Delivering a Tough Message in the First Two Sentences

Welcome to Connecting to Admired Leadership, where twice a month we explore the behaviors and routines that make great leaders extraordinary. I'm Wes Bender, and I have the distinct pleasure of hosting some of our firm's partners, coaches, and clients to discuss leadership in ways you won't hear anywhere else. Let's dive into this episode and make people and situations better together. All right. Good afternoon, as it is for those of us in the Eastern time zone here in the US. Good morning, good evening for those of you who may be joining in, in and around the world, or happy day to those of you who might just be listening to this recording as you're on a run, maybe mowing the grass, who knows, on your commute, whatever that may be. Very excited to have Katie. Those of you who have been on prior to this, you know Katie. Katie is one of our partners, executive coaches, leaders, advisors within our strategic communications practice here at Meyer Leadership. Katie is just incredible to talk to. I have many stories of Katie, but my favorite thing to do is share family stories with Katie. In fact, we were just doing that prior to the webinar today in regards to kids and taking some of our leadership concepts and how they apply to our families and those of us who are leading and growing our adolescent children as well. Before we jump in today, I did want to share a great question that I had on a call last week. One of our listeners asked me, Wes, why do you do these webinars? And it caught me a little off guard. And I started giving a roundabout answer, which I try to be pretty clear in my responses, but my roundabout answer was all over the place. And then she kind of stopped me and she said, tell you what, do you want to know why I listen to these? And I said, yes, in fact, that's probably where I should have started, is asking you that. And she kind of stopped me in my tracks and she said, Wes, these helped me understand what genuine leadership coaching should look and feel like, both what I should be looking for from a great coach for myself, but also how I should be coaching and making the people better on my team. And she said, in addition, this is giving me lessons on how to approach Alex. Alex is our AI executive leadership coach. And she said, I won't forget these words. She said, Wes, I don't think we're talking enough about the fact that good executive leadership coaching is now scalable and what that means. And she said, what I have— I'm joining this along with having the rest of my team because I'm trying to help them understand how to use an executive leadership coach because we're now able to put it in their hands. So just really interesting in regards to all of that. If you're not utilizing Alex, we can give you a free trial of that coming up too. So just really fun as we build this community of listeners and people along the way too. So without further ado, let me pull in Katie to our discussion. Katie, for those of you who may not have listened to you in the past on these webinars, who are you? And let's use kind of tag back into Alex and say, how is Alex or any other AI right now making you a better leader? Great, thank you, Wes. Happy to be here, and thanks everybody for making time out of your day. This is a true investment in you and your own development, so good on because this world moves fast and sometimes we lose sight of making time for ourselves. I'm Katie Eingstad. As you mentioned, I'm a partner at CRA and Myer Leadership. I actually just celebrated my 18-year service anniversary in May, so I've been around for a while. I'm based out of Philadelphia. The question related to how I'm using Alex right now, Alex is my go-to preparer and thought partner. So whether I'm preparing to deliver a keynote, whether I'm going to be leading a dialogue session with a client, Whether I'm doing an executive coaching where I know I want to go into a conversation and I want to pressure test some of my assumptions related to how I'm going to engage in that moment, Alex is exceptional at helping me think through difficult conversations and just preparing for those moments and practicing. So preparation and practice. And then I also have to admit, I used Alex quite a bit in preparing for this conversation. This is a topic we talk a lot about. It's one of the most popular topics that we talk about with rising leaders, how do we deliver tough messages and do that with credibility? And so, when you've talked about something for as long as I have, you just want to make sure, like, am I missing anything? I don't want to have any blind spots around these sorts of things. And so, it was really good helping me think through different scenarios for these types of things. And so, I'm hopeful that it'll make it a richer conversation today than if I hadn't used Alex. Excellent. And Katie, you'll be pleased to know that Alex in our chat box has encouraged your use of it and exactly the way that you're doing it. So a little encouragement from Alex there. All right. So let's jump into this topic, which is one, as you mentioned, Katie, we speak to, we coach a lot of leaders around delivering that tough message in the first 2 sentences. Could you just frame this for us? Why is it important? How should we be looking at this? Yeah, as I said, this is probably one of the more universal leadership challenges. And I would probably say one that is often most mishandled. When I talk to some of the