How Do I Communicate With More Tact?

MURIEL WILKINS: I’m Muriel Wilkins, and this is Coaching Real Leaders, part of the HBR podcast network. I’m a longtime executive coach who works with highly successful leaders who’ve hit a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them so that hopefully they can lead with a little more ease. I typically work with clients over the course of several months, but on this show, we have a one-time coaching meeting focusing on a specific leadership challenge they’re facing. Today’s guest is someone we’ll call Valentino to protect his confidentiality. He works in the technology space and is looking to advance his career, but he’s taken a bit of an unconventional move to get there.

VALENTINO: I’m not in the leadership role. I actually took a step back. I felt there’s some things I needed to do to enhance my career, and in order for me to take several steps forward, I had to take a step back, move back into an individual contributor role.

MURIEL WILKINS: Valentino reached out because he knows where he wants to go, but feels like there’s some gaps he needs to close and skills he needs to work on to get there, and work is not something he shies away from.

VALENTINO: I grew up with very strict parents. It’s typical immigrant parents, early rising, following strict disciplines. When you’re doing something, you do it right or you don’t do it at all. So I think my background, it’s a very disciplined-based background. Then in terms of my career, I did not grow up in the technology industry. I grew up in a different discipline. However, the trajectory of my career has informed the different roles that I’ve been in the technology industry, and I think it’s been very useful and helpful because I tend to see things from a different perspective. It’s very refreshing in some ways. It also informs leadership as well as myself and my teams to make decisions.

MURIEL WILKINS: Valentino wants to make sure he’s developing the skills he needs to move ahead and brings a few concerns to our session today about his expertise and the way he interacts with others, but in order to look deeper at his challenges, I also wanted to know more about what outcomes he’s driving to. So I started by asking him about why he took that step back and what are the longer term goals that he’s pursuing.

VALENTINO: Career-wise, I think my next role will have a C in front of it. I’ve been one step below the C level or the executive roles. However, I tend to bump into different ceilings, for whatever reason, and that’s really why I’m here today. From my perspective, I felt that the reason why I’m not getting where I need to be is because I’m lacking a technical acumen. I have the business acumen, I have leadership skills. However, I sometimes just bump into things. So my theory is it’s either technical or it’s the ability to communicate effectively, getting my message across effectively.

MURIEL WILKINS: Getting your message across effectively. So you mentioned that’s why you’re here. So articulate that for me a little bit. Why are you here?

VALENTINO: So, I’m here to answer a question, and the question is, “How does Valentino effectively deliver a message without causing angst, dissonance, confusion or feel as if I am being disrespectful to leadership? I have gotten feedback in the past that I sometimes tend to kick up, kiss across. I have a real challenge with leadership who I consider is not up to the task or inept. I have a serious challenge with it, and I do not always communicate effectively.

MURIEL WILKINS: All right. So you’ve had a career that you transitioned into from in terms of going into technology. You’ve done relatively well recently or I’m not sure what the timing is, but it sounds like you took a step back to build some skills that would then prepare you for that next level leadership, and that happened after or as a result of hitting certain bumps in the road, and there’s two hypotheses for those bumps. One is, is it technical acumen, and the second, is it something around the way that you communicate?

VALENTINO: That’s spot on.

MURIEL WILKINS: So, the technical acumen, obviously, I can’t help on because I know absolutely nothing about the field that you’re in, but you’re looking to drill down on the communication aspect of it and make sure that you are effectively communicating, and it sounds like specifically with those who are higher up than you. Is that right?

VALENTINO: That’s correct.

MURIEL WILKINS: So, tell me a little bit more about the feedback that you received.

VALENTINO: Well, the feedback that I received is you make very good points. However, sometimes when you come across, you have to be very careful in terms of how you communicate your point across the leadership, especially those who are several rungs of the ladder from you.

MURIEL WILKINS: What did you take that to mean?

VALENTINO: I took that to mean that, yes, I did make a good point. However, the delivery could have been more diplomatic, it could have been softer. It was very unambiguous, and I think sometimes in my quest to be unambiguous, it comes across as being disrespectful or condescending.

MURIEL WILKINS: Is this feedback that you’ve received primarily with those who are more senior than you or does it also apply to other stakeholder groups, your peers or folks more junior than you?

