Melody Wilding: Every week I talk to mid and senior level professionals who tell me the same thing. They want to become enterprise level communicators, and when I ask them what they mean by that, it goes so much deeper than I just want more executive presence, or I need to be able to command the room. Being an enterprise level communicator means something specific.

It means that you can walk into a conversation with a frontline team and speak in a way that motivates them without talking down to them, and then turn right around and brief a board of directors with the exact right altitude for them, the right level of detail, the right framing for what they need to make a decision.

It means you’re communicating across dozens, sometimes hundreds of people across functions that don’t share your context across stakeholders who have competing priorities and limited patience, and your message needs to click with all of them. Being an enterprise level communicator means you know, instinctively when to bring data, when to lead with the implication.

And when someone asks you a question, you are not just answering what they said, you’re answering what they really need to know under the surface, and you can translate complex, technical or operational realities into the language of impact. This is what enterprise level communication looks and feels like, and that’s exactly what today’s guests wanted and needed to be successful.

Daryl is a program manager with 22 years at his company who recently stepped into a role on the operations leadership team, and now is working alongside directors and VPs. He is brilliant at his craft and he is someone who describes himself as an executor. He can take anything and he can figure it out, but when the scope of who he needed to communicate with and how when that expanded dramatically, he started getting feedback, that stung a little. He started hearing, I still don’t understand what you’re trying to tell me. And Daryl was freezing in meetings when things would go sideways. He was watching his credibility take a hit despite the quality of his work. In this episode, you’ll hear how he went from a functional expert and a trusted executor to someone that leadership now describes as strategic collaborative, and the person who just gets it.

You can borrow both his mindset and his specific strategy because what he figured out is entirely doable and learnable. Daryl is an alumni of Speak Like a Senior Leader, and I do want to mention that doors are open right now, but only for a few more days.

We have sold out every cohort, so if you have been thinking about joining us, don’t wait. You can get all of the details at Speak Like a Senior Leader.com or in the show notes. Now let’s get into it.

Daryl So excited to have you here, to have you on the show. Thank you so much for making the time.

Daryl Caver: Nice. Thank you, melody, for having me on the show.

Melody Wilding: Yes. Before we dive into your experience and Speak Like Senior Leader, just tell us a little bit about what you do, who you are, so people have some context.

Daryl Caver: Okay. I am a program manager, working at Tom Tom. I am in our operations unit. I’ve been with the company now for 22 years, and I work very closely with the platform engineering team to revolutionize how we’re making maps today.

Melody Wilding: Very cool, and I mean 22 years, especially in that industry. I am sure you have seen so much, so much evolution in that time. And for particularly for this conversation, I want to talk about what your work and environment like was like. From 2025 heading into 2026. So paint a picture for us. What was shifting around you and what was making communication in particular, mastering this higher level of communication? What was making that more urgent and top of mind for you?

Daryl Caver: Yep. A lot of dynamics, in a very dynamic time in the company, doing a lot of changes, with some very demanding customers and constantly having to change our priorities, shift our focus, and I realized that I needed to be able to speak more the same language, ’cause I’m communicating more with other directors as well and trying to also advocate within the teams of like, Hey, this is a priority for us in operations.

We need to keep this moving. and so I realized, I needed to change how I was reacting. I wasn’t necessarily as good of a job, you know, if I think of like the 30,000 foot view, like I could get down into the weeds and could do a good job there communicating out with people. But the higher up I got, I realized I needed to do a better job of communicating the challenges, the needs that we had, and how to also to understand where they’re coming from, when I would get the feedback that I did.

Melody Wilding: What was the type of feedback that you were getting?

Daryl Caver: There were times, where the feedback was, it wasn’t as, I wasn’t able to clearly articulate the issue, even though I thought from my perspective, I had summarized, Hey, here’s the challenge. we’ve got a lot of requirements. They’re not clear. it’s changing in a daily basis. One day we’re told, Hey, this is the top priority. The next day it’s a different priority, and it’s like. What are we supposed to do? I thought I’d communicated that clearly, but based on the feedback I was getting, it was not resonating, because back and forth with a director of some emails of like, well, I don’t still understand what you’re telling me, Daryl.