executives that I coach or leaders that I coach, I'll say, well, how did it go? How did you approach it? And their intent is always right, spot on. I mean, I think that they really want to you know, do good and do the right thing. But I think unknowingly, sometimes they kind of prioritize the conversation in a way that actually leaves it feeling flat or in a way where the person on the receiving end of the feedback isn't hearing it. And so, whether it's about, you know, the performance conversation that you've been putting off just because you don't want to have it, or the, you know, an executive who has made a tough decision about maybe it's canceling a program or something to that effect. That they bury that decision in so much context that they actually miss the fact that there was a hard message that was getting delivered. And sometimes even we see leaders who are given a decision that they then need to communicate to someone or to a team, and they find themselves distancing themselves from the decision as if it's not their own. And so that's, you know, that, that in and of itself too can be quite a mishandling that doesn't lend itself well to the credibility of the leader or the broader leadership team and where the organization is headed. So, you know, what makes this topic worth it's worth a real conversation because leaders know they need to have these conversations. Avoidance is a real thing in lots of times. And the reason why they're avoiding it is because it's usually the emotional weight that comes with it, right? It's the fear of damaging a relationship. When someone says to me like, "I know I got to give them that feedback. I just haven't yet." And I'm like, "Well, why? Tell me why." And they're like, "Well, you know," and they'll talk about their calendar and they'll have all these excuses. But at the end of the day, when we get to the bottom line, it's like they don't want to hurt their feelings. They don't want to make that person feel some kind of way, and then that damages the relationship and maybe damages the effort that person's now going to put forward because they feel some kind of way. So a really important conversation that I think hopefully today we can hit on some things that will help make these conversations feel less scary and less like we want to procrastinate or avoid them. Yeah, let's go one level deeper into the framing. One of the things you mentioned to me when we were having our prep call on Friday that really resonated was not all tough messages are the same. And that's the first place to start. And one of the places that I knew you wanted to take us today is that it's not just the first 2 sentences and what you're doing in that. The preparation for the conversation starts way ahead of time too. So walk us into that. Sure. I mean, you'll hear folks from our firm, if you've heard any of these sessions or you're getting coached by anybody or you're involved with us, but we will often say the best feedback conversations are carefully scripted. And what we mean what I mean by that is that you're prepared, right? You're, you're not just going to go in and, and kind of wing it and hope for the best. But what I will say is the majority of the leaders that I've coached, you know, oftentimes won't do the practice or the preparation, and they'll get into it, and the first time they give the feedback is the first time they've heard it out loud themselves. And so just, I think the nuance to your point is there's a couple of different ways that you need to be thinking about these conversations. There's the performance conversations and recognizing that those conversations in particular are likely going to have kind of more identity wrapped up in the feedback. So have a higher likelihood that someone might feel defensive or want to push back or want to disagree. The one I also mentioned too, unwanted changes or decisions that are coming down, whether it's from that direct leader or coming down from above, and it has to be then shared on behalf of that leader. So, Decisions that people want to challenge or disagree with are also tough conversations. And I think there's small nuance in the 3, and it's important to recognize and anticipate, right? As you go through that preparation, one of the most important things you can do is say, "OK, how are they going to respond? What questions do I think they'll have? What can I anticipate so that I can be prepared, better prepared for that moment if it happens?" Yeah. Based on the leaders that we coach, Do you find— do we find that more leaders naturally lean into direct, very harsh, or more compassion? Just out of curiosity. In my experience, I would say there is a tendency to— it's either avoid or be really direct. And what I would say is the leaders who are really genuinely good at this have figured out something that is relatively counterintuitive to that. Which is these conversations are about creating clarity in lots of ways. And this is going to kind of feel like, we have a colleague who says, "Oh, that feels like a warm hug." But clarity is really an act of care. Okay? So, being able to deliver a message cleanly, directly, with genuine compassion is more respectful to the other person and avoiding that ambiguity. And so, what I would say is oftentimes, the frame that people have for giving feedback is, is, you know, this is going to be hard, they're not going to like it, they're going to disagree, this is going to hurt their feelings, this isn't going to feel