VALENTINO: No, I think it’s usually the leadership. My peers, we get along very well. I’ve been on teams in my recent move. I’ve had my former team members calling me, begging me to come back. I provide mentoring to those folks because they trust me the way I communicate to them. I think it’s with less of a, I think, anger behind it or whatever it is. I think the struggle I have with leadership is my perspective is if you’re a leader, it comes with certain aspects, meaning you are held to a higher standard. From my perspective, if you’re not carrying out your remit or you’re not being responsible with the position given to you or the position you’ve earned, then I have a challenge with it.

MURIEL WILKINS: What’s the challenge?

VALENTINO: The challenge is I think if I am going to report to you or you’ll delegate words to me, I struggle with trusting someone who does not have the requisite skills or is, again, in my words, inept or should be in the role that they’re in.

MURIEL WILKINS: Okay. So you don’t trust people who you, particularly leaders who you feel are not up to par in terms of the skills that they should have?

VALENTINO: I wouldn’t say I don’t trust them. I think it’s confidence. I don’t have the confidence in following a leader who does not understand the path, does not have a North Star or is unable to recognize that you’re in unchartered territory, which I think it’s okay if you do not have the chops, so to speak, to carry out your remit and you display vulnerability, I think I would have more confidence in you. In my mind, if you’re not able to do what’s expected of you, it’s going to have negative consequences down the line, not only for the team or the leader, but for the organization.

MURIEL WILKINS: So I want to imagine that I’m a fly in the room, fly on the wall when whatever it is that goes down goes down because I have a feeling something goes down, right? So play the scene back for me. You’re in the meeting room, you’re in the presence of a leader or some leaders who aren’t up to par, you’re losing confidence, you have to deliver a message. What does the delivery sound like? Feel free to give me an example if you want.

VALENTINO: Let me provide some context. We’re shifting strategy. So we know that the current strategy that we have in place is not working. So we’re changing the way we do things. So we had a call. However, the delivery of the message was very ambiguous. Following that call, each leader within their silo had separate calls to explain what the leader intended to say. So today in the meeting I said, “That’s not the best way to communicate your message.” Then I went into a rant, I would say, of saying, “Well, perhaps better preparation was needed so that the message is deliberate effectively and we would see less water cooler talks. We would see less breakout or silo sessions, which is a drag on productivity. So, what are we going to do to fix the situation?” Immediately after I said that, I could not edit those words because they were already out of my mouth, and I knew that he understood my intention, but again, in a room of peers and other leaders, it was probably not the most effective way of delivering a message.

MURIEL WILKINS: So what was your intention?

VALENTINO: Well, I think my challenge is during those water cooler talks, some of the leaders participate and then we all sit in the meeting and we’re faced with the problem. We know what the problem is, and no one wants to address the elephants in the room. I felt that in order for us to address the problem, we have to put it in front of us and we have to discuss it. Feelings may get hurt, but the purpose of the meeting is not to discuss feelings, it’s to address the problem, solve the problem, move on, and have a successful organization. I think no one chose to do that, and it was very frustrating, and so I forced the issue.

MURIEL WILKINS: So what I hear right now is how you feel about what happened. What I’m not hearing still is what was your intention.

VALENTINO: The intention was to address the issue that was at hand so we could move on.

MURIEL WILKINS: So we could move on. So what would’ve been a successful outcome?

VALENTINO: I think a successful outcome would’ve been, “Let’s talk about that. Let’s drill into that. Let’s figure out how we can save the company money and be productive and perhaps even provide training to our leadership so that the next time around when a new strategy is communicated, it’s communicated in a manner that’s effective, it drives the point home, and we don’t have to perseverate on the issue.

MURIEL WILKINS: So it sounds like what you wanted as an outcome is for those senior leaders to explore different ways of doing this, delivering the message that they had to deliver in the future.

VALENTINO: Yes. I think that’s part of it. I think it’s also about how do we as an organization move forward and can we identify the hurdles that are in front of us in order not to be unproductive, in order not to lose money because I think if we cannot communicate effectively, then we’re going to continue to spin our wheels.

MURIEL WILKINS: I think it’s interesting that you were focused and holding your leadership team accountable for how to communicate effectively, and yet you’re here asking, how do you communicate effectively.

VALENTINO: Yes. I’m not-

MURIEL WILKINS: No judgment. I just think-

VALENTINO: It’s funny because I recognized that I have this problem is when one of my mentees asked me a similar question. I know I could empathize with her, but I did not have an answer because the very thing that you’re trying to avoid is exactly what you’re doing.

