The Art of Executive Communication

The more you’re communicating to top executives, the more you need to try to tie metrics to the metrics they care about. And generally, for the board and for the CEO and even for the CMO, that’s generally tying it all the way to the outcome. The bookings or the revenue launches, what do they really care about, and how can you show that simply and clearly in data? This is Revenue Makers, the podcast by Sixense investigating successful revenue strategies that pushed companies ahead. Hey, Adam. What do you think is the most important skill for you, not just at work, but in life? Most in in not wow. Skill. And I’m not saying characteristic or, like, breathing, like, skill. It’s probably communicating, talking, or just not crying in the middle of the day. But that’s no. I’m just kidding. It’s definitely communication. But, yeah, communicating and communicating effectively and getting your point across whether you’re negotiating with a fifteen year old as I am these days or whether you’re, you know, presenting to the board. And so today’s episode has someone who I’d consider a master communicator, Carrie Lou Dietrich, who has been CMO at a number of big tech companies, including Atlassian where she took them public. And since then, advises dozens of companies and sees suite leaders in the tech space and and outside of the tech space on not just communication, but strategy and so on and so forth. And Cary List picked up a thing or two, you know, in in these roles. Yeah. And I think it was interesting to kind of really get into, like, how to talk in the c suite. We got into board meetings. We got into, like, a lot of different things. And it was really interesting to me because I had just had a conversation or multiple conversations, actually, with a couple of folks that I know, either getting into kind of their first executive adjacent role, we could say. Right? So it’s a VP at a company where they’re reporting into c suite, and they haven’t had the interaction. And definitely trying to understand, like, this is gonna be a change for me. I gotta, like, figure this out. And there were some really great actionable tips from Kayla right in there that were perfectly relevant. One of them being be succinct. And so let’s just end it right here and go straight into the episode. Let’s do it. Too much detail makes you look junior. Carrie Lou Dietrich, I read that on LinkedIn last week. Tell me about it. It was a surprising LinkedIn post that went viral. Many years ago, Christine Heckert, who was a former CMO of Cisco, was talking to a CMO group and told us that too much detail makes you look junior as if you don’t have mastery of the detail. And it really stuck with me because coming up, my mastery of detail was something that made me exceptional. So I might think that the same is true for you. Going above and beyond and looking at the data, analyzing the data, understanding the context and the landscape. We know whether I was in product marketing, demand generation, or brand and advertising. Getting the detail right meant doing better advertising. But as you become more senior and you’re attacking to senior audiences, they want you to synthesize and not derail them with all the detail that you know. And so this really struck a chord on LinkedIn in part because I was also promoting a class that’s not by me but another company that I took when I was younger to help you be more precise in the questions you ask and the answers you give. It’s interesting because, we’ve heard this again and again. Right? What got you here won’t necessarily get you there or get you to the next level. And communication and the way we, more importantly, communicate up is a skill that nobody really formally teaches you, but you have to start to change and evolve your communication patterns and habits. Tell us more about what you’re seeing and and what you learned in the class that you did take. When you’re first learning, you dig into a lot of detail, And then also you’re not quite as good at seeing the beacon in the middle of the blizzard. You might not have the pattern recognition, so you might detail things out much more substantially and justify your opinion. Whereas someone who has more experience might need less information to justify their opinion. There’s the logic gap. How do you organize your thoughts? There’s the experience advantage, and then there’s the skills. And so I was really lucky at Oracle. I worked for a gentleman called Scott Clausen. And Oracle, at the time I started, was eighty thousand. And when I left, it was more than a hundred and twenty thousand. I was running awareness advertising and had a budget of forty million dollars that I spent, and then I had oversight over eighty million dollars kind of across some different departments, that added up to to mine. And because awareness advertising was so important to Larry Ellison, we had to do a lot of communicating with him. So to communicate to a CEO who has eighty thousand employees, you really have to hone in on what is desired. And, also, for anyone that knows anything about Larry Ellison, he’s not really a soft, warm, empathetic, patient leader. He will give you his feedback very directly and sometimes harshly. So the learning environment is accelerated by feedback. Feedback is a gift. And so at Oracle, one of the things we did was be very specific about how we emailed. My boss literally taught me how to write emails. And you would think it was pedantic, but it was very practical and helpful. We had this format where in brackets at the beginning was the action that you desired. Approval needed by date, FYI, as requested. It had a small number of words that referred to exactly what do you want them to do with this email, And then it would have a brief title that was actionable or summarize the conclusion. And it would have any, like, critical dates or information. And the goal was, if they never ever opened the email, could they