How to Have Tough Conversations

Tough conversations are inevitable in leadership. We all know that. The best leaders lean into tough conversations even though they’re uncomfortable. That’s because great leaders understand that tough conversations usually spark an opportunity for growth and expansion. Whether you’re delivering bad news or correcting someone’s misstep, having the tough conversation with someone honors their potential.

This week, John Maxwell teaches how to lean into the conflict and make our people, our organizations, and ourselves better. For the application portion of this episode, Mark Cole and Jason Brooks discuss where leaders often get it wrong when it comes to conflict and how people who tend to avoid necessary conflict can confidently lean in.

Our BONUS resource for this episode is the “How to Have Tough Conversations Worksheet,” which includes fill-in-the-blank notes from John’s teaching. You can download the worksheet by clicking “Download the Bonus Resource” below.


Mark Cole:       Hey, welcome to the John Maxwell Leadership Podcast. We are committed to your growth because we want you to lead better. And that's why today, I will be joined by Jason Brooks, and I'm so thankful for Jason and him joining me today, because today, we're going to dig deeper into this concept of tough conversations. In fact, John Maxwell is going to bring a lesson in just a moment on how to have tough conversations.

See, tough conversations truly are inevitable in leadership. We know that. We embrace that as a leader. But see, the best leaders have learned how to lean into the tough conversations, even when they're uncomfortable. That's because great leaders understand tough conversations usually spark opportunity for growth and expansion. So whether you're delivering bad news, whether you're correcting someone's missteps, whether you are challenging the way someone is thinking, the tough conversation with someone truly should honor their potential. So John is going to come to you today. He's going to teach a little bit on helping you have tough conversations. Then Jason Brooks and I will come back and apply that and demonstrate how we do that at the John Maxwell Leadership Organization.

Now, if you would like to get the show notes and download them and follow along as John teaches, you can go to, and you'll be able to download the show notes there. Here we go. We want to balance care and candor, and here are nine steps to help you have an effective tough conversation. Here is John Maxwell.

John Maxwell:  Let me really kind of drill down here for a moment, because this was a major disconnect that I had. I don't want you to have it. In my book The Five Levels of Leadership, in level number two, which is a relationship level, I talk about the challenge as a leader to balance care and candor. Let's talk about it. In other words, I want to care for you so I want to relate well to you, but I also want to have candor with you so that I can be honest with you so that we can have some movement and progress. And that means that we're going to have some maybe very difficult conversations. And here's what I said in the Five Levels book. It's in your notes. Care without candor creates dysfunctional relationships. In other words, I love you, but I won't be honest with you. That just creates dysfunctional relationships.

Candor without care creates distant relationships. In other words, if I don't care for you, but I'm just bluntly honest with you, the good news is, I'll tell you, but the bad news is you'll pull away as quick as you can. There'll be some walls of separation. But care balanced with candor creates developing relationships. And there are some key principles to learn about the tough, difficult conversations we need. Principle number one. Caring values the person while candor values the person's potential. When I care for you, I say I value you as a person, but when I'm honest with you and have a tough conversation with you, you know what I say to you? I really care for your potential. In other words, I care enough about you to tell you some things that are going to be difficult so that you can grow you and develop you. I see your potential.

Number two. Caring establishes the relationship, of course it does, while candor expands the relationship. It grows the relationship. And number three, caring should never suppress candor while candor should never displace caring. You have to have both. So how do you and I have these tough conversations? If I just could come on and sit down and grab a chair and kind of sit at the desk with you and say, "Hey, my name's John, I'm your friend." And introduce myself and meet each one of you personally. And then if I could get into a conversation with you, and if I ask you right now, in fact I am asking you right now, how many of you have a situation right now where you have someone that you need to have an honest conversation with, but you're kind of putting it off because you know it's not going to be an easy conversation.

I'm going to bet that every one of you right now would raise your hand and say, I've got this situation. In fact, I love it because I'm in the studio here with some of the John Maxwell company. And so when I looked and I asked, how many of you would raise your hand saying you got a tough conversation that's for somebody, I'm looking over at my own people and they're on the computer, they're getting questions from me and doing all the work, and they're all raising their hands. I've got a tough conversation. And just let me time out for a second. Let me talk to the John Maxwell Company. We'll be right back. How many of you are sitting beside the person that has to have that tough conversation? Yeah, that's what I thought now. Now probably I've lost them for the rest of the teaching. They're probably going to have that tough conversation now. Hey, do it later. But here, when you do it, let me give you some tremendous principles on how to conduct that tough conversation. Number one, meet privately as soon as possible.