What is the challenge? And I was like, okay, this is not, and I’m, I looked at it again and I was like, I stated from my perspective, at least what I felt was. These are the issues. This is what we need or we’re trying to deal with it. and so that was really for me, kind of the eye-opener. Like, okay, I need to think about this further.

How do I communicate more clearly, to not cause that confusion? ’cause that’s the last thing I want to do is create confusion further. I’m trying to bring that there is confusion here and looking for guidance of how do we move this forward to address that confusion.

Melody Wilding: Yes. Yes. And I do, I do wanna get into, now with having gone through the program, what you do see, the, the disconnect was, but everything you’re describing gets at a, a big, evolution for you was that you went from someone who led a key program to now sitting on the operations leadership team alongside directors VPs.

So how was that elevation, that progression, how did that change what was expected of you in how you were articulating yourself, presenting yourself?

Daryl Caver: It was to be more, I think, clear and concise, with what I’m doing and where I need help with if I’m blocked on anything at all. Not that I wasn’t doing it before, but it needed to do it at a higher level. I needed to be more, especially with the dynamic level as well too, where things were constantly changing, priorities changed from one day to this.

I needed to be able to better communicate out. Okay. We’re shifting our priorities because this has changed. Here’s why we’re doing it. And make it clear and concise so that others that I work with on the leadership team and with another directors are understanding, okay, this is where we’re coming from.

This is why we’re doing this, and this is what it means to what we’re doing, and we’re gonna stop work on this, and we’re gonna work on this instead and pick it up. So.

Melody Wilding: And what I’m, what I’m hearing or just reading, analyzing between the lines of what we often see when, when people come into the program is that it’s making, it’s making the shift from being a strong and communicating like a strong functional operator, to some, to someone who can make the translation at that enterprise level of what should be happening, especially with people who are not as in the weeds of a certain program or project or product as you are, and who may not have been following along with the narrative this whole time of, well, we were focusing on this priority, now there’s this new thing.

They don’t have that context, right? And so it can be a challenge of how do you bring them up to speed, quickly without being too long and rambling, but also making sure they understand why we’re changing from this to that. Yeah. All of that can be a big challenge. Does that sound apropos to what you were facing?

Yeah. Yeah.

Daryl Caver: Yeah. Trying to find that fine line between not overloading ’em with all of the background information that I have that helps me do my job, but to give them kind of the,The high level summary, so they, again, they know what’s changed, why it’s changing, and they can either say, I don’t agree with this, let’s talk about this further. Go, this is the right choice. I support it. Let’s move forward with it.

Melody Wilding: So now having gone through, speak like a senior leader and I fully recognize that things are always an evolution, and you’re probably still working on this, we’re also talking about working with other people, and so there’s going to be naturally ups and downs or friction, but what have you realized or changed, evolved about how you used to communicate some of these challenges or, disconnects in the priorities to what you are doing now.

Daryl Caver: I would say for me, there were a couple of eye-opening things. first was the different styles of communication. as soon as I started taking that lesson, I was like, oh, I know what I am. I’m commander and a controller, and I can immediately pick up on that. I realized my immediate boss, fit within that same commander and controller window. and I’ve been able to pick up on others and understand how, at least they might the world, knowing that it’s not a, you know, a black and white and that you’re not just one style that you’re, you know, a mix of styles. But that was very helpful. And then being able to understand, what do I need to communicate, to them to give them the information that they need. so I’ve been able to streamline my communication further by going, okay, I don’t need to include every single thing. Can I summarize it into a couple of key bullet points so they can get enough of the context? And then if they want to ask questions or go deeper, can, but at least give them enough details, to give them that.

I’ve also changed, how do I indicate what I’m doing to resolve the problem. ’cause that’s one of the key things in my role, is not just to come to someone and go, well here’s this problem and then, you know, look for them for guidance. But to say, here’s this problem, here’s the approach I’m taking. Do you have any issues with this approach? Do you see something that maybe I’m not seeing as from your perspective, know, they’ve been doing this longer, they’ve got that more strategic, enterprise view that I’m still trying to learn and think about. ’cause I’ve come from a, what I would call an executor role like. I don’t need a lot of black and white. Gimme something gray and I’ll figure it out and execute it. And now I’ve gotta execute and also be thinking, this make sense strategically? Is this the right value for the operations team? Is this the right value? Is this where I want to invest the engineering resources? And so I’m doing a lot more of the strategic thinking as well too, I’m leveraging that to go, these are my thoughts, these are the actions I’ve taken, is how I’m moving forward. If you see something different, please speak up. But this is what I’m doing.