do what we needed or understand the conclusion or the timelines? And then within the email, we also had some structure around whatever the ask is is in the first sentence. You really only get the first two sentences to hook a top executive. You can have a couple of bullets, no paragraphs. Time is the most precious resource for top executives. And so figuring out how to really compress information into the essence of what they need to know is critical. And I was lucky to be taught some of those skills and some skills in and of the class I mentioned as well. I’m working on my email right now asking for a hundred and twenty million for awareness advertising to our CFO, but I have your template. Anyway, talking about awareness of the details. Right? But it doesn’t actually forego the need for that. Right? It’s like how you synthesize. And I’m sure we’ve all dealt with CEOs where you’re presenting that high level, and then the deep dive question is so so minutia, so, like, whatever. For some reason, they’re thinking about it that it can’t be expected to know everything, but that mastery of the details that you learned earlier in your career is still gonna suit you well. Because to get to those conclusions, you probably have still gone through and have that most of it top of mind. I’ve talked to people that are moving into their first sort of, like, VP role where they’re having executive c suite or CEO interaction, and they’re worried about like, I’m always in the details. How do I synthesize it? But if they start asking me questions and I’ve spent more time on the bigger picture and I don’t have the little details, then I’m gonna look like I’m not aware, but I have to go back and ask. Like, that’s a balancing act too at a certain point of, like, provide the executive overview, the insight, but then you’re gonna get those questions that are just gonna be random. Absolutely. I mean, to be a top executive or a successful middle manager or a successful individual contributor, you have to know your job and your business inside and out. What makes you successful is knowing a lot of information that helps you come up with better answers. So one of the points of contention on that viral post was anger over middle managers who delegate too much and don’t know the detail and how managers think they can be out of the detail, and I’m telling them they can be strategic by having less detail. The focus for Christine and for me is about how you talk to top executives, not what you know. Let’s take board meetings as an example. This is one of the places leaders start to to need to really synthesize, talking to your CEO internally, talking to c suite or vice presidents. But what’s important is that you know lots, but you identify just what they need to know. Like, what’s the recommendation, and then what are some of the details? You know, what’s the most important data point that shows your hypothesis might be right? And how do you show that in a really clear and straightforward way? Like, the worst thing to do is dump a whole data deck on an executive where they have to do the analysis. Executives want people on their team who are closer to all the detail, to look at the detail, to analyze the detail, and then say, is it going up or down? Why or why not? How do you fix it? Why or why not? And the same thing holds true at the board level. You don’t wanna send the board sixty seven slides with every data point. You wanna figure out what’s important to the big questions they’re trying to ask. And that’s why this class I was talking about was called precision questions and answers because part of it is knowing what question you’re asking and clarifying questions. What are they trying to get at instead of giving a long soliloquy about everything you know on the topic and then them interrupting you to say, no, no, no. Like, this is what I’m looking for. So yep. You’re right. You need to know the detail. And if you don’t know the detail, you need to be really honest and not use thousands of words that say yes, no, or I don’t know, and I’ll get back to you by this date. Yeah. And that’s the biggest part. Right? How do you communicate up the right level of detail, but having your talk track rooted in knowledge, details, insight that you’ve taken on? As marketers, we should be better at this than other people because there’s three important things that you need to know to simplify and hit the mark. And the first is, what does the audience care about? If you’re talking to the board, they care about often the financial performance. So awareness metrics and every click through is less interesting than the metrics from lead to revenue. So who are they? What do they care about? And then what questions are they trying to answer? And how do you provide just the level of information you need to first answer that question? And then in marketing, we tease about threes. Everything’s in threes. There’s three reasons. There’s three bullets, three memorable things. How do you take your ideas and put them into a structure that you can communicate that helps people follow along instead of having a stream of consciousness of lots of words and details? And, there’s this one funny story out of parenting book. Often when kids are start to be interested in their bodies or sex, you know, they might ask a parent a question like, what is sex? And a parent might go into graphic detail about all these things that make them uncomfortable. Or if the kid’s six, they could be like, it’s how we make babies. And they’d be like, yay, and run away. Right? So, like, how much detail does your six year old need about sex or your twelve year old or your twenty four year old? Like, who’s the person? What’s the question? What’s the context? What do they really need to answer? And then how much progressive detail do you know need to share? Yeah. So true. And and you’re so right that marketers should be better at this, frankly, than maybe some other folks on the c suite. Carrie