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This week Paul and Rich respond to a mailbag question! A listener reached out seeking advice on how best to deliver a project pitch to higher-ups at a company. From keeping your presentation short to showing up with deliverables, Paul and Rich break down the best ways to make your idea land with the C-suite.


Paul Ford God, Ruben, sounds like you should be the CEO. [Rich laughs]

Rich Ziade I didn’t sound like a video guy just now! [Pau laughs]

PF No, ‘be Rich Ziade’ is bad advice just in so many ways. [music ramps up, plays alone, fades out] Richard!

RZ Hello Paul Ford, how are you today?

PF I’m doing alright. Got my allergies. Allergy season.

RZ Ohhh snap!

PF Whatcha gonna do? Took a Claritin. I’ll be alright.

RZ Reminds me that song “bad boys, bad boys, whatcha gonna do?” you know that song?

PF Course! It’s a classic. I listen to that every morning when I wake up. Enough about me and my allergies. How are you doing?

RZ I’m doing well. I’m doing well. Postlight’s hummin’. Feeling good, personally. I feel I can see the light at the end of the proverbial New York City pandemic tunnel. So I feel pretty good.

PF It’s a bumpy transition. It’s not like, “Hey, everybody, let’s get back to work just the way it used to be.” So there’s a part of me that’s like, I’m looking forward to July. I’ll be frank. That’s what I think the new world takes shape. 

RZ Well, I think there’s just a lot of exposed nerve endings out there and to make any assumptions about exactly what they should do, on their behalf is very scary. People have been told exactly what to do for about a year and a half now, like exactly what to do.

PF Yeah, that’s true. Don’t go outside, go outside.

RZ Wear masks, six feet, 12 feet, 10 feet. So now they don’t, they’re really not in the mood for one more. [Rich laughs]

PF That’s right. That’s right. We’re kind of done. Right. 

RZ We’re kind of done and we’re sympathizing with that we’re looking at you know, how work is changing over to new normal. I hate the phrase ‘new normal’. Did I mention this to you?

PF Oh, we’ve been hating new normal since the new normal was the new normal. Alright, so look, enough about us. We got the mailbag! The mailbag was full this week.

RZ Ohhhh, I love the mailbag. Okay.

PF Our friend, Trevor. So we didn’t check in. So I won’t give a last name. But Trevor wrote us an email. And it’s great, because it’s not directly from our world. It’s not like, “do I use PHP?” It’s this. “This is a question for the podcast.” I guess I could have left that part out. But you know, let’s keep going. “I work in video.” This is Trevor. “And I often find myself pitching video concepts to C-suite level folks. They’re smart. But they don’t tend to have the ability to close their eyes and imagine the thing I’m trying to describe. When I pitch up to other creative friends, they get it right away! Because they’re used to using their imagination. But the suits don’t have that skill. So my question is, how do I get better at explaining abstract ideas to people who would rather see the finished product and approve it?”

RZ It’s a great question.

PF This is good. I got this like two days ago, I’ve been thinking about it non stop. 

RZ It’s a good question. I mean, we should point out that you and I reside in the C-suite.

PF We do!

RZ It is luxurious. It’s velvet, couches, floor to ceiling glass. It’s really something. Actually, we’re in a unique position, Paul. First off, we are executives, we got a relatively I mean, it’s a growing organization, we’re coming up on 100 people, knock on wood, all goes well. And we are also interfacing all the time with very senior people, right? It’s a pretty common thing for us. So we kind of know this part of the game, right? And we’re very well positioned to speak—

PF Being an agency leader is weird that way, because you’re like, you’re the leader, but my job, like, every now that it’s fun to see partners and people as they’re coming up in their career, and then you go into a pitch and you know, and the client just throws a brick at your head. And you’re like, yep, that definitely felt like a brick. [Paul laughs] And you come out on the other side, and it’s, it’s wild to see people look at you, and you look back and you’re like, yeah, no, I eat the same shit everybody else does. That’s just part of the job. It’s, it’s Yeah, it’s never gonna change. So yeah, we go into this situation all the time.

