Why comms deserves its own spot on the exec team — Aaron Zamost’s lessons from Square

Aaron Zamost - First Round

Brett: [00:00:00] Great. Well, Aaron, thank you so much for joining us.

Aaron: Thank you for having me. I love being invited to things like this. It's so fun.

It's also nice to be talking with a comms person who speaks for a living, so that's, that's nice. Yeah. I get, I get paid to do this, so I'll try to be as authentic as possible and remember that I'm wearing the hat of myself as opposed to any other hat.

Brett: So, one, one place just to, to use as a jumping off point, I, I'm super interested in, you know, the things that you believe about the roles of, of comms that maybe most don't or they maybe don't understand or that that took you a while to sort of figure out anything kind of come to mind for you.

Aaron: Oh yeah. I mean, I have religion on a whole bunch of crazy things. Probably don't sound that crazy, but I would say definitely are unorthodox when you talk to people who are not communications people. Um, I think the main one, and it's super self-serving is I actually think communications deserves a seat on the [00:01:00] executive team as a direct report to the ceo.

When I've talked to companies about, um, roles or I've given advice to other senior comms folks who are friends of mine, my first question is, to whom does this job report? And the answer is usually the CMO. Somebody in marketing, somebody senior.

Occasionally it's a COO or head of business. And very rarely do they say, oh, this job, it reports directly the ceo. And then sometimes they'll give you some hemming and hawing, like, oh no, it's on the executive team, but it reports to this other person. Well, okay, then it's not really on the executive team, right?

When the CEO calls her or his, uh, leadership team together to make some crazy important business decision, does this person get brought in the room and get to give the, their boss, the ceo, their advice? most people don't follow that as a rule, and I think it's really a mistake. I think most boards similarly would benefit from having this perspective on two, do you know how many problems in the last, you know, few months alone or through c you know, companies have found themselves in, and a person at the table who had an eye for reputation could have said, Hey, [00:02:00] you know, I don't know if I would do that, and I just think that's a perspective that most CEOs aren't getting. 

Brett: why do you think that is? Or, or why is it, you know, historically under the role of CMO or why is it not maybe the defacto kind of exec team role?

Aaron: Oh my God. How long is this podcast,

Brett: Well it's called in depth.

Aaron: Well, I'm a communications person. Let me give you the positive and message first, which is I think communications people, the best ones have skills that the rest of the leadership team doesn't have, as everybody on the leadership team should have skills that other people don't have, right?

You're building a team of rivals, people who compliment each other and make the CEO and the company better. And communications in particular, I think, are capable of seeing many, many steps ahead. I mean, they can see second and third order effects of decisions. I, I always start, when I'm looking at putting out news or information, I start with the faq.

You know, Amazon famously starts with the press release. I start with a list of hard questions and I take the questions down rabbit holes. And for me, this is a way of sort of seeing. Where things will go. And often you're surprised by the follow up question to the follow up question. And I think marketing people at their best are also thinking of perception of the company, but they're thinking about it from a, from a brand, you know, positioning related to have value propositions and how to sell the service.

And when they run an ad, how they want people to perceive or feel about the company. And communications is a great, you know, cousin to marketing and they work really well together. But at its core, the best communications people just can look at problems and spot exactly what the issue is going to be.

Right. I learned this from, um, a boss of mine, many, I mean many bosses that I've had, but Jill Hazel Baker, she's the current CMO and head of communications at Uber. She was my boss at Google and she just used to walk into a room in the middle of a fire. [00:04:00] Be able to so quickly identify the one fact or the one issue that was more important than everything else.

And I really picked that up from her. I picked that up in law school also, a lot of lawyers do what's called issue spotting. You're looking at a giant fact pattern and you're picking out the issues that matter the most. And just to have a person in a room for really hard, terrible situations who can give you that lens?

I mean, why wouldn't you want that in the room? So to answer the other part of your question, well, why aren't they in the room? I think the answer is because most CMOs are an earlier hire for founders because they're staffing up their marketing and they're go to market teams faster. And so they're most senior leadership early in that realm is somebody in marketing.

And that person says, oh, you know, we would benefit from a PR person. Then they go hire somebody with, call it six years experience communications. And that person rolls into marketing and that's that. But communication should not just be some like vestigial part of marketing. It needs to be something completely different.

And the best comms people, we'll take a job [00:05:00] on the leadership team where they can offer that kind of background and perspective. And those people probably aren't gonna work for a CMO. And so it's a choice that I think a lot of founders have to make.

Brett: Is any piece of it that there's just a low percentage of outrageously talented and strategic comms people, or no?

Aaron: No, I mean, I might be a personally self-loathing communications person, but I won't shit on the profession. Right? Like I just think the training of communications people are very different. 

I worked at Google back in the day in 2000, Seven to 11. And the Google comms team when I joined was like 30 people. And then by the time I left, it was 300. And they just scaled it with the scaling of the company. And the Elliot Shrag, who was the head of communications at Google at the time, was an ex policy.

And he, he went on to be a head of communications at Facebook and he had this weird idea that he was going to hire non traditionally trained PR people. And so all my best friends from back in the Google [00:06:00] Days who are now running communications all over the valley are lawyers policy people. And investor relations people who just came in and learned how to do communications.

You know, the head of financial communications became the head of IR at, at Google was um, uh, was a financial reporter. And so I just think there was a different training to people in that way and that encouraged people to think about communications differently. There's a lot of great communications people out in the world who, you know, didn't have that kind of training, worked in agencies and all that kind of stuff, but from a like really truly, you know, I like to joke seeing in the Matrix, you know, that seeing in the matrix where Neo.

 realizes he's the one and he sees everything in code. Like great coms, people see the world in code. Like they can look around and go like, oh, I know exactly what that is. And they can bend things to their will in that way. And, and, um, yeah. I just, I I just think that it's, it's a skill set that's honed from certain kinds of companies.

If you were at a Google or at a Facebook or Twitter and you're just like dealing with shit every single [00:07:00] day, you're gonna get good at that kind of stuff.

Brett: So I wanted to loop back on a couple things that you talked about in a second, but I, I wanted to kind of continue down this path of things that you're evangelical about as it relates to coms. So the first one is the idea, the sort of role of coms and how it sits on the exec table. What, what are some of the other things that you're just a deep believer in

Aaron: I think 99% of PR agencies provide little to no value to the companies that hire them. I, I, I wrote a blog post when I launched my little boutique consulting firm that I titled, no, you don't need to hire an agency. There are exceptions. I'm happy to talk about the many exceptions for when it really would benefit a founder or company to hire a PR firm, but for the most part, it is just you're just flushing good money after bad, and you find seven months into your contract with them that you've spent God, at that point, $30,000 a month, $210,000.