Melody Wilding: Yes. Yes. And this. It’s at something we talk about in the program is being able to answer questions behind the questions because someone may say, can you tell me where this is at? I don’t understand where this project is at, or why we’re focusing on this priority. And we launch into a whole explanation of the timeline and the dependencies and the logic of why we took, took this over that.

But we talk about in the program how to, yes, speak like a senior leader, but also think like an executive. So you have those razors as you were alluding to that, that cut down the fluff and allow you to focus on, okay, I know these are the types of things this person is going to be concerned about. And in particular, the question behind the question.

They’re usually looking for one of three things. Assurance. Tell me, this is on track. It’s not going to blow up. Guidance, right? Tell me how I should be thinking about this. What’s the point of view or action? What do you need from me? Do you need approval? Do you need more money? Do you need an introduction to somebody?

And it sounds like you’ve, you have been using that lens to make your communication more precise or targeted for the different groups of people, which is powerful because then I, I can imagine they may feel like, oh, he gets it right. He gets it now, versus them having to go through the cognitive load of Daryl.

I don’t understand what you’re saying to me, which, then has this ripple effect of the perception on, unfortunately, like, is this person capable of this role of navigating this complexity? Is this the type of person we need in the room making these decisions or not?

So what have you, what have you noticed as you’ve been making, some of those pivots to how you present challenges or ideas of the direction you do need. What are some of the results you’re noticing or changes you’re noticing about your projects or people’s level of reaction and respect towards you?

Daryl Caver: I’ve been getting more, I would say compliments probably is not the right word, but it’s the word that popped in my head of, Hey, this is great feedback. You’ve summarized it clearly. I understand what we’re doing. and it’s good status updates as well too. So I’m definitely seeing that. The appreciation and the acknowledgement that I have made that change and that folks are seeing that kind of, communication from me. I would say that’s the first thing I, I’ve also been, it gives me that insight as well to start even thinking more strategically. Before I would’ve just sent the email off, summarize the points. Now I, like you said, taking the time and looking at it and going, is this the right information in the right context that I need to share?

do they need all the background information? If they do, I’m trying to structure it differently to go, Hey, here’s the high levels, and if you really want to read the details and understand it further, further down the email, here’s the additional information in the context in case you do want to deep dive into it. I know my direct line manager, right now does not have that bandwidth. He and I have talked about that in our one-on-ones that right now he does not have the bandwidth to dive into the topics, and I know he wants to, so I’m trying to keep him apprised with that so that if he chooses to do that, or, and he’s even told me, he goes, Hey, if you need me to look at something, tell me, be direct and go, Daryl, you know, go, Peter, I need you to look at this.

This is where I need your involvement at. So, and that’s been great as well too. It lets me know that I’ve. that trust that he knows what I’m doing and that if I need to reach out, I can go to him and say, Hey, I’ve got questions. Please review this. Are we on the same page? ’cause that’s the last thing I want to do is have a bigger meeting where it’s him and me and others, and I don’t want the engineering team to go. looks like Daryl and Peter are not on the same page. They’re on different pages. and so I’m trying to get that as well too, is build that consensus within the operations team so that there’s not this disconnect when they’re like, Daryl, you tell us this. We’re in other calls with these other stakeholders, and they’re like, it’s this.

And I, so I’ve tried hard to, it’s helped me to see that, how to build that consensus as well too.

Melody Wilding: Fantastic. And the, that is such a, a connection. I have never put words to that. Yes, we talk a lot about managing up and communicating up in the program to your leadership, your other stakeholders, even powerful customers and things like that. But what you just said about, the being on the same page and having a united front with your leadership and the effect that has on your team buying into it and their attitude and investment in the project.

I had never put words to that, but that’s so important that I don’t, I think a lot of people focus on building rapport and trust with their team by let me understand how to manage each person individually and have good one-on-ones with them. All of that is incredibly important and we should be doing that too, but that’s very overlooked. Having that united front and alignment with your leadership to make sure your team feels motivated. So thank you for mentioning that. ’cause I, I had never made that connection. Yeah. Yeah.