MURIEL WILKINS: So I think there’s a bit of a mirror reflection that’s happening, and I’m glad you’re here because I think maybe let’s start with looking at you rather than others around this aspect of communicating effectively, which is what you’re doing. So that’s what we’re going to do. Let me ask you this. What do you see as your role relative to… I’m just going to take a step back here because it seems to be particularly happening with people in authority who you feel are not deserving of the authority that they have. So what do you see as your role relative to that dynamic?

VALENTINO: That’s a very good question, and I don’t know if I have the answer, but going in, I think reflecting back, I’ve always been in situations where I could have said something and the outcome would’ve been different, and I said nothing, and it was a disaster. I recently read an article about Bob Ebeling. I think he died a year or a while back. He was the guy who worked with the Challenger. He knew what was wrong. He said nothing. I’m not comparing myself to a rocket scientist, but I think I would say it’s regret of seeing that we’re going down a path that is undesirable and staying on the train without pulling the horn or initiating a course correction.

MURIEL WILKINS: Let’s pause here. Valentino reached out because he feels as though the way he communicates with the people above him might be hindering his ability to advance in his career. He knows what he wants and aims to communicate directly, but it’s not always coming off the way he wants. In evaluating his options, right now he feels like he can really only do one of two things, continue speaking up when he disagrees at the risk of negatively impacting others or keep quiet. Something Valentino said really stuck with me: “The very thing you’re trying to avoid is the thing that you are doing.” Let’s keep this in mind as we think through how he can communicate more effectively and still meet his goals. We’ll jump back in now to look at those two options as I ask him whether they are really his only options or is there another path. So are those your only two options to say something in a way that makes those folks feel a certain type of way or say nothing?

VALENTINO: No, I think both are counterproductive. I think the third option would be to perhaps question in a way that’s constructive, not destructive, engage in a way that you don’t necessarily curse the dark, you light a candle, in a way that’s diplomatic, in a way that others will find it receptive. So I think that would be a third option.

MURIEL WILKINS: All right. So why don’t you do that?

VALENTINO: That’s a great question. I think reflecting back on it, hindsight is 2020, but I didn’t look at it that way. I’m an avid reader. I love to read, and there are several books that I’ve read that talk about that, but when you’re in the heat of the moment, and I think sometime emotions, the amygdala gets hijacked, you tend to lose focus and you tend not, I tend not to focus on the outcome rather than focusing on the moment. Maybe it’s just an emotional reaction instead of responding in a way that’s much more productive and has much better long-term consequences.

MURIEL WILKINS: Look, it happens to all of us, and I think that part of it is recognizing when you do go into that emotional hijack and you go into reactive mode, what are you reacting to and what is driving you at that point? So you can only recognize it if you can actually see it and feel it and hear it. So in those moments, what is it that’s driving you those times where you are not diplomatic and questioning and trying to find that middle ground, but you go to, “I’m just going to call you out,” basically, what is it that is driving that?

VALENTINO: I think it’s anger. The reason why I say that is because a lot of times, leaders, they all know what the problem is, and I’ve had these conversations with my leadership and my leadership’s leadership outside of the conversation, and I’m sitting in the conversation and I’m looking at them and they’re saying, “Well,” and I think the fact that they’re remaining silent when my expectation is, “You’re a leader. You have the opportunity to move the needle here. Why not say something?” I think my attention then focuses on, “Why are you in the position you’re in if you’re not able to affect change in a positive way?” I think that’s where the amygdala hijack comes in, and I think I lose sight of the vision.

MURIEL WILKINS: I think you just said it really beautifully. You have an expectation that’s being unmet, and when that expectation is being unmet, it makes you angry, right? You’re like, “Come on, what’s going on?” and then you go into-

VALENTINO: Overdrive.

MURIEL WILKINS: Overdrive. Exactly. So it sounds a little similar to something you shared about your background in terms of how you grew up and what was expected of you.

VALENTINO: Absolutely. I think it’s not a therapy session, but I do think it does have an impact. The expectations that were set when I was much younger by parents, my community was you hit things on the head, don’t dance around the issue. I think in that situation, my community leaders, my elders, so to speak, my parents, if there was an issue, we would bring everyone to the table. We would bring the village, so to speak, to the table. The way the leaders in my community, and I’ve been privileged and fortunate to work with leaders outside of my industry, and I’ve seen them at their best, the caliber and the pedigree of leaders that I’ve worked with, they challenge the issue, they put the issue on the table, and I think here what I’m seeing is that lack of assertiveness, that lack of, “Let’s challenge each other.” I think to your point, instead of reacting, respond in a way that’s productive because it’s ironic that the very thing that you’re trying to address, you’re compounding it by reacting in a way that’s counterproductive.