good. Um, but what I would say is the best leaders reframe that confrontation into care. And that's where the real coaching happens, which is, this isn't, I'm going to tell them because they're doing it wrong, this is, I want to tell them because I want to make them better, I want them to be successful, I want to invest in them, and I need them to believe that. And that's a really important part. I know not for today's conversation, but like getting people to actually hear your feedback, they have to believe that you care about them first. Yeah, yeah, I was going to ask that because the intent of the individual, of the leader who's giving the feedback becomes incredibly important with the tough message. Is my intent here to get through this? I think of the Office episode with Michael Scott who has to fire somebody and he ends up start talking about a deer that he killed, but it took him an hour to kill the deer. You know, what does it begin to look like on the receiving end of that? And what is the true intent of that leader? Is it truly to develop this person and make this person better? Then whether I am the uber candid person or the person that's trying to avoid the actual tough message, that intent should motivate and inspire me to, to find my range within that. So that would be my next question. How do we coach both the candid leader and how do we coach the compassionate leader to find a balance and the importance of that? Yeah, I think first and foremost is even the acknowledgment that the compassion piece is important and more about like how you want your relationship. What do you want the relationship to look like? So your point, Wes, when we think about, okay, the best conversations, the best feedback conversations you're preparing for, you're asking that question like, what's my intent? What's my goal? People can smell intent from a mile away. And if I'm smelling intent, that's like, this person just wants me to feel bad, or this person isn't being active in how they're giving me feedback, I'm going to show up in that conversation differently, and I'm going to walk away from that conversation differently. And so, I think understanding what your goals are, both from like, what's my message, what's my intent, and then the third one, which is what we just talked about, I mentioned a little bit ago, which is how do I prepare for how they may react to this. And what am I doing in those moments? So let's dig into that for a little bit, because that's where most people's avoidance of the tough message or adding an endless amount of context before they actually get to the tough message in some way, shape, or form, they're trying to control the response of the person that they're talking to. They're worried about how this is going to land. They're worried about the person that's there. So how do you deal with or prepare yourself for any potential emotional response that you could be getting from the person you're talking to? I think there are a couple things that the best leaders do to do this effectively. One is they're actually priming the person for the conversation before the conversation even happens. So first and foremost, it is— let's just say, you know, that you have your weekly meeting with your direct, and you need to give them feedback about something that happened recently. You are anticipating it's going to be a tough conversation. I'm actually not. And if you use your weekly conference, that may not be the right time to give it. Timing is really important for people to hear feedback. But let's just, let's just build on this example. If you are thinking to yourself, okay, well, typically in these weekly conversations, we have a very set agenda. We talk tactics, we do this, we do that. You are going to blindside that person if you come into the conversation and in the first 2 turns you say, hey, by the way, you know, here's the feedback. They might feel a little ambushed. And so instead, what I would suggest you think about doing is how can you kind of drop some breadcrumbs before you get into it, where it might be like, hey, I'm looking forward to our catch-up on Thursday. I want to carve out some time to talk about last week's presentation, just some things that I want to focus on and how we can get better for next time. So let's come prepared, right? That is a simple way to get them thinking. And then, you know, if they're self-aware, they're gonna be like, oh man, I'm gonna get some tough feedback. And where they might say, like, give it to me right now. Right. And so I think you are priming them even before you get into the conversation so they don't feel like they're being attacked or that— and that— and you may not be attacking them, but people receive things in different ways. And so it's important to recognize, I think, that breadcrumb drop and kind of leading, leading them there before you get to the conversation is one way. So that's one. And then the second thing, what typically happens, and you've alluded to this already, Wes, which is this idea that you get into the conversation and you're already creating excuses for the other person's behavior. Whatever it is, whatever you're giving them the feedback on. So, yeah, I know the markets are tough right now, and I know that you have this happening. So this is actually really fresh right now. So if I'm gonna— I'm coaching someone who's a senior leader in an investment, global investment bank, and, um, this one junior person who was exceptional— I mean, talk about high