Stop Trying to Win Tough Conversations (Win the Trust Instead)

Research from Notre Dame says more than 80% of workers are holding back at least one tough conversation at work. So when leaders DO finally have those conversations, they're walking in with the wrong goal — trying to win them.

In this episode, you'll learn:

• Why "winning" the tough conversation is the move that actually loses you the team
• The 30-year-old Harvard research that gets the goal of these conversations right
• The Three Pre-Conversation Questions that change what happens when you walk in
• The two language shifts that signal you're there to learn, not to deliver
• The right way to know — one week later — whether you actually handled it

Walk into your next tough conversation trying to learn, not trying to win. The trust you build is the only scoreboard that matters.

The Three Pre-Conversation Questions (Colby Morris)

Before any tough conversation, ask yourself:

1. What am I missing?
2. What do they need me to understand?
3. How do I want them to feel when they walk out?

The One-Week Trust Test (Colby Morris)

Evaluate a tough conversation one week later, not in the moment, by asking:

1. Are they still bringing me things, or did they go quiet?
2. Has the team-wide energy shifted?
3. Would they take the same conversation from me again?

When to apply this guidance:

• You're a middle manager or senior leader with at least one tough conversation in your queue right now
• You've handled difficult conversations before but are seeing the same issues come back six months later
• You manage a team where people seem to agree in the moment but don't change behavior afterward
• You suspect your team isn't telling you the full truth about projects, peers, or the work itself

Research referenced in this episode:

• University of Notre Dame, NDDCEL: 80%+ of workers are holding back at least one challenging workplace conversation
• VitalSmarts (Crucial Learning): Each unheld or failed workplace conversation costs roughly $7,500 and seven workdays
• Brené Brown — Dare to Lead: Seven-year research on the consequences of avoiding tough conversations, including the "dirty yes"
• Stone, Patton & Heen — Difficult Conversations (Harvard Negotiation Project): The shift from "message delivery stance" to "learning stance"
• Chartered Management Institute: 43% of senior managers have lost their temper, 40% have panicked and lied, and 80% have had no formal training on tough conversations

Related episodes:

• Tough Conversations Part 2: When the First Conversation Didn't Work
• How to Have Tough Conversations with Employees
• The Conflict Series, Episode 2: How to Say Hard Things Without Burning Bridges
• Difficult Conversations for New Leaders

Connect with Colby Morris:

LinkedIn: linkedin.com/in/colbymorris 

Website: nxtstepadvisors.com

About The Things Leaders Do:

The Things Leaders Do is a weekly leadership podcast hosted by Colby Morris — Founder of NXT Step Advisors. The show delivers practical, immediately actionable leadership tools for middle managers and senior leaders navigating real workplace challenges. No corporate jargon, no theory you can't use — just real guidance you can implement before your next one-on-one. New episodes every Tuesday on Apple Podcasts, Spotify, and wherever you get your podcasts.

• Colby's LinkedIn Profile
• NXTStepAdvisors.com

Transcript

The Hidden Cost Of Silence

SPEAKER_00 0:00

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

SPEAKER_02 0:11

There's research out of Notre Dame that says more than 80% of workers are holding back at least one tough conversation at work right now. 80%. Now, I want you to sit with that for just a second. Not as some you know HR statistic, not as some interesting fact that you'll forget by tomorrow. But as a leader. That means that right now, today, this week, four out of every five people on your team are sitting on something they need to tell you. Something about the project, something about a teammate, something about you. And you know what? They're not saying it. So while you're walking around your office or your Zoom calls thinking, you know, your team is doing fine, your team is actually sitting in the meeting after the meeting. You know the one? The the Slack DM after the Slack message? The parking lot conversation after the parking lot conversation. The text exchange that starts with, so how do you think that went? And it's never about how it actually went. It's about how it really went. Look, that's not a culture problem. That there is a leadership problem. And here's what makes it worse. The few tough conversations you are having, you're walking into them trying to win them. You you prepped your talking points. Okay, you walked in ready to deliver the message and get back to your day. And maybe, maybe it felt like it went really well. Okay, maybe they nodded. Maybe they said, got it. Maybe you walked out thinking, cool, handled. And then nothing changed. Or worse, they got quieter. They pulled back. Maybe they quit three weeks later.