You haven't really accomplished much. [00:08:00] The CEO is constantly asking why they're not on the Today Show. You're getting these really long coverage reports that don't have your company in them. It's just, I don't understand the business model because every single company I talk to says the same thing to me, which is I'm really unhappy with my agency.

How is that possible? How can everybody be unhappy with their agency? Some agency asks their people have to be happy with. I know some of them that are very good, but they do niche things that are, and they do them very well. But I at Square, in the United States in particular, we never hired an agency period in my almost 10 years there.

And we went public without hiring an agency. 

Brett: What are the exceptions?

Aaron: I think there's a couple, right? Let's imagine you are a company who explodes, right? Like you are a 40 person company and suddenly you strike gold with product market fit and your consumer tech in particular, and suddenly everyone is calling you.

You know, sub stack is an example of a company like that. I think open sea. Was a company [00:09:00] like that about a year ago. Just like, boom. Everybody wants to talk to you and there's just no way you can scale with that. You go and you hire an agency to do that, right? Here's our messaging. You work with them, they block and tackle with reporters and help you prioritize and make the recommendations about what press is worth your time That's a totally legitimate reason to hire someone. Another one is, you know, the classic, uh, CEO co doing something horrendously bad and you have no expertise with the massive corporate disaster you're now in the middle of. Um, so you can hire a firm who knows how to help you navigate the release of that information and the weeks of fallout, right?

Totally legitimate reason Also, um, another one, this is when we hired agencies at Square. Uh, when you're expanding internationally and you don't quite know where you need full-time support, so you're starting in the uk. You're not sure if you need someone there full time, you might, someday you [00:10:00] can hire a firm to help you in a market.

Or even when you're a scaled international communications team, there are markets probably doesn't make sense for you to, to hire one person. So I love the, uh, mishmash of countries called like Ben Luxe. Like you probably don't need someone Belgium, another lens or Luxembourg. So you hire an agency that can handle those, those, uh, countries.

Um, and then the fourth one I think is vertical expertise, the best communications people have fantastic relationships with people across, you know, business press, tech press, national, local, that kind of stuff. But let's imagine you're in music, or you are acquiring something in a vertical that's brand new to you. You know, you need to know people at Variety, Hollywood Reporter, billboard board, all that kind of stuff. And so there are agencies that have that kind of expertise, right? If you asked me to go run communications at some Hollywood studio, I would fail miserably. I don't know anybody in that world, but you could hire somebody who does. So I'd say those are the main exceptions.

Brett: So if you are, an early product market fit company and you're scaling, maybe you're 30 [00:11:00] people or something like that, Your recommendation is not to have a PR firm in general and it, it, and other than, other than hiring your first comms person, we're gonna talk about early comms people in a second.

What, what's your advice to that person to, to do a DIY kind of approach until they hire their first person?

Aaron: Well, it depends on what you need. You don't put tactics first. This is not rocket science to say, just like any part of the business, you need to have objectives at the top. So I would ask you to ask yourself, what are my objectives? Am I about to fundraise and I need to get my story in front of the movers and shakers who are gonna give me money?

Did you just fundraise and you're trying to recruit and you need to get in front of engineers? Um, I hate communications as a tactic for customer acquisitions. This is why I don't think it should live within marketing. But are you really trying to drive awareness and downloads? So are you just trying to drive consumer…

Brett: Why do you, why do you [00:12:00] hate that? I'm super interested, particularly cuz I feel like anecdotally when you look at a bunch of the big consumer businesses like Airbnb, that long tail press and reporting and writing around the world was sort of a driver of their growth. But curious to hear more about it.

Aaron: It was definitely a driver. I'm not saying it doesn't help, but if you are reliant on communications for customer acquisition, your marketing team is broken, right? So let's imagine Airbnb has decided early on that they're gonna really double down on Chicago. What is the best way to drive usage in Chicago?

Is it, you know, you run ads against hotel search queries. I'm not a marketing person. Some marketing person listening's gonna say, these are terrible tactics. I apologize, But the, the point, the point stands, which is, do you, run campaigns showing some of the most beautiful, you know, high rise apartment buildings in Chicago.

Um, there are ways to create a direct conversation between Airbnb and the potential customer. I view communications as a [00:13:00] bank. Okay, so you're pitching the Chicago Tribune on this person who's, this is the early days, uh, rents out their guest room and that has helped them make rent when they lost their job.

Like that's just not the fastest, best, most direct way. And so I always think that if you're asking communications to carry the weight and driving customer acquisition, then your customer acquisition numbers aren't very good. And so communications is just a bandaid trying to get you to where you need to be.

And when communications ultimately A, either fails or B doesn't fail, but can't demonstrate, you know, the exact tie between the number of people who read the article and the Tribune or the Sun Times and then uh, rented an Airbnb, It's just not the best tactic, right? There are ways to measure success and communications, but asking them to drive customer adoption I always think is just a great way to be really unhappy with your comms team.

Brett: So, you mentioned this a little bit, but can you kind of force rank [00:14:00] good, jobs to be done for comms? If, if that's an example of sort of a bad job to be done.

Aaron: Yeah. I, uh, I think communications job is to inform and persuade the public. Now we can break the public up into different audiences, customers, the government, investors, but is to inform them about your company or, about you and persuade them to have a perspective about you and persuade them to think about you in a way that accomplishes your bigger picture goals. Right? So if you're an actor and you're trying to go from comedy to action films. this is why you see like Chris Pratt on the cover of Men's Health , right?

Like there's a tactic in support of your objective, and that is to persuade people that you are a viable [00:15:00] action movie star. And so with companies, it's the same thing, right? We'll, take Square as an example. Where I used to work our job was to inform people that we were more than just payments, right? At the early days, it was just, oh yeah, you're the cute card reader.

But they didn't know anything about the other stuff they were doing. So that's the inform side. And then persuade them. Persuade them that Square was a company that people would root for, that they were, not like traditional banks and actually cared about you and your experience with your finances.

And so I think about it as those two things. It's inform and persuade.