Lee, you have five pillars of effective communication that you you’ve kind of detailed out. Can you quickly hit on those? Yes. So, again, I have a blog at carrie lu dot com, where I share all sorts of details about this. And now I’m embarrassed because I had brought up all these other articles, but not the six. So let me make up a few, and hopefully, they overlap, with the fixed topics. But first is really knowing your audience. The second is really understanding what they need to know and what you’re trying to get across. And so, again, if we go back to this email concept, you know, when you keep synthesizing it to the most critical information, what do they need to know? And then if you get a title plus three bullets, what do they need to know? And if they get a title plus three bullets plus paragraph, what do they need to know? I have read this one blog about the three phases of preparation for board decks because board decks are this quintessential communication challenge. So often, if you’re on a marketing team, you’ve contributed to some board slides. Maybe at first, you’ve made forty board slides, and then the CMO says, no. No. I want them to be different. Change this and look at this and answer this question, and you create fifteen more slides. And then it goes to the CEO, and the CEO changes a bunch of things. And then in the end, maybe only four slides go to the board. And at first, when I was trying to communicate from different levels of marketing, I get so frustrated. They’re like, oh, what wasted time. But the act of these processes of analyzing as a team and trying to visualize and articulate and then getting feedback and synthesizing for the CEO, which is a second and different audience, and then ultimately synthesizing for the board are three separate phases of learning and articulation that have different goals and different learnings. And so, again, if the first is to understand the audience, the second is what are you trying to get across, and the third is exploring different ways to synthesize that. It takes way longer to write a short email than a long email because you really have to to work on pulling it together. So I would say those are those are the big three. Is there something else in the article that stood out to you that I’ve forgotten? I thought just coming with hypotheses and recommendations. Right? We’ve kind of hit out on. Right? What do you wanna talk about and how do you wanna say it? But goes back to not expecting the reader or the consumer of your information to come to that conclusion. You should be coming to it with all of sort of the analysis that you’ve done. Yes. Right. It’s difficult, and I see it at all sorts of stages. Like, you would be surprised. I’ve talked to some CMOs of billion dollar revenue or more whose marketing analytics teams are just delivering them a lot of charts and slides and not the analysis and insights. And so the board wants you to come with a clear point of view. The CEO or CMO want you to come with a clear point of view, and you could be wrong and they could want the other one, but they want you to predigest for them because you’re closer to the information. So, again, on this balance of too much detail with makes you look junior, talking about too much detail without articulating what is critical makes you look junior. Knowing all the detail and being able to quite senior. So I definitely think that the hypotheses is a critical aspect. And the other aspect that’s interrelated to that, now I found the article so I can say the same five topics, is having data and return on investment that shows business outcomes instead of activities. And I worry about even saying this out loud because for so many experienced business people, that would be a duh. But for the learning journey across your marketing career, you know, you might not be tied to revenue if you’re doing social media marketing. And so you share followers and engagements because that’s what you have. But the more you’re communicating to top executives, the more you need to try to tie metrics to the metrics they care about. And, generally, for the board and for the CEO and even for the CMO and CRO, that’s generally tying it all the way to the outcome. Like, the bookings or the revenue material launches, What do they really care about, and how can you show that simply and clearly in data? I have a favorite data guru. So there’s this guy named Edward Tufte, who was, like, the grandfather, maybe he’s the father, of infill graphics. And he has a series of books, and I sent lots of folks on my team and myself to his trainings over the year because he talks about how to use visualization better to articulate your conclusions and analysis in a very visible way and how changing graphs in different ways can disrupt people from making the right analysis and conclusions. And so that’s a big skill. So you’ve sat in I mean, I mean, a lot of boardrooms in your day and just in a lot of c, you know, c suite meetings and so forth. And we talked about the too much detail. Would you say, like, that is the number one mistake, the number one communication mistake that folks are making with c suite executives? Or maybe even describe a scenario where you’ve just seen it go. And I ask this question a lot, so I don’t know if I’m living in a dark period of my life where I’m like, it goes really bad. But just, like, digging a little bit on that, I guess, of of, like, what’s the the top one, I guess. Well, I just did a presentation to a number of CMOs on the topic of trust, not to over index on my blog, but it’s been really interesting to write a blog to see what resonates with people and why. And so Heidi Milin, who is the CMO of Marketo and Hyperion and a number of other companies, invited me to CMO summit she was hosting for, for a number of CMOs, and and we talked about trust. And there were four aspects of trust. One is competency. Do you trust someone’s competency? One is reliability. Do you trust