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Published on:

13th Mar 2025

The Art of Difficult Conversations | Ep 51

Brian and Justin tackle the challenge of having difficult conversations—a crucial skill for any leader. They explore why people often avoid these discussions, how to approach them with both empathy and accountability and strategies for ensuring clear and effective communication.

Drawing from personal experiences, they share insights on managing emotions, setting expectations, and following up to drive real change. Whether addressing underperformance in a sales team or discussing workplace standards, this episode provides actionable advice for leaders looking to foster a culture of openness and accountability.

The Logistics & Leadership Podcast, powered by Veritas Logistics, redefines logistics and personal growth. Hosted by industry veterans and supply chain leaders Brian Hastings and Justin Maines, it shares their journey from humble beginnings to a $50 million company. Discover invaluable lessons in logistics, mental toughness, and embracing the entrepreneurial spirit. The show delves into personal and professional development, routine, and the power of betting on oneself. From inspiring stories to practical insights, this podcast is a must for aspiring entrepreneurs, logistics professionals, and anyone seeking to push limits and achieve success.

Timestamps:

(00:00) - Introduction

(00:42) - Why difficult conversations matter

(01:53) - Leadership and accountability in tough talks

(02:48) - The importance of clear expectations

(05:06) - Why managers avoid difficult discussions

(06:15) - The power of trend-based observations

(07:32) - Creating a culture of open communication

(08:17) - Balancing empathy and accountability

(09:34) - The risks of inconsistent leadership standards

(11:02) - Setting firm yet fair workplace expectations

(12:07) - Constructive feedback vs. criticism

(13:18) - Actionable strategies for better conversations

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Watch the pod on: YouTube

Transcript
Justin:

Majority of the time, you have a relationship with the person that you need to have a conversation with. Whether it's a strong relationship or you don't work with them too much. You have a relationship regardless.

But it's uncomfortable to have those conversations because most of the time, you're speaking facts that that person probably doesn't want to hear. Welcome back to the Logistics and Leadership Podcast.

Today, Brian and I are going to be discussing something that not a lot of people like to talk about, and it's having difficult conversations. Brian, what comes to mind when I ask you your thoughts on having difficult conversations?

Brian:

It's hard, man. I think it's only easy for a certain amount of people.

But I know that as leaders in any organization, any industry, if you're overseeing a sales team, you have to keep them accountable. And there is a certain level of standard that you have to keep. You need to figure out how to have these conversations. Individual or a rep or met.

They might not be meeting a certain metric, and we got to hold them accountable. And how does that conversation happen? How do you have a. A difficult conversation? Hold them accountable to what is expected of them.

Justin:

I would even relate this to just life in general. Having difficult conversations with across the board, with anyone you're, you know, you have a relationship with.

What's your advice on trying to get my wife to stop leaving her coffee mug? Random spots around the house. It's tough.

Brian:

I don't know how to load the dishwasher. Yeah.

Justin:

Any advice there?

Brian:

Well, yeah, I think we text about this every now and then. But, yeah, I think the same thing goes for my wife. She loves to put an Amazon empty box on top of the recycling bin.

And I'm like, man, just open the bin and just throw it right in there. Right. Like, that's just, like, the easy way to do it. But, yeah, do I really want to pick a fight over an Amazon box?

Justin:

If they listen to this, we're probably going to have a worse conversation. So let's not turn this into a venting session. As much as I'd like to.

Brian:

But no, to answer your question, I think it is hard. I think they're, you know, especially as a leader or anything within your organization, obviously, we're.

We oversee everything in the company, and sometimes we do have to have those conversations, and it's hard.

It's not something that is easy to do, but I do think it has to go back to a level of expectation, a level of standard, you know, within the group or what you set out on the front end.

Justin:

I look back on my career and there's a handful of really tough conversations I've had to have.

Brian:

Sure.

Justin:

With employees, with bosses, you name it. But with anything even related to the expectations of showing up on time.