RZ We do. And one of the most important things you can do when you’re talking to someone, and when you say C-suite, you’re talking about it, CEO, CFO, CTO.

PF You know, in big orgs those are EVP, like you know, you can be the CEO of your lemonade stand, but like VPs, EVPs, and large orgs, all people with budget. I’ll tell you where it’s not a problem to pitch, Postlight has a great, we do a great job when we’re pitching to the head of product on the other side. If you’re pitching video production strategies and sort of how our conceptual piece is going to go the person on the other side used to be a video director, you’re gonna have a pretty easy time.

RZ Yeah, this is one of my points. I have numerous points to make. I came armed with bullets. One of the key points is you know that audience, that recipient of your pitch, what do they care about? CFOs care about very particular things.

PF Well, you know, it’s funny, hold on, you know, before you get there, because this is where you’re going, you just skipped like five steps, typically the answer to this question, you know, how do I get these people to pay attention? The typical answer is I’m going to give a presentation. And we need to use tools like storyboarding, or, or the more tech side, it’s like wire framing, or mock ups or whatever, we need to illustrate and tell a story about what we’re going to do. But the point you’re making, I think it’s a good one, I can sit there and give you forms and structures and techniques for making ideas simpler all day, you already know those, everybody knows those, like, I have to draw pictures, or I have to draw, you know, narrative use cases or whatever, right? But the thing that you jump to, and this is what’s real is that you have to sit there and and have empathy for the person on the other side and figure out what their priorities are, and then speak to those. See, they don’t want to understand your world, actually, most of the time, they don’t want to know what’s going to be in your video that’s going to make it so special, or why you’re good, or something, they just want to know that they can stop worrying about you.

RZ They want to stop worrying about what’s in front of you, what you’re responsible for, right? Like they don’t want to be roped into the process. And that’s not because they’re arrogant, or they think it’s below them. The thing you have to keep in mind about executives is that they do tons of context switching, they skim across many, many things. And they are very wary of diving in anywhere. One of the big mistakes, so let’s number these so we can come away with some wonderful pieces of feedback. And I think you’re orbiting around the most important one, which is understanding where they are, empathizing with how they will think and work and tailoring a message to them. Right, which is probably the biggie.

PF Let’s roleplay, why don’t you be an exec for a minute. Be a CEO, and I’ll be the video guy. We’ll call you, Mike, Mike’s a good name. Hey, Mike. I’m Ruben the video producer. Glad we have this time to talk to you.

RZ Ruben! I’ve heard good things. Listen, apologies in advance. I know we have 30 set aside but I’ve got to jump in 15.

PF Okay, well, that’s a problem. Okay, so Well, let me let me sit down. I have I do have 30 minutes of slides. So let me I think we can just go really fast. Is that okay?

RZ You know what, Ruben? Go, just go.

PF Okay, so what we’re gonna do is we’re gonna start with, so the product is called Sunset. And I want to, it’s a tool—

RZ I’m sorry, hold on a sec. Hold on a sec. Let me give me a second here. Vegan bread. I said, vegan. Yeah, just send it back to send it back. Okay, bye. Sorry, go ahead.

PF So what we want to do, I created a mood board to show you the different kinds of Sunsets that I think we could capture in this video, is what we want to do is give the sense, because you know, this is a thing for taking legacy software and making—Ah! End my pain, Rich. Come on. I can’t do it anymore!

RZ Alright. Ruben, look, I see where you’re going with this.

PF I’ve been Ruben. About 10 years ago. [Paul laughs]

RZ We’ve all been Ruben. So I think let’s, let’s come away with bullet one, Paul. Do not think that because you’ve got 30 minutes that you’re going to jam 90 minutes of information down some executives throat, or if you’ve got 30 minutes, 15 minutes, and you’re going to jam 45. One of the big mistakes people make is they think it has to be information dense because they’ve got such limited time with that person.

PF Well, they also want to, it’s a way to demonstrate and prove value, which is very tricky. They’re actually not looking for you to prove your value.

