Maybe you’ve got someone on your team who’s struggling, and you’re dreading the conversation. You don’t want to demoralize them, but you also can’t ignore the problem.
So how do you have the conversation in a way that leads to improvement and not fear? That is what we’re diving into on today’s episode of The Chris LoCurto Show.
Leading people is one of the toughest things you’ll do in business. And it gets even harder when a leader on your team isn’t performing well. Do you come down on them? Do you let it slide? Do you hope they’ll figure it out on their own? (Spoiler: That last one never works.)
Today, I’ll walk you through how to handle these conversations the right way—so you can actually fix the problem instead of creating fear or resentment. We’ll cover the two main types of underperforming leaders, how to approach these conversations with curiosity instead of criticism, and how to get real solutions that actually stick.
And, of course, I’ll share real-world examples along the way—because I want you to see how this works in action. Let’s dive in!
Episode Breakdown with Timestamps:
IBM Story (00:01:30)
Before we dive into strategies, I share a powerful story from IBM’s turnaround, showing how their CEO led tough conversations with curiosity and clarity—leading to one of the biggest business recoveries in history.
Understand the Two Types of Underperforming Leaders (00:03:03)
Not all struggling leaders are the same. I break down the difference between the ‘aware but stuck’ leader and the ‘oblivious’ underperformer—and why each requires a different approach. (With examples!)
Start the Conversation with a Gentle Hand (00:09:21)
Tough conversations shouldn’t feel like an attack. Here, I explain how starting with empathy and curiosity lowers defenses and makes leaders want to improve.
Get Their Perspective Before Jumping to Conclusions (00:12:57)
You may think you know why someone is underperforming—but until you ask the right questions, you don’t. This section shows how to gather key insights before making assumptions.
Shift the Focus to Solutions and Ownership (00:16:02)
Instead of guilting someone into improvement, guide them toward real solutions they can take ownership of. I give practical steps to make this work, especially for leaders struggling with delegation.
Next-Level Leadership LIVE Event 2025 (00:18:54)
If you’re tired of your business running on stress and frustration, this is the event for you. I break down what you’ll gain at Next-Level Leadership LIVE and how it will help your business run without you having to do everything yourself.
Set Clear Next Steps with Encouragement (00:21:46)
Telling someone to ‘just do better’ doesn’t work. Instead, I explain how to set clear expectations, check in consistently, and ensure long-term improvement.
Additional Resources (00:24:49)
Want to go deeper? I recommend two past episodes where we role-play tough conversations, so you can see exactly how to handle these situations in real life.
Underperformance doesn’t have to be a crisis—it’s an opportunity for leadership growth. If you handle these conversations with curiosity, empathy, and clarity, you’ll see stronger leadership on your team and better results across the board.
So ask yourself: Who on your team needs this conversation today? And how can you approach it in a way that leads to real change—not just temporary compliance?
Do this well, and you won’t just fix performance issues—you’ll develop a team of leaders who want to improve and take ownership.
That’s it for today’s episode! Now go take action. Change your leadership, change your business, change your life!
616 | How to Address Underperforming Leaders Without Crushing Their Confidence
Maybe you've got someone on your team who's struggling and you're dreading the conversation. You don't want to demoralize them, but also you can't ignore the problem.
So how do you have the conversation in a way that leads to improvement and not fear? That is what's coming up on today's episode of the Chris LoCurto Show.
Welcome to the Chris LoCurto show where we discuss leadership and life and discover that business is what you do, not who you are.
Welcome to the show, folks. I hope you're having a fabulous day wherever you are. Today we are going to be talking about sharing some key strategies and some common pitfalls as well.
Some real world examples to kind of help you coach leaders effectively while keeping morale intact.
Now, this is a, this is a very difficult conversation. This is not an easy one. This is a place where a lot of leaders struggle.
And, you know, normally we struggle with this by just trying to lead a team member in one of these situations when somebody's failing.
But it's also difficult to look at a team leader and figure out, how do I lead this person to success? They're not doing as well as they should, they're failing somehow. What do I do? Right?
IBM Story (00:01:30)
So before we dive into all of that, I just want to kind of share a quick story because you hear me kind of talk about this a lot on the show, but I want to kind of give you a different perspective.
And that's a story about IBM for those of you, for those of you who are old enough to remember IBM, yes, the company, I believe, is still out there operating.
