headshot of Nathan Calland with two business professionals in the background who look to be having a difficult conversation at work


How to Have Difficult Conversations with Employees

Many leaders get uncomfortable when it comes to having difficult conversations with employees. In this podcast, Nathan Calland offers strategies for how leaders can tackle challenging conversations.

Publish Date: December 15, 2020

Episode Length: 27 minutes

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In this Episode

Many leaders get uncomfortable when it comes to having difficult conversations with employees. In this podcast, Nathan Calland offers strategies for how leaders can tackle challenging conversations.


In this episode of the Leadership 480 podcast, we interview Nathan Calland, a leadership consultant based out of DDI's London office. He joins us to discuss difficult conversations in the workplace, and specifically, tips for how leaders can most effectively tackle those really tough conversations with their teams. 

Beth Almes:

Hi everyone and welcome back to the Leadership 480 podcast. I'm your host, Beth Almes, and today our topic is about how to have tough conversations with employees. My guest is Nathan Calland, who is a leadership consultant in DDI's London office. Nathan has more than a decade of experience coaching leaders and helping them build the skills that will get them through those really tough leadership moments. Nathan, welcome to the podcast.

Nathan Calland:

Hi Beth. Thanks very much, good to be here.

Beth Almes:

Tell me a little bit about why conversations are so important for leaders.

Nathan Calland:

Yeah, thanks Beth. I think before a lot of people come into their first leadership role, I think many of them have a lot of misconceptions about what leadership actually means day by day, and how they imagined what being successful as a leader looks like. I think, looking back to when I was younger, I used to have this picture in my mind of kind of a group of peers standing around me, congratulating me on making a great decision, and me kind of smiling with my hand on my chin. That was my idea of good leadership. And now good decisions are certainly a key part of a people leader's role, but it's only really a piece of it.

And what I know now from working with people over the years, is that people leadership really is a series of interactions. So for example, when you're coaching a team member on a new tool, maybe you've got to influence someone in a senior leadership role to change a policy that affects your team, moving the needle on most of your key outcomes is going to require high quality interaction. So even thinking about the decision making piece, you're most likely going to have to canvas your peers and your manager for their opinions, right?

Beth Almes:


Nathan Calland:

And so here's a great way to reinforce this point. I'd really like maybe yourself and our listeners as well, to think back over their careers to a moment when someone who led you really made an impact on you. So perhaps they inspired you to do something great, for instance. Think, how did that happen? Was it a conversation, or was it in an email, or was it something you read on a website? If you could hold that thought, and I'll share my example when we're finished talking.

Beth Almes:

It's funny, Nathan, when you bring that up, because I think it's both. As I think back, it's been both for the positive and the negative. So when you say those conversations, I can also think back to some of the negative conversations that, it was a two minute interaction or maybe even less, and it was so frustrating. 

It could kind of derail you for the rest of the day, of things, you're like "Oh, I should have handled that differently." And at the time I would have had a lot of those that would have been with my own boss. And yeah, so I think it's one that really resonates with me on both sides, both the positive where I've been encouraged, but also the negative where you get really thrown off track.

Nathan Calland:

Absolutely, yeah. That's a really good point. You want to get these right, and that's a sign of the outcomes of an interaction that didn't go so well. So yeah, maybe we can get people to think of some negative examples as well, have one of each.

Beth Almes:

Yeah, don't hold that one with you too much on those, but I think what stuck with me with some of those negative ones is how much time it wasted. It's too much energy, if you had a negative interaction, it wasted my time thinking about that instead of going forward in what I needed to be focusing on instead. And I've heard you talk sometimes in the past about conversations being the ninth form of waste in a lean organization. Can you tell me a little bit about what you mean by that and why it matters?

Nathan Calland:

Sure, Beth. This is something I've become quite passionate about, because we work, not just DDI, but me specifically just by default, really. I've ended up working with a lot of high-tech and industrial organizations over the years, so become really involved with this concept. Probably to talk about lean manufacturing, just so our listeners have an idea of what we're talking about, lean manufacturing and lean production is something. 

