Things Leaders Do

Tough Conversations Part 2: When the First Conversation Didn't Work

• Colby Morris

Share episode

You had the tough conversation. You thought you were clear. But nothing changed.

Now what?

Most leadership advice stops at "have the conversation" and never tells you what to do when the issue repeats. In this episode, leadership consultant Colby Morris walks you through exactly how to handle the second conversation—and why it's often more important than the first.


What You'll Learn:

  • Why the first conversation probably didn't work (and how to avoid the same mistake)
  • The two bad paths leaders take when issues persist (and the real cost of avoidance)
  • When to have the second conversation (and why timing is non-negotiable)
  • The "recap method" that creates accountability while protecting you as a leader
  • How to shift your language from coaching to accountability without losing respect
  • When to escalate to HR or start a PIP (the two-strike framework)
  • Step-by-step guide to preparing for and conducting the second conversation


Key Statistics:

  • Every avoided conversation costs organizations $7,500 and 7 lost workdays
  • 53% of employees handle toxic situations by ignoring them
  • 70% of employees feel disengaged when poor performance goes unchallenged
  • 25% of managers postpone difficult conversations for a year or longer
  • Low performers without accountability cause a 30% decrease in team productivity

Perfect for middle managers, directors, and team leaders who need practical guidance on accountability conversations that actually work.


Related Episodes:

  • Episode 31: How to Have Tough Conversations with Employees 
  • Episode 26: Difficult Conversations for New Leaders


Connect with Colby Morris

Website: nxtstepadvisors.com 

LinkedIn: linkedin.com/in/colbymorris

Email: Colby@NXTStepAdvisors.com

Services: Executive Coaching | Leadership Training | Keynote Speaking | Tough Conversations Workshop

Enjoyed this episode?

  • Subscribe to The Things Leaders Do on Apple Podcasts or Spotify
  • Leave a 5-star review
  • Share with a leader who's avoiding a tough conversation right now

Remember: Keep having the hard conversations instead of avoiding them. Keep being clear about expectations and consequences. And keep giving your people a real chance to succeed before you move to termination. Because those are the things that leaders do.

#ToughConversations #LeadershipAccountability #PeopleFirstLeadership #MiddleManagement #PerformanceManagement #DifficultConversations #LeadershipDevelopment #HRLeadership


SPEAKER_00:

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

SPEAKER_01:

So you had the tough conversation. You thought you were clear. I mean you addressed the issue, you laid out the expectations, you felt like you handled it well. But then nothing changed. The same behavior showed up again. The same mistake was repeated. The same problem is still sitting there on your desk. And now you're wondering, do I have the same conversation again? Do I go straight to HR? Did I fill as a leader? What am I supposed to do when the first tough conversation didn't work? Well, here's what I want you to hear today. The second conversation is often more important than the first. And how you handle it determines whether you're actually leading or just hoping problems go away on their own. Hey leaders, this is Colby Morris, and this is the Things Leaders Do podcast. I'm all about giving you practical strategies that make you a better leader faster. These episodes are short, 15 to say 23 minutes, so you can listen on your commute and then put something into practice the moment you hit the office. No fluff, no theory, just real tools you can use right now. Today we're talking about what happens after the tough conversation doesn't work. Because most leadership advice stops at have the conversation, but never tells you what to do when nothing changes. All right, so let's start with why the first conversation probably didn't work in the first place. Because understanding this helps you not make that same mistake twice. I see this happen in two ways usually, and it usually depends on how long you've been leading. See, new leaders tend to kind of brush around the topic without actually delivering the message. They just dance around it. They hint at it like a LaCroix taste. They say things like, hey, I noticed that sometimes the reports are a little late. Yeah. What they really need to say is, hey, your reports have been late three times in the last two weeks, and that really creates problems for the entire team and that needs to stop. They think they had the conversation because they mentioned it. But the employee walks away thinking it was just a casual observation, not a serious issue that needs to change. Look, I've done this myself early on. You think you're being nice, but you're actually just being unclear. On the flip side, more experienced leaders sometimes go the opposite direction. They mention the issue once and figure that because the boss brought it up, the person would just understand that it's been addressed. Like, well, I've said something, so they know it's important. Here's the thing. Just because you mentioned something doesn't mean the message was, you know, actually delivered. Both of these approaches fail because there's no clarity. No clarity about what needs to change, why it matters, what happens if it doesn't change. So if you're sitting here thinking, I had the conversation and nothing changed, ask yourself honestly, okay, honestly, did you actually deliver the message? Or did you dance around it and hope they'd figure it out? Because if the message wasn't clear the first time, the second conversation is your chance to get it right. And you need to get it right. When the first conversation doesn't work, I see leaders go down one of two really bad paths. And I bet you've seen this too, or maybe you've done it yourself. Path one is they go straight to termination or a pip, you know, a performance improvement plan. They skip the second conversation entirely. They go straight to HR and say something like, I want to start the process and let this person go. Or we need to put them on a performance improvement plan. And look, sometimes that is necessary. I get it. But a lot of times, it's premature. You're going nuclear when there were steps you could still take, or steps you still could have taken. Okay, you're jumping to the final option without giving the person a real chance to course correct. And then pass two, they just avoid it completely. This is actually way more common, and the numbers back this up. 53% of employees handle toxic situations by just ignoring them. That includes managers. We avoid the second conversation because we either don't like conflict, maybe nobody ever taught you how to deal with it in a healthy way. So we just, you know, hope it gets better. We convince ourselves maybe it was just a one-time thing. Maybe they'll figure it out on their own. Maybe it'll just magically resolve itself if we give it time. But here's what the research shows: every conversation failure, every time we avoid having the conversation we need to have, costs an organization$7,500 and more than seven lost work days. Hey, that's per conversation. So when you're avoiding that second conversation, you're not saving yourself discomfort. You're actually costing your organization real money and real time. And meanwhile, the behavior continues. The problem gets worse. And here's the part that kills me. The rest of your team is watching. Nearly 70% of employees feel disengaged when they watch someone underperform and see nothing happening about it. They're thinking, why am I busting my butt when that person isn't even trying and gets away with it? That's the message you're sending when you avoid the conversation. You're not being nice. You're being unfair to everyone else on your team. Don't take either of these paths. Okay. There's a better way, and we're going to walk through it. So here's the rule, and this is non-negotiable. When the issue repeats immediately after coaching, it must be addressed right away. Not, you know, not next week, not when it's you know more convenient, not when you finally work up the courage. Immediately. Because when you let it slide, even just once, you are sending a message. And that message is what we talked about wasn't actually that important. I didn't really mean it. Here's a stat that's going to blow your mind. 25% of managers have postponed challenging