RZ Don’t ever do that. All they want to see is that you’re about to lock in to their wavelength around what they care about. Right. So let me be Reuben, now you be Mike, you’re chewing on your vegan bread right now me come at you a little differently.

PF Ah, hey, Ruben. Alright. Look, I’m really sorry. I’m really sorry. 

RZ No, just eat, don’t worry about it. Just chew in front of me. 

PF Just gonna drink this diet coke.

RZ Our goal here is to make this we’ve got a minute, nobody watches videos more than a minute. I’ve got a minute. And I need this to resonate with decision makers. So they’re feeling like man, I’m they’re gonna take the pain away. That was the goal of this video. So the point here is to make it simple, impactful, straightforward, so that people can make a decision quickly. We can watch it if you want or I can leave you the link. But that’s what I’m going for. Don’t persuade, go in believing in your position and stat it. Instead of thinking I don’t have them there and I need to get them there. When you go into persuasion mode, immediately the suspicion kicks in.

PF And then they’re like this person’s a fraud. That’s all they’re looking for. They’re looking for—

RZ Don’t persuade! You gotta walk in ready with your position, believing in it. A strong case for it. Keep your words brief, and leave it on the desk. I have to use, I’ve been using this phrase lately, just leave the memo on the desk. Right? 

PF The other thing, see, and this is a default for you because you are an exec, it’s why execs sell to execs so well. Execs sell well to execs because they they’re in a relaxed position about knowing that the other person also has no frickin clue what’s going on, like, literally, this person you’re talking to is like, “oh, what the hell is this thing? I got to bless it, I don’t really know what’s going on.” And if they’re talking to another exec, it’s like, “oh, hey, man, I got your video. Look, I put my best people on it. I just want to show you what some of the ideas that we’re having here. And I just need, I need to get you to say like three things so that I can figure out how to do this right for you.” Right? And it’s just sort of like, here’s what they need to know. And this is an ego thing, but it’s also real. Have you valued their time appropriately, and figured out what their goals are? If you have, you’re going to find that 15 minutes is more than enough time.

RZ Absolutely. Absolutely.

PF What does this person need for the video, right? First of all, the video has a budget, it has a goal, it relates to some larger project, and it will be evaluated based on the impact that it has the impact is that lots of people will like it, he will not be embarrassing, or do any damage to the company and that it will meet whatever the goal is the marketing goal, the internal communications goal, whatever. So first of all, no one has trouble visualizing and understanding, talking head profile, right. So clearly, you’re trying to do something with the facts, you’re trying to make something new and novel and show a little creativity.

RZ This is another key point I want to share right at this point where you’re talking about which is don’t describe a sunset to an executive, come to the meeting with 30 seconds of something, show them something, let them talk off of something, do a little bit of work, we do this in sales all the time it at Postlight. The greater the fidelity of what you’re sharing as you talk, the more impactful it is. We’ve landed business by overstepping and over designing and going going even further than just words, an executive “walk with me”. When the executive says “walk with me” that’s a very tricky moment, right? They’re essentially saying I gotta go to another place, just walk and we’ll have this meeting walking, and then you’re pitching a video idea to someone while they’re walking from conference room A to conference room B. Good luck, right? So unless this person is, you know, you have a rapport with them. And you’ve been able to figure out how to communicate, communicating how great a mobile app is going to be with a conversation or how great a video is going to be and the ideas behind it, in a conversation—

PF And you know what? Don’t make the storyboard. Don’t give the full thing. So A) what are our goals? How will we measure success? B) here is one minute of the video. That’s what I would do.

RZ Trailer. Right? Make it sizzle and let it be impactful.

PF Doesn’t have to be original. Just go grab stuff, just whatever you can get, pull it from your reel, just be like, I want to do this. I want to do it with you know, your director of marketing, whose name is Olaf. You know, I want to just like make, yeah, we’re gonna put them on screen. And then we’re gonna actually we’re gonna show this software, yeah, we’re gonna show it changing lives. And we’re gonna actually make the people fly. And they’re gonna go, they’re gonna see one minute to 90 seconds of video, and they’re gonna see that you value their time. And then they’re gonna see that you have this model of their success. And then you just say, like, I want to get your feedback. We have a really good plan here. I want to know what you’re worried about.