But in the early 90s, IBM was on the verge of collapse. They were losing billions and they were stuck in outdated ways of thinking. And that's when Lou Gerstner stepped in as CEO and he knew the company's survival depended on its leaders stepping up.
But instead of tearing them down, he approached tough conversations with curiosity and clarity. You hear me talk about be curious all the time.
Be curious, be curious, be curious. Write it down, put it on a post it note, put on the top of your, you know, if you use the same yellow pad all the time, whatever, put it on your computer, be curious. So he stepped in with curiosity and clarity.
Listening first, challenging second. So some leaders embraced the change, but others didn't. But accountability became the norm. That shift helped IBM go from the brink of failure to one of the biggest turnarounds in business history.
And that's what we're talking about today. How to have a tough conversation or have tough conversations, depending upon what you have to have with underperforming leaders in a way that drives improvement, not fear. So let's dive in.
Understand the Two Types of Underperforming Leaders (00:03:03)
Now, the first thing I want to talk about two types of underperforming leaders that are probably going to be the kind that you see the most.
And, you know, are there other kinds? Sure, but these are probably the two you're going to. You're going to focus on the most and see regular. The first one is the aware but stuck leader.
Now, as we get into this, one thing I want to mention, there is a question you should always ask.
I've been telling you guys this forever, and it's easy to forget to ask this question when you get in the leadership hiring mode.
There's one question you should always ask before you even go forward with the process, and that is what makes me think this person can lead people to success?
If you cannot answer that question, do not hire that person in the role. If you do not already see on the front side that there is a way that a person can lead people to success, then do not put that person in a leadership role, period.
If you can't answer that question, what makes me think this person can lead people to success? So that's the first thing. Right.
Another piece of information is if you have somebody in a leadership role and they're failing in an area, the thing you have to ask yourself is, what makes me think they understand how to lead in this area?
What makes me think that they're strong and they know how to lead through this, this failure, this situation, this opportunity, whatever it is. Right.
Just because they have the title leader, just because they've been with you for a while, does not mean that they actually understand how to lead through the situation.
I've been on leadership teams in the past of my early days, sitting there, looking at people failing and wondering, where in the world did we get the idea that this person knew how to solve this and what are we doing to help them?
That's been one of my frustrations in my early years of leadership, is looking around going, nobody else around here knows how to solve this problem. This person's failing, and they're the issue. Right.
And if we would just come together. One of the things that I teach a lot over the last couple of decades is making sure that we're taxing the collective intelligence. Come together, get the brain power, find out how to solve the problem.
So important things for you to be thinking about is just because you have a team member failing, a leader failing, ask the question, do they know how to solve the problem? Start with those.
All right, now jumping in, we're talking about the aware but stuck leader. So this is probably somebody, they probably already know that they're underperforming.
They probably feel frustrated, they probably feel guilty, they may even feel shame, and most likely they feel fearful, Right?
So think of like a department head who's, who knows their team isn't hitting targets, but they keep making the same decisions without success.
We've probably all seen that to some extent, right? We, we've probably all done that to some extent.
Or you don't know what you're doing, but you just keep pushing forward, thinking, if we just keep doing it, eventually it's going to work.
And, you know, sometimes you may experience something like that in life, but it's probably not going to work out well in leading a team. Right?
So you need to start all discussions, all approaches with empathy. So I just gave you some examples of people who not even understanding how to solve the problem, right?
What makes us think that they know how to. You've got to start with empathy. You've got to put yourself in their shoes. They probably feel pressure already.
They probably feel like, you know, you think they're terrible. So start by putting yourself in their shoes.
Approach them with empathy, acknowledge their struggle, and then work together on solutions. All right, we're going to get into some ways of doing that, but I just want to kind of give you that upfront.
First type, the second type is the oblivious underperformer. There are, there are some folks who do not realize that they are underperforming.
This is often a leadership gap. Someone should have been giving them feedback sooner, but they haven't. You know, there's, there's a massive lack of accountability.
There is a lack of possible tough conversations. But if you have a leader who believes they're performing well, then you're not on the same page with them.
And that means that you have not done a good job getting them to a place of understanding what success looks like. That is a terrible place to be. That's a horrible place to be.
So this is something that. It's going to be considerably tougher because they're not aware and they're going to be shocked and surprised and they're probably going to look back and go, why haven't you said something?
Why have you waited this long? Right? Like, if it's a sales manager who's unaware that they're not coaching their team effectively because they're too focused on numbers, we see that a lot.