You were mentioning meetings, and this is another topic I want to go to because you had, shared with us that when meetings would go off script, which let’s face it, many times they do, but when someone would push back, a conversation would go somewhere you didn’t expect, it would throw you off a bit.

So tell us what would happen for you in the recent past.

Daryl Caver: Yep. So anytime conversations got difficult, I would freeze up on the screen. I would not. Answer. ’cause in the back of my head, my brain’s racing and looking around. I’m like, are we disconnected? Are we not connected at all? it would cause me to also like start second guessing, like, well, am I making the right decisions?

Am I doing the right thing? and I would say I’ve gotten, silenced those, not silenced. I’ve managed to. Manage the critics. So I don’t have those doubts anymore. And instead, what I try to do now is take it to a different place to go, okay, how do we get aligned on this? Because clearly there is a disconnect.

So I try to bring it back to not let it derail anything and not let it, reflect on me personally going, oh, I’m, I’m in over my head. I don’t know what I’m doing. But it’s instead going, okay, how do we get on the same page? you know, is it something where we need to disagree and commit? It’s one of our leadership principles here at Tom Tom is.

Do we need to disagree and commit? And, and I’ve done that in the past where I try to make a, for what I thought was the right approach. We had a good back and forth discussion, and ultimately that was one of the strategies they employed. I said, okay, you know, we disagreed and committed with the potential to go back and revisit the decision in the future and go, maybe now is not the time to make this change in the system, but let’s revisit it.

And in the future there might be a point where it makes sense to break this up and say, we’ll implement this new functionality and do it that way in the future.

Melody Wilding: Yeah, what, what I hear there is, another sort of meta concept we talk about in the program that you’ve really internalized. Which is most people, come from the, the perspective when they are communicating of what do I need to share? What am I trying to get across here? Versus what I hear you asking is, what do they need to hear?

Right? How can I convey this in a way that they’re going to hear more? So it’s less this, individual, personal focus and more thinking about the audience. And that is a very subtle shift, but it completely changes your, your attitude and helps you see from a more calm, grounded perspective, how do I find a win-win here?

Right? This is not about me trying to prove myself. It’s me trying to find the best path forward for all of us. And what have you noticed change or shift as a result of this different way you’re showing up in meetings? Mm-hmm.

Daryl Caver: I am much more comfortable and confident in meetings, than I would’ve been before. I would’ve been like nervous of like, oh God, please don’t bring up this topic. Let’s not go down this road. Let’s, hope everyone’s on the same page. and there’s no need to have discussion. So I, I’ve improved from that of realizing discussion is great.

Let’s have it, let’s talk about it. Let’s get to the consensus, and then ultimately. Really, it’s just, let’s disagree and commit on a path forward may not be the path I like, may not be the path other people like, but let’s just pick a path and let’s focus on moving forward and putting all of our energy on that and not revisiting or rehashing or going, wow, okay, I don’t really like this decision.

Let’s revisit again. No, no. Let’s really focus on a decision we can all live with. Like you said, melody it. How can we make this a win-win? so that everyone feels like they’re winning. I don’t look at this as like a competition of like, ha, I beat you down. I got what I wanted. I don’t pick up from people that are like, oh, well I got one over on Daryl, so I got win.

It really is about how to get that win-win so that we can move forward with all of our energy and effort on that and not revisiting and rehashing the topic. Let’s discuss, and then kind of move forward. I definitely don’t have those feelings anymore of like, well, I’m on the wrong track, or I’m not, qualified. I’m much more comfortable in the, yeah, I know what I’m doing. It’s not always easy. There’s always challenges that come up, but again, it’s the win-win mentality. That’s what I’m trying to go for.

Melody Wilding: Mm-hmm.

Daryl Caver: So.

Melody Wilding: Well, and, and the level of conviction and, Composure that it takes to set the frame. And this is one of, in our first, orientation session of speak like a senior leader, we talk about how one of the, pillars or tenets of speaking like a senior leader is the person who controls the frame, controls the outcome, and it sounds like you have become more comfortable, again, not in a like my way or highway. This is what we’re going going to do it. But you know that setting the expectation and the frame that we’re not all going to agree here, but let’s find the best compromise that we all can do a bit of give and take and live with, and then we’re going to move forward.

