149 | 5 Essential Leadership Questions

Discover the 5 essential leadership questions every leader must ask—and how our Mastermind Retreats help you find the answers in the right room.

Leadership doesn’t grow in isolation.

It grows in rooms filled with intentional conversations, honest reflection, and leaders who are chasing clarity, not just success. That’s exactly what happens at our Mastermind Retreats—and it’s the heart behind this episode.

In this powerful episode, we share the five essential leadership questions you need to be asking if you want to experience your greatest growth. These aren’t surface-level prompts. They’re deep, reflective questions that help you uncover what’s working, what’s not, and what might be standing in your way.

These are the same kinds of questions we wrestle with at our in-person Mastermind Retreats, where we gather three times a year with our clients—and a few outside guests—to break through what’s holding them back and unlock the next level of leadership.

Yes, the teaching is strong. But what leaders tell us most often is this: “It’s being around other people who are going through the same thing—that’s what changes everything.”

The truth is, when you step away from the day-to-day and into a room of like-minded, growth-oriented leaders, you don’t just learn… you transform.

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Here’s What You’ll Learn in This Episode:

• The 5 critical leadership questions that reveal if you’re ready for your next level
• Why leading in isolation limits your growth
• How to recognize the hidden roadblocks that may be keeping you stuck
• The difference between working in the business and truly leading it
• Why feedback, challenge, and environment matter more than you think

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Want to Experience This In Person?

Our Next-Level Mastermind is for business owners and key leaders who are serious about growth—both personally and professionally.

We host three Mastermind Retreats a year where our clients come together to learn, connect, and grow alongside other like-minded leaders. We also open up a limited number of seats to outside guests, so even if you’re not in our coaching program yet, there’s an opportunity for you to join us.

These retreats combine powerful teaching with intentional social moments—giving you time to reflect, recharge, and build relationships with other leaders navigating the same challenges.

It’s not just about learning. It’s about shifting how you lead.

→ Learn more about the Mastermind experience here.

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Final Thought

If you’re wrestling with what’s next in your leadership, you’re not alone—and you don’t have to figure it out alone. Start with these five questions. Then consider stepping into a room where growth is the expectation, not the exception.

🎧 Question for you: What’s keeping YOU from your greatest growth?

Continue reading for the episode transcript:

Welcome to The Chris LoCurto Show where we discuss leadership and life and discover that business is what you do, not who you are. Hey folks, welcome to the show. We are so glad you’re joining us today. We are talking about five essential leadership questions. There’s five, five questions I want you asking yourself that every leader should be asking themselves. And this is coming on the backside of our Mastermind Retreat.

We just finished that up, we just wrapped that up and we do that a few times a year. And it was powerful. It was so fantastic. The things that came out of it that were so great was the community aspect of what we do now. This is for our coaching clients, this is for our Mastermind group clients and we open it up to the public. But usually there’s only, only a few tickets available and those go pretty darn quickly.

Hopefully in the future we’re going to be able to open that up even more. But this, the thing that I wanted to talk about on this is how powerful it was and is every time this group comes together, the bulk of the group, they all know each other, they are in our groups together. And this is an event where we actually are pushing them even harder and further for growth.

To grow their businesses, to grow their leadership, to grow their top line revenues, to grow their bottom line, you know, growing their teams. Every aspect of running a business, we are pushing these leaders and these business owners to do better. And in this next phase of our coaching and mastermind groups and all that, the, the next level stuff that we’re doing, there’s a lot to it. We’re pushing for more accountability, we’re pushing for more growth, more growth mindset.

And it was such a pleasure to see everybody being not just happy about it, but super excited about it. That is what we’re talking about today is what came out of that and the joy that they have by coming together every single week and discussing these things as well as coming together in person what will now be three to four times a year, which we’re really excited about that as well.

So out of that, I’ve come up with five questions that are essential for you to be asking yourself. And this is the growth side of your leadership, the growth side of your business. That what’s keeping you back? Are you isolating yourself? Because we know that that is one of the worst things you can possibly do. Isolation is horrible. So I’m just going to jump right in. Here’s the first question that I want you to ask yourself.

