Things Leaders Do

When to Address Underperformance (Part 1 of 2)

• Colby Morris

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Quick Answer

When should you have a performance conversation with an underperforming team member? Address it immediately the first time you notice an issue—not the third or fourth time. The first time, approach it with curiosity: "What happened?" The second time, express concern and document the conversation. Waiting only makes the problem worse for everyone involved.


Episode Description

How do you know when it's time to address underperformance? What are the early warning signs that someone's struggling? Why does waiting to have the conversation make everything worse?

Most managers wait too long to address performance issues—hoping the problem will fix itself or waiting for the "perfect time" to bring it up. But waiting doesn't help. It just lets small issues escalate into formal performance problems.

In this first part of a two-part series, Colby shares the four signs that tell you it's time to have the conversation, why you need to address issues immediately (the first time, not the third), and why early intervention is actually the kindest thing you can do for someone who's underperforming.

This episode sets the foundation. Next week, Part 2 will give you the exact framework for what to say and how to follow up.


Key Takeaways

  • The four signs that tell you it's time to have a performance conversation
  • Why you should address issues the first time you notice them—not wait for a pattern
  • The immediate intervention approach: first time with curiosity, second time with documentation
  • Why waiting makes the problem worse (the timeline of doom from Week 1 to Week 12)
  • Why early intervention is actually kinder than avoiding the conversation
  • Key statistics: Employees are 3.6x more likely to do outstanding work with daily vs. annual feedback (Gallup)


Who This Episode Is For

Middle managers who've noticed someone on their team underperforming, who want to know when to intervene, and who need the confidence to address issues early instead of waiting until they become formal HR problems.


Connect with Colby

Don't miss Part 2 next week where Colby walks through the exact six-step framework for what to say in the conversation and how to follow up to make sure it sticks.


SPEAKER_00:

People first leadership. Actionable strategies, real results. This is Things Leaders Do with Colby Morris.

SPEAKER_01:

You're three weeks into doing consistent one-on-ones with your team, or at least a couple weeks now. And you start to notice something. Something uncomfortable. One of your team members isn't making the progress that you expected. The goals that you set together in January, yeah, they're they're not hitting them. Not even close, actually. The project you thought would be done by now, still not finished. Still working on it, still almost there. The improvement you were hoping to see, it's not happening. In fact, you're not entirely sure anything is happening. And every time you have a one-on-one with them, you can feel it. You know that that tension in your chest, that uncomfortable awareness that something's not working, that little voice in your head going, We need to talk about this, but maybe not today, maybe next week. You know that you need to say something, right? But you're dreading it like a root canal. You don't want to demotivate them, you don't want to make it awkward, you don't want them to think you're micromanaging them and you don't believe them, or that you're one of those terrible managers who's just impossible to please. So you keep hoping it'll get better on its own. Maybe next week. Maybe they're just having a rough month. Maybe I'm just being too impatient, or maybe my expectations are too high. Maybe I'm the problem. But deep down, you know, this isn't going to get better on its own. This is getting worse. And you're running out of time to address it before it becomes a thing with a capital T. Here's what's actually happening. Most managers either wait too long, hoping the problem magically fixes itself like a software bug that resolves on its own, or they come in way too harsh, making it feel like you're, you know, you're failing and we need to have a serious conversation moment. Neither one works, but both make everything worse. When you wait too long, the problem gets bigger. Okay, your team members keep underperforming. Your other team members start noticing and wondering why you're not doing anything about it. And by the time you finally work up the courage to have the conversation, it's turned into a formal performance issue instead of a quick course correction. Congratulations. You've waited so long that what could have been a five-minute conversation is now a documented HR situation. Well done. But when you come in too harsh, when you make it feel like they're in trouble, like they've disappointed you, like they're on thin ice, you destroy trust faster than you can say performance improvement plan. They get defensive, they shut down, they, you know, they stop being honest with you. And now you've created a bigger problem than what you started with. Plus, they're probably updating their LinkedIn profile during your team meetings. So you're stuck, paralyzed somewhere in between I need to say something and I don't know how to say it without making it worse. You know you need to address it, but you don't know how to do it without either seeming like you don't care or coming across like a jerk. But here's the thing: there's a framework for having this conversation early before it becomes a formal performance issue, before HR gets involved, before anyone uses the phrase pip in a way that's direct but not demoralizing. It's not about waiting for the perfect time. Spoiler, there is no perfect time. Okay, it's always going to be at least a little uncomfortable. And it's not about building up the courage to have big scary confrontation where you channel your inner tough boss and deliver hard truths. It's about treating this like any other conversation you have in your one-on-ones. Direct, honest, focused on helping them succeed, not on making them feel like garbage. This is part one of a two-part series. Today I'm walking you through when to have this conversation, how to spot the early warning signs, and why addressing them immediately matters. Next week, I'm going to give you the exact framework for what to say and how to follow up. By the end of this episode, you'll know exactly when to intervene, the four signs that tell you it's time to have that conversation. You'll understand my approach to immediate intervention and why waiting makes everything worse. And you'll be ready for next week's episode where I walk you through exactly how and what to say. Here's the truth: the longer you wait, the harder this gets. And your team member, they're probably already aware something's not working. They can feel that tension. Okay, they're just waiting for you to bring it up so they can stop wondering if they're about to get fired. So let's talk about when to have that conversation. Hey leaders, this is Colby Morris, and this is the Things Leaders Do podcast. Again, this is part one of a two-part series on having early intervention conversations. As always, I'm trying to keep this, you know, 15, 23 minutes of practical, actionable tools. Okay, it's just real guidance. I try not to put a lot of fluff out there. I'm trying to give you the tools that you need to be a better leader faster. All right. So let's start with the question every manager asks. How do I know when it's time to have this conversation? Because you don't want to be that manager who panics after one bad week, but you also don't want to wait six months while the problem gets worse. Here's what I look for. Here are the warning signs that tell me it's time to intervene. Sign one is the pattern is consistent. One missed deadline, not a pattern. Could be anything. Bad week, family emergency, their kid threw up on their laptop. Life happens. One rough week, that's also not a pattern. We all have rough weeks. Sometimes you're just off your game and you know, you can't really explain why. Your brain decides to take a vacation without telling you. But two weeks in a row of the same issue? That's starting to look like something. Three weeks? Yeah, that's that's a pattern. That's not bad luck. That's a that's a thing. A real, actual thing that you need to address. If you're seeing the same problem show up in multiple one-on-ones, whether it's missed deadlines, incompetent work, lack of follow-through, the I'll get to it next week, or something like that on repeat, like a broken record, that's a signal. Okay? Don't wait for that to get worse. Don't hope it's a fluke. Don't convince yourself that week four will magically be different, even though weeks one, two, and three were all the same. Address it early, while it's still a course correction and not an intervention. Sign two. You're starting to work around them. This is a big one. And it's sneaky because you don't always realize you're doing it. If you catch yourself reassigning their work to someone else because it'll just be faster if Sarah does it, or doing it yourself at 9 p.m. because you don't trust they'll deliver, or building in extra time to every deadline because you assume they'll be late anyway. Yeah, you've already waited too long. The moment you start working around someone instead of working with them, you need to have that conversation. Here's what's really happening. You think you're being nice. You think you're protecting them from failure or giving them grace. You know, you're being a patient manager. But really, you're protecting yourself from having an uncomfortable conversation. And they know it. Trust me, they know. They can tell you don't trust them. They can tell you're tiptoeing around them, and that's way more demoralizing than a direct conversation would be. Sign three is other team members are noticing. If other people in your team are starting to ask questions, is Tom okay? Why am I covering for them again? When is this project actually getting done? Yeah, that's how you know it's time. Or worse, if they're not asking questions, but you can see it in their faces during team meetings. You know, that look, you know the one. The are we seriously not going to talk about this? That look. Because underperformance doesn't just affect one person. Okay, it affects the whole team. It's like a bad smell in the office. Everyone notices, but no one wants to be the one to say something. And if your high performers are picking up the slack while you avoid the conversation, they're going to resent it deeply. I tell people this a lot. High performers do not want to work with low performers. And they're starting to wonder if performance actually matters on this team. Or if you just reward the people who show up and breathe while the people who actually work carry the load. Guess which group starts looking for new jobs first. All right, sign four. They're avoiding accountability in one-on-ones. I want you to pay attention to how they show up in your 101s. Are they taking ownership of their work? Or are they making excuses? Like, I didn't have time. I didn't get the resources I needed. Someone else dropped the ball. The system was down. I was waiting on