RZ That’s another thing is you think you got to jam in your pitch in those 15 minutes. You don’t. You actually want to take about five. So let’s recap, we’ve said, we said a lot of different things. First off, come understanding what their drivers and motivations are. Right? Second, don’t come with a script or too many words, don’t jam up the set the channel. 

PF Don’t tell the whole story. 

RZ Don’t tell the whole story. State out loud their interests when you meet them, you say “we’re looking to elevate CIOs to really understand what they’re buying here. And that’s the division behind this.”

PF Well, we want actually, we’ve worked this out, you’ll be Ruben, I’ll be the chief technology officer, we’ve got a software as a service product that helps you, you know, optimize some all of your travel in your giant organization. We have to sell it, we have to sell this thing. We need YouTube videos. And we also need to we need to actually announce it at the big conference.

RZ Okay. Alright. And you’re Mike.

PF Ruben, really good to see you. I only got about 10 minutes here if that’s okay.

RZ We’ve got some exciting stuff queued up, what we didn’t want to do is hurt people’s eyes with a bunch of screenshots, right? We’ve targeted exactly who the audience is going to be. And we wanted to create essentially, something no longer than a trailer, that’s going to really resonate with decision makers and like, it’ll be the pre-roll to the the pitch of the product at the conference too. So thinking it ends up on YouTube, it ends up in a lot of different places, in ads, but also at the conference, that’s the first time anyone will ever see it. So we’ll say a few words, play the one minute video. And the goal here is to you know, get an emotional reaction a little bit and also just tell people, they’re gonna, this is gonna solve a lot of problems for them around the travel platform.

PF I mean, that sounds fine, but do you have the brand guidelines, like I just saw, your worlds a little bit of a mystery to me. 

RZ Yeah, let me, obviously we adhere to the guidelines. Let me show it to you. I’ve got it.

PF No, no kidding. That’s great. Okay.

RZ This is a draft, 90 seconds long. Watch it all the way through. And then let’s talk about it for a couple minutes.

PF Alright, fast forward 90 seconds. Alright. Well, I mean, look, I wasn’t, this is great. Like, I see a lot of what you did here, I don’t really, we’ve got an organizational focus on positivity. Like, that’s one of our big goals. And so like, I do worry a little bit. It’s almost a little serious. You know, it feels like it feels a little somber, we want people to be really excited about this enterprise transportation logistics program. Also, sustainability is another big thing here that we really need to hit, I gotta hit sustainability really hard. Look, I think overall, you’re on this, I mean, are we going to be able to show the five product pillars and actually show the product?

RZ We don’t want to do that in the video, we want to walk people through that. There’ll be other videos, by the way, we’re producing a whole suite of them. But this is the launch. This is the ‘here we arrived’ right? So there’s gonna be a lot of other videos. 

PF This is what goes up on YouTube?

RZ This, this amongst others will go up on YouTube. But this is sort of the reveal. I’m using the wrong word. This is the reveal. Like we have been doing all kinds of HR software. And now we’re gonna tackle travel.

PF You’ve been talking to Cathy, Chief Marketing Officer, Cathy, you’ve been talking to her?

RZ Absolutely. Pause. This is something executives love to do, by the way, the way they sooth themselves, is by making sure that you’ve spoken to other people they trust. [Rich & Paul laugh]

PF We’re all going down together. That’s what’s gonna happen. Cathy and I are going straight to hell.

RZ Yeah. Cathy has been in the loop throughout. She’s been actually great. And she’s on board with this. She’s in love with it. I gotta tell you.

PF The move here, right, is kind of like we got it. Listen to we’re absolutely we’re covering those bases. So the critical moment in there that we’re both playing out, we’re improvising this right, is that there is a point where there’s a basic trust established, you showed me a video, there’s something real here. My next move, if you get an executive to start keyword matching, meaning like does this have sustainability? Does this have that? Does it have positivity? You’re very close to victory, okay? Because that means that they actually are just going through the final checklist in their brain before they release control. Because there’s there’s 10 things in their head that are that they perceive as risks. And so it’s just like, okay, okay.