How do I see myself compared to How I see others. You know, so many people think that they’re the only ones that do not have it together. Now, I’ve got a fantastic story from M. One of our guys that was here at the event, and he pulled me aside in the hallway, and he goes, Chris, I have to. And he’s okay with me sharing this with you. He goes, Chris, I have to tell you.

Very emotional moment. He’s like, I have to tell you, this is so powerful for me. Being here at this event is changing my life. And the main thing is, is that when I came into this, I thought, I’m going to be the one who doesn’t have it all together. I’m coming into this room full of leaders and business owners and Chris, and everybody’s got it together, and I don’.

And I just started laughing. I started laughing. And he goes, well, I know you laugh at that, but I’m very serious. And I said, mike, the reason why I’m laughing is because I’ve been doing this a really, really long time. And that is the common myth, that is the common broken belief system that so many leaders and business owners have. So many people think I’m the only one who doesn’t have it together.

Everybody else does. Look at Chris. He’s got this show. He’s been teaching people for a long time. He’s doing events. He’s got all this information. Yeah, well, guess where that came from. It came from not having it all together. And so it was great to be able to talk to him and just say, dude, you are in great company. And so I said, hey, do you mind if I share this when we go back into the room?

When I get up there and start teaching again, do you mind if I share? He goes, no, absolutely. So I went back in the room, and about the same time I laughed, I shared with the group. I said, you know, Mike was just sharing with me about how, you know, he coming into this, he was thinking that, you know, everybody else has it all together. Everybody started busting up right there.

Everybody starts laughing. And it’s so funny because it is true. We all think that everybody else does, and we don’t. We’re the ones that don’t have it all together. We’re the ones that are screwed up. We’re the ones that are making the mistakes. But look at everybody else. They’re so successful. Folks, you have to understand, champions are not people who have it all together. They don’t so many times they don’t have a lot of things together, but they are the people who are willing to find out what it takes to make them better and push themselves to make it happen.

That is what a champion is. It’s not somebody who has it all together, but somebody who’s willing to find out what it takes to make them better and push themselves to get there, to make it happen. That is what we have here. We have a room full of champions. We have a client base full of champions. And so many of them are messing things up and are having problems in their leadership or having problems with, you know, team members or having problems in growing the business or whatever it is.

But the difference between them and everybody else is that they’re here because they know that there’s a better way and they want to find that better way. So I want you to ask yourself that question. How do you see yourself, and how do you see yourself compared to how you see other people? Do you think that you’re the only one who screwed up? Because if so, I can tell you that you’re wrong.

You are not the only one. The difference is, what are you going to do about it? One of the best compliments that we get as a business from our clients is as we pull all of these people together. It is powerful to have people in their industry, you know, other people that are doing the same thing that they are, but a ton of people who are not in their industry as well, because then they get perspective from both sides.

Not just getting people from inside your industry, because, you know, they may be doing the same, making the same mistakes, but folks that are struggling through business just like everybody else, struggling through leadership just like everybody else. Some people are further along in one area, some people are further along in another area. But the great thing is, is having that input from people who’ been there when you may not have been.

The second question I want you to ask yourself is, do I have a network of challenging minds? Again, this is so powerful for everybody who comes to this event because these are people who want to challenge each other. These are people who are looking to push themselves and push others. We usually, and I’ve talked about this in a couple of podcasts before, when you take a look at the people that you have around you, when you take take a look at the top five people, the top five influencing people in your life, it usually comes down to family and friends.

And a lot of the time, family and friends, they’re not business owners, they’re not leaders. So you have people that you’re sharing information with that sometimes they don’t get it? Sometimes they just can’t digest it. Sometimes they can’t understand it. And unfortunately, a lot of times, depending upon what their influence in your life is, they may be telling you all the things you’re doing wrong or suggesting things that aren’t going to work anyways.

That is why you need to have a network of challenging minds. You need to have people around you that are willing to challenge you, not put you down, not bash you. And you need to be willing to challenge yourself. Where are you getting pushed and challenge. Ask that question, who’s pushing you? Who’s challenging you to be better at your leadership? Now, don’t hear me saying who’s pushing you to add more work?

Now, we’re gonna get to that in just a minute because that is not what I want you to be thinking. Instead, I’m talk, talking about challenging yourself, challenging your, your thinking, challenging your growth, challenging the way you do things without it. How are you growing? Are you growing at all? If you’re not being challenged and pushed, then are you growing? That was one of the things that, as we offer that to our clients, we’re saying we’re literally using the term guys.