Brett: So maybe to take, take it in a slightly different direction or get at the idea in a slightly different way. Let's say you were to join a 30 person company in a comms role.

Aaron: Oh, I'd be terrible at it. They would hate, they would hate me.

Brett: Well, just as a thought exercise, we're in the realm of imagination. Um, and you showed up. What would your first few months look like?

What are the actual things that you would do with the team? Kind of going zero to one in a calm sense. They haven't really done anything. [00:16:00] Tech Crunch wrote about their series A and that's kind of the extent of comms in their mind.

Aaron: Well, I would hopefully take the job because at some point during the interview process, I came to understand the story of the thing, like the company. Right. Um, andI would probably try to manage their expectations that over the first three to six months, I would not be in any way trying to drive coverage.

I would spend six months trying to answer, to start three questions. Right. Which is, I realize it's a cliche, and it's a very bad communications cliche, but I really do subscribe to the belief that you should be able to describe things in a way that your grandparents would understand them. And so I would spend time trying to figure out a very pithy, clean, compelling answer to the question, what does this company do? Right? And then once I felt I had a good answer there, we'd move down to step two, which is, okay, how does the company do that? [00:17:00] Right? And now you're partnering with the pmms, you're partnering with other folks in the company who have, you know, head start on this to really clearly articulate now what we do and how we do it.

And then question three is, why do we do it? Which is ultimately the mission statement of the company in many ways, or the purpose statement, And so you're really trying to crystallize. Just clean, simple way of describing the company and answering those three questions, and that will give you 80% of the messaging you need for any interview you're going to be doing between call it series A and series B.

Right. You know, I work with a number of startups so much bigger than others, and with the small ones, that's the exercise really. We spend the first two months just getting the CEO founder to a place where they can just in their sleep, just barf out messaging that sounds clean and, and, and compelling and simple, and explains exactly what it is that they do, and doesn't use shitty buzz words that no one understands.

And that's it. That's, that's [00:18:00] half the battle.

Brett: And on that point, you, you just sort of mentioned this a little bit, but my guess is that if you're gonna spend two months to get to that, There's, there's a lot of hard work that's required to do this. Well describe the company so that effectively anyone could understand it and make it pithy and clean and simple.

And so what does that look like when it's done well? Can you maybe walk through some of your favorite examples of what great looks like and maybe what bad looks like?

Aaron: Well, to be clear, that's not the only thing you're doing in two months, so I don't wanna make it sound like there's, that's not other things that you're doing. Um, you know, you're also building relationships with reporters. You need to know and having a bunch of meetings internally, getting to meet your business partners across different teams, right? but you're, you're just sort of hearing the way other people in the company talk, right? They've been there before you, right? They've gone through, if you're at 30 comp people and they're hiring you, they have hit product market fit and had insights that you do not know.

And so I love reading customer case studies, right? I think sales [00:19:00] is such a useful, intelligence function for communications because they're talking to customers who say things to them like, oh my God, I fucking love you. I've never been able to accomplish X, and now I can. Right? That's always how startups start to really take off, especially B2B one s.

And so I love talking to those customers myself. A, it's super helpful cuz someday when you're pitching stories, it's going to require you to give reporters customer to talk to. So you're already building those relationships. But B, you're just hearing people who know how to speak about it passionately.

And that is, goes to the persuaded part, right? You're gonna be the best person at informing, you're gonna have all the information cuz you're in the company. But the persuasion that comes from like real belief in the thing that you're doing and getting people excited about it. I love starting there. Um, bad.

I think look, everybody thinks they can do communications, right? It's not rocket [00:20:00] science, but it's unique in so far as everybody thinks they can do it, right? I don't go to the finance team and see them building models in Excel and go like, fuck you, I can do this.

I don't go 

Brett: just go to the software engineers and just start ripping out some code

Aaron: no. Totally. Like, why are you coding it this way? but communications, everyone talks, everyone reads the news about their company and therefore everybody thinks they can do it. so being overly deferential to what some people think are, well, you have to communicate the value prop in this way, or, um, and this is the buzzword thing. It's just like technical speak that sells to customers is not the non-technical speak that sells to the public. Like imagine you're a security software startup company and you're talking about, I don't know anything that's backend infrastructure related to security and compliance.[00:21:00] 

Aaron: Okay. If you make a big billboard off of 80 in San Francisco, you might put all that stuff on it because you're trying to sell the product. But when you're talking to, you know, the Wall Street Journal about why they should care about your business, you can't go into that much detail or they're not gonna care.

Brett: Is there, is there an example of something you've worked on over the last handful of years that's like a clean articulation of, of a really good description?

 Square came out with a product called Square Capital, which was its first real non payments company product, right? It was advancing money to people and loans come with all sorts of fun, confusing language and requirements about APRs and payback periods and square reduced the message about Square Capital to the message about Square.

Aaron: Generally, everybody knew Square, right? Oh, it's [00:22:00] that thing. You plug it into your phone and you swipe a credit card and you sign with your finger, oh my God, what a clean distillation of, of why you would use it, right? I can take a credit card payment anywhere. And so We just did the same thing with loans. We said, while you're taking payments, you're gathering insights about your volume and payment activity, and we're able to know how to advance you just the right amount of money. And all you have to do is click okay and it appears in your account.

I mean, what a clean explanation. That has nothing to do with, you know, going to a bank and having to fill out applications and triplicate and then waiting six months and then only 33% of people who do that even get the loan in the first place. And we did all of this messaging secondarily, but the core message of Square Capital was, you know, you don't have to wait in line at a bank.

Were able to just basically give you an advance based on your usage of the product, period. I mean, it was just very simple and spoke even at its best to [00:23:00] the things that people already felt about Square, easy to use, beautiful, clean on my side, all of that kind of stuff.

Brett: What was the path into that? Was it just a number of internal conversations or, or was it immediately evident or like what, what was the process to land on that language to describe the product?

Aaron: Well, it's the same thing of that we talked about before, which is what is the product? Well, it's in advance that allows you to take capital and invest in your business. Okay? How do you do it? Right? And the how is very complicated, right? Where there's algorithms that, um, uh, are able to discern your payment volume and know your likelihood of being paid back, paying back in advance of this size.

You know, if we give you X dollars, it will take you six months to pay back. We give you y dollars, it will take you nine. And then we have the payments back to the loan come out [00:24:00] when people swipe their credit card with you. So when they spend a hundred dollars, we take the 2.75% that we usually take, but then we take a little bit more in order to pay back seamlessly over time.