Schweitzer said, “Truth has no special time of its own. The hour is now always.” In other words, when you have a tough conversation, as soon as possible, privately have that conversation. Number two. Assume good motives. William James said, whenever you're in conflict with someone, there's one factor that can make the difference between damaging your relationship and deepening that relationship, and he said that one factor is attitude. When you assume good motives, you'll go into the conversation with a real good attitude and you'll be giving the other person the benefit of the doubt. Number three. Offer observations of specific behavior. In other words, when you sit down and have a tough conversation, you can't be nebulous. You've got to give tangible, specific things that you're seeing that you need to discuss. Number four. Explain the negative impact of these behaviors. Basically say, here's what I've observed, and let me tell you, because of that, let me show you some of the negative fallout that's happened.

Number five. Ask them their side of the story. Because Peter Drucker was right when he said erroneous assumptions can be disastrous. So sit down and say, look, this is how I see it, but I could be seeing it entirely wrong. Do me a favor. Share with me from your perspective how you think this works. Number six. Find points of agreement. Whenever I have a tough conversation, I always look for common ground because that's where you build relationships. So before I talk about what makes you and I differ, I talk about what makes you and I similar.

Number seven. Set out a future course of action. Sit down with that individual and say, okay, this is what we're discussing, this is what we're finding. Let's get a game plan. Let's have a target that we can aim for. Number eight. Validate the value of the person and the relationship. I think Goethe has a tremendous quote when he said, “Treat people as if they were what they ought to be and you help them become what they are capable of becoming.” Validate the value of the person, validate the relationship. And then number nine. Express your commitment to help. What can I do to help you? What could I do to come alongside of you? How can I add value to you?

Mark Cole:       Hey, welcome back. Jason, I'm humored by the fact that Jake has you and I in the studio today, because I'll tell you, I don't recall having to approach you for a tough conversation. And for those of you that do not know, Jason and I have been leading together, Jason has it been five years now?

Jason Brooks:   Yeah. Over five years.

Mark Cole:       Over five years, we've been leading together in several different roles. And in fact, Jason, as you and I kind of debrief this lesson, I didn't even tell you this before Jake put us into the record mode, but I can only remember one tough conversation with you and it was you having it with me, which is funny. In the world of organizational structure, I guess, Jason, you would be by direct report. But I think the only time we've had a tough conversation is one to where you really pointed out some things that really helped me see myself as a leader that needed to grow and a leader that had a lot to learn from a couple of interactions, both with you and one of your teammates in times past.

But here's what I know. If you're listening to this leadership podcast and Jake just gave us a great illustration of another tough conversation that he was a part of, here's what I know. No matter where you are in your leadership journey, no matter whether you are the reporter are the reportee, whether you have a very hard work environment or whether you have one of the most people affirming environments ever, you will need to have, perhaps in the next seven to 10 days, you will need to have a tough conversation. Jason, John did a great job today giving us some real tangible things to do.

Jason Brooks:   He really did. And it was interesting. I was joking with Jake before we started recording. I'm not particularly known for having tough conversations. I'm kind of the guy that leans way more towards the care than the candor. I tend to hedge things and try and frame them in a way to just be positive and not really touch on the sensitive points. But the few tough conversations that I have had have come in a couple of different contexts. And I wanted to start here before we really get into John's points because it's easy to think about tough conversations in terms of maybe conflict or tension with an employee. But I had to have, and we've had, you referenced we had a conversation similar to that earlier on in my leadership that really, A, defined what I could become, but also showed me what we could become together.

But then more recently we had to have a tough conversation when I had to call you and tell you about my cancer diagnosis. And that wasn't necessarily a interpersonal conflict or a tension or you're doing something wrong, but it was still nonetheless one of those things where it was really difficult to know what to say, how to say it. And I think John's principles still apply even in a context like that. And so I just wanted to ask you, do you think that these points, or the how to steps that John provides here, do you think they're equally applicable for not just a confrontational conversation but also a conversation about just an uncomfortable subject or a transitional phase in someone's life? Do you think that these are malleable enough to cover both contexts?