It's a production method that originated in Toyota's operating model back in the 1930s. They called it the Toyota Way. And then somebody, I can't remember who it was, repackaged it as the concept lean in the late '80s, I think, and it went on to be successfully implemented in production environments all over the world, so really a global concept. And a key part of lean is focusing on minimizing waste in your process to improve efficiency.

And as you mentioned, there's eight principles that cover things like defects, over production, things like inventory sitting idle, extra processing. So when you're thinking about supervisory conversations in a production environment, they could certainly be added to this list as number nine, as a recognized form of waste. 

Now this sounds a bit counter-intuitive initially, until you think about it. So you have to think about a supervisor briefing their team on a new process. The expected outcome is that they'll go back to their roles and implement this process efficiently, right?

Beth Almes:


Nathan Calland:

But what if not everyone involved in that conversation has clarity on the key points that were being discussed? Or what if they didn't feel comfortable enough to raise a question that would help them understand what this means for their particular contribution? 

So the consequences for that kind of ineffective interaction are real. We're talking about possibly hundreds of hours of lost efficiency there. And also, if you think more longer term, investing time in building the capability of the teams is also a way to reduce waste.

So as that production supervisor, if I'm able to coach my team members to successfully execute tasks that typically, I've needed to delegate, it's a win-win. So their capability increases over time, and hopefully this means they're getting more out of their role. And then I'm not trying to accomplish everything myself. 

But once again, if those coaching conversations are ineffective, then over time, my team isn't going to expand their capability, and so their level of effectiveness stays the same, and I'm going to have a lot more to do myself. So overall, efficiency is definitely going to be impacted. So I hope you can see that it really is something that isn't often measured, but hundreds, possibly thousands of hours every year.

Beth Almes:

Yeah, just from a bad conversation, if things weren't clear. But what about those leaders who might be reluctant to have these tough conversations, either because it's faster to just solve the problem themselves, or because they're simply uncomfortable with it? How do you help them have those really hard conversations when they might naturally try to avoid it?

Nathan Calland:

That's a really good question, Beth. And in my experience, this is where so many first time leaders particularly struggle with this when coming in into that first people leadership role. That transition to getting things done through others is a mindset shift. Now, what holds new leaders back is a lack of confidence or that anxiety around actually having the conversation. 

So they might be thinking not only, "What am I going to say?" But more importantly, "How do I say it?" So there can be a real anxiety here that holds leaders back from initiating these conversations, which can sometimes be really difficult. Can you imagine providing feedback on a team member's performance issue? It's really difficult.

To explain this a little bit better, I'll tell a quick story, because who doesn't love a story? Roughly about five years ago, I spent some time on site with one of DDI's key partners, and the main reason was I wanted to get to know the organization, to meet some of the leaders that DDI was developing. 

And one of the guys I spoke to had actually recently been promoted to his first team leadership role, and he'd also just attended one of our programs. He confided in me that he was aware that he'd probably been promoted for his technical ability more so than his people skills, which is very common, especially in a technical organization, we see this a lot.

And he also shared that he had several complex people issues to deal with straight away, as soon as he came into role. Some of these were inside his new team, and some of them were scattered across the business, so not just in his immediate team, either. Now, he viewed these as real challenges, but he said that he thought that what he'd learned in the program actually was going to help him, so some of the stuff that DDI taught him. 

Now quite a bit of time elapsed, I think it was about maybe a year or maybe more later when I actually caught up with the same guy, and it was super inspiring to see the change in him and how he felt about himself. Because what he'd done is he'd begun planning his discussions, particularly difficult ones in advance. So by doing this, he was able to ensure that he was meeting that person's personal and practical needs that we talked about.

So not only would he be able to do that, he'd also have clarity on the key points he wanted to make during the conversation, and this allowed him to, having done this, make ample time for the good stuff like the active listening. So over time he was following this process, and he became more and more confident. 

Then he confided that these days he addresses any issues that come up in his team straightaway, there's no avoidance because of the anxiety. And he said he actually really enjoys his interactions now, and he just seems really empowered, which is great. So that worked for him.