So that way you're not paying a monthly payment fee. That's a really long answer, right? And it's how it works. But then you reduce it to something like every time you take a payment, a little bit goes towards your balance. we really tried to reduce it to something. I, this is just my mania on it, right?

I love editing docs. I love taking someone's statements or blog posts and cutting stuff from it, right? It's that great silly mark Twain quote. Um, I would've written you a shorter letter if I had had more time. My team would write blog posts and statements and I would hack them apart and I would say, this was great.

And they would say, how is it great? You just like cut it in half. But the point was we were just constantly reducing to something very simple. the person who looks at your blog post or your statement for you should be deleting, not [00:25:00] adding.

Brett: So you kind of outlined, describe what you do in an exceptionally simple, simple way. Um, why do you do what you do?

Aaron: Yeah. And then we didn't even get to that. We didn't even get to that part for capital, right? So why does Square make it so easy for you to get a loan? Well, we think most people are kept out of the financial system unfairly.

So many people rejected from taking credit cards. from getting loans. And we think that, uh, opening up access to the financial system for everybody is why we get up in the morning. So now you have your what, which can be basically any square product you have your how, which is a description of the simplicity with which it works.

And then you have the why, which is economic empowerment. And you just, you just do that over and over and over again.

Brett: And is that sort of how you think about balancing sort of a high level, uh, a high level mission or something that's not particularly functional on one end with the other end? Something that's like very functional and specific. So like functional would be, [00:26:00] we make it easy to accept credit cards. You couldn't do that.

sort of this higher order bit is, um, economic empowerment, because I often think throughout the course of the company, you tend to move in general from messaging that feels more functional to messaging, that feels more aspirational. You know, maybe Nike started out with like, you know, great performing athletic products and then it got, you know, we enable athletes to do X, Y, or Z, or you know, it's 

sort 

Aaron: a picture of Colin Kaepernick about racial

Brett: Exactly, exactly.

And so you kind of had this arc, but is this sort of simple three step framework a way that you're balancing those two at any given time?

Aaron: Yeah. It, it forces you to do both and you can see how those talking points allow a founder or anyone giving the interview to touch on things that inform you and persuade you about their company. my startup does X and It's been a really hard problem for people to do X and we do it by [00:27:00] doing y And the reason why we do it is because we care about Z. Right? It's, it's, you're able to do both and you're, you're bringing yourself up to the high level pitch of why people should care about you.

Right? So much of persuasion is making people want to root for you and liking you more than other, right. I think one reason Facebook can't convince anybody of anything in their positions, cause nobody wants to root for them. Right. So the, the balance between informing and persuading comes from your abilities to sort of tie all those different pieces together.

 So we were talking about kinda the first few months, three, six months, if you were to kind of build a calm strategy and begin to execute it when there was nothing there, what, what, what then happens after this? So you spend time, you've edited these things down and, and, and then,

Aaron: So why am I still working at the company after six months?

Brett: No, just once you go through these three things, you do it well, then. Then what is the work to be done?

Aaron: Yeah. [00:28:00] Well, and then it's a question of, again, objectives. Who should we be speaking to? What do those people need to hear? And building relationships with reporters who, a will understand what you're doing. B I won't say are sympathetic to your position 

But I mean, open to your ideas and might be personally interested in, um, your industry or have written things that make you think that they'll. Interested in what you do and you just start building relationships with them again. it's okay to just meet people and get to know them and build relationships with them.

There's a whole, you asked the question early on what are other things I freaking hate about communications and how it's done. I think there are hundreds of standard coms tactics that are just taken as gospel and that make no sense now if they ever did. And so I would encourage people to just go out and.

The reporters that might cover them. If you're a hardware company, give them a tour of your factory. If you're a consumer company, just take them [00:29:00] out to coffee and ask them about their interests. And hopefully you already know in advance that they like the thing that you do. If you're a, you know, you're a fitness company, go get the tech reporters for super into fitness apps, right?

If you're, um, if you're a pet company who gave the reporters that are constantly tweeting about their dogs, uh, and just build relationships with them, and then someday the fruits of those efforts will result in coverage. I think there's so much like brute force by bad coms people and, and the agencies that you hire in which you send an announcement of your news to a BCC list of folks within embargo time they didn't agree to, and you're like, here's our announcement.

It goes live tomorrow. And the reporters who get that are like, what the fuck is this ? And, and so many early stage companies think that's the way to do it, right? I just have to break through with volume. Right? You know, that's why reporters are constantly getting emails. It's like, hi, here's a bio of my executive.

They are capable of speaking to this thing that you wrote about this week. Would you like to interview them? No one's gonna respond to that email and [00:30:00] agencies are, you know, they're just playing a quantity game, not a quality game. And so my advice for the next few months is build relationships with these reporters.

It'll be way easier to get them to write about you when you know them.

Brett: Well, I want to come back to the reporter thing in just a second, but what are the other venues or outputs when you think about early stage coms? One is, um, you figure out what is the goal from a coverage perspective, and you execute on coverage, and we're gonna come back to that on a second. Are there other core tenants or, or, um, parts of what good coms looks like?

Aaron This is not 2012. This is not 2007. The idea that you can go get coverage of your company the way you might have years ago is over. Like so much has changed in the past, let's call it five to seven years, about how communications is done in tech perception [00:31:00] of the media, from certain tech executives perspective of tech companies from the media, I think we need to break folks of the idea that good coms is like, I got an article in TechCrunch and then I got an article in Fast Company and then I was on the list of the 10 most exciting, you know, founders in this area. And then we did an office tour, right?

We used to pitch office tours, right? Like, oh, check out our new office. And reporters would come and they would see like the food in the glass conference rooms and they'd write these swooning portraits. No one's writing those anymore. I can't believe we got away with them for so long.

But the expectation from some members of, let's call it the tech glitterati, that like the the press is super adversarial now because they won't write that shit. Like that's just not how it works anymore. So when you ask what good coms looks like, the answer is not always, I think what people would expect of a steady drumbeat of coverage about your company.

You're a series A company with. a couple thousand customers or God help us. And I [00:32:00] love B2B companies, right? I worked at a payments cash register company for crying loud, but B2B companies ain't getting impressed with any great frequency. And so you have to ask yourself what are my objectives?

