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How To Deal With Difficult Conversations

Episode #724

Are you struggling with difficult conversations in your personal and professional life?

Ever wondered how to navigate these challenging interactions successfully?

In this enlightening podcast episode, Tim and Doug delve into their experiences with handling tough discussions, offering valuable insights into the art of effective communication.

In this episode, you’ll learn how to approach difficult conversations with a sense of curiosity and an assumption of the best intentions.

Discover the power of removing emotional charges and setting the stage for a safe, productive exchange.

Whether you’re facing a sexless marriage, a tense business situation, or any other challenging discussion, these tips will help you build stronger relationships and achieve better outcomes.

Hungry for more?

Head over to our BONUS page for special access to some of the deeper tactics and techniques we’ve developed at The Powerful Man. 

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Doug Holt  00:01

Hello, guys! Welcome to another episode of the Powerful Man Show. I’m here with Tim, and we’re going to talk about how to deal with difficult conversations. [Inaudible 0:00:26] That was a horrible intro. But anyway, let’s talk about difficult conversations.

Tim Matthews  00:31

Yeah, let’s. Wow. So much to go into with this one. I’m curious, what’s one of the most difficult conversations you’ve had to have?

Doug Holt  00:40

Wow. On the spot, it’s not like one jumps out at me right away. You and I have had difficult conversations together. I’ve had difficult conversations in a lot of areas of my life with my parents, with you, and other business situations, friends with my wife.

Tim Matthews  01:00

How have you handled them?

Doug Holt  01:02

Usually, I’m super nervous. I’ve had them in two different stages. Right? The past, I was really trying I’d avoid them, right, when I was thinking myself as a business owner in my early 20s. And then I’d rush into them like a bowl in a china shop and just like going in with ultra-aggression to push past that fear. Now I think the way I handle them is I come into them with this idea we talked about in a previous episode of Clearing the Mud Off the Glass. When I come into those difficult conversations with that metaphor in mind, it allows me to be — what are you laughing?

Tim Matthews  01:43

I’m just thinking about some of the frames you’ve used with me in the past when we have these conversations. It’s just funny.

Doug Holt  01:50

Well, yeah. In the past, you and another coach, Arthur, have accused me of being too nice around him, and then he told me to be more straightforward. Since then, you told me to go back to being nice, you know, right now I just shoot it straight. I’m like, you know, just I think I’m so secure with myself and with who I am that I’m not as worried of the outcome, you know, so. I value the outcome. If you and I were to have a difficult conversation, I value our relationship. I don’t want that to end. But I’m not worried about what you think of me, because that’s on you, not me. So if I come across directly, your interpretation of that is your interpretation, and it’s not my baggage to handle.

Tim Matthews  02:45

So I agree. And I’m curious, though, what about having a conversation with somebody who may not necessarily see it that way? All right?

Doug Holt  02:55


Tim Matthews  02:56

Somebody who may not do the work. Because we do the work, right?

Doug Holt  02:59


Tim Matthews  03:00

The work.

Doug Holt  03:02

Yeah. Usually in that case so in that case, what I try to do in the best version of myself, which doesn’t always show up, then I try to go back to what the older version before you and Arthur told me. So I try to do it nicely. So I’ll use a version, know, with the sandwich compliment. Right? Compliment, critique, compliment.

 So it could be something like, you know, Tim, one of the things I love about you is you always show up as your authentic self, you know, you always do that, and you always honor your routines. Sometimes it can be frustrating when you don’t show up on time for meetings and other things that I’m waiting for because I showed up at a respect. But when you do show up, we always get the work done, right?

So that’s an example of compliment criticism. Compliment kind of a classic way to have those conversations, but you can also do it in difficult ones. And I want to hear your version, too, but something I’ll do is call it out. So it might go like, hey, man, this is a tough conversation for me to have, but it’s something that I think is holding us back from our friendship, and I think it’s something I just need to get off my chest. Is that cool with you? Right?

So you’re nodding your head yes. So I’ve already gotten buy in for the conversation, and I’ve already kind of called the elephant out in the room, because if it’s difficult for me, then there’s going to be some kind of energetic exchange or whatever. You’re going to know something’s up, whether you believe it to be the same difficulty or not. There’s something for you, too. There’s a charge.

Tim Matthews  04:38

Yeah, definitely. Yeah. I think for me, I’m thinking of when I had to have with my dad right before literally in the airport coming here.