You have set that as, this is the mindset we are all going to go into this. With versus just kind of passively showing up and whatever happens, happens, and then you feel railroaded by other people. I sense more of this assertiveness, for lack of a better word, or this, this presence of, in a calm, collaborative way saying this is how this is going to go. And I’m doing that because it’s in best service to all of us getting the outcome we want here. And, that sounds very different, the willingness to be the one to set that frame. Yeah.

Daryl Caver: Yes. Nope. You’ve interpreted it very correctly. I’ve done that recently. Even within our operations leadership team. We were discussing the program that I’m leading and I reiterated, I got feedback and I said, these are the priorities I’ve chosen. the priorities based on the feedback I got from stakeholders as well too.

Again, part of it was being able to read between the lines with my boss of there was something I had deprioritized. I read between the lines and it’s like. Let me fix that. I will bring it back up in priority ’cause I can see how it’s valuable, to him. And it made sense strategically. It wasn’t just me caving, it was me, like, you’re correct. This is something that’s important. It’s gonna bring value to a lot of our teams that we work with in operations. So I’ll reprioritize it. but yeah, it, it’s framing it like that as a, having that, it comes back to the collaboration. How do I build the consensus and the collaboration make it a, a topic where we can free flow and have disagreements and go, why are you prioritizing this, Daryl over other things?

And explaining very quickly, these are the reasons why I’ve made these choices. If you guys see something that I’m not seeing, let me know, right? Because it helps me right now. But it also helps me the next time I’m in that position again to think I’m looking more strategically going, all right from last time I didn’t think of this. Let me put that lens on and look at it from that lens and going, okay, yes, this makes sense to do. I’m gonna prioritize this accordingly. So.

Melody Wilding: Yes, yes. And you have earned social capital with those people because you’ve been willing to listen to them. So you can draw on that next time. You need to ask them for a favor for them to make a concession. And what also strikes me with all of this is you are crafting the personal brand you want people to have of you and how you want people to see you.

I imagine what’s going on in rooms that you’re not in is people say, oh, Daryl brings people together. Right. He’s really great at helping us broker these different priorities and navigate some of these tensions that we’re facing, which is really powerful for creating that sort of leadership brand.

Have you noticed anything there in terms of, how that has been forming or changing for you.

Daryl Caver: I’ve definitely received that kind of, accolades is probably not the right term, is the one that popped in there of that collaborative nature of, okay, not that I am, you know, a walkover or someone we can, we can just push Daryl over and get what you want of it. But they understand like, hey, he gets it.

He’s thinking more strategically. He’s collaborative and he’s working then with the team, the operations team, to go and breathe their, you know, I’ve gotta bring the message both in the operations side, but also from the engineering side of like, we know you guys want this, but this is gonna take us a longer term. So can we deliver this in the interim? And I’m making those kind of trade-offs, but then I also need to communicate with both the engineering stakeholders and the operation stakeholders just to make sure that everyone’s understanding, again, these are the changes or trade-offs that I’ve made. Here’s why I’ve made them and build that kind of. so yes, I would say I feel much more collaborative and I definitely feel that, respect and appreciation for, I’m trying to be collaborative and build consensus and relay both sides of the, the challenge, the engineering side and the operation side.

Melody Wilding: What other results have you noticed or experienced so far by, implementing some of the things you’ve been learning?

Daryl Caver: More clear crisper communication, coming from me. So again, I’m taking a little bit more time to think about it. I’m looking at and feedback that I get in a more, in different lenses now, trying to understand like, is there a question behind the question that I’m getting? So thinking about it more from that perspective, the confidence is there. No nervousness at all. So I’ve definitely learned a lot to see things differently as well too. I don’t think of an executive. I think one of the things recently we’ve discussed is a lot of times they’re on their phone. I’m on my laptop. I’ve never really considered how does something look on the phone versus the laptop, and that was kinda like an aha moment.

Like, oh, okay, I need to keep it short. I need to keep it simple. It’s hard to scroll, like, yeah, if I’m on my phone. I don’t wanna have to scroll through a long message and go look at it. So all of those, it’s the, it’s little pieces of things that have made me think of seeing things differently, and how to be more concise.