They don't know how to coach, they focus on numbers and nobody has said anything, nobody's talked to them, right?
So they're probably going to be shocked. They're probably going to be very surprised. You have to lead them with curiosity, not criticism. I'm not saying you can't get to criticism.
What I'm saying is you've really got to step into this and ask them how they think, how they're doing it, how do you think this is going, how well do you think you're doing? How well do you think the team is doing?
If they feel challenged from the very beginning, they're probably not going to respond. So, and by that what I mean is if you come in hot, then they're probably going to walls up and you're not going to get good responses.
So ask them how they feel like they're being challenged in the role. Ask them if they feel like they're addressing performance issues. Go through all those pieces and then that will get you on the right path.
Start the Conversation With a Gentle Hand (00:09:21)
Now what about those conversations? You have to start the convers--, any conversation with a gentle hand. People naturally want approval. They naturally fear disappointing a leader.
Now you might not think that a lot of the leaders that we work with are very self effacing. You know, they don't look at themselves as somebody that a team member is going to be fearful of disappointing. And yet that's exactly what's happening.
That has happened to me my entire leadership career. I do not think people look at me that way. I, I do not think that they're looking at me going, man, I want to do everything I can not to disappoint Chris, I think they're in the same boat with me.
I think, you know, we're doing this together, we're making this happen, right? Let's, you know, get in there, get our knuckles bloodied and make some things happen, right?
But you will be shocked to find that a lot of times people really do not want to disappoint you. So if they're approached wrong, and this is not surprising, but they can shut down, they can become very defensive.
So you know, instead of saying, hey, you're not hitting your KPIs, right, there's a lot of times with folks and a lot of you leaders that have come through StratPlan probably recognize this, that you have these conversations with other leaders and think we're on the same page.
I could talk to this person like this and you don't realize how much your directness is shutting them down immediately. Now, once again, I'm not saying that it's a, you know, that it's an okay thing.
It's, it's. They're probably struggling with some stuff from their Root System. There's a lot of issues. You know, they probably have a big fear of failure.
If you just approach it differently, if you just think that you can talk to somebody the way that you know that they're on the same level as you, then you're probably going to be more direct than you need to be, which is going to affect things, right?
It will probably shut them down. Don't go in, hey, you're not hitting your KPIs. Maybe try and start with something like, hey, I want to check in with you about how you think things are going, right?
What's been working well for you? Where have you been struggling? Get that curiosity out, get that perspective gathering out, right? Why?
Because this will help to lower their defenses. And believe it or not, it's going to make them more open to feedback, right?
It's going to, it's going to show that you care if you do this well. It's going to show that you care. And it's going to put them in a position where they can receive and they can give. Right?
They can be vulnerable because they can trust you with their vulnerability. Next thing you need to do, please, please do not jump to conclusions. Even if, even if you're pretty darn sure you know exactly what's going on.
Get their perspective before you jump to conclusions. You probably do not have the full picture. Well, there's. The numbers are sucking. They're not doing a good job. What perspective do I need to get?
You may not understand. There could be a ton of problems. There could be a software issue. There could be a piece of information that they were never trained on, that they were never taught.
They might believe that you have an expectation of them that is totally not the expectation that you actually have.
I have discovered this a bunch of times in my own leadership and thousands of times leading leaders where leaders believe one thing and they're very, you know, they assume someone is slacking.
And because they didn't get in and really find out what the perspective is of the other person, they end up bullying that person.
Maybe they don't even think that they are, but they end up talking, you know, potentially harshly to somebody and affecting that person and they still don't know the answers.
I've talked about this a thousand times in my early leadership careers. I'd have a leader come in and try and rip my head off. What's going on with this?
And I go, do you want to ask any questions? Why would I ask any questions? Well, because if you did, you'd find out I have absolutely nothing to do with that. Well, who does? I don't know. And then they just storm off. Right?
Those are bosses. Those are horrible people. Those aren't leaders. I should say that. I shouldn't say they're horrible people. Those are horrible leaders. Right, because they're not actually leading.
So instead of coming in, you know, assuming everything, go in and gain quality perspective. Be curious what's been your biggest challenge with hitting your numbers.
Help me to understand where have you struggled? Can you walk me through how you're prioritizing your tasks?
You know, maybe they're focused on something that's not getting you the information that you want. And it's because they have horrible priorities.
Because they believe you have different priorities. You might have said something once this happens.