competence, really, really good at what he does— but he has a reputation that he can be, um, not a very good team player, and he interjects, and he does a bunch of stuff that makes other people on the team feel marginalized and small. And so this leader has let this go on for far too long, so much so that a couple of people from his team who are peers of this person have asked to be moved to different parts of the business. And so it also reflects on the leader, you know, this leader, people, there's perceptions now. Can this leader actually handle this tough person? Are they giving them feedback? Um, and so when we started working together, one of the things that they shared with me was this Here's how I approached the initial conversation. And it was so much context, like, "I know the markets are tough, and I know you're really busy, and I know you have a lot going on," and making a bunch of excuses for this person's behavior. So, by the time the feedback was actually delivered, the person was like, "Well, I'm doing that because of all the things you already said." So, that I think are the things that are the biggest barriers to people wanting to do this well, is that they don't want to hurt feelings, and they create all these excuses, and then they wonder why behavior isn't changing. And so, when we go back to this idea about creating clarity, we've all been in conversations where we're like, "Get to the point. Like, what is it that you're trying to say?" And when the person finally says what they're meant to say, it feels a little disingenuous because you're like, "Why'd you bury the lead? Like, why wouldn't you just— if you really care about me, why wouldn't you have just told me?" And I know that sounds— there's some art to how you deliver that. But that's why we say, in the first few turns. Because if I've done the pre-work, I've warmed— I've warmed them up. And you don't always have that luxury, but I, I would encourage you to, one, do the prep, write your goals, your intent, you know, what are your main messages, how do you plan for things that might go awry, and then what do you do. And we can talk about that emotional response and how we manage it. Um, but I think those pieces are really important. And then when you get into the conversation, you got to lead with that because that's what's top of mind for them. They're almost going to be like, okay, so let's talk about what happened last week. You said you wanted to talk about it. What is it? And so you have to then think about the reframe, which we talked about, which is if you really care about this person and you want to make them better, what's the feedback that you want to give them? And you can say that, you can make that connection. Hey, you are, you know, I want to talk about what happened, and in the spirit of me helping you and getting you to the next level, because that's what I'm here to do, I'm here to make you better, like, I want to give you this feedback. It's going to be hard to hear, but you got to hear it because I know it's the right thing. So those kind, that kind of language can be really powerful in getting them to say like, okay, they really do care about me, they do want me to feel You know, but, but if you don't have that relationship yet, you got to start there. Yeah, that's great. Just a reminder, if you're joining us live, feel free to drop in the chat box any insights, thoughts, or any questions you might have too. And Alex has put another great field note in there for us too. I love what you just said, Katie, and I kind of wrote it down. You know, if you want to ensure an emotional response, then blindside them with the information. If you want to ensure the feedback does not land, give them some excuses on the front end before you even let it land. And that's, that's probably a good way to move into that, you know, because we— those are the two things we're trying to control a lot of times that are really out of our control. But there's some things we can do ahead of the conversation. So let's, let's dig in even one level deeper, maybe even some more utility and what this looks like on a very practical basis. But look at it both managing up and managing down. Or we might say leading up and leading down. How do folks approach this? Because I guarantee we've got some people on the webinar who are like, boy, I wish my leader was here. I wish my supervisor was here. I wish my boss was here. They could really use that. Or I wish my other team person was here. How do we move from not only doing this effectively ourselves, but using it in a way to develop the team, whether that be up or down the, the, the tier, the organizational tiers there? Yeah, while a lot of these conversations do tend to focus on superiors talking to direct reports and folks below them, up, down, and across, the principles are really regardless of direction. Those core principles still stand, which is kind of lead with intent, be clear, don't bury the lead. I think what does shift is the understanding that the risk of that positional authority doing too much of the work when you're kind of giving that feedback down. And the other person may not push back even when they maybe should, right? Because you have that positional authority. And so, I think delivering up is a different challenge entirely. You don't have authority to fall back on. And so, how you frame that message really matters even more. And what we tend to say is the most effective approach is to lead with genuine