MURIEL WILKINS: The thing that you’re reacting to is your expectation. You’re reacting to your expectation of the way that they should be rather than realizing, “This is where they are. Therefore, what do I need to do? How do I need to be do to communicate based on where they are?” which is however it is that they’re communicating? I also think that I wasn’t necessarily going back to, as you said, this is not a therapy session, I wasn’t going back to how you were raised. I was going back to what your expectation was that you shared around when you do something. I think the way you said is when you do something, you do it right or you don’t do it at all.

VALENTINO: Exactly, and I think that’s the rob is if you’re doing it, why waste your time? Why make it half-baked? Because we’re talking about shareholders’ funds, it’s given to us. It’s a trust that our shareholders have a certain expectations of us. Why not perform, behave, lead in a way that if your shareholders see you, they would be proud of you. I think that’s tangential. I think what you’re saying though is how do I manage my emotions, how do I manage my situations, and how do I manage my reaction or my response to folks that I interact with, with colleagues that I interact with in such a way that I meet them where they are.

MURIEL WILKINS: You meet them where they are and not based on what you think or how you think things should be because even what you said, listen, in an ideal world, yes, everybody does exactly what they’re supposed to do, and they do it right, and they’re responsible and they’re not half-baked. They are … I get it, Valentino. You seem like a guy who is like 350% in on everything, right?

VALENTINO: Absolutely.

MURIEL WILKINS: So you’re like, “If I’m that way, and I’ve seen other leaders be that way, every leader should be this way. Why should it not be?” So there’s something that’s happening where people are not leading according to Valentino’s rules, and as much as those rules are great, I would love to live in a world where everybody lived by those rules too. That’s not the reality of things. So you’re having a little bit of a mini tantrum in these meetings. It’s just the adult version. You boldly call them out.

VALENTINO: Mature tantrums. I love it.

MURIEL WILKINS: Mature tantrums.

VALENTINO: I love it.

MURIEL WILKINS: So I only bring this up because, yes, we could talk about communication skills and we could talk about the diplomatic way of doing it and the delivery, which we will, but if you don’t go back and kick the tire on what is the assumption and the expectation that is then leading you to react in this way, it’s all for not. You’ll end up right back here, and by here I mean here and what you experienced with your senior leaders today even, and maybe even here coaching with me because you’ll be like, “Dang it, Muriel. I did what you said to do and it still brought me back here.” So we’ve got to start with your expectation or not even your expectation, your assumption around how leaders should be. I know it sounds cliche, but there is no should. There just is. So the leaders you’re dealing with right now are what?

VALENTINO: Are not at a level where I expect leaders to be in their position.

MURIEL WILKINS: Yes. “They’re not at a level at which I expect them to be,” there’s a judgment there because who made up the definition of what the level is? It’s relative to what you think. It’s subjective. So I would like to hear a fact, meaning, the leaders I work with today did not communicate X, Y, Z or did communicate X, Y, Z.

VALENTINO: That’s a tough one. I get where you’re going and I think it’s going to be a transition, but I think if we were to go through the exercise, I would say the leaders that I work with today without judgment did not communicate in a way that was received. This is a tough one.

MURIEL WILKINS: What’s tough about it?

VALENTINO: You talked about two things, the assumptions and the expectations, and the fact that I am struggling to put together one sentence. It says a lot. I have to unpack that because I think what you’ve said is I’ve created a world where I think I have a certain set of standards, which, by the way, are subjective, and leaders should behave this way. I expect them to behave this way. They are given a title, and this is what I assume of them. So I think I have to do a lot of unlearning and introspection because that’s why I’m here today. It’s not the communication. The communication is the output of everything else that comes before what’s being said or what you say.