I've had this happen to me probably a hundred times over, over the decades where I'll say something and somebody attaches to that thing I've said, and that becomes their new priority. I didn't say it was our new priority.
I said it's something we need to do, it's something we need to get to, something we need to make happen. And then, because I was saying it possibly in passing, most likely, that's usually when this happens.
Somebody attaches to it and it becomes their biggest priority. So when you come back and it's like, hey, what's going on? Well, you, you told me that to go after this thing.
Whoa, whoa, whoa. Let's go back to the conversation. When did I say that was your number one priority? Well, I just assumed. Okay, now we have a different conversation, right?
These things happen, folks. So if you will go in with a gentle hand, if you will go in with curiosity, if you will go in gaining their perspective before you jump to conclusions, you could actually get to proper information.
So think of like a marketing leader who's continuously missing deadlines, right?
After asking you find out that maybe a last minute project from another department is consuming their time and it's something you didn't know about, but they thought it was a high priority.
So that gives you the opportunity to find out should they be working on that project? They did somebody come over and get them to work on something that they shouldn't have?
Do they not have healthy boundaries with a potential leader somewhere else? All of these things can give you different perspective and help you to make the right decisions going forward.
Another thing you need to do, shift the focus to solutions and ownership. Shift the focus to solutions and ownership. Most leaders will guilt somebody.
I shouldn't say most. A large number of leaders will just come in with like a guilt trip, you know, why, why aren't you doing this?
Well, you need to make that happen. You better get that done, yada, yada, yada. Instead of helping them get to the solution.
Folks, if they didn't know how to do it before you entered the conversation, what in the world from your fantastic conversation is going to make them know how to do it now?
Why do leaders lead that way? Because the leader probably doesn't have the answer either. And so instead of jumping in and helping out, they try to guilt somebody into getting something done.
You just dumped a bunch of fear on this person and they're going to do a worse job. Now, some people out there might, might hustle it out, they might make it happen. But I can tell you, you just dump so much stress on them that the solution is going to be desperate.
It's not going to be great. It'll be desperate. Get your butt in there and help out. So if a leader is struggling with, let's say, something like delegation, right, don't just tell them you need to delegate better.
That's always worked in all of man's history. That's always worked, right? You better do a better job delegating. That doesn't do crap for anybody, right?
That doesn't help out, ask questions and help them to get to, you know, discover what the problems are and then help them to get to solutions.
Hey, what's making delegation tough for you, right? What are you struggling with? What's one thing that you can delegate this week to free up your time?
Now I'm barely hitting this delegation piece and you know, again, you've heard me talk about delegation in the past that it needs to be proper delegation.
For all of those who've gone through our Killing the Leadership Crazy Cycle lesson, it's got to be proper delegation.
I just don't have time to go through all of those steps. So help them to create an action plan that helps them to delegate properly, right?
If you do that, then they're going to be more likely to follow through. They're going to be more likely to do it correctly. If you don't do that, then what you're going to find is, is that you're going to be the one who's handling all of this stuff.
All of this is going to end up on your shoulders, all the responsibility is going to end up on you. You might end up having to let somebody go because they didn't do a good job.
And that's going to come back on you at the end of the day.
Next-Level Leadership LIVE Event 2025 (00:18:54)
Stuff like this is the major reason why so many leaders are overwhelmed. So let's be honest, one of the hardest parts of running a business isn't the work itself.
It's managing people. Now, if you've ever felt like you're constantly putting out fires, struggling to get your team to take ownership, or frustrated that things don't move forward unless you personally push them, you're not alone. Not at all.
And that's exactly why we created the Next-Level Leadership LIVE event. The Next-Level Leadership LIVE 2025 is happening April 2nd through the 4th.
And this event will show you how to lead a team that actually operates without you being in the trenches every single day.
So here's just some of the things that you're going to walk away with. How to develop leaders on your team so you're not the only one making big decisions.
The keys to getting buy in and accountability are so you're not micromanaging every little thing in your business. How to create a culture where people take ownership so you don't have to chase them down. And here's the best part.
You'll leave with a clear plan to implement these strategies immediately. No guessing, no hoping things change. You'll know exactly what you need to do next.
Now, I know some of you are out there thinking, Chris, I just don't have time for this. But let me ask you, how much time are you already losing dealing with people problems? A few days at this event, two and a half days can save you months, maybe even years of frustration.