Doug Holt  04:50


Tim Matthews  04:51

Yeah. Because of how he spoke to Amelia. Quite honestly, Amelia didn’t even recognize they’d spoken to her in a certain way. But because I’d grown up with him speaking a certain way and been overly critical and all that, I think there’s just I’ve got such a short fuse for it now. I just won’t tolerate it whatsoever. And her and I just that’s one of the rules. Her and I, we speak to each other respectfully, which includes not calling names and so on.

And my dad was just outright rude. So much so, I was going to get up from the we’re in a restaurant, at a table. I was going to leave him there, time to get a hotel room. That night, I was done with it, but I didn’t I was able to breathe like I am now. But anyway, in the airport, when I was coming here, I hadn’t had a chance to speak with him about it. But equally, there’s no way I was going to let that happen again.

So in that conversation, I went into it assuming the best and maintaining some level of curiosity with it, which isn’t always easy to do, depending on the person you’re doing it with. That looked something like I called it out, just like you said a moment ago, too, hey, dad, just have something I need to share with you. And I’m sharing it because you’re important to me. Our relationship’s important to me. I want to continue, enjoy spending time with you together. And I know you never mean to offend anybody. I know you never mean to upset people.

And when were at dinner the other night with Amelia, it wasn’t cool how you responded to her when you said bum bum bum bum bum. I get that it wasn’t a big deal for her, but for her and I, we don’t speak to each other that way. So I’m not going to allow anyone to talk to her that way. So for you and I to spend time together in the future, I just need you to know where I stand because if this comes up again, it’s not going to work for me. That was a little bit of a firmer boundary delivered in a soft way still, but he got the message. He didn’t validate, but he got the message.

Doug Holt  07:05

Yeah. But we did that. Let’s break that down for a second because you did that really well. You and I do this all the time. We coach it all the time, so it comes naturally. But for the guys listening to this, it wouldn’t. Right? So what you did there is you called it out, you also said it in a positive way, like looked at I know you would never mean to offend anybody, which is just a global truth. Right? Most people don’t want to be dicks or at least come across it just comes out.

And you also said, hey, you pre framed what the outcome is. Your relationship means a lot to me and I want us to be able to add so we use this in the Hidden Motives Technique. A version of this is you’re leading with the outcome, here is what I want. And you came up with that at the beginning of it. So your dad knows this conversation is not going to be good. Or I shouldn’t say good…

Tim Matthews  07:53


Doug Holt  07:54

But you get what I’m saying. Yeah. Or it’s going to be about him and it’s not going to be something you enjoyed. At the same time, you’re also saying, hey, dad, you’re okay? I’m okay, I’m not abandoning you, I’m not leaving you, I’m not ending our relationship as friendship or whatever else it is. So you’ve set the stage for this being somewhat of a safe space for him to receive it.

Tim Matthews  08:18

Yeah, I didn’t even think of it like that, but yeah, I think you’re right because, yeah, he definitely received it, which was great. I think in the past we either not said anything and just out of fear, quite frankly. Then, similar to you, I think the second phase would have been anger. That would have been the second evolution of how I handled those conversations, which equally wasn’t healthy or good for me or for anyone.

And the third phase and I’m always looking to get I mean, we’re both always looking to get better at these things, but the third phase has been more so this I think you’re great with it. I think you do a really good job. I think communication in general, you’re really good with.

Doug Holt  09:06


Tim Matthews  09:08

So at the moment of insight, yeah, I think you do a great job with it. I think for me, this concept in particular, how to handle hard conversations, the thing that keeps coming back for me when I think about how I do these is assuming the best.

Doug Holt  09:25

Yeah, that’s a great one.

Tim Matthews  09:27

I always do my best to assume the best in the other person, and typically, whenever I do that, it lowers their guard, and then it just becomes easier.

Doug Holt  09:39

Yeah. Something I’m struggling with right now is, there’s somebody that’s in my life that I’ve had difficult conversations with, but they don’t receive them? They’ll come back and say, yeah, you’re wrong. I thought about it. You’re wrong. And the difficult conversation is around how they’re showing up. Right?

And we like to use the word in our space. They’re not coachable, and they’ve asked for feedback in general. And you come back and say, hey, man, you may not know this, but you’re showing up in this way. You’re gossiping about other people behind their back. You’re politicizing. You’re calling people to insert your opinion ahead of time, which is very Machiavellian or strategic. And I’m in a position for this person in particular that I have some control in a business realm.

