How to Have Difficult Conversations at Work: Boundaries, Timing, and Leadership

Hard conversations are part of the job, and avoiding them costs more than most leaders realize.

In this episode, Shelby and Belinda share a practical framework for navigating difficult conversations at work with clarity, boundaries, and discernment. They share executive-level strategies for adapting communication styles across different contexts, setting boundaries without overexplaining, and using silence as a powerful tool. Shelby also introduces a practical framework for hard conversations, clarifying the What, the Why, and the How, so leaders can prepare intentionally instead of reacting in the moment.

The episode also explores the limits of chat-based communication and why leaders must choose the right tool for the message to build trust and real community.

Transcript

SPEAKER_01 0:01

Welcome to the Leadership Tea Podcast, brought to you by Grounded in Global Advisory, where we are grounded in leadership and global in impact. Today, Belinda and I want to talk about the difficulty that we see in having conversations. Sometimes it feels like we don't know how to talk to each other, particularly when it comes to having difficult conversations. And it's beyond giving constructive feedback to someone. It feels like with social media and all of the chat groups and the different ways that we can communicate with the advances in technology, it has degraded the quality of communication skills. I will turn it over to Belinda to get your thoughts on some tips that we can share with our audience that reflect how you and I have adapted as executives when it comes to having conversations.

SPEAKER_00 1:16

We come from a space where both oral and written communication is really important and where we really value the nuance, especially when you're talking to people in other languages or other cultures and things like that. And so I think I've really had to adjust to this idea that I am now regularly engaging with people who communicate on a wide spectrum of ways, and I'm constantly adjusting and constantly having to claim my space in the communication space and becoming comfortable with ways of communicating that may be effective in certain spaces, but uncomfortable for me. And I think that's probably one of the biggest lessons I've learned over the last few years is that I really have to adjust my communication style to the place or the person with whom I'm communicating. And if I don't, that's to my detriment. I can be quiet in the wrong space and look weak. I think I'm looking diplomatic. They're perceiving me as weak. Or I can be assertive in certain spaces, and I think I'm just being really clear and direct, but it's received as, you know, I won't say bullying, but you know, just being, I hate to use the word aggressive, but for lack of a better term, aggressive. When in fact it's like you asked me for the truth and I'm just giving it to you, right? And so recently I've been reflecting a lot on some volunteer work that I'm doing that is in a space that has a lot of momentum, lots of different people with different skill sets and people who are really passionate about the work that's being done. And I have had to really work hard and we're because people are passionate, they are direct in ways that make me really uncomfortable, that for my diplomatic ear sound rude. Like, like really. I mean, like I'm like, wow, you said that out loud, like, oh, is that what we're doing? Like, oh my God, right? Like, and that's me and the baggage I bring to the room, right? And so I've had to really drill down into two things that are helping me right now. One is really being clear about what I want to communicate. And to do that, you need to understand the mission, understand what behavior you want out of people, but also understand what your boundaries are. Right. So I'm now doing a better job of going into conversations with I understand what we're trying to do, here's what I'm capable of, right? And here's what I'm gonna do. Like that's my negotiating strategy. And then being comfortable saying it in the least number of words, not rambling, right? I hear you. Oh, and then using a coaching technique where I repeat back what I think you've said. So what I hear you saying is X. Great. I can do Y.

SPEAKER_01 4:20

I heard you, right?

SPEAKER_00 4:22

But I'm doing Y, you know, and then being comfortable. This is the most important piece. Yeah. Being comfortable with silence, right? And I have said it. And now I'm not gonna, I'm just gonna let you absorb and react. So that is something, those are two things that have been really helpful for me, is just knowing what my boundaries are and what I want to talk about, and then being comfortable with the silence as you absorb it and react, and taking a pause and just kind of, you know, and then responding from there. But that's been enormously helpful for me.