Now, registration is open, so go to chrislocurto.com/liveevents. That's chrislocurto.com/liveevents to get your spot. Your business doesn't have to run on stress and frustration.
Let's fix this once and for all. All right, what's the final thing we need to focus on here?
Set clear next steps with big with here encouragement. Underperformers need clarity, not ambiguity about improvement expectations. You need to do that. You need to do that better.
That doesn't mean anything. They need clarity on what they're going to do. So instead of saying, you know, let's work on this and leaving it at that, which a lot of people do try, hey, over the next 30 days, I want you to focus on improving X.
Fill in the Blank, whatever it is, I'll check in with you weekly. How does that sound? Right. Ask them the question, how does that sound?
Do I need to check in with you at the end of the day each day, whatever the thing is. But make sure that you're spending time with them and don't just leave it with them again.
Go through the other steps. Tax the collective intelligence. Find out what some of the struggles are. Find out what they think solutions are. Don't just leave this in their hands. Help them to get to an answer.
Lead, lead, lead. Here's the thing you need to do now. Are you good with going and working on that? And I'll check in with you every week over the next 30 days.
Or, or does it need to be more often? Or whatever. Find out how they feel about it now. Just understand a lot of folks are going to be like, oh, yeah, yeah, oh no, I got this.
If they feel like they can trust you, if they feel like they can be vulnerable with you, then they will tell you where they're going to fail. So don't just leave it at this. Ask questions.
Hey, where do you think you're going to fail with this? Where do you think you're going to struggle with this? Where do you think you're going to need help with this? Go through all of the pieces of information to set them up for success.
So when they go tackle this thing, they're going to be successful. Are they going to hit some road bumps? Probably, but the goal is get them as much info so they are set up for success.
Now, why would we do this? This ensures commitment because you've helped them get to a place where they see you're on their team, they see that you're all about them being successful, where they see that you're not just going to rip their heads off.
So it gets commitment, but it also ensures progress and it also shows them that you believe in them. Right? Massively, massively important.
But Chris, what if I don't? Then figure it out. Learn how. Understand that you have two options here. Help them to fix this and get it done right.
And grow your leader and help them to become stronger and help them to become better, or fire them and try all over again, do the same thing you've been doing.
How well has that worked out? So all of what I'm sharing with you today is going to help you to get that team member, that leader, to a place of vulnerability and growth. Right? So be gentle as you go into conversations.
Get Their Perspective Before Jumping to Conclusions (00:23:57)
Gain perspective before jumping to conclusions. Make sure that you're focusing on solutions and ownership and make sure that you're setting the next steps with them. Help them to get to those next steps and then encourage them.
Make sure those steps are clear. This is what we're going to do. So some action items you can do today. Identify the leaders on your team who may be underperforming.
Sit down and write it down, right? Assess if they are aware or unaware of the issue you need to stop and think about. You probably have some things that you've already known. They're in the back of your head but you haven't done anything about it.
So identify them. Assess if they are aware or unaware. Plan a conversation that starts with questions rather than accusations. Listen first, clarify the situation, then guide them towards solutions and then set clear next steps and follow up with encouragement.
Additional Resources (00:24:49)
So here's some things that you can do as well. Episodes that are great resources 379 | Leading Through Tough Conversations.
This is where our company president Joel Fortner and I act out this scene so that you know you can have more understanding of what it's like.
We're role playing this scene and it shows you how to navigate tough conversations and it can be very beneficial for both sides of the conversation, believe it or not.
Also 595 | Face the Facts: Stop Avoiding Tough Conversations in Business – Part 2. So this episode is all about learning how to have tough conversations and gaining tools to handle them effectively.
So folks, underperformance doesn't have to be a crisis. It's an opportunity for leadership growth. Think about this. If you grow your leaders in this, you will teach them how to grow their team members.
So how you handle these conversations is going to determine exactly whether or not you're building up a leader or you're breaking them down. You probably have some people in your past who have broken you down.
You may even have some people in your past who have lifted you up, right? Who've built you up. So be the one who builds people up.
So when you approach underperformance with curiosity, empathy and clarity, you'll see better results and stronger leadership on your team.
So take action today. Who on your team needs a conversation and how can you approach it? With a gentle but firm leadership hand. Do those things and you will build up leaders, not break them down.
Well folks, I hope this has been helpful today. This is all the time that we have. As always, we want you to take all of this information. We want you to change your leadership, change your business, change your life, and join us on the next episode.