How do you handle it? This is my question, because I’m really struggling with this is how do you handle it with that individual when you’ve gone to them multiple times and tried to give them feedback and they keep coming back, and this feedback can be consensus based. In other words, hey, five people have talked to me about your behavior, or whatever the number could be, and I’m the one communicating it to you. And they come back and go, yeah, I really thought about it. No, they’re wrong. You’re wrong.

Tim Matthews  11:09

Wow. Yeah, it’s a tough one. The thing that comes to mind for me, so if I was dealing with that, I think how I would probably handle that is I begin to question, are they even aware of how they’re showing up? That’s probably the first thing I’d ask, are you interested in changing? Do you care about our relationship? Because I’m trying to think, if someone came to me and they said to me, hey, this is how you are being received, and I didn’t necessarily agree with it. If I respected that person and if I cared for that person, if I cared for that relationship, even though I didn’t see it necessarily, I would be open minded to how might I be able to change my behavior to help that person get what they want?

So if it was you, for example, and I didn’t see it, then I’d probably ask you some more questions around what it is you’re looking for me to do and why. I’d want to understand why as well and where it comes from. And then, honestly, I’d make an effort.

So if that person isn’t making an effort, I think what I’d ask them is, hey, I’m curious genuinely, does our relationship mean anything to you? And if they said no, okay, that’s great to know. If they said yeah, they’d probably say, Why? Well, do you understand what it feels like? Do you get what it comes across like when you respond this way? And I imagine they don’t. If they did, do you see the juxtaposition between those things? So that’s how I would handle it anyway maintain curiosity, continue to assume the best, and ask them. I don’t know if that’s helpful or not.

Doug Holt  13:10

It’s not, but that’s okay. I get what you’re saying. In this particular situation, it’s a little bit more unique. Difficult conversations are difficult, right? They are by nature, to have them. And in business, we talk about we use new paradigms. So instead of firing somebody, we let somebody find a better career. Right? We use these paradigms in business to make ourselves feel better about those conversations, like, oh, I need to let somebody find their actual true passion, which is another way of saying, I got to fire Steve, right? Steve’s an ass hole, or he’s not performing. I got to fire him. Nowadays, we know I need to let Steve go find his true calling or whatever.

But when it comes to other conversations, like, a lot of guys that listen to the show are having problems in their marriage. Very common for us to talk to men who either have had affairs emotionally or otherwise, but more commonly, the woman has had an affair, emotionally or otherwise. And so how do they have those conversations in a way that has tact that’s a difficult conversation to have. Or they’re in a sexless marriage, right? They’re in a sexless marriage. Let’s use that as the scenario.

Okay, let me just come up with a guy that both of us know. I won’t say the person’s name. So this person’s in a sexless marriage, and their wife is checked out. She’s on Instagram all the time. She has zero interest in him, almost as a human. How does he have the difficult conversation of, hey, we either need to both work on each ourselves or we need to cut ties?

Tim Matthews  14:44

Yeah. Just came to mind for me, then, when we keep saying difficult conversations, I think it’s a good thing to just drop in there. A difficult conversation is difficult because we care.

Doug Holt  14:55

Yeah, that’s a good point.

Tim Matthews  14:57

Yeah. So if you’re in a sexless marriage, it’s because you care, and you don’t want to be in a sexless marriage, and you want to be intimate with this particular person, and I think it’s a great thing to remind who your partner of. Right? You’re going to bring up the topic, so let’s just say it’s Steve.

Doug Holt  15:16

I’m going to interrupt for a second because I’m going back. I want a slight tweak to what you’re saying. It’s because we care, but sometimes it’s because we care what other people think of us or about us. So you may not care about Steve, but you’re worried of what Steve thinks about you or what other people are going to think about you when you fire Steve.

Tim Matthews  15:35

Got it? Yeah. Okay. So going to the suckless marriage piece.

Doug Holt  15:41

Sorry, Steve.

Tim Matthews  15:44

We can never bring anyone on the team called Steve. I just think anyone on the team called Steve? No. Yeah. Because I’ve had these conversations before, and when I’ve had them with Amelia, I’ve just reminded her that, hey, I want to be intimate with you. I’m frustrated right now because I want this, and I want this with you. If I were you, I’d be more concerned if I wasn’t bringing it up. Because the likelihood is if I’m not bringing it up and I still want it, then that’s going to lead to unhealthy things. Right?