MURIEL WILKINS: Look, Valentino, here’s the thing. If you want to communicate effectively, you have to be able to see the situation effectively. I’m not dismissing your expectations. Like I said, I would love to live in that world. Not dismissing them. I’m just saying that it is tinting the way that you then see those leaders that is then creating these emotions of anger, which then is leading to the communication delivery issue that you have. So what we’re trying to do is neutralize it a little bit so that you can see the situation clearly and then determine, “Okay. Based on seeing the situation clearly without filter, then how do I or what do I say relative to the outcome?” So if I give you an example, I think I’ve used this example a lot, but the version of what I’m asking you is like if I ask you, “What’s the weather today?” and you say, “Oh, my gosh, the weather is amazing.” That tells me nothing about the weather except how you feel about it. It doesn’t tell me if it’s sunny, hot, cold or gray or rainy or snowing or hailing outside because your perception of what’s amazing weather might be very different than what my perception of amazing weather is. The data-driven response would be, “Oh, what’s the weather? It’s 35 degrees outside, and I’m looking, there’s water falling from the sky. It’s raining.” That’s the no judgment response. It’s what’s happening. Let’s see the situation clearly. So when I asked you what’s the situation with your leaders, what’s happening, you’re giving me the, “It’s amazing,” or, “It’s not amazing,” weather report rather than the, “Here’s the temperature,” and it’s either sunny or raining or hailing or snowing or whatever, something that is actually evidence-based.

VALENTINO: I get it.


VALENTINO: I think you’re absolutely right. It’s being able to label it with any color or baggage, so to speak. So it’s not what happened when the leaders communicate, and I’m still struggling. I get what you’re saying. It’s putting it in practice. When the leader communicated with the team, the team didn’t fully understand the message.

MURIEL WILKINS: So let’s leave it at that. This team did not fully understand the message, and how did you know? The team did not fully understand the message?

VALENTINO: It’s evidenced by the fact that there were a number of water cooler conversations. There were followup meetings.

MURIEL WILKINS: Side conversations.

VALENTINO: Questions of clarification after the meeting. There were several sessions that took place to clarify the original message.

MURIEL WILKINS: So, we’re not labeling it. I love the fact that you used the word labeling rather than the word I use, which is without judgment. I think labeling is actually a simpler way of thinking about it. Without labeling it, your assessment is something was communicated by the senior leaders. It was not understood by the receivers of that message. My interpretation of that it was not understood is based on the fact that there were a series of followup conversations that needed to happen, side conversations.


MURIEL WILKINS: 100%. What do you think the impact would be if you were to state that?

VALENTINO: It would’ve been very different.

MURIEL WILKINS: In what way?

VALENTINO: The fact that my interpretation of what happened maybe followed by, and it could have been different, and it’s not the ideal way of communicating it, but I think it took some of the edge off because even though it was a bit subjective, I clearly stated that it was my perception of what happened, and here’s the evidence that I bring forth to support my assumption or to support my thesis.

MURIEL WILKINS: That’s right. So you’re owning your interpretation rather than demanding that others see it the way that you did it.

VALENTINO: Yes or projecting it.

MURIEL WILKINS: … or projecting it. That’s the fancy word, but yes, or projecting it.

VALENTINO: Yes. Absolutely.

MURIEL WILKINS: Exactly. Exactly. Exactly. So that’s part one. What it does then is allow you, when you’re able to say, “It’s my interpretation, my perception, I own it,” what does it then allow you to do in the next step of your communication?

VALENTINO: I think what that does is it creates an environment in which we can go back and forth. It does not come across as being condescending, as being subjective, as being pushy. It comes more across of, “Let’s explore this. Let’s understand …” and I think it creates a more collaborative environment because then I would be more receptive if I was on the receiving end of what I just said rather than, “Well …” and even though I didn’t say this, it would come across as, “Well, you guys don’t know what you’re doing. You’re inept and you should probably think about updating your resume.”

MURIEL WILKINS: You’re going straight to that.

VALENTINO: So I think it’s a different tone. The modality of the delivery is very different. It’s very receptive.

MURIEL WILKINS: I think what you said around, it allows for opening. If you own that, it’s your interpretation, you then have a chance to check it out. So again, going back to the weather, if I say, “Hey, it’s sunny outside. That’s amazing. It’s amazing. Isn’t it amazing?” and you go, “No, that’s not amazing. I don’t like hot weather.” “Oh, okay,” versus me saying, “Hey, it’s sunny outside. It’s amazing. It really is amazing. You should go put some shorts and a tank top on,” and you’re like, “What? What did she tell …” “No, no, really, let me convince you that that’s what you should do,” and if you’re like, “I don’t understand,” and then I’m like, “Oh, my God, what’s wrong with this person that they don’t want to wear flip flops and shorts and tank tops and it’s sunny outside?”