Mark Cole:       I really do. And the beauty of our podcast is some days we'll sit and just have a great conversation after listening to John and then develop some things that we want to talk about. Other days, like today, we knew that John's part was going to be short. This will be a shorter podcast than normal, perhaps, but today we went straight into listening to John and then coming right out of there, Jason, and talking about our takeaways. And I will tell you that I'm glad we did that because you have just truly rocked my thinking and how I was contextualizing this whole conversation. Because I came out of John's lesson and I went, man, you and I have no had but one tough conversation and that was you with me. And then you give two minutes and go, oh my gosh, I've had one of the toughest conversations I've ever had with a direct report and there was no confrontation at all.

It was a very life altering, very life revealing, very transitional conversation that you're alluding to when you called me that day back in early 2020. And I'm sitting here going, yes, I absolutely think that many times when we hear how to have the tough conversation, we're thinking a very conflicting, very difficult, very two separate people, two at odds with one another, trying to come together, or I got to let you know, I'm letting you go. And that's not always the context of a tough conversation. And I'm glad you brought that up because you really expanded our thinking on application to John's content today.

Jason Brooks:   Yeah, because, it's easy sometimes. Like I said, I have a tendency to sugar coat things and try and dial things back and maybe make them not sound as bad as they are. And I do that for a couple of reasons. One has just been my own insecurity, but two is you want to keep the other person engaged and not offend them and keep them in the conversation. But whether you're talking about conflict or you're talking about just difficult circumstances, John's methodology here where you just address the whole truth, even in its difficulties, it equally applies. And it was really necessary for me, in both of the conversations that we've referenced that you and I have had, for me to be able to sit down and just go, okay, here's what I see, here's what I know, here's what I understand.

Help me better understand how to move forward with this. How do we move on from here? And so I do think as leaders, and we can approach this more from the conflict side, because I did surprise you with that particular observation, but I just wanted to say, as leaders, it's beneficial for us to remember that not every tough conversation is necessarily going to be an oppositional conversation. Sometimes the toughest conversations are with people that we deeply love and we enjoy being with, and there's no animosity between us, but maybe life circumstances or something has changed, and we need to have an honest conversation in order to continue the benefits of that relationship. Does that make sense?

Mark Cole:       It does. I was thinking, I think both contexts that you've given today are very difficult conflicting conversations or very life transitional conversations. And now my mind is flooding with many difficult conversations that doesn't have conflict at all. It just has reality of some very needed changes that happen. But here's what I will tell you. John does a great job with laying out. And again, guys, download the show notes. Because it's really helpful to stare and look at these points and the exercise of filling in the blanks. John does a good job of talking about balancing caring and candor at the beginning of the lesson, the key principles to learn. I won't repeat those, but let me tell you something else that I think is really foundational, no matter what context that is driving the tough conversation. It's really the foundational component of do you care for the other person? And not a caring candor care, but is this conversation really about bringing benefit to the other person?

John talks about a lot, we've talked on the podcast a lot, about this concept that we're in a leadership deficit. There's not enough valuing people, basing our leadership on the people's agenda, not the leader's agenda, and this idea of servant leadership. There's just not enough of that. So with that context of values-based, people-centered servant leadership, the reason always to have a tough conversation comes back to this. It should be for the benefit of the person you're talking to. Too many times, we walk into a difficult conversation because we got to get something off my chest. Something's been bothering me and I need to have a difficult conversation with you. I want to get rid of this burden I'm carrying. That should never be the impetus of a difficult conversation. It should always be on the foundation of, I want to bring this to a point of conversing so that I can add value to the other person.

Now, if I come into a difficult conversation with you, Jason, and we've talked about a couple of those that we've had, if I come to you with a difficult conversation and my whole attitude and persona is to be about business that will make you better, will that not change the tenor, the tone, the attitude of our presentation? Because it's all about making you better. One more thing I'll say. I remember in the 21 years I've led alongside John, specifically the last 11.5, 12, making the senior decisions for John's organizations. I've made some difficult conversations. I've let some people go, I've transitioned some people.

