Carolyn Penner on Fearlessness & How Founders Should Approach Comms

Carolyn Penner is one of the most sought-after comms consultants for a reason. The Mixing Board community member has only worked for interesting companies in interesting moments. She joined Google in 2007 and then became Twitter’s second comms hire as head of product comms (hired by Mixing Board founder Sean Garrett). She parlayed the trust she built at Twitter into running marketing and comms for Vine (RIP), and then later ran North American comms for Dyson. Along the way, Carolyn has created a well-deserved reputation for being both a savvy strategist who gets great results and someone who deeply understands the ins and outs of a product at least as well as most product managers.

Here are excerpts from this Mixing Board Studio Session between Carolyn and Sean. The two talk about why press doesn’t solve everything, trying new platforms and getting comms people on boards of directors.

SG: What is the common thread to that first conversation you have with a founder?

CP: Most conversations start in one of two ways. It’s either, “I’m launching a product and/or announcing a round of funding for the first time and want to make sure we get a lot of coverage.” Sometimes there’s specific publications referenced, but usually they come to me with a very specific goal in mind of how they want their launch to go, and they want help making that dream a reality, usually in a matter of days.

Or they come to me through a lens of product positioning, product marketing and messaging — when a product is new, or a product has been out on the market for some time, but we just haven’t really figured out how to talk about it yet. We’re getting to a stage of growth where we need to wrap our hands around that a bit more.

I’d say in both instances, it’s very common for there to be a really tight timeline of a week or two of, “can you get this done for us really, really fast?”

SG: What do you tell them? And which conversation do you like having more? The one about the positioning or the one about the sudden news?

CP: It depends a lot on the person, the company and the product. Products that can get instant coverage are increasingly rare given the media environment. They tend to sit in a very specific category — it’s a consumer product, it’s tech, it’s probably built by a founder who’s already had some success, it probably very directly competes with the existing player who’s getting a lot of coverage. If you’ve checked all those boxes, you can possibly launch by next Thursday and get coverage. That’s such a rare beast.

I prefer the second type of conversation because at a minimum, the deadline is arbitrary and you’ve come this far without having what you need and you’re still kicking. You’re doing alright, so let’s go through this process of getting you a good story, of getting you a good message, of getting you good positioning that can really sustain you over the next year or two. With early stage companies especially, it’s hard to see past even a quarter. But let’s do it right, and to do it right, it’s going to take time. That’s usually an easier conversation. With launches, it’s harder. Sometimes that toothpaste is already out of the tube, “We’ve already told our investors and we’ve told our company and this launch date cannot move.”

SG: What is wrong with these people who put in years of work and then they’re like, “Oh yeah, let’s go get a PR monkey to get us some stories.”?

CP: It’s a handful of challenges. One is that a lot of founders have worked in a company that’s cool. They’ve worked at Uber, Twitter, Facebook, Stripe, Square — the list goes on. They’ve been an engineer, they’ve been a PM, they’ve been a leader in these companies and they’ve seen and felt what it means to work in a company like that. And they’re like, “Oh, I want that for my company.” What they don’t understand is that the world looked really different when they worked at that company five years ago, eight years ago, 12 years ago. On top of that, I love this about founders, they have to believe that what they’re building is the coolest thing in the world. They are literally dedicating their life to it and it’s part of what allows them to do the thing that they do. And they’re surrounded by people who have a similar belief, whether it’s investors or advisors or colleagues. The people who are the closest to their circle are like, “What you are building is so fucking cool.”

It’s a weird conversation because they come to me with, “Hey, what I’m building is really cool. Can you just help me make sure the rest of the world knows about that through press coverage?” There’s a double conversation that has to happen, which is first, “Let’s talk about whether your company is really cool to the outside world.” Second is, “Based on that answer, whether it is or isn’t, let’s figure out what you can do to really get the most out of this moment that you’re creating.”

I will say too, there is a false belief that the only way to have a good launch is to get a lot of coverage. That coverage and getting on Techmeme… that used to be the key metric. When I worked at Google, it was, ‘oh, this mobile feature launch is only on the additional news section of Techmeme — that’s too bad, you didn’t do as well as you could have. Two weeks ago, we were at the top of Techmeme for announcing Chrome.’