discussions for a year or longer. A year. Think about the damage that does to performance, to team morale, to your credibility as a leader. Don't be that person. Now, sometimes the repeat can be an accident. People make mistakes. They're human. I've made plenty of mistakes myself, God knows. But sometimes, and you need to be aware of this, it can be someone testing you. They want to see if you're actually going to hold them accountable, or if you're just blowing smoke. This happens all the time. Especially if you're new to leadership or new to the team. People will push boundaries to see what the real boundaries actually are. And it's not always malicious. Sometimes you're just figuring out, you know, what kind of leader you are. So the second time the issue shows up, you address it. No exceptions, no waiting, no hoping it goes away. Here's what's interesting. The second conversation is actually easier than the first one in a lot of ways. Because now you have a pattern. You're not making assumptions, you're not wondering if it's a one-time thing. You know it's an issue because it happened again. You have evidence. And remember this. When low performers stick around without any accountability, research from Harvard Business Review shows it leads to a 30% decrease in team productivity. 30% decrease in team productivity. Your high performers start wondering why they're working so hard. Your middle performers start thinking, well, maybe they can coast too. That clarity, that pattern makes the second conversation more straightforward. Okay, you're not guessing anymore. You know what needs to happen. All right, so let's talk about what actually changes in the second conversation. First, your tone doesn't change. Okay, if you're a people first leader, you're still respectful. You're still calm. You don't raise your voice. That doesn't change just because this is the second time. In fact, the tone that you hear me using right now, that's the tone I use like 24/7. If I'm coaching someone, if I'm correcting someone, whatever it is, this is the tone I use. I don't get upset, even if I am upset. I don't, I don't put that in my voice or my tone. Okay. But your language absolutely must change. The second conversation needs to move toward forward action and concrete consequences. It needs to sound different from the first one. Okay. Now, you do need to ask what caused something, right? So give them a bump to just explain what has happened, you know? Hey, this happened again. What's, you know, what happened? Can you help me understand why you're missing this deadline, that kind of thing? If they don't really have a great reason, I didn't say excuse, a great reason, then you kind of bump it up a little bit and you say something like, Look, this happened again 10 days after our last conversation about it. Okay, we specifically discussed that your reports needed to be on time. And here we are two weeks later with another late report. Okay, this does have or could have an impact on your future here, and I need you to understand that. See the difference? It's still respectful, but it is direct. It connects the dots between their behavior and the consequences. It removes that ambiguity. The first conversation might feel more coaching heavy. Okay. The second conversation feels more accountability heavy, and that's appropriate. Now, here's the approach I use for the second conversation, and I think this is really effective. I start by asking them to recap. I'll say something like, Can you recap for me what we discussed last time you were in here regarding this situation? What did we ultimately decide was the issue and how did we address it? And then I just let them talk. I want them to own this conversation. Here's why this works. As a people first leader, I've had multiple conversations and coaching with this person, especially in our one-on-ones. So this isn't like coming out of nowhere. They know and they can speak to it. When they recap it for me, it's an acknowledgement that we've already addressed this. It's not a surprise to anyone at this point. They know it, I know it. And whatever this conversation leads to is the next step. This approach also protects you, by the way, okay, because if they can't recap the conversation or they act surprised, that tells you that the first conversation wasn't clear enough. And that's valuable information. And it's on you. You have to own that. Because if you aren't communicating clearly the first time, it's not their fault. You have to make sure they understand. Okay. But most of the time, they know exactly what you're talking about. And that makes the accountability piece much easier. So let's talk about when you do need to escalate beyond just the two of you. Because at some point you might need to involve HR or start the formal process. Here's my framework. I involve HR when I've coached someone at least twice, depending on how serious the issue is. Now, if it's severe enough, like a major policy violation or something that puts the company at risk or creates a hostile work environment, it could either be immediate termination or a final warning right out of the gate. Those situations absolutely exist, and you need to know your company's policies and involve HR immediately when those happen. Don't try to handle those on your own. But for most performance issues, the you know, the everyday stuff like missed deadlines, quality problems, attitude issues, after I've addressed it twice, it becomes like a two-strike situation. We're at a point where something more formal needs to happen. HR usually needs to be involved in a pip anyway, because there's legality around the language and the process. You want to make sure you're protected and the employee is treated fairly. Okay, don't skip this step. But here's my standard. And this is how I know when it's time to move. When I know that I know that