their reliability? One is, affinity. Like, do you have stuff in common, and are you connected to one another? And one is integrity. You know, are you playing on the same values and moral goals? And I think that communication is very important in the boardroom. It’s important to be clear and articulate, but I don’t know that communication and affinity can win alone. Like, the board actually wants competence. They want you to set goals and predict if you can hit those goals, hit the goals, and then recommend changes to accelerate growth or to get back on growth track. So I think any good communication starts with having a shared understanding of what the objectives are that you’re trying to reach. So in your very first board meeting, you don’t really have any control over your department yet, and your first board meeting is generally articulating your outsider’s perspective of the company. You did a lot of research before you joined. What is the market perspective before you get inundated and drink our Kool Aid? And what are your observations of the team once you join, and what are you know, what’s your kind of strategy and focus and and how will you sequence things? So you you’re kind of off the hook the first time. But the second, third, and fourth is we’re trying to hit these goals. Did you hit these goals or not? And I think where sometimes people fall down is haven’t hit the goals and you talk about everything else and there’s waving hands. I think that undermines trust where you could say, hey. Look. We set really aggressive goals. We haven’t been able to hit them. This is why. You know, there’s three areas I see of challenge in the business. This is what I’ve done to address those three areas of challenge in the business, and this is when I’ll know if it’s working or not. So again, you know, you might have had come up with seventeen hypotheses and have forty two programs you’re gonna run, but how do you put them into some categories so that they’re digestible? And then only provide a lot more information if they ask for more information. Yeah. It’s a good reminder. We’ve spoken a lot about the board in relation to the topic at hand, which is communicating up, communicating effectively to executives. I wanna almost take it to a different lens where the job market is what it is. There’s a lot of turnover. There’s a lot of folks interviewing for roles, and it’s just very competitive right now, particularly for CMOs and other c level execs. How would you take some of these tips and frame them for folks who are actively interviewing with multiple people on the c suite? So I think it’s important to understand the audience and what’s important to them again. So let’s say you’ve already gotten an interview because I think, you know, we could talk about how you customize your resume to the words that they have on the job opening. I think we have to do that. You know, how you network your way in to someone who knows someone, I think that gives us a better chance. How to research the market and have a point of view on the company’s challenges, opportunities, and strategies, I think we need to do that. But if you’ve already gotten an interview and it sounds like the question is talking to multiple different stakeholders, it’s it’s really important to not come in talking, but come in listening and asking questions. So at the very beginning of my career, I was in sales, and a lot of sales methodologies recommend spending maybe a majority of the meeting getting to understand the pains of the customer and what’s really their urgency and what drives them. And if you can spend twenty minutes understanding the strategy and ten minutes really customizing your solution to their words and their pinpoints, it’s considered a more successful meeting than one where you come in and just walk them through your default slide deck. So if you’re meeting with the head of engineering, you might wanna talk more about how product marketing interfaces with product management and how you think about tiers for launching products. If you’re reading with the sales org, for sure you wanna have orientation around revenue. But, again, I would challenge people to spend more time asking questions. Like, what worked about the previous structures? What didn’t work? You know, what kinds of leads are you looking for? Tell me more about the sales process. Do you really trying to understand your audience and ask precise questions to provide precise answers? And then going back to the marketing skills, I often come up with threes, and I often list three on my fingers, and I often count them out. And sometimes I’ll come up with a three at the beginning. Like, the reason I’m right for this job is because I’m, like, values focused on the same, like, long term mission you are to to change the world to this technology. You know, two, I have the scale and experience to do what the challenge in front of you. And three, I have the network to hire the best team to to really scale our company. And then maybe I’d talk about some of those things, and I’d I’d mention them again at the end, because that skill of listing some things, talking about them, listing them again, it makes them memorable. And these are the same skills we teach a CEO or a vice president in their keynote speech for our conferences. Right? We’re gonna write a keynote. It’s gonna have an intro, three sections, a conclusion, and a restatement of the three sections. We’re like, we wanna try to use that in our own lives to help people process all the information we’re giving them. I was just thinking too about as you’re going through that, back to your Oracle story. There’s a company culture component here too a little bit in terms of and I if you’ve ever like, the Amazon way where they write these seventeen page I mean, not seventeen. But whatever long memos outlining everything that’s gonna go on to the meeting, And then they sit there and they read them, and PowerPoint is verboten and and