And then start to think through nontraditional media relations, ways of accomplishing those objectives, right? Owns channels. Editorial, maybe you hire a content marketer or you have an influencer strategy. I think communications is so much broader now than it was 10 years ago when it was primarily thought of as media and public relations.

And so when you ask of what it good looks like, it's some multifaceted strategy that is informing and persuading people publicly in a way that's not just calling the reporters all the time.

Brett:  you talked a little bit about this in terms of nurturing reporter relationships, but let's say you have cleanly articulated what your goals are from a comms perspective and from wanting to engage with the press and you're starting to nurture relationships. What advice [00:33:00] do you have for people preparing for an actual interview with a reporter and for a founder CEO who, who hasn't spent much time with the press, maybe what are things to be mindful of or careful of, or maybe even How do you understand what the goals of a given reporter are and maybe how that maps into your strategy with engaging 

Aaron: Well, I think you have to find a balance between not sounding like some horrible robot, being authentic and interesting such that more people wanna talk to you, but then also, let's be honest, conveying your message. Right. Yeah. There's a great, um, Henry Kissinger quote, this will be the only time I positively quote Henry Kissinger, but he walked into a press conference and he said, I hope you have questions for my answers.

That is such a funny thing to say, and in many ways exactly right. Right. You have a message you wanna convey and you cannot allow the reporter to derail you from delivering your [00:34:00] message. That having been said, especially for early stage companies, which do not have the luxury of being a Mark Zuckerberg or an Elon Musk, where anybody will take any interview with them, you have to convey some value in talking to you.

And so it's a really hard balance between being yourself and being willing to talk about different things and being unguarded, but not. At the end of it, wondering why you did the interview cuz you did talk about the thing you wanted to talk about and so that's just practice, right? We talked about how everybody thinks they can do communications.

The greatest way to make a person humble in understanding of the unique role and and skills of communications is to make them give an interview and record them, and just then they listen to themselves back and they just think they're the worst.

I can't wait to listen to myself on this podcast. I'll just critique everything I said. And so you make people practice like crazy and that is just learning how to answer the question.

I really do believe you have to answer the question, but you don't always have to answer it exactly the way they want. You don't even have to answer [00:35:00] yes or no question if you're unwilling to say yes or no. But being authentic in how you do it is hard. And so the answer is practice.

Brett: And so you're a CEO of a 50 person company. What does that practice look like? You, you write up the questions you're most likely gonna get, you start with the points you wanna make. What does it actually look like?

Aaron: Well, you have your what, your how, your why, right? You should hopefully at this point have internalized how you talk about the company in its most basic form, right? 50% of questions about who you are, what you do, and why you do it. You can handle with your basics, but you get a friend if you don't have a comms person in the company to write a bunch of questions that they think you're gonna get, and you have them ask you them, and then you see how you did.

And if you like what you said, great. And if you didn't, Ask the question again and learn how to answer it in a way that you feel more comfortable with. It really is as simple as that. this does not require you to hire somebody for a $10,000 a day media training session, where at the end of it, you know, they spent six hours with [00:36:00] you.

 any founder, CEO who has six hours in one day to do a media training session is not focused on the right things. However, spending 30 minutes one on a Monday, doing a practice interview with somebody, and then 30 minutes on Thursday in the two hours before the meeting in the afternoon.

Aaron: Right? So you spent an hour practicing and going back and forth. That's, I'm, I'm not asking the world of, of founders. I'm just asking them to spend a little bit time thinking about how to do this. I mean, hard thing, right? Speaking publicly, speaking intelligently, trying to cut out your ums, making sure you answer the question well, how not to get trapped.

 these are skills they take practice.

Brett: You mentioned sort of not being overly robotic, or maybe not, not completely avoid every question, but are there other things to keep in mind if you haven't really done this before?[00:37:00] 

Aaron: I could give you a list of 50 things probably. I really think if we're talking about level one right. Zero to wanting how to be good at giving an interview, it's sounding like yourself and cutting out the corporate blah. It's very easy for you to retreat to the thing that makes you feel comfortable, especially if you're a technical founder.

Um, and to just go to the language that lives in your, you know, your roadmap or the product specs. I work with a, a CEO who, the advice I gave him was, you're a terrific interviewee if you are a product manager, but you're a ceo and you need to be able to speak at a little bit of a higher level. You need to be willing to opine on, on bigger picture topics.

You need to have opinions that makes people want to ask you questions. [00:38:00] So it's, it's, yes, not just being robotic, but also learning how to convey your message in a bigger picture way. Right? When you pitch a VC for funding, there are slides in that deck that are highly technical and there are slides that are super high level, the high level slides.

Those are your talking points.

Brett: Any thoughts on how to prepare for the handful of most difficult questions that if you're with a good reporter, they're always going to ask?

Aaron: You have to just hear yourself answer these questions to know what you're going to say. And I know that sounds really weird and sort of circular logic, but until you answer hard question, you have no idea what your answer to the hard question is. And after you've given it in your practice, you'll know whether it was good or not.

And so you should not be afraid of hard questions, right? if you're a security company, you're gonna get questions about privacy and data [00:39:00] and. Give an answer and decide whether you're comfortable with that quote being the only quote that they use of you, right? You have to know when you're on the record that literally any one sentence in your 30 minute interview can be the only sentence that they use.

So every sentence that comes outta your mouth better be one that you're comfortable with being put in quotes. And if you think that the reporter is gonna spend the majority of their time on harder questions with sticky answers, then you have to get really comfortable with those questions, right? At a certain point, you should be just as comfortable with a question of how did you found your company as, what do you do with the data?

It just has to become second nature to you.

Brett: How about any thoughts on navigating topics around competitors and do's and don'ts in that line of questioning

Aaron: Well, it depends on your size. Obviously there's the obvious answer of we don't talk about our competitors. Yes, you [00:40:00] do. Uh, I think, I think the answer really is don't shoot down. There's absolutely nothing wrong with shooting up. If you think your competitor is a bigger company or a unicorn and you think you do better than how they do it, do talk about your competitors all day.

 You know how many articles we read about Square that said PayPal releases, its square killer Amazon releases. Its square killer Google working on its square killer. Right. We had no problems just saying like, sure, Amazon thinks they can build hardware. This was the early two thousands before.

Aaron: Before they actually did start building hardware, or you know, we said PayPal customers hate PayPal. So if PayPal customers think that they would benefit from taking payments with PayPal and having their money held like it always is, sure, use the PayPal product, right? There's nothing wrong with being punchy up, but the key is don't punch down.