I know that they know it's time to escalate. Colby, what does that mean? It means we've talked, we've discussed it multiple times. I've been clear. They've acknowledged it. There's no ambiguity left, zero. At that point, if the behavior continues, it's not about me, you know, giving up on them. It's about acknowledging that this person just isn't a fit for this role or this team. And that's okay. Hey, not everyone is a fit everywhere. But as a leader, you have the responsibility to the rest of your team and to the organization to address performance issues. You can't let one person's poor performance drag down everyone else indefinitely. I don't ever want to feel like I gave up on someone. That's just, that's just not who I am. I want to be able to say to myself, to them, to HR, to my boss, that we exhausted all of our options. We coached, we documented, we gave them every opportunity to course correct. We were clear about expectations, we were clear about consequences. And at this point, the decision is clear. And you know what? They know that too. It makes it easier to have what might be that final conversation when it's time because they know at this point that they haven't made it, they didn't cut it. And that's how you approach it with integrity. That's how you sleep at night knowing you did the right thing. All right. So let's get really practical. If you need to have the second tough conversation this week, here's exactly what you do, step by step. First, schedule it quickly. Look, don't wait. Stop waiting. Okay, that thing you're thinking about, stop waiting. Don't let days pass while you work up your nerve. Okay, as soon as you see the behavior repeat, get it on the calendar. Same day if possible. Next day at the latest. The longer you wait, the weirder it gets and the less effective it becomes. Second, prepare your language. Look, write it down. Okay, don't wing it. Write down things like what was discussed in the first conversation, what you both agreed would change, what actually happened since then, and be specific. You know, give dates and examples. What needs to happen going forward, what the consequences are if it doesn't. Okay, be specific. Use concrete examples, no vague language like sometimes or often, say three times in the last two weeks, or on Tuesday and Thursday. And then third, start with the recap. Can you recap for me what we discussed last time about this and let them talk? Let them own it. Don't fill the silence. Just wait and let them talk. And then fourth, acknowledge the reality. We had that conversation, you know, six days ago, and this issue has happened again. That tells me something needs to change, either in how you're approaching this or whether this role is the right fit for you. You're connecting the dots for them. You're making it clear that this is serious. Fifth, let me be clear about next steps. Here's what needs to happen from this point forward. Here's what success looks like. And here's what happens if this continues. No ambiguity, no sugar clothing, just clarity. And then sixth, document everything. Okay, this is crucial. Send a follow-up email summarizing the conversation. Okay, keep notes in a file, date everything. If this ends up going to HR or a pip, you need documentation that shows you addressed it multiple times. Okay, protect yourself and be fair to the employee. And here's the emotional part that nobody talks about. This can be hard. Okay, even when you know it's necessary, even when you've done everything right, sometimes it's still hard to have these conversations. It doesn't feel great. But you know what's harder? Letting the behavior continue and watching your team lose respect for you. Letting poor performance drag down everyone else who's working their butt off. Avoiding the conversation until you feel like you have no choice but to fire someone without warning because you never actually address the issue properly. The second conversation is an act of leadership. Yes, it can be uncomfortable, but it's necessary. And your team, the ones who are doing the right thing, they're counting on you to have it. So here's what I want you to do this week. If you have an issue that didn't resolve after the first conversation, don't avoid it. Don't go straight to HR and don't skip the second conversation. Have the conversation. Do it right. Use the recap method, be clear about consequences, document everything, and give the person a real chance to turn it around. That's fair. That's leadership. And if you're listening to this thinking, man, I wish I'd done this differently with someone in the past, that's okay. You can't go back and fix that. But you can do it right the next time. Learn from it and move forward. Leaders, if your organization needs help building leadership skills around tough conversations, conflict resolution, or people-first accountability, I'd love to help. I work with leaders and teams through keynote speaking, executive coaching, and leadership training to build people-first cultures that drive real results. You can connect with me on LinkedIn or my webpage, and those are both in the show notes. And hey, if this episode resonated with you, would you do me a favor? Subscribe to the show wherever you listen to podcasts, and please leave a review. And share this episode with another leader who's wrestling with how to handle a tough situation. Maybe they're avoiding a conversation right now. Send this to them. Let them know they're not alone and finding this stuff hard. That's how we grow this community, and that's how we get the word out to make a bigger impact in the workplace. And remember, keep having tough conversations instead of avoiding them. Keep being clear about expectations and consequences. And keep giving your people a real chance to succeed before you move to termination. 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.