approvals. My horoscope said it wasn't a good day for the project work. Okay, maybe not that last one, but you get the idea. Look, sometimes those things are true. Systems do crash, other people do drop the ball. Resources are something, you know, sometimes that they're just genuinely missing. But if every single one-on-one is a list of reasons why things aren't getting done, that's a red flag the size of a parade float. Here's the tricky part. Sometimes they don't even realize they're doing it. They genuinely believe that all these external factors are the problem. They've convinced themselves they're a victim of circumstance rather than someone who has agency and responsibility, which is why you need to help them see the pattern. Because if you don't, they never will. Here's my approach. Address it immediately. And here's my guideline. And it's different from a lot of what you know leadership books are gonna tell you. The first time you see an issue, I address it right then or that day. Do it in your next one-on-one or in a quick conversation. And it's not aggressive, okay? Not like they're you know in trouble, just address it. Something like hey Tom, I I noticed you can get that report in before the deadline. That's not really like you. What happened? And that's it. Empathetic, curious, assuming the best, but and this is a big but, also making it clear that you noticed. Because here's what you're doing you're establishing that you're paying attention, you're you're setting a like a baseline and you're giving them a chance to explain. Maybe it was a one-time thing, maybe they had a legitimate reason, maybe they didn't realize it was you know a hard deadline, whatever. But now they know that you noticed the second time, that's when it gets more serious. Okay, Tom, I'm I'm starting to worry about this. Two deadlines in a row, and you know, you've messed with the report. I know we talked about this last week, and I felt we had a good conversation. So what is it that's happening? This is not like you, and I'm I'm worried you're on a bad trend at this point. And then, and this is critical, I send them an email later, just summarizing our conversation. No, that's not a formal write-up, not a you know, you're in trouble email, just a summary. I'd say something like, you know, hey Tom, just wanted to recap our conversation day. We talked about the missed deadlines on this date and this date, and you mentioned, you know, whatever it is they said. We agreed that moving forward, you'll, and then whatever that specific, you know, commitment is. Hey, let me know if you need anything from me to help make that happen. Why the email? Because two times is a big deal. Okay, especially when you're starting the new year with momentum and someone immediately starts to struggle, that's tough. Or, you know, hey, if if it's in the middle of the year and suddenly there's a pattern, okay, it's the same thing. The email creates documentation, not in a punitive way, but in a we're both clear on this way. Here's the key principle. The more you let things go without having some sort of conversation, the more it seems like you're just allowing that issue or behavior. If you wait until the third time or the fourth time or week eight to say something, you've already told them it's okay. Your silence is permission. If you didn't write that down, I'm gonna say it one more time. You've already told them it's okay. Your silence is permission. So don't wait. Address it the first time. Escalate your concern the second time, document the second conversation. By the time you get to a third occurrence, if you get there, everyone knows where things stand. Okay? And you're not starting from scratch to explain why this matters. You've already been having the conversations. Here's what the research shows. Employees are 3.6 times more likely to do outstanding work when they receive daily feedback versus annual feedback. And 80% of employees who receive meaningful weekly feedback are fully engaged. Wouldn't you like to know for sure that 80% of your employees were fully engaged? You know what that means? Your team members want to know where they stand. They want feedback, they want the course correction. So when you notice a pattern early and addressed it early, you're you're not being harsh, you're being helpful. Okay. So you've spotted the pattern. You know it's time to have the conversation. But maybe you're thinking, I'll wait one more week. Maybe it'll get better. Maybe I'm overreacting. Let me tell you why that's a mistake. Here's a hard truth that's going to sting a little. Performance problems seldom, if ever, get better on their own. I know. I know. You're you're hoping this one time it will. Okay. You're you're hoping that if you just give them a little more time, a little more grace, a little more space to figure it out, they'll magically turn it around. Like one day you'll show up on a one-on-one and they're like, great news. I've completely fixed all my performance issues overnight. I don't know what happened, but I'm suddenly amazing at my job. Yeah, that that's not gonna happen. I've been doing this for 20 plus years. I've seen a lot of performance issues. I've managed hundreds of people. I've had all the conversations. You know how many times I've seen someone, you know, underperforming that just suddenly turned it around with any intervention, without any conversation, without any support or course correction? Yeah, not many. It doesn't happen. Because if they knew how to fix it, they would have already. Either way, waiting doesn't help. Waiting just lets the problem marinate and get worse. The longer you wait, the more it escalates. Here's what happens when you wait. I'm going to show you the timeline of Doom here. Week one, small issue, easy to fix with a quick conversation, five minute tops. Hey, I noticed this, let's course correct, done. Week two, issue continues. Now it's a pattern. Still fixable, okay, but requires more discussion. Now it's a 20-minute conversation set at five. Okay. You're explaining the impact. They're explaining what happens. It becomes a thing. Week three, issue is affecting other team members. Now it's not just their problem, it's a team problem. Your high performer is in your office asking why they're covering for someone else. You're making excuses that you don't believe. They're working on it, you'll tell them, knowing full well that they're not. And then week four, you're frustrated. They're defensive because they can tell you're frustrated even though you haven't said anything. What should have been a five-minute course correction is now a formal performance conversation complete with written documentation and serious faces. Week eight, you're documenting everything for HR like you're building a legal case. They're updating their LinkedIn profile and responding to recruiter messages during work hours, and everyone is miserable. By week 12, you're sitting in HR's office having the is this a pip situation conversation while your high performers are interviewing at your competitors. See how fast that escalates? It's like a snowball rolling down a mountain, except the snowball is made of anxiety and poor performance and your own regret for not addressing it sooner. The longer you wait, the worse it gets. For really, for both of you, and for everyone around you who has to watch this slow motion car crash. Your team is watching. Okay. Here's the thing nobody talks about. Your your high performers are watching how you handle underperformance. When you when they see you avoiding the conversation, they s when they see you reassigning work or making excuses for someone who's not delivering, they draw conclusions fast. Okay. You probably have seen exactly what I'm talking about. Okay. They're thinking to themselves, oh, so performance doesn't actually matter here. Got it. The people who work hard and the people who don't get treated exactly the same, cool, cool, cool. Why am I killing myself when Tom is coasting and nothing happens? What what am I? An idiot? And eventually, your higher performers check out. They stop going above and beyond. They start doing the bare minimum because why work harder than necessary if it doesn't matter? Or worse, they leave and they take their high performance to a company that actually rewards it. So when you avoid the conversation with one underperformer, you're not just hurting that person, you're demotivating the entire team. You're sending a message that mediocrity is acceptable. And high performers hate that message. Here again is what I've learned in over 20 years in operations and leadership. The kindest thing you can do for someone who's underperforming is to tell them early. Okay. I know that feels counterintuitive. I it can feel mean, it can feel harsh. You know, you think if I just give them more time, that's the nice thing to do. But it's not.