SG: How do you reshape that perspective on a launch? The common theme of why people are coming to you — they’re either preparing for a big moment or they’re having a big moment, right? There’s some imperative, there’s some time sensitivity, they feel it’s this huge thing everyone’s been zeroing in on. There’s a countdown clock somewhere either mentally or physically. What’s helpful about that and what’s damaging about that?

CP: A lot of these conversations, as you know, become like therapy. Just being able to have a really honest conversation about where there is wiggle room. Are you willing to push this launch date back? Is press coverage super important to you? Basically, what are the non-negotiables of the launch and what of those things are within our control or not? Because press coverage is very outside of one’s control. As comms people, we do the best we can to shape a story but at the end of the day, a reporter is going to write what they’re going to write. Their timing might shift because of other priorities, they might think that they’re going to be able to work on a story next Tuesday and then all of a sudden something happens in the world, which is increasingly common. It’s helpful at the get-go to get a sense of how realistic this founder is and what is achievable.

What’s challenging is, there’s very little understanding around how much time it takes to do communications work well. Messaging takes a ton of time, it takes a lot of iterations. It takes writing, walking away from a computer, sitting with it, thinking about it, coming back to it, deleting everything you’ve written, rewriting it again. Even getting to the state of being able to write something, takes a lot of deep conversations with the founder around, “What is this? What are you building? Why?”

The questions that have been answered in the conversations a founder has had up until the launch, are usually very investor focused or recruiting focused, which is this business narrative of, “We’re going to build a big business.” That’s just not a narrative that journalists and consumers tend to be interested in. They want to hear about companies and products that are going to be useful to them, that are going to be additive in a crowded world of products. A big business does not mean a big press announcement.

SG: If you had a red button that you could press and it would teach one concept to founders and investors prior to hiring comms folks like yourself, what’s the one thing that they would suddenly understand?

CP: Founders should find an ally in a communications, product marketing, brand person really early on. Make them an advisor, bring them on as an investor who’s heavily involved. The sooner founders can start having conversations around the realities of this work, the better. Investors should say, “Hey, we’ve invested in your company now. Part of our thing is we set you up with advisors who know about the areas that you’re not familiar with. Over the next year you and your engineers and designers are going to be building, but we think it’s really useful if you have a — even if it’s just a one hour, once a quarter or once a month — check-in.” There’s a lot of value that can be had there. You’re always building the rocket while flying it with a startup. But it’s really hard to simultaneously try to wrap your head around what communications is before you need it. What would your red button be?

SG: It gets so reductive when it comes to the desire for press coverage. The question I always ask is, “You guys seem to be doing perfectly well, why do you need this? What is it going to do for you?” It forces people to have this conversation, think about it and take a beat and step back. And certainly you get the BS answers that are really wrapped in ego. But, at the end of the day, for a lot of companies, it’s, “We’re trying to hire a VP of engineering, we need to improve our internal morale, we want partners to take us more seriously.” And then you say, “Well, if you’re trying to hire people or improve your internal morale, for example, are there better ways you can go about doing that other than simply press?”

Media coverage may be part of the solution, but it becomes this weirdly lazy mechanism that allegedly solves for so many different things. It becomes a silver bullet that the PR person is going to solve for, which, btw, the founder has so far given zero investment, zero time and zero space for. But now they are going to reach out to a stranger and expect in two weeks that hiring problems and internal culture issues will be solved by outside validation? Oh, and also, it’s going to set the company up for its Series B?

Ironically, a definition of good comms is helping do all of the above — once armed with thoughtfulness and time — and perhaps without any press coverage at all.

So my red button is, not considering press as a shortcut to solving near term problems.

CP: Too often, companies wait until there’s a problem or an urgent need to reach out to comms people. Companies need to approach communications with a long-term view — just as they would other parts of the business. You wouldn’t expect other core parts of the business to come together in two weeks. The same approach should carry over to how you bring a product and company to the world. And similarly you don’t need to do it all at once. In fact, rushing out press can do more harm than good if the product isn’t ready or the narrative isn’t there or the time isn’t right. And the best use of a strategic communications person’s time is probably not going to be going out and getting coverage. A really good communications person can help solve for some of those other problems through other types of suggestions. As a consultant, what I look for is a founder open to other solutions to those problems. Or are they fully convinced that there is no other option other than pieces of press coverage? That reveals a lot about what it’s like to work with that person and how rigid they are. They’re talking about a space that they don’t understand, but they also have a strong belief in what they think is the right path? That’s a red flag.