And I got to tell you, the advice that Dan Reiland, the long time executive pastor leader under John Maxwell gave me when he said, Mark, in a difficult conversation, make the point of the conversation obvious in the first 30 seconds and make sure that you're settled that this really is the best for the person that you're having the difficult conversation with. And he gave me those two pieces of advice, Jason. Get to the point quickly, and before you even have the conversation, make sure that you can honestly say this is for the best of the individual that I'm having the conversation with. And those two critical components have helped me through a lot of difficult conversations.

Jason Brooks:   I love that, one, because I think too often, the reason people dread tough conversations is because in our current culture we have made these conversations more about what we want to say when we see something wrong, when we see something off. And so we're trying to address our needs as opposed to the needs of the other person. And maybe there's something going on in their life that is affecting performance that we don't know about. And so if we genuinely make the conversation about their benefit, then we're going to, A, eliminate a lot of assumptions that would make the conversation tougher than it need be, but we're also going to be able to better balance care and candor because we're coming at it, like you said, from that perspective of we're doing this to add value, not just to get something off of our chest.

So I want to talk about John gave us a great how to, in terms of conducting tough conversations. We don't have to touch on all nine points, but I will say this. I did something a little different as John was teaching. I decided to turn this into a checklist. And so, as he listed each point off, if I didn't typically do that in a tough conversation, I put down an X. If I did, I put down a check mark. And I was pleasantly surprised that five to four, I do more of what John recommends than go against John's recommendations. Narrow margin, but I was still, I was like, I'll take five.

Mark Cole:       You're still on the right side.

Jason Brooks:   Still came out winning. And so, the very first point actually is one that I do want to touch on because it's one that I've always struggled with, and that is meet privately as soon as possible. It's not the private part. That I get. But as soon as possible, that's always been the challenge for me. I'm a processor, I'm a thinker, and I'm just introvert. I've got a whole bunch of junk, just different mixture going on here that makes it easier for me to delay a needed conversation than to say, all right, let's go ahead and have it. So how do you as a leader, how have you learned to have these conversations? What are some signals or signposts that, okay, this needs to happen and needs to happen within the next X number of days or whatever? How have you learned to have these conversations as quickly as possible while still keeping it in mind that this is for the other person's benefit?

Mark Cole:       Well, I'm glad you gave that context of how you are a processor and you like to think out your process and write out your process before you launch into the process. And there's many people listening to our podcast today, Jason, that really relates to that style of leadership, of processing and going. And there's a lot of tendencies there to the introvert, but it's not only introverts. There's some extroverts that likes to process, get it written out, and then go implement. And then I'm going to bring the other side of the spectrum. I process out loud. I process while I'm verbalizing. I process on the go so to speak. There's no right or wrong there. In fact, there's some real challenges to my approach to processing. I process before I really did the due diligence to see if this was just an emotional response or if I really do have an issue.

And so I have to really check that, I have to work on that, but that's not the subject of today's podcast. Me privately, ASAP for me is when I feel there is a challenge between me and a co-leader, somebody that reports to me. I'm going to go and address that quickly. And I'm going to get it out on the pay on the sheet that says, hey, we're having an issue. I'm not sure if I can clearly articulate it, but let me give you some thoughts that I think could be contributing here. And in the first conversation, a lot of times, Jason, I'm going to give a lot of what ifs, but what if nots as well. Man, it feels like you're really not performing very well, Jason. Is it because something's going on in your life? That's the what if or what if not. Jason, it really feels like you're showing up late to the meetings. Are the meetings not really important or is there something else going on that's causing this tardiness?

I'm going to give you two different A and B factors. Is it A or is it B? And I'm going to work through that. Now, I think that I do that ASAP. I do that privately, I do it very quickly, because I don't want to be sitting over here. There's too much at stake for a chasm to be widening in minding your co-laboring together. Got to get it out and got to get it done quick. Now, in decisions, when I'm going to make a decisive tough conversation, I am very process oriented. I'm very this is why, this is what happened, this is what's going on, and this is going to be the net result. But in tough conversations, know the difference. Is it time for a decision or is it time to really process this out?