and all that. So which that exercise in love itself seems to be get into the details so everyone knows every little thing you’re gonna talk about versus what it sounded like at Oracle, at least from an email perspective, was like boom, boom, boom. You gotta be a bit of a chameleon because you move from especially wherever you sort of, like, spent your time training, you could say, or getting sort of, like, that that c level talk down and that that working that way. And then suddenly, you move over to a different company. In your mind, how do you navigate that where there’s certain tenants that you follow, but yet the company is saying, well, that’s great, but, you know, write ten pages of everything that we’re gonna talk about over the next twenty minutes. Like, that one the Amazon thing has always fascinated me, but curious what you think about that. I think a lot of the skills transfer, and then, of course, you have to customize them. So just to clarify, my understanding of the Amazon is that they’re only allowed to use two pages. Oh, really? Okay. That I didn’t quite part. You know, I heard years ago that it was six pages, and then it was two pages that I heard from the last Amazon executive. And, actually, I really wanna write a blog on that. Maybe that’s gonna be my blog, but I wanna even even a blog person on it. But two pages and so the challenge is how do you synthesize a whole concept to two pages? And, like, what’s the background that’s most relevant? You know, what information do you need to know to make this decision? And then here are some links to the resources that we could learn more or something. The biggest challenge for me in something like that would be you need to restructure your day to have time to write memos instead of just meeting all day. But I think that’s the right focus of time, having someone do focused thinking so that everyone else doesn’t have to sit there for an hour while we brainstorm what we’re gonna talk about. Oracle is very direct. Atlassian was very warm. Oracle was email, Microsoft shop, PowerPoint. Atlassian was obviously Confluence and Jira tickets. And in Confluence, I really miss Confluence because I don’t use it with all of my clients necessarily. But, in Confluence, you could put a whole bunch of detail on a page, and then there was this way to shrink things up. So you could have three sections and then I’m forgetting the word. But, like, shrink up. Collapse. Collapse. Thank you. Collapse the detail so that you could have a whole bun you know, you could have something that someone could scan and they could scan the detail if they wanted. Sometimes when it last seen, we would get into these QBRs, though, that were like an arms race of detail. I think I prepared for one QBR executive QBR by reading for, like, twelve hours to read everyone’s information because I’m a detailed person who wants to know the detail. So it can be dangerous. You’re right. Different cultures can can be dangerous. Although, one of the best pieces of advice I ever got was from the CRO at Atlassian, Cameron Deach, who I had worked with for companies before. And he, at one point, said, Carrie, your slides are so rich, but why don’t you take everything on the slide and put it in the notes and put three words on the slide? And at first, I was so annoyed. I was like, no. This is the important detail to, like, support whatever we need to do. But he’s right to challenge me in some ways because you don’t always need all the detail on every slide. You can have some, like, what I’m trying to get up this is the big point that you need to take away and then have something that’s collapsible or a follow-up or, like, a hidden slide that you could open as you need it with some more detail. So I think there’s really a yin and yang to finding the right balance of detail and strategy high level, both for yourselves and for different companies’ cultures. Yeah. Twelve hours of reading to prepare for a QBR could qualify as the answer to this next question, but it’s a question we ask everyone, Carrie Lou. It’s the last question. What is the most ridiculous thing you’ve been asked to do in your career? Good or bad? Well, are we talking about DE and I topics? Like, being asked to go to a strip club with, like, elderly accounts? Like, that stuff doesn’t really happen anymore. I don’t know. You know, it’s funny because I’ve only worked for first time founders. I mean, even Larry Ellison is a first time founder who still runs his own company. And so I’ve always felt like it was my job to help them realize their vision. And sometimes their vision might have been misguided to me, but it’s only crazy if it doesn’t work. And sometimes their crazy ideas work. So I don’t know. One of the craziest ones might be Larry Ellison did want to sponsor, the world’s strongest man, which was this, like, late night TV show where guys drag car parts. Like, maybe they’ll carry a car or, like, massive tires from a construction, vehicle or something. And we had to tell him why we did or didn’t think it was a good investment for Oracle. And, you know, my recommendation was I didn’t think it had as much brand alignment, and I didn’t think it reached as many business buyers as some other alternatives. And originally, it was just, like, coo pooed and laughed at by some of the folks on the marketing team. I tried to take it seriously. Like, he watches it at night. Maybe he’s right. Like, some, like, late night direct response stuff gets amazing results. So I don’t know. I think I look at things with an open mind and a sense of humor and, enjoy the ride. That’s good advice. Thanks, Carrie Lou. This was fantastic. You’ve been listening to Revenue Makers. Do you have a revenue project you were asked to execute that had wild success? Share your story with us at six cents dot com slash revenue, and we might just ask you to come on the show. And if you don’t wanna miss the next episode, be sure to follow along on your favorite podcast app.