RZ It’s not final.

PF No, no. And in fact, what’s going to happen, and this is where especially creative folks can really get in trouble. Because it’ll be like, what the hell you mean positivity? You’re going to figure it out. They’re going to pay you money, and it’s going to be annoying. And you’re going to figure it out. Just say absolutely, absolutely. Because, if you don’t give them that, if you put friction in there, because you don’t understand what they’re asking for, you’re not part of that conversation. That actually resets everything to zero. So you’ll find you’re not actually just saying yes to say yes, you’re basically saying the absolute magical words that every single executive wants to hear and Rich, do you know what those are?

RZ What?

PF I can figure that out. We can figure that out. We can figure that out. You don’t have to say yes, or I have a solution, or absolutely or no problem. Just say we can figure that out. They just want to see you nod and say I’ve got it, I will take that away.

RZ How do you get ahead? This is what this is about, right? This person is asking you in a roundabout way how they win with the leadership in their organization. That’s what they’re asking you right? And I’ll tell you how you win, you win by being self propelled writing three words in a notebook when they talk to you and then you are able to move it forward with near zero involvement or participation on their part. Your ability to propel change forward based on a five minute conversation, a 10 minute conversation is gold to executives. It is absolutely the one of the most valued things.

PF Now if they’re poisonous, if they’re poisonous, you’re screwed. If you’re going to go do a lot of work, exactly what they tell you, they micromanage you and you come back and they’re like I hate it. Now, everybody has to be wearing purple hats, you’re screwed. That happens.

RZ Yeah, yeah. It does happen.

PF Most people are just struggling through.

RZ Most people are just struggling through. Look there are monster customers, monster quote unquote “customers” out there that are just, it depends on who you get in the meeting.

PF Oh god yeah, that’s really, trust your instincts if you’re, if you’re talking to people before the meeting to prepare for the emotional state. If you’re being asked for things that you simply can’t understand. And if everybody is kind of in a flurry of anxiety trying to protect each you know like around this person’s mood, you got an absolutely toxic person and that’s just real. Sometimes you’re in a position where you’re not gonna be able to win. Soldier through. Hopefully you’re freelance, get some distance. If you’re not, what can you do?

RZ Believe in your position and treat it less like a sales pitch and more like communication. Like I’m sharing you with you where things are out, the train is moving really well, right now, we feel good. Saying the words, “we feel really good about this” that exec even though they have their anxieties, and I’m as anxious as they get as far as executives go, when someone feels really strongly about a certain position, my inclination is to let them use that motivation to keep going.

PF I’ve seen you stand down. They’re gonna go prove it. The other thing and look, going back to it. This is unfair, it is unfair that when you have you have to demo work before you’re ready, it’s unfair that you have to make a minute of something. But the closer you can show them, the real artifact, even a tiny sample of it is so much better than any kind of storytelling, you could do. 

RZ I think that might be the biggest, one of the biggest takeaways here.

PF  it feels just like, but that’s not the process. That’s not how this works. Being at you know, me, I’m not being paid for that. All of that is true. But if you can simulate the real artifact and put it in front of them, your chance your likelihood of success shoots through the roof, especially if you’re pitching. There’s a lot of times we have lost work to competitors, because they have gone ahead and done full designs before we even got there. And we’ve been told like well, they did the whole design. Other times we’ve done designs, and we’ve gotten to work because we had time and capacity, we really wanted to land something and what we knew, we often do that if we know we’re going up to very high level management, because it’s very, these are the people who need to see the real artifact in order to understand what they’re buying.

RZ It’s really, really hard to just describe the thing and hope that person spins it up in their imagination. Let’s recap all. We gave a lot of different kinds of advice. 

PF Alright!