But if you sense there is, I'm going to use a old school word for you. If you said there is ought between you and your brother, or you and your co-leader, in other words, if you sense that there is something off, something disconnecting, ASAP, ASAP, ASAP, even for you processors, because you'll process something to the point of an emotional uncertainty and it will cause there to be a problem when there really wasn't a problem. Get on it quick, whether you are a verbal processor like me, or whether you are a thinking, writing it out processor like Jason. If there is a relational distance between two individuals, if there is a potential challenge on the horizon, get it out quick. Jason, in the example you gave at the beginning of our podcast here of when you realized you were fighting cancer, I was one of the first people you called. I'm the boss.

I'm the guy that could be going, oh my gosh. I got to replay, I got to do all this kind of stuff. There was a lot to lose by having a instantaneous conversation with me, in some cases before you had even talked to some of your closest family members, your kids. You were letting me know. You know why? We had a trust together that we were going to work on this together and it wasn't all of a sudden going to be the employer going, oh my gosh, my employee's get ready to have a very difficult year. Get tough conversations out quick because together you can work on them and come up with the right solution.

Jason Brooks:   I love that. And that's really helpful for me because I tend to attend to delay because I want the right answer. And you're saying that if I delayed too much, I not only risk the right answer, I risk right relationship. And so by moving faster, I'm preserving the relationship. We can get to a better answer because we're working together, because it's on the table, as opposed to me coming and saying, okay, I've got it figured out. Here's what we're going to do. And I think that, for me, that's really, really helpful in having some of these kinds of conversations. I did want to move on. Assume good motives. I think that goes back to if we truly value people than we think the best of them, we give them the benefit of the doubt. But point three, John says we need to offer observations of specific behavior.

What is he, I mean, it seems fairly obvious on the face, but what does he really mean by that? When we say specific behavior, is it as detailed as, hey, on Monday, August 23rd at 9:23, you came into the office seven minutes later than you said you would. You went and got a coffee. You stood and you talked to your coworker for 15 minutes before you finally made it into your office. You didn't check email in the first. Do we get that granular or is it something a little more? Is there another way of approaching it, I guess, is what I'm asking about?

Mark Cole:       The answer is yes. If you've got that level of specificity to it, then yes, you get that answer, or you get that detailed. What John's really cautioning us against doing is words like, hey, it looks like to me that you might not be as engaged. It feels to me like you really don't care. That right there is not going to help any kind of productive conversation. But if I go, hey Jason, the last four times that we've had a leadership meeting, you showed up 15 minutes late. I'm taking that that you don't care. Is there a better way that I should interpret that?

I have given you specifics that there is a reason that I'm coming to you, not because generally I just feel like you don't care. It seems to me, words like it feels, it looks, it seems should be eradicated from tough conversations. Words like, hey, I asked you to do this four times. You haven't done it. I can't get you to respond to an email. There is distance between us because you are not putting the work effort into this. Jason, usually you bring this kind of quality to work, but the last two times you brought this quality of work. As clear as you can be with less I see or it seems, it looks, it feels, the better off you're going to be.

Jason Brooks:   So you've just talked about eliminating some of that emotional soft language. Is it also wise to try and avoid sort of hard definitive language like you always, you never, you rarely? I mean, should we try and avoid that kind of language too? And if so, why?

Mark Cole:       Because it's never always. There is no such thing. I forget. Somebody was telling me just yesterday about something that always happens. And I said, well, does always mean like three days ago when actually the opposite had happened? Well, okay. Almost always. And so words like always, sometimes. Because the first thing I do when somebody says this always happens, I think of the exception, so you lost me on your whole point. You're going to lose people when you deal with those kind of specifics.

Jason Brooks:   Yeah. There's a difference between specific and absolute. I think that's really important to remember. Well, let me flip it around. I've been driving the conversation here and kind of telling you what I've noted or what's been benefiting me. What about what in these nine points or in this lesson jumped out to you? Maybe reminded you of your own journey as a leader or sort of made you stop and go, okay, I thought I had this down, but I realized I've maybe drifted here. Anything like that that's jumped out to you that you feel like would benefit the listeners through hearing?

Mark Cole:       Yeah. So it probably goes to the very last one that John named. Validate the value of the person in the relationship. And I have done that at the beginning, going back to Dan Reiland's suggestion that in the first 30 seconds, let people know, hey, today's going to be a tough conversation. I'm choosing to go a different direction. I'm going to let you go. In the first 30 seconds, if that's the point, get it out there. Because everything said before that feels bogus once you say that. And most everything you say after I'm going to let you go is considered bogus too. So just get it out at the beginning so that we can see how we can navigate through this together. Now, let me say this. Because validating the value of the person in the relationship is so important to me, I do use things like the sandwich philosophy. Jason, I really appreciate you.