VALENTINO: Absolutely.

MURIEL WILKINS: Very close ended if I do it the latter way, okay? You’re right, then you jump to, “What’s wrong with this person that they’re not getting and making the same assessment that I’m making?”

VALENTINO: I laugh, but it’s very profound because the weather example, a farmer may say, like you said, a farmer, “It’s raining. Great. My crops are going to blossom.” Well, I may not like the rain because I have a parade today. So now the farmer’s projecting, and then it creates a lot more animosity, for lack of a better word. It creates a negative environment, which, again, the irony of it all is the exact thing you’re trying to do, you’re undoing or creating, you’re exacerbating the problem by projecting, by me looking at the world through my tinted lens of, “This is how it should be. These are my assumptions, and I’m therefore projecting it on you. What’s wrong with you? Why don’t you understand it? Are you okay? Why don’t you get it?”

MURIEL WILKINS: So this is key because if you’re trying to get somebody to a certain destination, basically what you’re trying to do is influence rather than get them to comply, right, Valentino? You do have to, again, a little cliche, but you have to take your glasses off and put theirs on and see the world through their eyes so that you can understand where they’re starting from and frame the message in a way that they’re going to best understand it. Right now, you’re framing the message in a way that you understand it and you’re sending the message in a tone that you understand it, meaning when the tone that’s used with you is when you don’t do something, you better get it right. That works for you. That’s the tone that works for you or that’s the tone that has worked for you to get you to the place where you are today. That tone doesn’t necessarily work for everybody else.

VALENTINO: Why not? No.


VALENTINO: I’ve never looked at it that way, but I think it’s a very profound way of looking at it because it then changes the delivery. It then changes the interaction, it then changes the expectation. It then allows me to challenge those assumptions and expectations.

MURIEL WILKINS: This session is bringing up an important facet of coaching, especially when it’s not an ongoing relationship. Part of the situation that Valentino outlined around his communication style is the sense that he gets that what he’s saying doesn’t land well with others. Not only does nothing change when he communicates, but people don’t seem to react well. This can be a bit tricky as a coach because I’m not able to talk to others and see how they experience Valentino or get a better sense of their side of the story, but there are a lot of things that we can do. So taking Valentino through why he communicates the way he does and what other options he has is really key. Now, it’s time to think about how some of this reframing might actually play out in practice. Let’s dive back in as we work through some scenarios. So let’s do a little bit of practice around this. If you were to put yourself in the shoes of these very leaders who you felt are not doing right by everybody, put yourself in their shoes, how do you feel you need to convey your message in a way that’s going to best land with them?

VALENTINO: I think the first thing I would do is take a step back, get a panoramic view of the situation, challenge the assumptions I have, look at my expectations, and then ask questions that are non-judgmental. Again, going back to the, “Oh, my God, it’s amazing.” “No, it’s raining and it’s 35 degrees outside,” I think that’s the approach I would now embrace, and using that mindset, I think the exchange, the back and forth will take on a different tone because my world, I’ve had the privilege or pleasure or whatever it is of living with myself for the last however many years. So my world is quite different from theirs, and it would allow me to bring grace, patience, understanding the situation before popping off at the mouth, so to speak. Perhaps in some cases, they may have challenges that they probably weren’t prepared. I think it allows me to not be so dogmatic about what I know is right and I know they should be doing, and it would add a bit of, I would say, levity, sobriety in terms of how I communicate, what my expectations are. It would really give me pause to think about what’s the outcome, one, you’re trying to achieve? Check your assumptions at the door and engage.

MURIEL WILKINS: Beautiful. So here’s the thing. We started off this conversation, and when I asked you what type of feedback do you get, the feedback you get is, “Look, Valentino, your message, the point you’re making is on point. It’s right. It’s the way that you’re delivering it.” So in no way do we want to dismiss this asset that you have around being able to laser in on what a solution might be or what an answer might be. It’s not all of a sudden like, “Oh, I don’t know.” It’s the way that you convey that. I also asked you what was your intention, and then we talked a little bit about impact and what you just said here around, “If I want to do it with compassion and with grace,” and you used other words. So part of what I think would be helpful is if you think about when you convey a message, when you’re about to deliver something to these senior leaders, how is it that you want them to feel after you’ve conveyed the message? How do you want them to feel about themselves, about the situation, and about you? So when I asked that, what are some of the words that come up for you? How do you want them to feel about you?