SPEAKER_01 2:20

Real talk? That that's not because you're a bad leader.

Why Leaders Avoid The Talk

The Real Price Of Failure

SPEAKER_02 2:27

It's actually because you've been taught the wrong goal. So today we're tearing that down. We're talking about why winning the tough conversation is the move that actually loses you the team. What the real goal of a tough conversation should be, and how to know you actually handled it right, which, spoiler, is not measured in the moment. We've got Harvard Research, we've got Bernie Brown, we've got a Marcus, and we've got a whole rethink of what these conversations are even for. So let's get into it. Hey leaders, this is Colby Morris, and you're listening to the Things Leaders Do podcast. I have got about 30 minutes of real actionable guidance for you today. No, you know, corporate jargon, no theory that you can't actually use, just practical tools you can implement before your next one-on-one. So let's talk about it. All right. So let me describe a scenario and you tell me if this sounds familiar. You've got a tough conversation you've been putting off. Maybe it's a you know a performance issue, or maybe a behavioral issue, or you know, maybe it's that thing your direct report did in the meeting last week that you just can't stop thinking about. Whatever it is, it's been on your to-do list for three weeks, maybe longer. And you keep saying, look, I'll do it Monday. And then Monday becomes Wednesday. Wednesday becomes, okay, I'll handle it after this big project. And before you know it, it's a month later, and you're still rehearsing what you're going to say in the shower like you're prepping for closing arguments. Look, I get it. I have been there. Crap, I'm I'm still there sometimes. There are weeks I'd rather rewrite the entire org chart than have one direct conversation with somebody. But eventually you do it. You know, you schedule the meeting. You you walk in with your three talking points, you deliver them, they nod, maybe they push back a little, maybe they don't. You wrap it up in you know 12 minutes flat, and you walk out feeling like a champion. But here's the thing: you didn't win anything. You all you did was pay the entry fee. I've talked about this number on the show before, and I'm I'm gonna keep saying it because most leaders are still acting like it doesn't apply to them. Vital Smarts research found that every conversation failure costs a company$7,500 in seven work days. Seven work days per failed conversation. Now, most leaders are going to hear that stat and think, well, yeah, that's about the conversations I'm avoiding. That's that's not the only kind of failure. The conversations you handle badly cost the same, maybe more. Because at least when you avoid the conversation, you know you avoided it, right? But when you walk out thinking you handled it and you didn't, that that's worse. Now you got a problem you'd even know you still had. And here's where it gets uncomfortable. The reason most of us walk out of those conversations thinking we won is because the leadership world has been training us with the wrong stinking scoreboard. We've been taught the goal is to deliver the message and change the behavior. Talking points in, compliance out. Done. But that that framing is exactly why your tough conversations don't actually work. Because here's what's actually happening on the other side of that table. The person you just won the conversation with isn't going back to their desk thinking, wow, what great feedback. Let me change everything. No, they're they're going back to their desk thinking, okay, okay, got it. Don't bring stuff up like that again. All right. Yeah, don't push back, just say got it and move on. See, you didn't change behavior. You taught them to manage you. And those are very, very different outcomes. Brene Brown, yeah, yeah, I I know every leadership podcast quotes Brene Brown, but stay with me. Brene Brown's seven-year research study on courageous leadership found that when leaders avoid or botch those tough conversations, what shows up next on the team is super specific. She found four things. Passive aggressive behavior, gossip, the meeting after the meeting, and what she calls the dirty yes. Let me break that down because all four of those are happening on your team right now and you probably don't even know it. Passive aggressive behavior is that snarky comment in the team chat. The one that's technically about the project, but it's really about that one person nobody wants to deal with. Gossip, that one's self-explanatory. The meeting after the meeting is exactly what it sounds like. Three people on a Zoom call after the actual Zoom call ends, finally saying what they wouldn't say while you were on the screen. But the dirty yes, that's the one that should keep you up at night. The dirty yes is when somebody nods, says, yes, got it, to your face, but then walks out and does whatever they were going to do anyway. They didn't disagree, they just stopped fighting you. Because fighting you didn't go well last time.

SPEAKER_01 8:39

And you know that moment. You've done it. Don't lie to me.