We’re going to have a group of people pushing you. So it’s not just going to be one person. It’s not just going to be me. It’s not just going to be yourself, but we’re going to push each other. People who don’t want to be push, they don’t want to hear that. They don’t want to. I don’t, I don’t want to be pushed in this area. I’m afraid of that.

Well, why are you in leadership then? Why are you a business owner if you’re afraid to be pushed? Now, I’m not talking again, do hear me correctly. It’s me. You’ve been following me long enough. You know that this is not the pushing that, you know, that doesn’t have healthy boundaries in it. That doesn’t have, you know, positive people trying to obtain great goals. That’s what I’m talking. We want people that are looking for that to help people in that.

So ask yourself the question, do I have if I do not have that network of challenging minds, what am I going to do about it? Third question, do I have a mindset of growth? Do I have a growth mindset for me? And every single time I always say, if you are not growing, you’re dying. You better have a growth mindset. I want you to be thinking growth. So many people are coming out of Bad cultures coming out of bad industries, having worked their butts off and stressed out and all of you know, just crazy places where they don’t want to grow anymore.

They just want to be, I just want to do something and it be easy. That’s fine if you’re healing. That is fine if you’re healing. But listen, let’s get healed. If you need to come in for a life plan, get your butts in here. Let’s do something to heal you in the process. But if you’ve done that, if you’re on the other side, then you’ve got to understand your leadership and your business must have a growth mindset.

It is so easy to become stuck. Let me say that again. Stuck in doing the same thing over and over and over again, but expecting growth. We do the same thing. We get into this place of sameness. We keep doing the same stuff, we keep overloading ourselves with work and we’re not growing. Why? Because we’re not doing the most important things that we can be doing as a business.

We’re not doing the most important things that we can as a leader. Instead, we’re doing stuff. We’re getting stuff done. Not the best way to grow. Next thing I want you to ask is, do I have proper accountability? Do I have proper accountability? Accountability is people that are willing to help you, to call you out, to push you to do things, to help you hold yourself to your own expectations.

Now, that’s the difference between proper and improper accountability. Improper accountability is people wanting to call you out on stuff that fulfills their needs, like telling you that you’re bad at something or bashing you or, or, or. Proper is not about that. It’s about helping you achieve your own expectations, those things that you have set. And that as we share that, we were going to have even more accountability within the groups.

That was one of the most powerful things. People are like, yes, that is exactly what I’m looking for. I don’t have that push at home. I don’t have that push in my peer group. That’s why I love coming here, is because when I come here, it’s people that want me to grow for me, not for them, not for them to beat me up, not for any of that junk.

So do you have proper accountability? While being in the group is about getting my needs met. So if I’m in the accountability groups, if I’m in the mastermind groups, the coaching groups, while being in the group is about getting my needs met as a leader or a business owner, our Setup keeps people from getting their needs met by being controlling or by manipulating others. Instead, they understand that pouring out helps others on a regular basis grow in their leadership, in their business.

So you have to understand that it’s not just about coming and getting somebody pouring into you. It’s about you practicing pouring out. It’s about you practicing teaching, mentoring, not manipulating, not controlling, but instead pouring out of yourself leadership, pouring out of yourself, mentorship, growth, direction. As you do that more and more and more. Now, keep in mind, I’ve been doing this a very, very long time. Every time I do it, I grow.

So the guy who does this for a living is constantly growing by practicing teaching, by practicing pouring out, by practicing helping others. So that is a huge part about that accountability. Do you have it around you and are you a part of it yourself? Number five, what is holding me back from reaching my goals? So if you are one of those people who sits down at the beginning of the year and says, well, here’s what I’m going to or the end of the year, here’s what I’m going to accomplish next year, and you write down a list of stuff and hope that you hit it, guess what, folks?

Those aren’t goals. That is a dream. That is something that’s going to end up in a drawer somewhere or end up in a file somewhere. And you’ll pull it out about October and take a look at it and go, oh, wow, we actually hit three of those. Eleven. That’s not good. That’s not goal setting. That’s not proper goal setting. You have to understand that as leaders and business owners, we’re all overworked.