VALENTINO: In terms of the situation, I want them to feel empowered. I want them to feel encouraged. I want them to feel good about themselves because if I’m stomping and stepping and tearing them down, the energy that they’re using to either fight that or to wrestle with that could have been diverted to actually solving the problem. So I think how would I want them to feel about me, that I’m someone they can work with, that I’m someone who’s collaborative, that I’m someone who understands the vision and who’s willing to work with them, not against them to achieve the mission so we can all be successful, our shareholders can be successful, our team members can be successful, you can be successful as my leader, and I can be successful as your subordinate.

MURIEL WILKINS: So it sounds like you want them to feel like you are on the same side of the table as they are in solving whatever issues you’re bringing up rather than being across the table pointing the finger.

VALENTINO: Absolutely. I think it would come across with less hubris or less, “I know what’s right, you don’t. Hahaha,” or it would come across more mature. I think you mentioned the mature tantrum I think becomes a constructive conversation, “Here’s the path. How do we go down that path and how do we work together to achieve our objectives?” not necessarily, “Well, you should be and why aren’t you?” It’s counterproductive. It does not add to the outcome. It’s distracting.

MURIEL WILKINS: So if I may, I’m going to suggest a practice for you post our meeting, which is prior to every conversation that you go in with these specific leaders that you visualize starting being and staying on the same side of the table, okay? Then ask yourself, “If I’m going to stay on the same side of the table, what tone do I need to use and what communication strategies do I need to use when I’m trying to get my message across?” So notice I didn’t say don’t say anything. It’s tone and strategy.

VALENTINO: Absolutely.

MURIEL WILKINS: “If I want them to feel, and in fact, I am on the same side, on the same team, same side of the table as they’re,” and then what’s going to happen is you’re going to be in these meetings, and every now and then you’re going to realize, “Oh, my gosh, how did I get to the other side of the table? I didn’t mean to do that.” That’s okay. That’s actually where the learning will happen is in noticing when you default and then you just want to step back to the other side, and how do you do that? So what are going to be your tools to course correct? Your tone and your communication strategy, and you already said what they were. You said, “Communication strategy, I need to probably start with more questions in a way that’s open-ended. I need to own what my interpretation is rather than demand that they see it the same way that I do. My tone doesn’t need to have any type of emotive around it. It’s neutral.” So when I say all that, what do you think would get in the way of you being able to practice that?

VALENTINO: My ego. The question I think has now been shifted from how do I communicate the message in a way that folks can understand to how do I manage my internal, my expectations, and my assumptions internally, being mindful of the tone, being mindful of the strategy, and obviously above all the outcome, how do I want to leave these leaders or how do I want to leave this transaction, this communication, this conversation? Starting with those I think will be key.

MURIEL WILKINS: Look, I think you hit the nail on the head there. Transfer the energy that you’re expending towards others and transfer it back to you to manage yourself.

VALENTINO: Absolutely.

MURIEL WILKINS: If you can manage yourself, you have a better chance of then being able to manage the communication that comes out of you and then hopefully influence others because you’re not going to be able to control them. All you’re doing is trying to influence. So bring it back a couple of steps. So exactly what you just said, revert the energy to managing yourself.

VALENTINO: Absolutely.

MURIEL WILKINS: So my sense is that you get it, right? You get what you need to do. Now, it’s a matter of doing it, and it takes practice.

VALENTINO: It’s practice. The theory is great. I think the rubber meets the road when you’re faced with the situation, and oftentimes we don’t always measure up to our highest standards when we’re in the heat of the moment, and I think it’s going to be an exercise that will not come easily because the default is to be emotional, to be reactive, and to say, “Why can’t you see it this way?” and then start projecting. I think it’s going to take some patience and some diligence and discipline to continue on the journey. I don’t think I’ll ever get there, but I think with practice over time, it will become better. I’ll be more self-aware. I’ll control the amygdala a bit more. It’s a very useful way of approaching conversations, not just with leaders, but I think I participated in a lot of sports. Sometimes taking that step back, meeting people where they are … A couple months ago, I was running with my wife and I love to run, and she’s not where I am. I think the lack of patience there was, now looking back at it, made me realize that, yes, sometimes my expectations and the way I project those expectations and assumptions can sometimes have unintended consequences. So this is extremely helpful.