curiosity. So rather than a conclusion. And so sometimes the most effective way to carry feedback is through asking a crafty question. So what could that look like? Well, that could look like something like, okay, I've been thinking about how we're handling this and I'd love your perspective. Not sure we're getting the outcome we want. That question alone is going to give that leader feedback. And then their response is going to be really telling. And what we typically find is then they engage in the conversation. And by that engagement, that leader is actually accepting that feedback because they're responding to the question. And so when you're delivering feedback up, how can you be curious about what the situation is and why the leader is doing that, or whatever is happening, and asking a question? And that will in and of itself create a conversation that carries feedback that that leader, it may or may not be, you know, very aware of. So in the chat box, I'd love to hear for those that are live, we've got a great group of live participants today for this particular topic. I'd love to know maybe just a yes or no if you want to add some context or if you want to add a specific question or something. Is there someone and some critical conversation that's in your mind right now that you know you need to have? Is that in your mind right now? Yes or no? So Clearly, that's the case. So I want you to think through that. And I would love to hear from the chat box. What are you— what is your biggest reservation about that? And then Katie, as those comments potentially come in, here's what I want to ask you. What happens when somehow a leader does avoid the real clear feedback? What is at stake? What is at risk? That's because I— what I want everyone to see who's joining us or listening to this recording, these conversations, this ability, and the small practical things you can do to deliver tough messages right off the bat is a game changer as it relates to team synergy moving forward. But the flip side of that, what's at risk is significant. Could you speak to that? Yeah, let's talk about that. And then there's already a theme around like strong reactions, yeah, volatile reactions, the emotional piece of it. And so, we can go there. But I think the risk is what I said earlier is there's a lot of things. I mean, one, you're not getting the performance out of someone that they could, right? So, how they elevate the team and the contributions they have. You are, you know, when we think about caring for people, you know, this idea that people don't want feedback because it's going to hurt their feelings. I actually would say like you're hurting their feelings if you're not giving them feedback. I want people in my life who are going to say, hey, like, this is going to be hard for you to hear, but I'm telling you because I care deeply about you. Like, that's the way that you— the reframe that you need to have. It's going to affect their credibility as a leader because everybody around is going to see what's happening, right? The example that I use with my coachee, they— I said, let's talk about your reputation. Like, how— and we did, we did a 360 at the beginning, and I actually had heard that in the 360 that I had done for this person, that they maybe didn't have the right team. They had one particular performer who was really, really excellent, highly credible, but was damaging to the culture and So, it affects how people view you as a leader and your own credibility. It affects the team dynamic. People want to, you know, are saying like, "Let me change teams." And so, I think there's so much risk to avoidance, not to like scare, but it is a huge, I mean, one of the most important responsibilities we have as leaders is to create clarity and make people better. And if you're avoiding these tough conversations, you're not making anybody better. You're not even making yourself better because then you're not getting the reps and the practice of actually delivering. These tough messages, which you need to become a master at. You need to be very, very, very good at that. The better you are, the, the better the talent is that you're going to help produce, right? And that's, that's all, that's all good in the end. So I've got, uh, we're gonna call her Kim in my mind. Sorry for anyone that might be named Kim on the call today, but Kim in my mind. Kim is volatile. Kim is hard to speak with. Kim is defensive. You know, Kim is that personality. Kim may be great, right? She may really be knocking things out of the park, showing some results, all those kind of things. But there's some tough feedback I've got to deliver, Kim. Judging from kind of the common theme we see in the chat box, how, how do I go? How do I prep right now? How do I get inspired? Well, my first question, if you're, if you're someone I'm coaching and you bring that to me, I'm going to say, well, have you talked to Kim about how she reacts to feedback? That's right. So that's the first conversation, right? Because she needs to have that level of awareness and she likely does at this point. We don't know if it's it's, you know, maybe she's very unaware of how she shows up, or maybe it's a tactic now she's employed because she knows that nobody's going to give her tough feedback. She kind of gets a pass because nobody wants to deal with how she reacts to it. Um, and so my first is going to be the prep is that much more important, and I'm gonna probably tell you it's gonna have to be two