The problem is when your startup becomes somewhat successful and then even smaller companies start to pick at you. And those are the ones that I think aren't worth your time addressing.

Brett: What did you think of the Slack full page ad to Microsoft?

Aaron: I hated it.

Brett: Why is that?[00:41:00] 

Aaron: Oh, it was so cliched. It was, it's so obviously just a rip off of what Apple did years ago and there's nothing original in it, and so many other people have done versions of it. There had to have been a better answer.

Brett: so sort of on this theme of reporters for, for founders or maybe technical founders who haven't spent a lot of time with reporters, how would you articulate the goals of a reporter given your experience working with so many over the last decade plus? Right. I think it's always helpful to understand what someone's objectives are.

And so, you know, a salesperson's objective is to exceed quota. You know, you can go down the list of different roles, different companies, and what people are trying to. And maybe it's too hard of a question to sort of answer in the generic, but can you give a founder just sort of a sense of, of what the average reporter they might engage with actually cares about and what are their motivations?

Aaron: yes. I will give you a silly version of this answer, which is I think the job [00:42:00] of a reporter is to please their editor. I hope some reporter friend of mine is listening to this and can tell me whether or not they agree with that, but they have a boss. Just as you, an engineer has a boss and just as a comms person has a boss a reporter has a boss, and that reporter's boss is the editor whose job it is to decide what is interesting in the newspaper.

And so I think this is a big misunderstanding today of. In how, expectations are that tech reporters should write these glowing pieces about the cool things that are being built in Silicon Valley If they take that to the editor, the editor's gonna go, why do I care?

How is this relevant to what people care about today? 

That's just truly the M.O. of the editors, to make sure that it is speaking to something newsworthy, relevant, potentially controversial, counterintuitive trend identifying. The editor is the decision maker. And so you have to give reporters something that their editor will go, you know, that is worth you spending [00:43:00] your time on, right?

Cause editors are asking reporters to prioritize the many stories they could write just as your boss is asking you to prioritize the 50 different projects on your plate. so if you're a tech reporter and you are covering social media companies, some series a startup is probably not gonna hit their radar.

And if they are gonna write about them, it has to be relevant to something much bigger picture than here's this cool new thing that we did and here's, uh, the customers that are using it that love us. And I know, again, that we would love a world in which those stories get covered like they used to when you and I were young , but they don't anymore.

And I think that's okay. You just have to learn how to evolve, which is why I'm a big believer again, as we talked about the own channel. Are a humongous part of a communication team strategy and need to be thought of as just as good in many ways, as as landing press. Because if your objective is to reach an audience, you can do that via article, but you can also do that via a Facebook post, a podcast, a Twitter space.

Anything really.[00:44:00] 

Brett: So, switching gears a little bit, we, we started the first portion of the conversation talking a little bit about if you were the, the fictitious kind of first comms person. Um, what about if we reverse the line of questioning and, you know, you're 50 70, you know, we can talk about maybe even what stage or company maturity makes the most sense, and you're gonna hire your first in-house comms person.

What, what coaching would you give to a founder that's about to do that? Maybe we could start with like the when and then move to kind of the what.

Aaron: So the when is hard. There's a moment in time where it makes sense, but it's largely dependent on the kind of company you are. So a company like, let's take Clubhouse, right? One of these companies that exploded and was probably 20 to 30 people when they were being written about all the time, right? So you're either hiring an agency to block and tackle for you, or investing in somebody [00:45:00] to be proactive in getting your story out in a way that is not just.

Taking what has been given to you from reporters who are interested in interviewing you. Right? So maybe it makes sense for a clubhouse at 2030 people to hire a comms person if you're a really awesome, successful B2B SaaS company that could be a hundred people, 200 people. Um, and I think it becomes a point where, uh, you realize that your communications goals are best served by people who do have writing and media relations skills, right?

I, I talked to a number of companies, like I said, I, I have the small communications consultancy and I've said to founders, you don't need me. You need a writer and a social person and an SEO person, , and you need to build a whole giant library of content and have it all lovely optimized. That way people searching for expertise find.

Your content [00:46:00] and point of view right now, I think that could live within communications, but when you ask, when should you hire a communications person? I don't think most founders think about hiring somebody called editorial director, right? They think about public relations. They think about somebody who has, you know, their title as communications manager or something.

And so it really is a moment in time in which the skills of the best communications people start to provide value beyond what a content marketing person can provide or a social person can provide. So it's, it's, this is a really unsatisfying answer I know, because there is no hard and fast rule, I'd say consumer companies earlier than SAS or B2B companies, is the general rule of thumb though.

Brett: And then, so moving past sort of the question of, of when, how do you think about the first hire or first couple hires and maybe how, you know, I assume you're gonna sort of map it back to, well, you have to start with what are the goals in sort of this area of comms.

Aaron: Well, I, I'll, I'll say it this way. I [00:47:00] think your first comms hire more than anything is an archeologist. They are digging for stuff in your organization, right? Imagine you're in their shoes, right? You're the first communications person. People don't really know what it is that you do. Uh, you probably had an agency on staff already that this communications person has to figure out how to manage, how to make the best use of, or get rid of.

And that person has to, on their own, find the stories in the company. That person needs to go talk to customers. That person needs to talk to marketing. That person needs to talk to product and look at the roadmap for the next 12 months and say, I know you all think that launch in.

Is the most important story for us. I think that's the most important launch for the business. But I think the most important story is the product feature you're launching in May, right? Like you're, uh, you're assessing an issue, spotting, as we talked about before, and just trying to surface stuff. And then I'm gonna keep going with my silly archeology metaphor.

And then you find a piece over here and a piece over here, and you have to decide if those two [00:48:00] pieces fit together and if they don't, whether you're missing another thing that will make it fit together. And you just have to be really industrious. And so I am constantly interviewing first comms hires for the things that I think industrious people are really good at, which is curiosity, intellectual horsepower.

Um, they can sort of spot patterns. Um, and yes, also tactically they need to have. Media relationships and they have to be excellent writers. But I am looking first and foremost for a person who by themself with no help or support in an organization that probably doesn't even really know what they do with a boss that isn't a communications person can still be successful.

Brett: building on that outline of, of what you want the person to do, how does that map to how you think about interviewing that person? What should I be doing in an interview process to make a high quality decision on on this first hire?