But I’m also now taking that to others that I work with that are not trying to impart that onto them of like, think about it from this perspective guys. Or, please give me, and I’m being more clear and direct with my communication to them of like, just need to hear from you guys like what is the issue and like what is the, if there’s a blocker, what it is. need all the extra background information because I don’t have the bandwidth myself. Whereas in the past, I would’ve loved to have dove into those. I don’t have that bandwidth, so I’m relying on others to give me the information I need so I can make the decisions to move things forward. So,

Melody Wilding: Fantastic. Fantastic. From both sides, you being able to show up more. Crisp, more articulate, but then also getting what you need from your team more efficiently, which I’m sure has a halo effect of your team, is having to send communications that go to these other stakeholders and teams and decision makers, and that has a, that has a halo effect of how it, looks on you and your leadership and ability to cultivate them and direct the product and the work. So, very cool to see how that’s all connected.

Okay, Daryl? In terms of the program itself, there are so many different aspects of speak like senior leader from the curriculum. We have the on-demand lessons, we have the, skill drills, we have our live workshops, the community. What have you found especially valuable for your own development and growth?

Daryl Caver: I would s in all honesty, it is all of it. I have enjoyed the drills, the videos. They’re bite-size, informative. I get the great examples. I can understand ’em. They’re not examples where I’m like, well, how does this, relate to what I’m doing for work? have, the community itself has been great. very supportive and collaborative. So the entire program from my perspective, is, I love it. again, do it at my own pace. I plan time on the weekends to go through those lessons. When my, I’ve got the free time, I love following them. I love looking at the, I’ll even look at the cheat sheet and the skill drills first before I do the lessons to kind of understand where things are coming from. I used to be proficient taking a lot of notes, and one of the lessons you were like, Hey, you try to limit yourself to a number of bullets. And I was like, she’s right. And then I was like. started trying to do it. I’m like, this is hard. ’cause I’d get through some of these and I’m like, I’ve already got a lot of bullets.

I’m like, do I need more bullets or not? so I would say the entire program I love.

Melody Wilding: I’m so, I’m so glad to hear how you use the different pieces together, and that’s why we do have so many different aspects to it is because your schedule, your bandwidth ebbs and flows, right? Some weeks you may have more time where you’re showing up for a the calls live, you’re posting in the community more.

Other weeks, you may only be able to watch the replay and do a skill drill on your own. So that’s what, that’s one reason why we have all of the options. Another is because that they do work together to reinforce different aspects of the material in different ways. And, you know, third is people have different learning styles.

So I, I think that’s so smart to kind of skip ahead to the cheat sheet and for anybody listening, yes, we do have one pagers that summarize each of the modules, so you can keep those on your desktop, you can reference back to them. It’s sort of just a refresher to keep this, the main frameworks and takeaways top of mind.

But I love that idea. Kind of figure out the end and then you, you at least have that top of mind as you go through the lessons themselves. It’s really smart. Really smart. Excellent.

Daryl, as we’re closing up here, I would love to understand from you, how would you describe your transformation over the past couple of months and speak like a senior leader from where you were before to where you are now.

Daryl Caver: I am much more confident. I would say comfortable. I’ve start again, it’s thinking things differently and trying to put myself and understand now from others that I’m working with, with it’s the other directors and VPs in that lens of where are they coming from, what are they looking for? They’re very clearly looking for, hey, is this on track? And if it’s not on track, it’s okay. But do you have a plan to get it on track to be green? So, and are you the right person to do that? And do I need to intervene and talk to someone else because maybe they’re not listening to you or they see a different priority? so I would say I have gotten more comfortable and confident and seeing things in that lens and operating in that lens myself.

so I think for me, that’s been one of the eye-opening things is how we’re. put myself in their shoes and go, what are they looking at and thinking about? And it’s kind of like the same thing of like, yeah, I wanna rely on others and go, you guys know what you need to do. If you have a challenge, give it to me. Let me know what you’ve tried to do yourself that I don’t go down the same path, but go, okay, you did this. All right, I’m gonna try this approach. Or I will intervene and talk to other people if I need to.

Melody Wilding: Really appreciate, all of your time here and so much to be proud of and to celebrate. So thank you for joining me today.

Daryl Caver: All right. Thank you for having me, Melody.