Brian:

Sure.

Justin:

The goals, you know, the expectation around goals or their activity throughout each day. As long as the expectations are clear and if someone's not meeting them, you have the right to have that conversation.

Because they're not meeting expectations.

Brian:

Sure.

Justin:

If the expectations are in the clouds and they're not attainable and they're unrealistic, it's a different story. But as long as they're clear and they're realistic and attainable, like, showing up on time is not that big of a challenge.

So if you can't show up on time, having a conversation around that, it's something that needs to be had or they don't need to be there. What are some things you keep in mind? Let's say you have an employee that's underperforming or you name it.

What are some things you keep in mind or you want to make a priority when having that type of conversation?

Brian:

There's a couple different things. And I think it has to go with the role. Right. Is the person in a sales role?

If it is, then they are hired to produce revenue for the company in themselves from that side of it. From that perspective, it's a level of expectation from the front end. Here's what's expected of you on the metrics.

That's from a revenue activity attitude, mindset perspective as well as, like I just mentioned, they have to produce revenue for the company. The same thing goes, if we were in a sports scenario or in a.

On a basketball team we hire, we bring somebody in to be a scorer, and they're not scoring any points. Okay, we didn't have a conversation. What's happening here?

And we brought you into this team, we're paying you all this money, which essentially we're paying them a salary plus benefits and IRA matching program, and they're not producing any revenue. Okay, we need to have a conversation. Well, let's go back to our expectations. Are you doing the things that we're asking you to do?

Are you putting in the activities on a sales dash? Are you making the phone calls to those clients? I think with that, there's a lot of those and we can track those things.

I also think there is an attitude, a mentality, a mindset that you have to have that we've seen and we have that experience with a lot of these sales reps And I think if we see that and we get it, like, there's a lot of times like, oh, man, like, I don't think Johnny's going to make it because we've seen it, we've been there, we had that experience. The metrics and everything might be good, but they're thrown in the towel or their attitude's not there.

They don't truly believe that they can do the job with that. Like, why do you think that some managers kind of let things slide?

Or like, oh, yeah, Johnny's, he's meeting some of the metrics, but not all of them. He's not producing, but he's a good kid. Why don't we have some of those hard conversations?

Justin:

Yeah. I can only speak from my own experience, but also can assume why based on the way I've avoided them.

And I still avoid some of these conversations because they're uncomfortable. Majority of the time you have a relationship with the person that you need to have a conversation with.

Brian:

Sure.

Justin:

Whether it's a strong relationship or you don't work with them too much, you have a relationship regardless.

But it's uncomfortable to have those conversations because most of the time you're speaking facts that that person probably doesn't want to hear or they don't want to acknowledge.

Brian:

Yeah.

Justin:

And it's uncomfortable for them as well. So you want to make sure you do your diligence and you're not blindsided.

I wouldn't have a conversation with someone that's underperforming and have them come in, high five them in the morning, pat them on the back as another week was, and then two hours later have them come in and say, listen, you're shit in the bed, you're terrible at sales, and just come at them in a way where they're going to get defensive.

Brian:

What's the inverse approach to that? What do you do? You set up like a meeting beforehand and put like in the subject line, like metric review.

And in that way, like seven days in advance, they say, oh, shit, I'm not doing very well. Is that what you should do or what do you think?

Justin:

I look at trends. I'm big on trends.

So if someone has a trend of showing up late or have someone has a trend of not meeting their phone metric or activity metric or BR metric, I'm looking for trends.

If I notice a trend, I'm having an initial conversation, whether that's like a one off, see them in the kitchen, or hey, swing to my office real quick, or catch him after work, give him A call, whatever. Hey, is everything going okay? Everything all right with you?

Brian:

Yeah.

Justin:

You're good?

Brian:

Kind of like a check?

Justin:

Yes, right?

Brian:

Like, yeah.

Justin:

Yes.