Aaron: So the funny thing is the thing that I have religion on, which is that communications report to the CEO is lovely. . [00:49:00] And most important, when you are building a larger organization with a, more developed leadership team, in the early days, a CEO probably has 50 other things that they need to worry about than the six to eight years experience communications person that they hired.

So it is totally fine for you to not put the communications person reporting to you in the early days, but the long term plan should be for that person to report and to the CEO when you have a robust enough leadership team. So putting that aside, whoever is interviewing this person, I, I interview for a couple things.

I interview and ask questions that are really trying to get at like how people think. I love hypotheticals. That's probably the law school background of mine where I just throw people random things and I see how they think through them. So I was interviewing an internal communications candidate, and the hypothetical I used was, um, imagine, uh, A bunch of people start a internal wine [00:50:00] tasting club and they start it on Fridays at 3:00 PM And I assume you have no problem with that, right? And the internal com person says, no, of course not. Okay. Now let's imagine that a month later, the, uh, weed smoking group starts and they say, we wanna smoke different kinds of weed because weed is legal in California now and we wanna do that at 3:00 PM on Thursday.

Do you have problems with that? And it's weird to ask an internal comms person that question because I think it is an internal comms problem because either the company says, I mean, your first instinct is probably no, you can't smoke weed at work at 3:00 PM To which I would say, why not? You're letting people drink at 3:00 PM How is that different?

And there's no right answer to that question, but watching the person navigate sort of the intricacies of the hypothetical, to me is super eye opening in how they solve problems. I'm [00:51:00] sure it's probably a little bit scary, but I, I try to make it a very comfortable environment where I, I admit that there is no right answer to this question.

I just wanna hear how this person thinks, and I want them to be curious about the problem and I just, I think that is such a great way of identifying the best sort of early stage comms people, because they are, as an archeologist, they're constantly digging and trying to solve problems on their own.

They're gonna find things that are unusual. 

Brett: How would you answer the question

Aaron: Oh, I think it's totally fine for them to smoke weed as long as they do it outside.

Brett: physically outside.

Aaron: physically outside, it's hard. I mean, it's hard to justify in an age where both marijuana and alcohol are legal.

It's a hard question, which is why I like it.

Aaron: The other one I use, uh, for internal college people was same sort of thing. Uh, a bunch of internal, um, social groups are forming and one group forms the skiing club. And on uh, weekends in the winter they go skiing together and they talk about skis and their favorite kinds of skis or their favorite kind of [00:52:00] snowboards or the best mountains in gear.

And then another group comes up and they say, Hey, you know, we're gonna start the automatic weapons. Weekend shooting group, and they post photos of them holding ar fifteens and shooting at shooting ranges and some employee reports that that channel and the content in it makes them really uncomfortable.

What do you do,

Brett: And what's your answer there?

Aaron: Oh, I don't know. It's more complicated than I think we have time for. We could do the entire podcast on that question.

Brett: That's a good way to deflect. I, I really admire that

Aaron: Thanks. well, I'm a communications person, but again, what's the point of that question? It's just to watch someone, the people who work with me would say, I just like watching them sweat, but it's not that, I just wanna see someone problem solve.

And for me, in communications, that's the way to do it. The way, you know, engineers will hand another engineer a, a dry erase pen and send them to a whiteboard for communications. There's no [00:53:00] way to really do that. And so I like testing them in that way.

Brett: So it's a good pivot point as we kind get into the back part of our conversation and talk a little bit about internal coms, which, which we haven't gone very deep on yet. And so I, I, I'd be interested to hear how do you define internal coms? done well and then kind of have a bunch of other questions that kind of come to mind for me.

Aaron: I think internal communications, like communications is, again, two things. It's inform and persuade, but the question is, what are you persuading employees about? Well, you're persuading them that the company is healthy, that the company is doing well, that they enjoy working there, that your benefits are good, that um, it's worth them having to stay late for this crazy launch, that they want to persuade other people to come work with them.

Right? And so it's the same thing, right? You're informing people about the goings on at the company, the roadmap, uh, this is why internal comms functions often have speakers, series and q and as with executives and, and so on the informed side, you're making sure that employees know what is going on in their own company, on their persuade side, [00:54:00] you're trying to get them to think something.

The company that builds culture and is consistent with your values.

Brett: And so what are the key touch points or the tools in the tool belt in the realm of internal comms?

Aaron: I often think about internal comms into parts, right? So if you think about it as inform and persuade, in a scaled internal comms team probably has a comms or corporate communications function. And what I would probably call a marketing function. Corporate communications is, uh, in January we are launching our performance review cycle.

It will be at the same time as our compensation review. Here are the next steps, and here's what we expect of you, the managers. That's, you know, corporate communications informing, making sure everybody has the information that they need. The marketing side is the speaker series that we're doing that gets people really excited and we'll bring a board member in who's really interesting to take questions.

And we will have [00:55:00] the following campaign over the month of October, around Halloween. And, we'll have a costume competition. I know that that stuff is all very corny and silly, but it, there is an element of like, making people have fun at work.

And, uh, I really do believe you should have fun at work. And I think the internal communications team plays a big part in that.

Brett: What's your thinking on when a CEO and or leadership team should comment on something that is happening in the world that is not directly related to the company or the mission of the company?

Aaron: I think this is so fascinating and hard right now, Like there is a dissertation to be written about how as increasingly dysfunctional American government gets and its inability to solve problems, the populace, as they might say, are demanding other solve problems for them.

And so if you're an idealistic 24 year old in [00:56:00] tech, and let's be honest, people do join to do something good and to make positive changes in the world. And that is noble and I, I actually am at my heart like a tech optimist and enthusiast.

And so if you are in that place in your life and you see major problems that you believe are being unresolved, but you think the company at which you work can actually influence that publicly, hell yeah, you're gonna pound the table and demand that your company speak out. And I totally understand that.

I was, in addition to being the head of comms at Square, I was also. Totally randomly for several years ahead of people. And so I came to realize the overlaps between those two functions in call it 2020, were also fundamentally changing the relationship between employees and their companies and the nature of internal communications.

So to actually answer your very hard question, which I've stalled to until now, yeah, it's, this is a flavor thing. This is entirely a taste. Some CEOs like, you know, mark Benioff, wanna [00:57:00] be out there publicly saying exactly what they think and some CEOs absolutely do not. And some CEOs at companies can get away with that and some can't.