SPEAKER_01 4:59

I love the being comfortable in silence part, as you mentioned. That is definitely a coaching technique. And as an introvert, I am like naturally comfortable with silence. It doesn't bother me. I don't panic when there's empty space. I'm good with it. And I think when it comes to communication, it really does give people a chance to absorb what you've said. It gives you a chance to regroup mentally in case you need to be even more clear than you already were in making your points. I think those are all useful tips on how to improve your communication skills. And being clear, I also like what you said about having boundaries and being deliberate in your word choice and not just vomiting out everything that you could, but just being very intentional in what you say. I think all of that dovetails nicely with one of the points that I wanted to make, which is what is the what when you're having conversations? This is something that I learned, or this is something that I practiced as a senior executive at the State Department when I was managing other executives. Sometimes I would practice in the mirror. Like, what is it that I want this person to walk away with as a result of this conversation? And I do want to be clear that, you know, how you deal with crisis communications is completely different from what we're talking about right now. We are talking about like when you have time to actually prepare and be deliberate and be intentional about the conversations that you're having. I would sometimes write out what is it that I want to convey to this person? What do I want them to walk away with? Because the more clear I am by writing it down and practicing out aloud, this is what I'm gonna say when I meet with this person. It really helped me hone in on the clarity of the message that I wanted to convey. Because I think sometimes we don't take enough time to pause and think about, okay, I need to have a difficult conversation. Let me prepare. Let me not just go off the handle and say the first thing that comes to mind, like I'm annoyed with this person, they pissed me off, they did this, they screwed something up. Okay, that might all be true, but am I doing them a disservice by just, you know, saying the first things that come to mind, or will the outcome that I'm seeking be better because I've actually taken the time to sit down and write out this is the what. This is what I want to say, this is what I want them to walk away with.

SPEAKER_00 7:50

I really agree with that. I think that being really clear about what your goals are in the conversation, but that idea of practicing, I mean, you practice in front of a mirror. For me, I play it over and over again in my head, but I think through all the different scenarios, and I'm rarely surprised then in the real conversation. It's like, oh, so we we've decided to go that direction. Okay, I'm ready. Like so I think that is, you know, I definitely agree with you on both of those points.

SPEAKER_01 8:26

The second part of how I think about communicating is the why. Why am I having this conversation? Why is it important for me to say these things to this individual? And sometimes I think because we have a tendency to not really step back and think about the why, that can be the reason why conversations get derailed. Like if I'm giving this person feedback because they messed something up, that's a clear reason why. If they have been performing in a way that has been bothering me for months, and I've now suddenly decided that this is the moment when I need to tell this person that they've been underperforming, then I owe it to them to explain why I haven't brought it to their attention up until now. And that's on me. But I think again, when it comes to having effective conversations, it's important that you're clear in why you have you decided to have this conversation with this person right now. Is it because you have a major project coming up? Is it because you see a pattern of behavior that is detrimental, you know, to the team, to the company? What's the why?

SPEAKER_00 9:56

I agree with you. As I think about it in the context of, say, like this volunteer organization, where there are times when you are the boss, and so yes, you're providing context, and that's helpful. And I think the person wants that. There are times where you're engaging with people, and this is what I mean by this different communication styles. This person was under stress, they're really busy, they're freaking out about all the things the organization's got to do. And so I had to keep the y as brief as possible. Right? You want me to do X, I can do X point five, like this is all I can do. X and a little bit of Y. Here's a little bit of just a glimpse as to why I'm putting up that boundary. Right. And that's what that person could absorb. So I think an important component of good communication is yes, you have your kind of framework and space in place, but you have to be able to read the room. You have to be able to adjust to the moment and the person.

SPEAKER_01 10:55

Yes. Your point on reading the room and adjusting to the moment and the person is actually a good segue to my final point, which is the how. Something that we've discussed in other episodes. It's on you as the executive to, you know, have the professional maturity to know is this person in any headspace to receive what it is that I'm saying? And maybe they never will. That's a that's a different challenge, that's a different problem. But that should not prevent you from having that difficult conversation. How they react should not keep you from delivering your message and having a difficult conversation. We are proud to be sponsored by State Department Federal Credit Union, a financial institution built around the realities of global service and frequent relocation. From competitive lending and rewards credit cards to international money management through WISE, SDFCU provides reliable financial access wherever members are posted. Learn more about their global banking solutions at SDFCU.org. State Department Federal Credit Union is federally insured by the National Credit Union Administration and is an equal housing lender. Membership and product eligibility is subject to approval. Yes.