RZ Number one, know your audience and know what they care about. CFOs care about money. CTOs care about risk and technology platform. CEOs care about the health of the business and growth, right? 

PF Marketing officers, CMOs care about the brand and the marketing.

RZ Correct. Don’t aim to persuade, instead communicate what you actually genuinely believe in and care about. Almost, I don’t want to say within a frustrated tone, but within excited and motivated tone around what you’re putting forward, you’re going in and they want that.

PF You know, it’s critical. Your focus on the artifacts, this is what three, four, focus on the artifact, not your discipline. A lot of times people want to describe what they do. Focus on what you’re making.

RZ Come with something. Don’t describe what the future is going to look like. It’s hard to pull off, they don’t have time, their brains, if you open up the skull of any executive, it is a scrambled mess. The amount of context switching I do on a daily basis is pretty staggering, right? So don’t make them work, come with something, make it slick, put a little polish into it. It’s what we do in sales at Postlight. Do it for them. And fourth, be brief, don’t jam words in because you’ve got very little time with that person.

PF We can figure that out, super powerful. The other most powerful words in the CEOs life are these “I know we have a half hour, I really only need about five minutes.”

RZ Oh my god. I mean, that’s very hard for a lot of people to process, because they can’t believe they got that time. But man is it valued. You’re showing value of your own time. Not just theirs.

PF You are the superstar. Especially if you’re coming in with something from a little a little bit outside, like making a video, odds they’re going to talk to you for 20 or 30 minutes, simply because you said I only need five minutes. Because it means they can relax, they can actually have a conversation because what they know is that someone has button this up and into five minutes so that instead of sitting there and pattern matching for 30 minutes to make sure something’s gonna get done, they’re gonna get an executive brief, they can then ask questions in a conversational way, and come to a conclusion. So it’s much less work for them. It’s much more natural. That’s a great question.

RZ It’s a great question. It touches on something very fundamental and basic about people’s professional ambition and how they communicate with others, right? We’re new executives, Paul, you and I, and we deal with many more of them now than we used to. So we have a good sense of how this works. I hope this has been helpful not just for someone pitching a video to an executive. But frankly, this is what we’re talking about here is communication.

PF The great fantasy of the executive is that they know something that you don’t know and that they’re going to kind of catch you and you’re kind of looking for their approval and worried if they’re going to like or respect you. They’re just confused—

RZ We don’t know anything. 

PF They’re on the other side of the table and they’re doing the best they can and it’s the thing about Postlight that’s tricky, right, is I think anyone could sit down right now and make a case that Rich and Paul, what are they even thinking? Except that it’s not an accident. We have a place to tier. We have a podcast we talk and we make good decisions and bad decisions, but most of our decisions have led to the growth of Postlight. And so we’re sitting there and it’s like, part of me is like, well, I don’t know what’s going on. But then another part of me is like, by collaborating with my executive team, we’ve been able to grow the business. That’s all I got. On the other side, I read the same newspapers, I got Wikipedia, like, that’s all I got. [music fades in] And so then you pitch me something. And I’m like, huh, it doesn’t mean anything. When I’m like, it just means like, okay, I want to, we got to move this forward together somehow. That is all that’s going on. Just relax. You are here in the room. The person on the other side doesn’t actually have any secrets. They have a little more power and that’s awkward, but you can work that out. 

RZ That’s very good advice. Speaking of advice, Paul, we love to hear from people. Send more questions like this, it’s really fun.

PF Yeah, it’s good. Mailbag! 

RZ That’s at also reach out to us if you need help. We’re a digital product studio based in New York and just about everywhere nowadays, digital transformation driven by great product management, product strategy, design and engineering. Check us out at you can see all sorts of fun case studies of the work we’ve been doing. Teams hummin’, Paul. We’re killing it these days.

PF It’s a wild year. We’re getting through it! And we’ve stayed busy. Hope you have to everybody hang in there and get in touch. We’ll be here for you to check out Lots of good exciting work and case studies that we’re gonna be talking about soon. 

RZ Have a great week.

PF Bye, everybody! [music ramps up, plays alone, ends]