conversations. The first conversation, you're gonna be doing much more listening than talking, right? You want to, you know, give that person— you want to give Kim that space to be able to share how she's feeling, so long as the conversation is productive to a certain extent. But if it starts to turn south, the advice is, look, I can tell that there, there's a lot that you want to share, and I'm here to listen to it. Maybe what we can do, let's take a beat, right? I want to, I want to go, I want to go away and think about it, and let's come back together tomorrow. It's that whole sleep on it thing, right? It's a very real thing if you sleep on it. And so I'm going to turn that conversation into maybe at least 2 different conversations because there's no way that you're going to get to a coaching conversation with her and how she gets better if she hasn't had a feeling, if she doesn't feel like she's had the chance to feel heard, so long as there's respect in that conversation. So I'm usually going to do, you know, advise much more listening in that first conversation, but I'm still going to follow all the principles we shared earlier, which is do the prep, know your intent, set your goals, what's your message, prepare for that moment, But recognize when you get there, let her be heard, and then maybe have a second, have that second conversation where you can give more coaching to her. And that's what great leaders do. They're eventually going to get to the point where they're coaching and going and looking forward as opposed to kind of litigating the past, which is what people who tend to be emotional or reactive to will say. Well, I didn't do that. That's not what happened. Let me, you know, let me explain myself. As soon as you get into litigating the past, it's not a productive conversation. You're not going to be able to move forward. So I don't know if that helps, but— That's really good. All right. So we only have 2 minutes left, which is wild. This time has gone by quickly, as it always does. Of course, these are designed— going back to my conversation last week— designed to hope you get a feel for what really great executive coaching looks and feels like, what it can do for your teams around some of these leadership topics and things. I am— I want to— and Katie, I'm going to give you some final words, just any kind of encouragement, anything like that you can give, give us and give you the final word. But I do want to make a special push. Our next webinar coming up is with our co-managing partner, Alan Nelson, and it's going to be a 1-hour special conversation, again, complimentary, just like the rest of ours, centered around what's at the intersection of AI leadership and strategic communication. And what we're going to be talking about, I'm very excited for, which is what, what does it mean that we can bring an executive leadership coaching experience at scale to any size organization? What we're finding is as people approach Alex, they're approaching it as they would ChatGPT or Claude or, you know, sometimes just a search engine. But the ability to truly utilize an executive leadership coach That ability has really been reserved to a small population of leaders, but that is now available across the board. So the ways that you approach Alex with conversations and topics like today is really important. So we're trying to get ahead of the training before we even put an executive coach in someone's hands. How do you truly utilize an executive coach, you know, in that way? So that conversation is going to be really good. I want to strongly encourage you— thank you, Sophie, drop that link in the chat box there. Would love for you to send that to somebody too. That's going to be a really powerful 1-hour conversation that I think many will enjoy. Katie, we're at our time, but any closing thoughts, remarks, encouragement for all of our listeners today? If you are one of the people who dropped something in the chat about not wanting to, you know, you know you need to have a feedback conversation, you haven't had it, or you're kind of dreading it, or you're avoiding it, you got this. Do the prep. Practice, think through your goals. And the only way that you get better at this sort of thing is by actually doing it. And it, you know, it may not always feel good, but at the end of the day, I think that reframe, if you can really reframe for yourself and understand why you're avoiding that and reframe this about— this is about getting, you know, making someone better, helping them be successful, being a good partner to them. I think leading with that as you deliver that message will hopefully open that other person up and And, um, just hope that you found a few nuggets that were helpful in today's conversation. And again, appreciate people making time. Fantastic. Thank you, Katie, as always, for all that you do for, uh, our firm, uh, and especially for our clients, taking the time with us this afternoon. I'm going to drop my email address in the chat box there today. So if you'd like any kind of follow-up or, uh, want to connect with one of our coaches for any particular reason, just let me know. Uh, this has been a great conversation. I've got some really good tidbits myself, so really appreciate the time today. We'll leave the chat box open here for about 2 or 3 minutes. If you want to grab any of those links that are in there, please do so. Katie, thanks again, and everybody have a fantastic rest of the day. Cheers, everyone. Thank you.