SG: Let’s talk about another reason why people reach out. You’ve mentioned this a little bit, but funding news. And personally, I feel like funding announcements are the most nutrient-free form of tech communications. There’s so much of it, so little of it is helpful. There’s a high expectation that every company has, that their moment is special. But the actual news and content of these announcements are so limited. It’s just about raising dollars. What’s a good funding announcement? How do you think about funding announcements?

CP: Funding announcements are interesting from the business context of where dollars are going. For a company that is early in its life cycle, sometimes that announcement can be the hook that is needed for the company to be able to have a moment. Good funding announcements though, use the announcement to support a broader story, rather than having the funding announcement be the thing. So if it’s possible, don’t announce your funding until you’ve announced your product. And when you announce your product, you say, “We’re announcing our product, this is what it is, this is why you’re going to love it. By the way, huge thanks to our investors who have collectively given us the money to be able to build this thing and get us where we’re going.”

SG: The funding becomes the proof point, but not the point.

CP: In the same way that you would also mention, if you’re a B2B company, you might mention a couple of key early customers, “If you think of yourself like these companies, maybe you want to check out our product.” That’s the ideal from a launch. When you start getting into a Series B, even a Series A, type of round, the funding announcement just becomes part of a broader momentum story. If the last coverage of your company was about your Series A and there’s nothing about you until you’re a Series B, it’s probably worth waiting to talk about your Series B until you have something else to talk about. Because otherwise, you’re just talking about funding in a vacuum, and it’s not terribly interesting.

As someone who’s worked at companies that have been in the spotlight or under a magnifying glass, there can be this belief that once you announce it, it has to be confidential. Sometimes companies will say, “Oh, well, we’ve done the Series B and we want to be able to talk about it with people we’re trying to recruit. We want to let them know we’ve got enough money in the bank, we’re going to sustain and last.” You should totally tell people you’re trying to recruit that you’ve raised that money and done that round. If they turn around and take it to a reporter or tweet it out, weird, but not a big deal. That shouldn’t be a big deal. It’s not a leak risk. You should be able to talk about it and have conversations about it. You should talk about it with prospective customers, you should talk about it with hires and if it gets out, then that’s an indication that your company is actually pretty interesting.

SG: The irony is that that’s probably actually the best way to get coverage for a funding round.

CP: If you’re holding back the announcement in service of waiting for a different announcement to talk about, you’ve still got the other announcement that you’re talking about. If the funding gets out before then you’re okay, you’re going to just reinforce it in your own message. A lot of founders have worked at a company where they’ve learned this type of stuff. There’s this learned behavior of, “If it’s not on our blog, it’s fully confidential and cannot be discussed.” That is the case at such a small number of companies.

SG: You are now an experienced hand. When you burst onto the scene at Google in 2007, it was the year that the iPhone came out. And shit’s changed. From being a college graduate coming into Google to 2021, you’ve seen quite a lot. In your eyes, what has shifted in comms? What’s changed? What do people not really recognize about that change that they need to understand?

CP: There’s definitely conversation within certain tech circles around the appetite and optimism for tech companies. In those glory days of tech press, where tech publications wrote fairly positive stories about tech companies, the industry was new and everyone was in it together. Tech blogs were less crucial, as far as publications go. The senior people at Google were the ones who talked to The New York Times, USA Today and the L.A. Times. It was the junior people like me who were allowed to talk to Gizmodo and Engadget and some other mobile blogs that don’t exist today or have been folded into other things. That’s a huge change. The entire industry was new. And at the time the approaches to making money weren’t focused on the usage of data and privacy. Because advertising itself was still in its early days and targeting technology wasn’t as advanced.Those things have changed.

Another thing that’s very different is the expectations that consumers have of the brands and the companies that build or make the products that they use. That you make a product that people love is awesome, but the more people love your product the more they expect from you. From participating in social conversation and political conversations, being vocal about support of real issues around women going back to work after having a baby, supporting people as they’re trying to form families and really supporting the whole person. That conversation started from a brand standpoint of, “Change your avatar on social media.” It’s really evolved in the last couple of years. This ties back to the funding stuff but, you have all this money, what are you doing with it except having it? The more successful a company is, the more the consumer and the employee demands of them. These are hard questions. But a lot of companies don’t spend time talking through and thinking about the extent to which they want to participate in those conversations and the resources they want to invest in them.