And I think it's honestly a personal decision. It's really hard to tell someone what the right answer here is. I think you are inevitably going to disappoint somebody. You either don't speak out publicly and you disappoint the employees who think you should, or you get put in a.

Roundup and buzzfeed of companies that refuse to comment on a anti-trans bill in North Carolina. And that sucks. Or you do speak out and you know, you run the risk that you become a less attractive company. People don't wanna be associated with controversy. The Governor of Florida decides to punish you.

I mean, it's just super complicated now

Brett: So in this realm of internal comms, how do you know if you’re doing a good job? 

Aaron: Uh, I guess the question is how do [00:58:00] you wanna measure success? I, I think, um, I think attrition is a good answer, but that's not necessarily a reflection of internal communications, like the market and the collapse of stock will cause people to leave. 

Um, I think trustworthiness, I think you can get a sense in the slack channels of your company, whether people are happy with leadership. And I think there are questions you can put in a pulse survey that get at the general sentiment of people. I, I think one really great question, that you can put in a pulse score that can get at this, which is something like, um, I can express a contradictory opinion and feel I have been heard. That's really all you can ask for, right? You know, I don't think that the product roadmap makes sense on X and Y, but I'm willing to disagree and commit, right? If people feel comfortable with that, you have a really healthy company actually.

Brett: A couple of [00:59:00] things on internal comms. What, what advice do you have for CEOs who are sharing tough news or negative news with their team? How to do it? Well, it could be. Something like a layoff. It could be a key executive is leaving sort of anything that's just negative. What are the things to keep in mind when you're, when you're communicating that internally? 

Aaron: You have to tell the truth. If you treat employees like adults, for the most part, they will behave like them. So tell them the truth. Tell them the background for the decision you made. When you have to do layoffs, tell them Here are are the things that led us to here.

We invested in X, we invested in Y. The market is showing us because of the volatility that we cannot sustain it at that present rate of growth. Unfortunately, that means we have to part with members of our team. This is completely my fault as the CEO because I call the shots, but that doesn't mean I'm not still going to have to make this really hard and difficult decision.

And I feel bad about it [01:00:00] but I hope people can understand that like we're running a business and we do our best with the information that we have. And in good times we hire like crazy and give you all raises.

And in bad times when we make mistakes, we. That's a, I'm not saying that that's like a great answer, but that is, that's real. That is giving people context and treating them like adults and giving them information and treating them well on the way out. And you know what? Because of that, we're giving you six months Cobra and we're letting you vest your stock even if you're unvested.

And, um, we're gonna let you keep your computers and, you know, just ways that show that you're a human. Just be a human. And this is actually, I'm gonna tie this back to why I think communications leaders should be on the executive team. Someone in the room needs to tell people when their ideas are bad. So like the CEO of better.com, there's, this is a sequence of real headlines.

Something like the better.com CEO laid off a year ago, [01:01:00] like, and I know the number 900 employees and the reason I know the number is cuz the headline for the article I read was better.com CEO lays off 900 employees over Zoom. That like somebody had to say, Hey, you know, putting all 900 people into a Zoom meeting and laying them off as a group is a really shitty idea and very bad for our company. Its reputation and you the ceo.

Brett: so to wrap up, we would love to sort of chat about one of my favorite topics, which is when, when you think back kind of in, it could be an internal comms orientation, external sort of however you wanna define it. Who is the person or the couple people that have had the, an outsized impact on, on how you think about the role or imparted something that was profoundly useful to

Aaron: well, one person that comes to mind immediately is the CFO of Square. For many of the years I was there with Sarah Fry, she's now the CEO of Nextdoor and I remember. I got promoted to the executive team in January, 2015. [01:02:00] I'd been at the company as the head of corporate communications for three

years and my boss left and Jack decided to break up what was a large communications and marketing team called Brand into separate functions.

And he decided the communications should report directly to him on this, on the staff team. And I felt like I was the oldest kid at Thanksgiving. You know, I could sit at the kids' table and I could sit at the adults' table, I could talk with the adults and I could also like throw food with my cousins.

And I had credibility at both tables, right? The adult table cuz I had worked with these very senior people forever as their head of communications And then, you know, the kids meaning everybody else in the company because they knew I was one of them. And I came into the leadership team, you know, room and had no idea really what my role was beyond being the head of comms at the time.

And a couple months in, Sarah said to me, you know, you only really speak up on communications related issues, [01:03:00] and that's not why you're here. You know, you think you're just representing the communications function. You're not leadership team of companies are people who have to represent the company and be willing to speak out on things, you know, respectfully outside of their lane.

And she says, I've worked with you for years. You've never been afraid to give feedback to, to her, to other execs, to jack the ceo. Um, you know, I've been through so many fires. She's like, I want to hear your thoughts on topics that you don't think you have decision making authority over, because it's not about that, right?

There is a discussion and then a decision maker makes a. And I want you to be in those discussions. And that was just so liberating for me. It's very silly to be a straight white guy and feel like you have imposter syndrome. But I was in that room looking at Sarah Fryer and Jackie Reeses and Jack Dorsey and Goel Raro and Jessie Douser and Franos Broker, like, I'm forgetting names here, but these are people who [01:04:00] worked at Facebook or GOCO invented ads.

Jesse, like all the hardware at Apple for Steve Jobs, the iPhone, he was, you know, working on. And, and these were just humongous people. And the fact that Sarah and others wanted to hear my perspective really changed me. And as long as you as a, as you do that in a way where you acknowledge that you are not going to be the decision maker because it is not your area of ownership, that's fine. Disagree and commit. It's a beautiful thing. 

Brett: Well, thank you so much for this wide ranging conversation. I really enjoyed it. and particularly, I actually think in the realm of comm. There's infinite amount of stuff on product, infinite amount of stuff on general management, infinite amount of stuff on, on scaling businesses, but not sort of in this specific dimension. So it's always, it's always nice to get to explore those topics.

Aaron: I, I wrote this silly post years ago about the, the communications clock, how narratives are forced on the companies by the press. And it is, it, it [01:05:00] is, it still gets so many hits on medium and I still see it randomly tweeted about, and I think that's because there's not a lot of people who are writing and or talking about communications almost academically.

 And that's why I find it really interesting and I write some of the things that I do and why I was absolutely happy to come talk to you about it.

Brett: Thank you. Thank you.