Switch From Winning To Learning

A Side By Side Conversation Demo

SPEAKER_02 8:45

We've all dirty yesed a manager in our career. The question is whether your team is doing it to you right now. Those those four people in your team holding back the tough conversations, they're not they're not holding back because they're disengaged. They're holding back because the one time they tried to bring you something hard, you treated it like a debate to be won. So they learned. And now they don't try anymore. And listen, I'm I'm not picking on you. Okay. The Chartered Management Institute did a survey of 2,000 managers, and you know what they found? 43% of senior managers admit to losing their temper and shouting in a tough conversation. 40% admit, and this one floored me. 40% admit to panicking and just lying. Just making something up to get out of the moment. And 80% of the managers survey said they'd never had any formal training on how to handle these conversations at all. I sorry, I just keep coming back. 40% admit to just panicking and lying, just making stuff up. But those 80% that never had any formal training on how to handle these conversations, man, 80%. Twins with our, you know, our other 80% from earlier. So we've got 80% of workers holding back, 80% of leaders untrained, and somehow we expect this to magically work out. No wonder you're trying to win these things. Nobody ever taught you what else to aim for. So look, let's just say it. This isn't about being soft. Okay, it's not about avoiding hard truths or letting people off the hook. I'm not telling you to host hugs and puppies hour every time someone misses a deadline. I'm telling you that the way most leaders define winning in these conversations is the move that actually loses them the team. And before you can do this differently, you have to want, okay, you have to want a different scoreboard. So let's talk about what that scoreboard actually looks like. So here's where we shift gears. There's this book, Difficult Conversations, How to Discuss What Matters Most. It's been around since 1999, okay, written by Douglas Stone, Bruce Patton, Sheila Heen, the people from the Harvard Negotiations Project. Same group that wrote Getting to Yes. And almost, you know, 30 years of research has gone into the framework they teach. Here's the one thing they argue that almost nobody internalizes. You have to shift from a message delivery stance to a learning stance. Now, in fancy academic Harvard language, that's a mouthful. Let me translate it into how I'd say it to a friend. Dude, you're not there to deliver. You're there to learn. That's it. That's the whole shift. You're not walking in to drop the message. You're walking in to find out what you don't know yet. But I can already hear some of you. Colby, I know what's going on. Marcus has missed three deadlines. There's nothing to learn. I just need him to fix it. Look, I I hear you. Okay, but that confidence that that I already know what's going on, confidence is exactly what's making these conversations fail. Because what you know is the what. What you almost never know is the why. And the why is the only thing you can actually do anything about. So here's the reframe in a way you can actually use. Before your next tough conversation, okay, before you walk into that meeting, before you even schedule it, I want you to ask yourself three questions. Just three. And yes, I'm gonna make you ask yourself questions before a meeting. I know how that sounds, but stay, stay with me. Question one. What am I missing? Okay, not what do I think they should say, not what do I expect them to push back with, but what am I actually missing here? What's true about this situation that I can't see from where I'm sitting? And then question two, what do they need me to understand? Not, you know, what do I need them to understand? Flip it. What do they need me to understand? Because if you can't answer these questions, you don't know enough yet to walk in. And then question three, and this one is is the kicker. What do I want this person to feel when they walk out of this room? Not what do I want them to do? Not what behaviors do I want them to change? Not, you