MURIEL WILKINS: Look, you’re not going to be able to get your wife to run any faster if you’re yelling at her 10 miles down the road because, first of all, she can’t hear you. As a fellow runner, let me tell you that, and running way behind her isn’t going to do it either. That’s the version of not saying anything. How do you coach somebody or how do you support somebody to run a little faster up the hill through the muck? How do you do it?

VALENTINO: You do it by being side by side, encouraging, responding, motivating.

MURIEL WILKINS: That’s right.

VALENTINO: I think going way ahead or staying far behind, both are counterproductive. It’s you meet them where they are, literally. In this analogy, I think we meet and we stay with each other, and again, it takes a great deal of patience, a great deal of self-awareness to be able to say, “Yes, let’s take this path together. Whether we’re going up the hill, going around through or over a barrier or we’re on the straits, we are together. We’re one team.”

MURIEL WILKINS: That’s right. Anyone who takes running seriously as it sounds like you do, I certainly do, one of the first things you do when you set out on a run is you set your intention, “What is this run about? Is it a fun run? Is it a training run? Who am I running with? How do I want to be with that? Am I going to stick by their side? If I know I want a hard training run and I already know the person is slow, should I even be going out with them?” You set your intention and you set your intention based on how you want the run to go and how you want to feel after the run.

VALENTINO: Begin with the end in mind. Absolutely.

MURIEL WILKINS: Begin with the end in mind. So you have that at your disposal to use as well when you go into these meetings, and practice with your wife. I think that’s amazing. All right. Beautiful. So I think we can wrap it up. I’d love to hear in a few words, you can use adjectives, how did you feel at the beginning of our coaching conversation and how are you feeling now?

VALENTINO: I think in the beginning I had a lot of questions, I had a lot of doubts. I was less sure of what the outcome is. I think at the end, I have the tools that are at my disposal that I can leverage, whether it’s in personal situations or professional settings to help my peers grow, to help myself grow and to work toward an outcome that’s mutually beneficial for not only myself, but for others. I think I feel I’ve grown tremendously from the beginning of the conversation to the end of the conversation because I now have the tools that will enable me to be successful.

MURIEL WILKINS: I think what happens in a coaching session like this is that the awareness increases.

VALENTINO: Absolutely.

MURIEL WILKINS: The awareness increases. The growth will happen through the practice. So you’ve got to go forth and practice now. That’s the only way that you’ll see if what we discussed, if the insights that you had today actually stick. So do that and then come back and let me know how it went.

VALENTINO: Absolutely. Thank you so much, Muriel. This has been very helpful.

MURIEL WILKINS: Communicating clearly and effectively while also building trust and influence is a key skill of any great leader. Valentino came to this session with the goal of eventually getting to the C-suite in his career, but also knowing that there are some communication issues that he’d like to work on, especially when it comes to managing up. We work through what a lot of his assumptions and expectations are around what leaders should be. By approaching his interactions more objectively, it can help reframe his reaction to the situation and to those around him because a key skill of leadership isn’t always about doing it your way. It’s about making sure how you communicate really lands with your stakeholders. That’s it for this episode of Coaching Real Leaders. Next time-

SPEAKER 3: I’m finding it a really tough decision because possibly for the first time in my life, I might have a bit of imposter syndrome. I usually feel very confident about what I can and can’t do. If I say I can’t do something, I probably can’t. I’m usually very confident about those decisions for myself, and I’m not confident about this one. I don’t know what I think. I don’t know how I want to move forward.

MURIEL WILKINS: Want more of Coaching Real Leaders? Join our community where I host live discussions to unpack the coaching sessions. Become a member at You can also find me and my newsletter on LinkedIn at Muriel Wilkins. Thanks to my producer, Mary Dooe, sound editor, Nick Crnko, music composer, Brian Campbell, my assistant, Emily Sopha, and the entire team at HBR. Much gratitude to the leaders who join me in these coaching conversations and to you, our listeners, who share in their journeys. If you’re dealing with a leadership challenge, I’d love to hear from you and possibly have you on the show next season. Apply at and, of course, if you love the show and learn from it, pay it forward, share it with your friends, subscribe, and leave a review on Apple, Spotify or wherever you get your podcasts. From HBR Presents, I’m Muriel Wilkins. Until next time, be well.

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