And he also shared that day-to-day now, he interacts with his team a lot more, more or less all the time. And I think previously, quite a bit of this was done electronically, messaging or over email. And he said that this had opened up a kind of informal feedback channel, and it really made the team atmosphere or how the team interacted a lot more open and enjoyable for everybody. But most importantly, his anxiety had gone and he was actually looking forward to having those effective conversations, even the difficult ones. It was fantastic to see.

Beth Almes:

That's really an inspiring story of really changing from that dread and anxiety over these conversations, to it really being a positive experience, both for the leader and the person that they are coaching and having these tough conversations with. 

As you mentioned, though, as we're doing this and we're moving now to the virtual work world, and where a lot of these conversations used to take place just impromptu, or there was a moment, say, "Hey, can I grab you for a sec?" That's a lot harder to do. How do you feel like conversations have changed in the virtual workplace?

Nathan Calland:

Yeah. Well, that's something that we're all coming to terms with right now, Beth. That's a really good point. It's pretty much a global mega trend, isn't it? I don't know, I think one thing that I know I've noticed and a lot of people I've spoken to about this noticed is that, in this a 100% kind of virtual context, you've only really got a set window to get your conversations right. 

So you mentioned before, some of the face-to-face stuff that would happen during the day, all of these things that we could do before or after a meeting to help make it successful, all of this is going to happen inside the 30, maybe 45 or 60 minute window. So for example, we've talked about how you've got to invest some time in meeting someone's personal needs before you can really dive into the practical meeting focus, like all of the things that you want to accomplish.

And I think we all know how it feels when somebody does that, right? Just starts a meeting and it's right onto the first agenda item without really checking in with everybody to see how they are psychologically. These days there's no walk down the corridor, you can't have a chat, or you can't speak to someone earlier in the day to do this, to warm up and find out how they are. 

So not only are we coming in cold, so to speak, we've also really got to make sure that everybody involved feels heard, and that they have the clarity they need, that when they leave the meeting, they're feeling satisfied and focused. And there's a real impact to getting this wrong.

And I'm going to share another story, actually, because I was speaking to a senior leader at another organization that we work with not so long ago. And they shared that they'd been involved in an internal meeting that really didn't go very well. So there'd been some healthy, I think we call it challenging during the meeting, which ended without everybody. Because of that challenging process, it got quite heated and they weren't able as a group to reach a consensus and move forward. 

So this really affected the leader in question, and it put them in quite a difficult, both heart and a head space afterwards, and took them quite a while to refocus. So the point is that there's no water cooler conversations to catch up and maybe smooth things over, so there isn't that opportunity to do that. And this is something that a guy we've started working with at DDI some time ago, Dr. Steve Rogelberg. Beth, you may have heard of him.

Beth Almes:

Yeah, absolutely. He's been around a lot talking about meetings. He's been on a lot of the talk shows, things like that. I've definitely heard of him with the meetings, yeah.

Nathan Calland:

Yeah, yeah. Yeah, he's a real expert in the science. It's kind of a data-driven approach he uses, the science of having great meetings, so he breaks it down. And he calls that emotion that people have, or the effect of a bad meeting afterwards, I love this term, meeting recovery syndrome. 

I really love that term because it's given all of us a way to articulate what that feeling is, and we all know it, I think. It's the psychological impact of having a poor interaction, and that effect or that feeling that stays with us maybe for a few hours, maybe a whole day. And I'm sure that feels familiar to everyone. So to answer your question, in the virtual world, we've only got a really small window to get things right, so that's a real challenge now.

Beth Almes:

Yeah. I think your point there too, around, maybe there's some opportunities there for inclusion, too. You mentioned everybody needing to feel heard, and that's hard. It's really easy to overlook people in a big virtual meeting. 

It's a little harder when they're sitting there face-to-face in the room. I think there's probably some aspects of inclusion there where you can maybe go a little bit more out of your way to make sure you hear people.