You've done a lot of good for the organization. Jason, today, I'm going to make a decision that you're going to do good somewhere else because we're going to make a translation. Now I've got to tell you, I value you like you just cannot even understand at this moment. But here's why this point number nine, Jason, as we kind of wrap up today. The reason that I think validating the value of the person in the relationship is so important, it goes back to the values that you and I defend every single day. We're people of value that value people. Now, as many of you podcast listeners that may not work in an environment that values people, and definitely makes it one of its top behavioral expectations, that validate the value of the person in the relationship may be very hard for you in a difficult conversation.

But for me, if I can't communicate the value of the person and the importance of the relationship, I don't have the tough conversation. It's that ingrained in the values of who I am and how I want to lead that without that component, I won't have a tough conversation. Because everything else is argument. Everything else is disconnecting. Everything else is for no advantage. And that's why I believe, and I'm glad John closed with this one today, because validating the value of the person, understanding the importance of the relationship, is why we have the conversation in the first place. One of my favorite, in fact, I have a consulting firm that I have, and I still do work out of, called the [Iron Leak 00:35:15]. And that's because of an old proverb, Proverbs 27:17 that says, "As iron sharpens iron, so does the countenance of one brother sharpen the countenance of another brother."

Here's the point there. The reason that we have tough conversations is to make each other better. And that's the point, that's the point, Jason, to be honest with you, of the lesson today. Hey, you've done that for me. We talked about it and I hope I have done that for you, even though we've not had very many tough conversations. Here's my challenge. Here's my challenge again. Some of you have conversations that you should have already had that you haven't had because it feels too tough to you. And my challenge for you today is to go take these nine key points that John brought out in how to conduct tough conversations and build a plan and go have some conversations that needs to be had. I know you can do it, I know it will be successful, and I know it will impact you. I'll tell you this, Jason, I could talk to you all day.

Not about tough conversations, but about any conversation. Jake's wrapping us up. But let me tell you this, podcast listeners. Jason and I, Jake, our entire team is committed to help you, whether it's a tough day, a tough day at the office, a tough conversation that needs to be had, whether you're in the leadership mode right now of some of the best years of your leadership advancement, our desire is to add value to you. So take this podcast, pass it along to others. Hopefully we're serving you. If we're not, please tell us. Give us some comments to let us know how we're doing. If we're doing well, give us a five star rating. That helps us in the podcast world. But more than anything, go be your best you, go have that tough conversation. Go love, go learn, go live and listen to others and then lead from that posture. Have a great day everyone. We'll see you again next week.

12 thoughts on “How to Have Tough Conversations”

    1. Apologies for the inconvenience! The audio file has now been updated. Please accept our apologies!

    1. Hi Carrie, that’s our mistake. We are sorry for any inconvenience. We have updated the episode to the right audio file. Please let us know if we can assist you with anything else!

  1. Just wanted to say thank you for this session. Used the concepts today with one of my people and it turned out fantastic! My approach was completely different from what I’ve done in the past. Very encouraging and can’t thank you guys enough!
    Huge fan of your podcast!

    1. Thank you, Tom! We are so glad that this episode helped have a tough conversation! We love hearing stories of impact like this and knowing this this podcast is adding value to your leadership. Thank you for sharing!

  2. This podcast is awesome. I just had a difficult conversation and I used many of these tools prior to hearing this podcast. The podcast truly affirms the conversation I had.

  3. Thank you always for providing such rich content, I’m an avid listener and reader of John Maxwell. I listen to the episodes 2-3 times and take notes. Thank you for being so generous with this incredible powerful lessons.

    1. Hi Matthew, sorry you’re having an issue downloading the Bonus Resource! Everything on our end seems to be working properly. What form pops up when you click the Bonus Resource Button?

      1. It comes up with a document that has “File Not Found” in the middle of it where the Bonus Resource content should be.

  4. Where can I find the worksheet for this “How to Have Tough Conversations” Sept. 29, 2021 podcast episode? The bonus resource download button does not appear to link to a document. I have attempted this using two different browsers.

Leave a Reply

Your email address will not be published.