know, anything along those lines, but how do I want them to feel? Because how they feel walking out is going to determine whether they actually trust you with the next thing, or whether they go full dirty yes for the next six months. Brene Brown calls this kind of conversation a rumble. Okay, not a confrontation, a rumble. The whole point of a rumble, her words, is to serve the work and each other, not our egos. See, that's the refrain. Not, you know, you're not winning, you're rumbling. You're not delivering, you're learning. You're not trying to walk out with compliance, you're trying to walk out with trust. And that's the actual goal. Okay? And here's the contrarian truth that you've got to sit with. You didn't win the conversation if they walked out feeling smaller. You didn't win if they're gonna spend the next week telling everyone else what happened. You won if they walk out trusting you more than they did when they walked in. Man, I'm gonna say that one more time. You won if they walked out trusting you more than they did when they walked in. That's that's the only scoreboard that matters, y'all. I know. I know it's a totally different way of thinking about it than what most leadership books tell you. But it's the difference between leaders who get the truth from their team and the leaders who get the dirty yes. All right. So I want to make this concrete. I want to play out an actual scenario for you. And yes, I'm gonna play both parts. I know it's gonna sound a little weird. Bear with me. We don't have a budget for voice actors, and frankly, I'm not sure I'd trust them with this anyway. So here's our setup. Marcus is one of your senior people. He's been with you for a few years. He's good, okay? But the last three weeks, he's missed deadlines. And on Tuesday, in a team meeting, he snapped at Sarah, your newest team member, over something pretty small. Okay, you've been putting this conversation off, but now it's Friday afternoon. You finally pulled him in to a one-on-one. I'm gonna play it two ways. First, the version most leaders run, then the version I'm asking you to run instead. And just want you to see how different they feel. All right, so version one again is the trying to win version. Hey, Marcus, so I want to talk about the deadlines you missed the last few weeks and how you handled the situation with Sarah on Tuesday. That can't keep happening. Well, yeah, look, I've been dealing with, I hear you, but the standard is the standard. We need to see this turnaround. Can you commit to that? Yeah, got it. Okay. Thanks for being open to the feedback. And that's it. That's a whole conversation. What, 45 seconds? The manager said the thing. Marcus agreed. Manager walks out thinking, okay, handled. Now watch what happens when you flip it. This is version two, the trying to learn version. Hey, Marcus, thanks for making time, man. Listen, I want to talk about the last few weeks, the deadlines and you know what happened with Sura on Tuesday, but before I say anything else, help me understand what's going on for you right now. Honestly, I don't even know where to start. You can start anywhere. Look, man, I'm I'm trying. I'm getting pulled in three different priorities. Every week it feels like the goalpost moves. Had Jen telling me one thing on Monday, you saying something different on Wednesday, and then leadership comes back on Thursday wanting the original thing. By the time I figure out what we're actually building, the deadline's already passed. And then Tuesday with Sarah, I know. I I shouldn't have snapped at her. That's on me. But I think part of it was I've been holding it together all week, and she asked a question, and I just I just didn't have anything left. Okay. But what am I missing here? Because where from where I'm sitting, I see the missed deadlines. I but I didn't see the rest of that. I I think you're missing that I haven't known whose direction to follow for about a month. And I haven't told you because every time I bring up the conflicting priorities, the answer is basically figure it out. So I stopped bringing it up. Yeah. That that one's on me. I should have heard that the first time. Let me ask you something different.