Nathan Calland:

Absolutely. It's about how you're drawing people in, making people feel included by involving them. And it could be back to that that personal needs thing around checking in with someone, seeing how their self-esteem is, and people maybe who aren't confident, who aren't normally included in the conversation, that little pep to their self-esteem and a question to invite them in can really make someone feel much more invited, and encouraged to participate in a conversation. So there's definitely lots of work that can be done around that for inclusion.

Beth Almes:

Yeah. I keep going back to that idea that you mentioned earlier around waste, and how if you don't have everybody on board with the concept after the meeting, if they're not really bought in kind of head and heart with it, it's much slower going, it's harder to win, it's harder to move forward. I think that's really an image that has stuck with me from our conversation here about how much waste there is when you haven't done these conversations right.

Nathan Calland:

Yeah, I was going to say, there's another aspect of virtual conversations that I think's worth mentioning, is that I think we've all read a lot of articles during the pandemic or through the crisis about what worked and what didn't. I think just about most of them anyway, or article or analysis talks about empathetic leadership, right? 

It comes out as one of the key success factors for leaders in a crisis. Can I empathize with my team? Can I be authentic in sharing what they're going through? In the last few months, we know that teams are super stressed, overworked, and facing probably the largest amount of ambiguity they've ever encountered.

And it seems to be leaders who managed to empathize with our team's emotions, and when I say empathize, I guess my description I normally use is not feeling sorry for, but feeling sorry with, if that makes sense. So teams who were able to do that were able to help their teams work through these emotions more and stay focused, because a problem shared or a feeling shared, is a feeling halved. 

So leaders who are able to do this were able to do the best job. I was actually speaking to our VP of assessment, Matt Paese, about this very topic, about interaction challenges in the virtual world. And Matt's always got a great turn of phrase. He said to me, "Nathan, empathy takes a lot more finesse to demonstrate in a virtual world." And I couldn't put it any better.

If you're thinking about looking through that little window in a virtual meeting, your words and your tone are really the two key ways that you can transmit that you're feeling your team's, whether it's frustration, sadness, or joy, it could be positive emotion, too, because we're all on a roller coaster during that crisis. 

So what I need to do as a leader, is I need to become more intentional and verbal with my expression. So perhaps in the past when I could just maybe lean in physically and say, "Oh dear. Jane, that must be really tough for you." 

Probably, I need to say something more like, "Jane, that challenge you've shared around getting digital content really at such short notice must've been really frustrating. I can kind of imagine the experience of the pressure, not just from the client, but dealing with our own tech team. That must've really taken up a lot of your time and energy." So that's a pretty straightforward example, but basically, I've just got to work a lot harder on demonstrating the empathy in a virtual world.

Beth Almes:

I really like the concept, defining the empathy versus sympathy. I will say that right now the hardest thing about this that has not really been around in recent years, is everyone going through such a tough time all at the same time. 

Normally in the past, it was you had one person on your team who might have a specific family situation, or one person who had something that was going on that was particularly stressful in their lives, and now it's everybody in the world all at the same time is really having a hard time. And I think your point around that team empathy of feeling sorry with, of we're all going through this together, there's no time to be sorry for anyone, but going through that together is such a powerful one in this particular time.

Nathan Calland:

Yeah, and I think that there's a theme building. Another example of the challenges you're facing in a virtual world is how do I go about building trust with people that I've never met before in a physical world. We've been talking a lot about this lately, once again internally and with people we work with. 

This challenge is particularly real for people who've just come to an organization, they haven't got a network, they're brand new. We rely so much on body language and the ability to observe people day-to-day to really find out more about them and slowly build trust and find out who they are. But in the virtual world, we haven't got these opportunities, so we've really got to be hyper-intentional with our approach. 

So, for instance, if I want you to trust me, you've got to feel that I care about you and really understand your world. And if I'm starting from scratch, this means that I've got to become really good at asking open questions and actively listening to the answers. Maybe like what your role challenges are, how you're feeling about your part of the business, do you like pineapple on your pizza (I know many people who do), maybe even how many kids you have. In the virtual world, this stuff isn't going to just fall into our laps like it could do in the past. 