What I've noticed is once they answer, because, you know, if they come out and say, yeah, man, I've been drinking a lot, or my mom's really struggling or butting heads with my spouse or my kid's sick, whatever it is, I don't want to just jump the gun and assume that they're dicking around and underperforming or showing up late because they don't care.

Brian:

Yeah.

Justin:

I want to make sure that they're okay, they're good. Because if they're good now, I have the right to say, well, it seems like. Or it looks like. Or I feel like, yeah.

I don't want to come out and say you're doing a terrible job producing. It seems like you're kind of going the opposite direction that we need you to go.

Brian:

Yeah.

Justin:

Are you struggling with something or are you uncomfortable on the phone or what's going on? Talk to me. I open it up.

Because when I open it up and bring their guard down, they're more likely and more inclined to tell me how they're actually feeling.

Brian:

Right.

Justin:

I'm not going to say, like, on the floor in front of everyone, hey, Johnny, you're at the bottom of the list. And again, like, you're really doing terrible. I'm going to do it in private where they feel more comfortable, they can open up.

I'll be vulnerable because I want them to be vulnerable with me.

Brian:

With the conversation that you're having with those folks, you open it up, you're getting them kind of to spill whatever's going on in their life, do you feel like, is there a point? Where are you relating to them? Are you still holding firm on the metrics? How are you handling that piece?

Cause I think a lot of times I think we're human and we say, like, damn, okay, this dude is going through a hard time, or this lady is going through a hard time. Maybe I need to hear them out a little bit. Do you take it that path? Do you stand? Where do you draw the line there?

Justin:

I want to be empathetic, and sometimes I think I'm empathetic to a fault. Where you want to make sure you're not getting taken advantage of.

Brian:

Yeah, yeah.

Justin:

So here are the expectations. And.

And at the end of the day, like, it is a business, you and I especially, but, like, if you're in a position and you have responsibilities and you're answering to someone or you're a business owner, you have the right, it's your business, you have the right to hold people accountable to the expectations that you set.

But I do want to be empathetic because if there is something that we can work through and they are a good fit and they, you know, they're a good fit for the culture, they're a good person, you can get value out of them and they like being there. We're going to be flexible and work with them.

Brian:

Sure.

Justin:

But if there's outside factors and internal factors where, you know what if it's just they don't like sales, they're uncomfortable on the phone, they tell you they don't like cold calling.

Brian:

Yeah. Okay, well this, we've seen that a lot.

Justin:

Yes. This probably isn't a good, a good role for you and that's my fault.

Like I do this a lot but like, yeah, I'll take fall or I'll pin fault on you and I.

Brian:

Sure.

Justin:

Because it's our responsibility to put them in role. I mean we're the ones interviewing higher.

It's our responsibility to put them in the roles where they can thrive and then we support them or give them the tools and contingent education to thrive. But yeah, I think, I think there's a fine line between being like too flexible and too empathetic. Getting taken advantage of.

Brian:

Yeah.

Justin:

But also like structured and holding them accountable because we've seen this too where they get a pass or he gets a pass, she gets a pass.

And then it kind of disrupts your culture where there's different expectations for this person, the same role and there's different expectations for this person saying, well, that doesn't work.

Brian:

It's funny, you know, funny story that comes up. I was playing high school baseball on like a summer travel team and the head coach guy's name is Dave Bingham and he would make a joke out of it.

And so it wasn't necessarily. He had a son on the team. His name was Brandon. And the funny thing is, is he always. He would joke about the, like these are Brandon's rules.

And he would do it in a way that's Dave was like the most hard nosed. Get after it, dude. Like, there's so many stories that I could tell from him just being so hard.

No, but he had a set of rules for Brandon and he would joke around about them.

But he would be so hard on Brandon where he'd make him be the first one or he would make him do certain things that he wouldn't let other People do, and he would joke around, so it's kind of like an inverse of that. But, yeah, I think sometimes we get into this, like, oh, those are Steve's rules. And not really. This stuff doesn't really apply to him because of X.