SPEAKER_01 19:37

What would help right now? That that conversation took about 90 seconds.

SPEAKER_02 19:46

And here's what's different. The manager didn't lower the standard. Okay, the deadlines still matter. Snapping it, Sarah, still not okay. Okay, none of that changed. But what did change is the manager actually now knows what's broken. And Marcus walks out of that conversation feeling like for the first time in a month, somebody actually hurt him. You see the difference? Same problem, same employees, same set of facts, completely different outcome.

SPEAKER_01 20:18

And the only thing that changed was the manager's goal walking in. All right, let's get back to it.

How To Measure Trust Later

SPEAKER_02 20:28

So here's what you actually take from the markets example. There are two specific shifts in language that that signal you're not there to win. And these are are little, but they're huge. Shift one is when you say, Help me understand instead of I need you to understand. Three little words, different posture entirely. Okay. Help me understand puts them in the seat of the expert on their own situation, which they they actually are. Okay. Guess which one gets you better information. Mm-hmm. And then shift two, the phrase, what am I missing? Used mid-conversation there, not not just before it. Okay. This is a power move, and almost nobody uses it. When they push back, when they say something that surprises you, when they get defensive, instead of correcting them, ask, what am I missing? And watch what happens. Their whole posture shifts because suddenly you're not opponents. You're investigators looking at the same stinking problem. Now, here's the hardest move of all. When they say something defensive or wrong or even unfair, don't correct it. I know, I know. Every fiber of your being is going to want to correct it, but don't. Okay. Sit with it. Ask what's behind it. Most leaders get to that moment of pushback and they they immediately pivot back to winning the point. Okay, but don't do that. The pushback isn't the obstacle to the conversation. The pushback is the conversation. Okay, that's where the actual information is. And here's a tactical one for you. After they say something hard or surprising, count to 60 in your head before you respond. 60 seconds. I know how that sounds. Kobe, that's gonna feel like an eternity. That's gonna feel so awkward. Yes, it is. And it will. Do it anyway. Because in those 60 seconds, two things happen. They fill the silence with more information, and you get out of reaction mode and into thinking mode. Last thing for this part the repair move. Some of you listening have been the manager who's been trying to win these conversations for years. Your team knows it. So when you suddenly start asking, help me understand, yeah, they're gonna be suspicious. Okay, they're gonna think you read a book or saw a TikTok or had a leadership coach yell at you. So name it. Just say it out loud. Hey, I've been approaching these conversations wrong. I'm trying to do this differently. It might feel weird at first, but please just bear with me. And that's it. That's the whole repair. Vulnerability is not weakness here. Okay, it's the it's a credibility deposit that lets the new approach actually work. Okay. So let's say you do all this, right? You ask the three questions, you walk in to learn, you have a real conversation. How do you know you actually handled it right? Here's where most leaders go wrong. They measure it in the moment. Did they agree? Did they apologize? Did they say they'd change? Okay, again, wrong scoreboard. Anybody can nod for 20 minutes and walk out and do whatever they want. The real test is one week later. Three questions to ask yourself. Number one, are they still bringing me things or did they go quiet? Okay, if they used to ask you questions and now they're not, you didn't win. You scared them. If they used to push back on things and now everything is sounds good, you didn't win. You you taught them to dirty S you. The proof is whether the relationship is still alive. Number two, has the team-wide energy shifted? This is one people don't usually talk about. Other people in your team watch how you handle one tough conversation and then make a decision about whether to bring you their own. So look around at the team a week later. Are people more open or they are they more guarded? Because that that one conversation with Marcus didn't just walk through the halls of you and Marcus, okay? It walked through the whole team. My friend Dan Collard says it this way: culture can't just hang on the walls, it has to walk the halls. The way you handle one tough conversation walks the halls of your team for months, maybe years. And then number three, would they take the same conversation from you again? If you had to have a tougher conversation or a tougher version of that conversation in three weeks, would they show up open or would they show up armored? Because the test of a tough conversation isn't whether you got through this one, it's whether you can have the next one. So the contrarian truth here, tough conversations don't end when you stop talking. Okay, they end three weeks later when you see what the relationship looks like. That's the real measurement. And by the way, if you're listening to this and thinking, okay, Colby, but what about when the first conversation didn't work? When you did everything right and Marcus's still missing deadlines, go back and listen to Tough Conversations Part two from November. That whole episode is about what to do when the first conversation didn't work. This episode is about not having to get there in the first place. Look, most leaders are addicted to winning tough conversations because winning is measurable. You said the thing, they nodded, done, moving on. It feels like leadership, right? But trust isn't measured like that. Trust is slow. Trust is invisible. Trust shows up six months later when somebody on your team brings you a problem that they would have hidden from a different leader. But trust is the only thing that compounds. Okay? Wins fade. Compliance fades. The dirty yes always comes due eventually. Trust is the only thing that's still earning interest two years from now. So here's what I want you to do. You have a tough conversation in your queue right now, right? You're avoiding it. We we both know it. You know which one. When you finally have it, don't try to win it. Try to understand it. Walk in with the three questions, use the help me understand, count to 60 before you respond, ask what you're missing, and when it's over, watch the next week and not the next 60 seconds.

SPEAKER_01 28:08

It's to know if you actually handled it right.

Coaching Help And Next Steps

SPEAKER_02 28:16

All right. If your organization is struggling with tough conversations, the avoiding, the failing the dirty yes culture that builds up when leaders don't know how to do this, that's exactly the kind of work I do. Okay, I work with organizations through keynote speaking, executive coaching, and leadership training to build people-first cultures that actually gets results. You can connect with me on LinkedIn or at my website, and both those links are in the show notes. And hey, if this episode hit, would you do me a favor? Subscribe to the show wherever you listen, and please, please, please leave me a review if you've got a minute. Okay, that's how we get more leaders listening, and we can get better leaders faster. And share it with another leader who's avoiding a conversation right now. Yeah, we we both know one of those. And remember, keep walking into tough conversations to learn not to win. Keep asking the questions that get you the truth instead of the dirty yes. And keep building the kind of trust that means people will tell you what's broken before it's too late. And you know why? Because those are the things that leaders do.

SPEAKER_00 29:29

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.