So a clear picture of the future is a great thing to have in our professions, but it’s also great to have personally. So in light of my future hopes and dreams, professional or personal, what is the wise thing to do? Lane, I think that most, if not all of our podcast listeners would agree that their greatest regret, their greatest regret links back to an unwise decision. Again, it may have been, as I said, a first domino, but our greatest regrets, the thing again, that undermine our success or undermine our future hopes and dreams or unwise decisions. That’s why again, this is such a powerful, powerful, even though it’s a simple question, what is the wise thing for me to do in light of my past experience, in light of my current circumstances, in light of my future hopes and dreams? What is the wise thing to do in light of my past experience, in light of my current circumstances, including my emotional state? And in light of my future hopes and dreams? What is the wise thing for me to do? Again, that question from those three angles brings extraordinary

Lane Jones (20:20):
Clarity. Andy, in the book, you covered just a lot of great things. I love the section on time, and I wish we could cover everything that

Andy Stanley (20:28):
You talked, but we don’t have time.

Lane Jones (20:29):
No, we don’t. But I hope we have time for one more question that you ask in the book that I think is so key. You asked this, you said, what if, after considering my past experiences, my current circumstances and my future hopes and dreams, what if I still don’t know the wise thing to do?

Andy Stanley (20:46):
Yeah, this is like the kept secret of all wise men and all wise women. This is how wise men and women became wise. And I say it’s a secret because when we meet people who make great decisions, we just assume they just have always been able to make wise decisions. But people learn this. And so the way I say it in the book is simply this, wise people know when they don’t know and they’re not afraid to go to those who do know

(21:10):
Wise. Men and women know when they don’t know and they’re willing to admit to themselves, you know what? I just don’t know. I really don’t know what the wise thing to do is. And they are willing to go to those who know. When wise people bump up against their own limitations, they stop and they ask for help. They don’t deceive themselves. They don’t pretend. They don’t act like they’re smarter than they are. They know their limits, and they find people who know what they don’t know. And that’s the secret to wisdom. It’s asking the question, acknowledging that even after asking the question, I still don’t know what the wise thing to do is, and I want to do the wise thing. So when it’s not clear on those few occasions when this question doesn’t kind of take away the mist and the fog, that’s when you go to someone else and you ask them the question, in light of my past experience, here’s what it is. In light of my current circumstances, here they are. In light of my future dreams lane, what do you think the wise thing is for me to do? Again, there’s extraordinary clarity that comes with asking that question from those three angles and listening to someone else, answer it in light of your past, your current circumstances, and your future hopes and dreams.

Lane Jones (22:17):
Well, Andy, as we wrap up today, do you have any final thoughts?

Andy Stanley (22:20):
If you have middle schoolers or teenagers, I promise you, you need to buy this book and you need to read this to them or pay them to read it. And we did this all the time with our kids. Here’s 20 bucks. Read a chapter because I promise you, and you already know this as a parent, you want your kids to make wise decisions, and creating a context for your conversations with them around wisdom is so extremely important regardless of your religion or if you’re religious at all. Again, the question, what is the wise thing to do? You are going to want your kids to ask it, and this book is designed to help you talk about it with anyone, but I think perhaps especially with your kids, your middle school and high school kids. So that would be my takeaway. I encourage you to check it out.

Lane Jones (23:02):
Andy, thanks again for creating this great resource as well as taking this time with us today. And I want to say thank you to our audience for listening. To hear more from Andy on leadership, please visit andy stanley.com.

 

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