SPEAKER_00 14:27

One mistake I made in the conversation I had yesterday with this volunteer group is I timed that conversation too late in my day. My day starts really early. And so I start getting tired by like late afternoon. And so this conversation happened late afternoon. And yes, the thing was about boundaries, but it really, I think it really was a little more. I was tired. Yeah. Right. It was late in the day. So I'm like, hey, look, I got nine nine problems, and y'all can't be one of them. It's late. I got like 10 more things to do. Look, boom, boom, boom. But if we'd had that conversation at like, say, nine in the morning, when you were fresh, you could have given it a different energy. Yeah. Right. And so I thought, like, that was a strategic error on my part. And I'm usually better about that, but it that was something that I would highlight for our audience. And then, you know, the other piece is really as you're thinking through that conversation that and that context and thinking about the person's reaction. You have to be honestly, and we talk a lot about bravery on the show, but like you have to be brave because not being afraid of a reaction and therefore not having the conversation. I feel like your silence is like a lie.

unknown 15:46

Yeah.

SPEAKER_00 15:47

Right? Silence is a lie, and that lie is going to start to snowball. It is better when it's very small to take that hit than to wait until it's a big thing. And like you said, some personalities are just, it doesn't matter if it's a little thing or if you wait for the big thing, the person's going to be crazy. So do it over here when it's small. Yes. But yeah, you cannot allow the lie of silence to grow.

SPEAKER_01 16:15

You cannot allow the lie of silence to grow. I love that. And I also love what you said about checking in with yourself and knowing when are you at peak performance to have these hard conversations? Because yeah, if you're spent, if you're mentally drained, that's probably not the best time to have that hard conversation because you're more likely to pop off if the person doesn't respond in the way that you that you want them to. So know yourself. Know yourself before you know you go into having hard conversations. One of the things that I've told other executives that I coach is that if you're not having at least one hard conversation a week, at a minimum, if you're not having one hard conversation a week, you're missing something.

SPEAKER_00 17:19

What are you doing?

SPEAKER_01 17:20

You are not doing your job because I guarantee you, even if you're working in the best office environment, everyone's great, everyone gets along, people are rolling in the same direction. Human nature dictates that something's gonna be off. Like someone's having an off day, someone's missing the mark. Like it's it, and it doesn't have to be intentional, but you know, life happens, mistakes happen. And I guarantee you that even in the top performing, best places to work, you know, in the world, whether it's corporate, government, whatever, something is gonna go wrong. And as a leader and as an executive, if you don't have your finger on the pulse, if you're not having, again, at least one hard conversation a week, I guarantee you you're missing something.

SPEAKER_00 18:10

I feel like there's a certain level that only the bad things are coming to you.

SPEAKER_01 18:16

Right.

SPEAKER_00 18:16

Right? There's a certain point where you have to make this switch from being a good employee to being a brave leader.

SPEAKER_01 18:24

Yeah.

SPEAKER_00 18:24

Right. Because if you're in a large enough organization, I feel like my last, I don't know, I feel like the last decade of my at least maybe 10 to 15 years has been like this. There's layers of managers beneath you. And so if those managers couldn't solve it, then by the time it gets to you, it's just bad. Right. Right? I feel like for many years I've been joking about how only the worst things hit my desk. And so I agree with you. Like if you're running from that, then you're fundamentally running from your job. Right. Like you're getting paid as an executive to do hard things, to think big thoughts. To have hard conversations. I mean, 100%. Like so I used to have this picture on my door, like jokingly, in one of my assignments of the from the whiz of um, I can't think of the character's name, but the woman who sings like, uh, don't nobody bring me no bad news. Right. And I was just like, it dawned on me. And I had it on the inside of the door where I saw it. Because it it dawned on me one day, like, oh, I'm in the job where everybody just brings you bad news.

SPEAKER_01 19:44

Yes.

SPEAKER_00 19:45

Right. And from the outside, every anyone else would have looked at that team and said, like, they're super high performing, everything's perfect, like they are amazing. And they were, it was an awesome team. But we still had to deal with bad news stuff. Of course. And so I feel like that's just, you know, and yeah, I had to have hard conversations and I had to do um make hard decisions, and that's just uh that's just a part of that's just a part of the job.