unknown:

Okay.

SPEAKER_01:

Brene Brown said, you know, clarity is the best thing. If you want to be nice, you have to be clear. Because every week you wait is another week they're building a reputation as someone who doesn't deliver. Every week you wait is another week your team members are noticing and resenting. Every week you wait is another week they're thinking everything's fine when it's not. That's not kind. That's cowardly. And look, I say that with love because I've been that cowardly manager more than once. I've waited too long because I didn't want to have an uncomfortable conversation. I convinced myself I was being patient and graceful. Really, I was just being scared. And every single time I regretted it. Because when I finally had the conversation, weeks or months later than I should have, the person would look at me with this expression of confusion and hurt and say, Why didn't you just tell me this sooner? I thought I was doing fine. And I didn't have a good answer. Because the truth was, I was being a coward and I didn't want to have an uncomfortable conversation. And you can't say that out loud, even though it's the truth. So if you're waiting because you think you're being kind, you're not, you're being selfish, address it now while it's still a course correction and not a formal performance issue, while there's still time to fix it. All right, let's bring this home. If you're cons, you know, if you're doing your consistent one-on-ones, and you absolutely should be, you're going to notice when someone's not making progress. That's the whole point. The one-on-ones give you that visibility. And when you notice that pattern, you have two choices. You can wait, hope it gets better, work around them, and watch the problem escalate. Or you can address it early the first time with empathy and directness. Again, here's what that looks like. Hey, I noticed, you know, you missed the deadline. That's not like you. What happened? The second time, I'm worried. This is the second time. What's going on? And document that second conversation with just a nice email summary. Because the more you let things go without a conversation, the more you're saying it's okay. Again, your silence is permission. Next week in part two of this series, I'm going to walk you through exactly what to say in that conversation. The six step framework that it's direct but not harsh. Okay. How to listen for what's actually going wrong and how to follow up and make sure course correction sticks. But for now, just remember, don't wait and address it early. Because the longer you wait, the harder this gets for both of you. And your team member, they're probably already aware something's not working. They're just waiting for you to bring it up. So bring it up this week and your next one-on-one. You've got this. Hey, if your organization is struggling with performance management, or if your leaders need help having these early intervention conversations, well, I'd love to help. I work with organizations and I do that through keynote speaking, executive coaching, and leadership training to build people-first cultures that get results. You can connect with me on LinkedIn or you can visit my website. Both those links are in the show notes. And hey, if this episode was helpful, would you do me a favor? Please subscribe to the show wherever you listen to your podcast. And please, please leave me a review. Okay. And make sure you tune in next week for part two, where I'll give you the exact framework for what to say and how to follow up. And remember, keep noticing the patterns, okay? Keep addressing them early and keep showing up for your team. And you know why? Because those are the things that leaders do.

SPEAKER_00:

Thank you for listening to Things Leaders Do. If you're looking for more tips on how to be a better leader, be sure to subscribe to the podcast and listen to next week's episode. Until next time, keep working on being a better leader by doing the things that leaders do.