If we are setting up our goals as dreams, only then we are not going to attain those goals. My air quotes. We’re not going to attain those because it’s not a true goal. A goal is the steps that it takes to accomplish the vision. So if you know what it’s like to go to Tahoe, where I’m from, and go skiing, what does it look like when you get there?

So when you’re there, what is it like when you’re on the mountain? What is it like at nighttime when you’re having dinner or if you’re in the town or whatever, if you’re crashing and tumbling down the hill, whatever that is, that’s the vision. That is the vision. What it’s going to be where we’re headed. That’s the vision. The goals are the steps it takes to get there. And if you are overworked again, we are so overworked as leaders and business owners, if you are overworked, you’re not going to do the goals, you’re not going to accomplish the vision because you don’t have the goals that it takes to hit that vision.

The problem, as my buddy Rory Vaden says, is efficacy. It’s the ability or the capacity which we don’t have if we’re continuously overworked to produce a desired result. So in essence, it’s being effective. Well, if you’re bogged down all day long and stressed out as a leader, then there’s no way you can be effective. You’re doing tasks. If you are task saturated and finding your identity and your worth in your tasks that you accomplish, then you’re definitely not focused on a more productive hour in your work week that is spent with champions who are focused on growth because you are getting identity and worth from task and you shouldn’t.

So let me first say, don’t get your identity from work. Don’t get your self worth, your affirmation, your validation from work. Now you’re going to get some of it there, but don’t let that be the bulk. The bulk of that should be coming from God, the One who owns you, the One who made you, the one that cares about you and loves you more than anybody else on the planet.

It he’s the one who loves economy as well. He created it and he loves you. So if you’re getting your affirmation there, if you’re getting your self worth there, if you’re getting your identity from God, then you’re not getting it in your job. So you can actually let go of the task saturation, the tons of stuff that is bogging you down, and instead focus on the things that make you the absolute best in your business.

So, for example, me, I should not be doing administrative work. It’s not that I can’t do it. I can do it. I’m the kind of person who can make anything happen. It’s just not the most productive thing for me to be doing. Instead, I need to be leading, I need to be teaching, I need to be guiding you guys. I need to be putting out content that helps you and changes you.

I need to be coaching in our coaching program and mentoring in our mastermind groups and all of that stuff. That is where I’m powerful. That is where I am the best for this business. But if I get stuck doing tasks, daily tasks, that takes me four hours. And yet if I hired somebody who was administrative, it would take them 30 minutes that is a complete waste of my time.

So when I am not bogged down by task saturation, it makes it much more easier for me to put an hour in my week to be spent with champions, to be spent with people who are really focused on growing, and not just growing themselves, but helping me to grow. So that’s what I need you to ask. What’s holding me back? Is it because I’m so bogged down in my week that I don’t have the time?

If you can’t create one hour a week to spend with people who are going through the same stuff you are, even if they’re not in the same town as you, then guess what? You’re going to keep doing the same exact thing you’ve done over and over and over again. And expecting growth, expecting change. We all know that’s the definition of insanity. Let’s not do that. So I want you to be asking these five questions.

How do I see myself compared to how I see others? Do I have a network of challenging minds? Do I have a growth mindset? Not just a desire to have a growth mindset, but am I doing something with it? Do I have proper accountability? And what is holding me back from reaching my goals? So, in other words, if I had time with champions week after week, how much more could I get accomplished?

How much better could I lead my team? How much better could I grow my business? If you will ask those five essential questions, you will discover the answers, and you may not like them. So be honest with yourself, folks. As always, our goal is to change every bit of your life. Our goal is to. To help you. Our goal is to grow you. Our goal is to expand you.

We want to push you past normal. We want to push you past your comfort zone. So hopefully this has helped you out today. Do me a huge favor. Tell people about this. If you would go onto itunes, leave a review. Let us know what you think, even if you just do the stars. But we’d love to hear what you think. We’d love to hear your reviews. So if you click on itunes, just give us a quick review.

Whether you like us or don’t like us, tell us what you think. That means the world to us. Not only do we get that great input back from you, but that also helps other people to see that we are here and that we can help them as well. So please do that right now, if you would, as always, we want you to take this information. Change your leadership, Change your business, Change your life.

And join us on the next episode.