I think it's hard. And I think as a leader, you can't have that because I think you. You have to do it. Like, inevitably there's going to be some of that.

But I think as a leader, I think you have to have a balance where if you give this person this privilege, you also have to give these other people a privilege that is, you know, more in line with. With what they want.

Justin:

Yeah.

Brian:

It's hard to execute.

Justin:

Oh, for sure. And you also. You don't want to create a culture where people are pushing the boundaries. This is the standard. We're going to stick to the standard.

And if you're not a good fit for a role or you can't meet the standard expectations, then it's okay. Like, it's. Nothing gets you, but you're not a good fit for the company.

Brian:

Yeah.

Justin:

So, yeah, it's something we've. And we're. We're first on business center.

So it's something that we've had to have a lot more conversations recently because both of us have avoided those conversations.

Brian:

Sure.

Justin:

But the one thing I will say about having those, and we're not specialists and having hard conversations by any means, but the benefit of having those is there's a mutual respect there. A lot of times people don't want to hear the truth, myself included. It's hard. It's feedback. You call it constructive criticism. I call it feedback.

It's direct and indirect feedback. But there's a mutual respect there where they might not like it, it might burn a little bit. It's tough pill to swallow.

But afterwards, I've never really had those conversations where they didn't benefit everyone involved.

Brian:

Sure.

Justin:

And I think when you go into those difficult conversations seeking to understand and listen and find a balance or like a resolution as opposed to winning and getting your point across and like being triumphant, you're going to have better outcome.

Brian:

Yeah. I think a lot of people have like a feedback aversion. Right. Like they, they want to avoid the feedback because I don't feel good.

Justin:

Yeah.

Brian:

Like getting feedback on anything. Right.

Like, even as a spouse, you know when your spouse comes to you and says, hey, I really don't like it when you leave your coffee mug on the counter. Right. Or I don't like it when you leave a empty Amazon box on top of the recycling bin. Yeah, yeah, exactly.

But yeah, I think the feedback, it doesn't feel good.

So I think that, you know, people depending on the person, they might put their guard up or they might have an not an excuse, but they might have some sort of justification. Right. So yeah, I think those, they are hard conversations. I think me and you have over the years, we have experience with it.

I don't think we're masters in it, but I do think we have some experience that hopefully we can help other folks out to make them or help kind of nudge them to have those difficult conversations, even though we all know that it's not easy.

Justin:

Last thing I'll add when it comes to having difficult conversations, and again, we're still a work in progress ourselves, but just in our experience, some of the tools or actions we've taken during these conversations is one. Emotional control. Don't ever go into those meetings hot, take a pause or schedule it for a time where you're cooled off. 2.

When you have those difficult conversations knowing that you are on the same page and you effectively communicated the point you're trying to get across. Great way to do that is either send a follow up and have the employee or other person sign off on it.

Or what I like to do, especially with newer sales reps, is ask them to send you a bulleted recap. Short, sweet, to the point. What are your takeaways on what we discussed today and what are your action items to follow through on that?

Because I want to know if they were engaged and absorbed the conversation as opposed to just nodding their head because they wanted to get out of the office. So we'd love to hear your tips or best practices around having difficult conversations. Like I said, we're still learning as well.

They're never easy, but for me they always seem to have a positive outcome after the.

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About the Podcast

Logistics & Leadership
Powered by Veritas Logistics
Join "Logistics & Leadership", where we redefine logistics and personal growth. Hosted by industry veterans Brian Hastings and Justin Maines, it shares their journey from humble beginnings to a $50 million company. Discover invaluable lessons in logistics, mental toughness, and embracing the entrepreneurial spirit. The show delves into personal and professional development, routine, and the power of betting on oneself. From inspiring stories to practical insights, this podcast is a must for aspiring entrepreneurs, logistics professionals, and anyone seeking to push limits and achieve success.

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