And if you don’t want it, that’s cool. I’m not going to put pressure on you to want to have sex with me. It’s fine. If you don’t want to have sex with me, I’m good. I will be having sex. I want it to be with you. But if you don’t want to have it with me, that’s cool. Just let me know so I understand where I stand. And then that way we can figure out what to do, right? In that instance, Emilio is saying, yeah, of course I do. Okay, great. At least that gives me that sense of clarity. Cool!

So she wants to have sex. She wants to have it with me. Okay, cool. How do we get to make that happen? Like, what is it you need? And for her, there was certain things that were going on for her with the contraception she was on, it was affecting her mood and her hormones and various things. So she chose to come off it, and she chose to change her diet, and she chose to do certain things. She felt better, and it put her in a better mood. And then from there, things changed.

But I think it started with that conversation. Not going into it with a charge or criticizing her or blaming her or calling her names or whatever, just reminding her that I love her, I care for her. I want the relationship. I want sex. I want it to be with her. Do you want it with me or not? It’s cool. If you don’t just tell me the truth. I’m a big boy. I can take it. I’ll be fine. I was very prepared for it to say, no, I don’t want sex with you. Okay. I don’t want to go into. I would handle that. I think it created a safe space for her, to be honest, and then she led herself to the decision of what she needed to change, and she just went there and things shifted.

Doug Holt  18:05

You just lay it out. You need to do this, you need to do that. Yeah. I think the thing you said also that reminded me of the coaching tip is you don’t want to have a charge around this, right? When you have an emotional charge, the other person could feel it. So get yourself centered, whatever that means to you. Breath work is a great way of doing it. Taking a walk, whatever it is. I think all too often, at least for me, when those conversations don’t go well, it’s because I’m doing so many things.

It’s like, let’s just use you and I as an example. If there was a charge and I’m going, doing with one thing, dealing with another, and then you’re there, I’m like, hey, by the way, you’re an ass hole, so change. It just doesn’t come across well versus taking a breath, taking a second, saying hey and then having a conversation, that’s important about whatever that is. So that emotional charge is big. And also, I would add on to that not having expectations of the outcome of the conversation, letting the conversation go where it needs to go.

Tim Matthews  19:05

That’s a big one.

Doug Holt  19:06

Yeah, that’s a big one. It’s a hard one, right? Because if I’m going to talk to my wife about a sexless marriage, my expectation is we’re going to come out of this having sex or it’s going to be better. Right? Ideally, we come out of the conversation with headboard banging sex, and it’s passion. She’s amazing, she’s screaming my name and the whole nine. But if I have that expectation, it goes someplace different. Then it sets up for disappointment, then sets it up for an argument.

Tim Matthews  19:35

Yeah, big time. You raise a great point. The charge, because I didn’t think about that too much, but so many times I’ve chosen to have a conversation at the wrong time.

Doug Holt  19:48

Not me.

Tim Matthews  19:49

Oh God.

Doug Holt  19:52

Too many times.

Tim Matthews  19:53

Yeah. And I’ve just walked away from that conversation. Like, that did not go how I planned. I just saw myself totally short because I’d played out beforehand and I’d gotten clear on things in my own mind. I’ve done this so many times with Amelia, then she just tied me in knots. And I’m like, oh, shit, because I’ve been in the wrong state. I’ve not been present, I’ve not been grounded, I’ve been calm enough. And as a result yeah. It’s just not gone well, to say the least.

Doug Holt  20:27

Yeah, I know. For me, when I go in with a charge, I can walk away more porn** off, more angry, which just then accentuates it. Right? Then the other person’s angry. Now you both walk away. My wife and I used to do this all the time. That was our routine. Is difficult conversations. We’d walk away really bad, and we talk about, like, why do some couples fight and then have just passion, full sex afterwards? And we fight, and we end up being more angry. No sex. It’d be like, no sex for, like, a week. Which I know some guys listening to this. Like, I’ll take that.

But for me, that was a bad time, right? No sex for a week. I was like, wow, there’s a problem here. And so when I looked at that, the reason was we had expectations of the conversation. We didn’t come into it, or I didn’t come with I’ll just talk for myself from a place of curiosity, and I came in with an expectation. I was right, of course, which I usually…

Tim Matthews  21:25

It’s a big one.

Doug Holt  21:26

Yeah – [crosstalk] what’s a big one for me, because I usually am. But we all know that as long as everybody else does, we’re good. But yeah, because a lot of times we have a difficult conversation, it’s because something is out of balance, something’s wrong in your eyes. You’ve already judged it. Right? That’s a fair assessment. And when you’ve already judged it, you’ve already assigned a right and wrong to it in some way.