SPEAKER_01 20:10

You know, the one thing that I would say to close out this conversation before we started recording, we were talking about the proliferation of chat groups. We're both in too many chat groups. All of us are in too many chat groups, too many platforms, too many, yeah, it's too much from a cybersecurity perspective, from you know, the perspective of just keeping track of who you're saying what to, it's too much. And I would just say, you know, because we talk about building community so much on this show and this theme of communication and having good communication skills and really connecting with people, you cannot build community in a chat group. Like chat groups have their purpose, especially, you know, I think one of the one of the biggest lessons or biggest best practices that we gained from COVID was uh pivoting to a world in which we had to find different ways to communicate. But I feel like that has it's gone overboard, right? Like we've lost the ability to connect with one another in person, to have genuine conversations. People get on these chat groups and they feel that they can say things that I don't think that they would say face to face in a one on one. And I do want to be clear that I'm not saying chat all chat groups are bad. That's not what I'm saying at all. Hybrid communications have their place and are very valuable. But I feel as though they've also taught us that we need to be even more intentional and More careful in how we say what we say to one another so that things don't get lost in translation because you're texting on your phone.

SPEAKER_00 22:09

So I agree with you. I think that a hybrid approach makes sense and that there are many different scenarios where people need, you know, different kinds of things. But I think about, say, when I was in Rwanda and during the pandemic, and I was in a lot of chat groups, and I might chat, chat, chat with you, hee, hee, hee, send some funny memes. But then there comes that moment where I'm still in an empty room by myself with my phone. Like, yes, we kikied a little bit, but I'm still alone. Right. And so I understand what it means, and you do too, to be geographically, you know, away from people that you're close to and having and struggling to build community, or maybe being in places where you it's really hard to build in-person community, or you know, having an illness or some physical impediment that makes that challenging. But I also recognize whenever possible, the power of having some human communication, some human direct communication. And it's something that we joke about at our house a lot. How for me, like you know, my family notices my mood is better. I'm super extroverted, so I'm better when I go outside and I have some contact with people. I understand that people are introverted, but there is a difference between like you and I trying to build a relationship of trust virtually when since we can meet, we are, you know, we are near each other to have that human connection really helps. A thousand percent. I also just feel like right now the other extreme is happening in my world where there's just a lot of work that's happening by chat groups. And I'm like kind of on the other side of you know how people complain about meetings should have been an email.

SPEAKER_01 24:06

Yeah.

SPEAKER_00 24:06

Sometimes I'm in chats and I'm like, yo, this should be an email. This could be an email, yes. This should be a document. Like, what are we doing right now? This should be a spreadsheet, like you're tripping.

SPEAKER_01 24:18

Right.

SPEAKER_00 24:18

So I think that we're like becoming overly reliant on this, using them as knowledge centers. Like, oh, I I put that in the chat, go search it. Like, whoa, it feels unsafe. Yes, and unstable. And I'm not sure we who owns this information and stuff like just less in the chat. Less in the chat.

SPEAKER_01 24:40

And how are we keeping track of like all of these documents? Like you're saying, people are waxing poetic in chat groups, and it's like, okay, this probably needs to be a document and memorialized somewhere so that we can go back and refer to it.

SPEAKER_00 24:55

That needs to be an email, right? It's like a bumper sticker, all of it. Your meeting, your Slack, your chat. It all should have been an email.

SPEAKER_01 25:06

It all should have been an email. Yes. I think what we're saying more than anything is, you know, don't be afraid of having difficult conversations. Make sure you're clear, make sure you're making the necessary adjustments, make sure that you're not letting fear get in the way of having that difficult conversation. Make sure you're in check when you're having these conversations and that you're at your best so that you can get the best outcome.

SPEAKER_00 25:34

And then build your community toolkit with lots of tools. There's some chats, there's some emails, there's some coffees, you know, there's some video calls. Like you've got a lot of different tools. Don't become overly reliant on one or two. There it is. Uh, with that. Well, look, Shelby, I would say for our listeners who are listening on audio, you're missing out on like all the good fun, the laughs, the great backgrounds, the wonderful camera effects. Like you're missing out on so much. Come over to YouTube and please subscribe to our channel. If nothing else, just subscribe to our channel and definitely please like and engage with some of our content. And we look forward to having a few upcoming episodes for you that I think are going to be really interesting. So stay tuned for those. And please come back and sip wisdom and stir success with us in the future.