What we really need to do is work much harder to understand it. Ultimately, I think this is a really good thing. We should all be having more of these curious conversations, so if that proves to be one of the positive crisis trends then I think we'll all be doing much better in our roles.

Beth Almes:

I think so, and the I think the important thing here is that no one should be ashamed to share that they like pineapple on their pizza. I do, and I think it's totally legitimate, so if there are listeners out there who do like pineapple on their pizza, they should know they're not alone, they shouldn't be afraid to tell their boss about this and connect on that personal level.

Nathan Calland:

If you're going to ask an open question, then you should be prepared to receive the answer. I still think you're in the minority, Beth.

Beth Almes:

I might be in the minority but I just think that there should be support out there for people who do appreciate the pineapple. I think your point overall of really making sure we're taking the time to connect, that people feel heard, especially as we switch to virtual meetings. A lot of people don't speak up in meetings. 

I am envious if there is anyone out there that can't relate to that 'meeting recovering syndrome' because it is so prominent that you have a bad meeting and it just sticks with you. Really challenging, and you feel like you weren't heard and everybody went on in a direction that you don't agree with. Or, maybe your ideas were completely overlooked about how to solve this problem. 

Leaders can go along way to check in with people afterwards, especially if the meeting was contentious. Checking in to see how did you think that went, was there anything that didn't come out that you wanted to share, that we might think about moving forward. I think that's really important as we switch to this virtual world and having those tough conversations. 

So, for a final question we ask everyone on the show, what was a moment of leadership that had an impact on you and your life?

Nathan Calland:

Thanks, Beth. This comes back to something we said earlier. I wanted people to think about an interaction that really impacted them, so it's great that you're asking this question. I'm going to go back to my earliest teenage years, to an interaction I had with a teacher at the time, an English teacher. His name was Mr. Mike O'Brien. He was super cool, he had a pony tail, he was pretty progressive. I really liked him. 

We had a book assignment, a book that we had to read and we had to prepare a review, and write quite a long essay about what we thought of the book, and answer key questions. It was probably five or six weeks into the timeline of this work, and I'll confess that I probably wasn't the most dedicated student when I was around 13 or 14, but here I was, up in the library in a study cubicle, pretty much hiding away from this work. 

And Mr. O'Brien came and knocked on the cubicle and said, "Hey, Nathan. How are you doing?" I was actually new to the school and he was checking in on me. He said, "How are you doing with the book assignment?" And I kind of umm-ed and awww-ed and made a few pretty poor excuses. He said to me, "Nathan, have you read the book?" Once again, I said I read a couple of pages, but not really, and sort of made my excuses. He sat down and looked me in the eyes and said, "Nathan please just read the book. I'm not worried if you don't even turn anything in. I really want you to just read the book. It's a great book." The book incidentally was a Day in the Life of Ivan Denisovich by an author called Aleksandr Solzhenitsyn.

So by engaging me in that very authentic and honest way, pointing out what the goal actually was, he just wanted me to read the book. He motivated me and I did read that book. And I really enjoyed it. To this day, it's still one of my favorite books. It probably led me on the path of some other really fantastic literature. I'd like to thank Mr. O'Brien. Mike, if you're out there anywhere, thanks very much. You inspired me to read a lot of really great books. So that's the one I'm willing to share.

Beth Almes:

That's such a great leadership story of how he addressed the uncomfortable. As we're talking about tough conversations, he addressed what was uncomfortable as you hadn't read the book but he helped you to see this is what the point of this is. And I think, even at work, for so many of us, that's the bottom line. That this just isn't another task, another thing. What is it that we're really trying to do here? 

Getting to that is such a powerful leadership skill of saying, "I don't need you on board to create these tasks, but whatever you are working on, whatever you are doing, here's the impact, here's what going to be important." That's a great way to engage. 

So thank you for joining us today, Nathan, and thank you to all of our listeners who spent part of their 480 with us today. Remember, don't let anyone tell you what you're allowed to have on your pizza. It is up to you. That is the message we are taking with us today. And we'll sign off. I'm Beth Almes, reminding you to make every moment of leadership count. 

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