So therefore, you’re right. So you got to let go of that. I really liked your point, and you do this really well. And I think when I reflect back after you said it, I’ve really noticed you doing this more in the last six months to a year, this assumption that the other person’s — how do you say it?

They have the best intentions. Right? I’ve noticed that in your communication, at least with me and with other people, that you’ve approached it from a much better way because we’ve had some charged conversations and you’ve come back and the languaging that you use, I know you were in that frame without you saying it again. You and I do this professionally, listening to people and coaching, which I’ve really noticed. And it takes the charge out of me, which porn** me off. Damn it.

Tim Matthews  22:44

I think it’s because I genuinely give a shit, quite frankly, about our relationship and that’s kind of I’m not in relationships with people that I don’t want to be in because I can’t fake it. What if I genuinely care about you, which I do, then I genuinely believe that you are doing the best. I sincerely believe that. I doubt it a lot, but I always arrive back at the same point. I sincerely believe it. I do. Because I know you are.

Doug Holt  23:16

You do doubt it a lot.

Tim Matthews  23:18

I know who you are. Yeah. I know where your heart’s at and where your intentions are. And yeah, you do? Even with my dad, he’s a complex guy. Even with him. I know he’s doing his best. His best looks different to yours. Very different. But to your point, typically, people don’t want to be ass hole, right? Typically.

Doug Holt  23:47

I think so, yeah. I think this is a really interesting thing. And a lot of these guys listening to this, one, they’re business owners. We have women listening to this too. Two, they’re married. So give a couple of takeaways here or one takeaway. Let’s bury it down to one. So you guys listening to this, take action. Just take one friggin thing and do it. Guys, you move your life better. What’s one thing they can do in the terms of having difficult conversations, in particular with their spouse?

Tim Matthews  24:22

Particularly with the spouse. I’m torn between removing the charge and assuming the best.

Doug Holt  24:28

I’ll give you two.

Tim Matthews  24:30

What would y’all be?

Doug Holt  24:32

Well, I thought about assuming the best when you said that. So I’m going to talk about something different, right? Because I have to be different. What I would do is it is removing the charge, but take a breath, take five minutes and do some deep breath work before having the conversation.

Tim Matthews  24:55

All the guys do that in the movement.

Doug Holt  24:58

Yes, the men do it in the movement.

Tim Matthews  25:00

Help them a lot.

Doug Holt  25:01

Yeah, that’s one of the things we teach them in the Hidden Motives Technique. I mean, I can give a laundry list of things. So guys, here’s my call to action to you guys is write down all the difficult conversations you know you need to have. How do you know they’re difficult? Because you haven’t had them and you don’t want to have them.

Write all of the ones you need to have in your marriage at work with contractors, people who owe you money, whatever it is. Write down a list of all the difficult conversations and then prioritize that list in order of relationship. So the hierarchy, the people who you are in most relationship with or people you love or care about the most to the least.

And the big challenge, big challenge is start at number one and have that conversation with this week. Be a Powerful Man. Have that conversation this week. Guys, we’re here for you. We have a whole community of men just like you within our alumni. There’s over 2000 men who are there who want to have that conversation with you and guide you along the way. You’re not alone. We’re in your corner, guys. We’ll see you next time on The Powerful Man Show.

All right, guys, that’s a wrap for this episode. But as I always say in the moment of insight, take massive action. You see, there are two types of men that listen to a podcast like this, those that go on from one podcast or show to another just hoping things are going to change and realizing that they’re going to be in the same place month after month, year after year.

You see, I was this guy so I completely get it. You may just not be ready. But there’s also a second man, a second man that listens to a show just like this. And this is a guy who takes massive action so they can shorten the learning curve, compress time, and get RESULTS to be the WOLF. See, WOLF is an acronym for Wise, Open, Loving, and Fierce.

Now ask yourself, which one am I? And just be honest with yourself there. And there’s no judgment on my end. But if you’re ready to move from deactivated DEER mode, which is Defend, Excuse, Explain, and React to activated WOLF, Wise, Open, Loving and Fierce, then go over to thepowerfulman.com/grow. And go there now. In fact, I’ll make it super easy for you. I will even put the link right in the description here so you can just click it and go over there now to learn more. Guys, in the moment of insight, take massive action. Go from deactivated to activated, because like I said, life is too short for average and I’ll see you on the next episode!