SG: How has the role of a comms person changed since you started?

CP: You have to be much more mindful of that stuff and companies are looking to comms people to make decisions on social issues, for example. It might feel obvious to change your profile picture on social media or post a photo of a black square on Instagram, “Well, everyone else is doing this. We should be too.” If the only activity you’re doing to support black people is post a photo of a black box on your Instagram, you’re totally missing the mark and not at all doing enough. Those movements from a superficial level, actually do more harm than good. In particular for the audiences that need the support.

I’m fortunate to have started at Google because the comms team was already massive and very good. I learned from very skilled people. That was part of the role even in 2007, but it’s become even more of an active part of the day-to-day. Being mindful from an internal communication standpoint too, a lot of shit is happening in the world these days. When the entire company is heads down in the work, sometimes founders don’t even know what’s gone on. They don’t know the Capitol was stormed.

SG: It’s what’s going on, both outside the company and around it in society but also inside the company. Can you tell me where comms fits into a listening role, both externally and internally.

CP: As my years have continued in this role, I have found internal communications to be almost more important than external. It’s a leading indicator of what your external narrative is. If your employees are hyped and they love the problems that they’re solving and working on, and they’re feeling really good about it… chances are, you’ll probably be able to tell a more compelling external story. Similarly, if the team is disgruntled and feels like you’re spinning a story in the outside world that doesn’t line up with what the employees are feeling, people will pick up on that eventually. It might take some time, we’re talking a two-year type of timeline, not a month. So that’s one thing.

With both the outside world and internally, there’s a duty that comms people owe the company to be honest in what the external message is — from the capabilities that a product has and its potential to the culture of the company. It can be tough when things are moving really quickly, but I always try to find and involve people within a company, the people that are closest to an issue and might feel an issue the most viscerally, and I talk to them.

It can be a tough conversation where it’s like, “Hey, I’ve been with the company for a couple months now, and there’s some conversation around what we’re going to do to celebrate Pride. I understand that you’re trans, can I run some stuff by you — what we’re planning on doing and see how this sits with you?”

SG: If you’re hiring and someone comes to you and gives you this binary, who should I hire first? The head of marketing or head of comms? Or head of internal comms?

CP: I don’t think it’s the head of internal comms as the first hire. Whether it’s a comms or marketing person depends on the company. It depends on the product. I think for B2B, a marketing person is probably usually better. I think for consumer, if we’re talking a CPG in a crowded space, a marketing or brand focused person is probably a better hire. If you’re talking consumer tech, differentiated product, building something that has never been built before — a communications leader is probably the right move. Because it’s that person’s job to write a story that’s never been written and that’s typically a skillset that is stronger for a comms person.

Putting internal comms within the remit of that communications person is wise. There are often some small systems that can get put in place for internal comms that can solve for a lot in the earlier days while that external stuff gets worked on. And by the way, telling that story is going to be helpful for internal communications as well, so that the company knows what they’re building and working toward and continue to feel inspired by their job and their work.

SG: What is going to be the Carolyn Penner of 2021 — some bright-eyed kid coming out of Stanford — impact on comms? What do they see that you don’t see now? You taught me so much at Twitter about all that I was blind to — what are you now blind to that someone young is going to teach you?

CP: TikTok is a very specific answer, but a real one. More broadly, what they don’t see, decades of experience and knowing what works and what doesn’t, is frankly a superpower.

SG: It’s what I was telling you in 2009 but you weren’t listening to me.

CP: It’s true. “I don’t know how to do this, I’ve never done it before.” Sometimes I wish I could just erase all of my experience. It’s an element of not knowing, just being more fearless and trying new things, because they don’t have the PTSD of knowing that that doesn’t work. Just having a finger on the pulse of what younger generations are paying attention to — how they’re getting their news, where they’re getting their news, if they’re even reading news. Being more seasoned, it’s really important to be open-minded to those perspectives. And to recognize that some of what a younger person might reveal is the elements of the work that feel good and right might actually be the wrong thing to be focusing on. Continuing to just have an open mind around what matters.

When I started working at Google, getting into the next day’s newspaper was the number one priority, embargo times were determined based on that. And that is not a conversation I’ve had in a very long time. That’s where that combination of fresh perspective and experience can be really powerful. Inexperienced people can be super strategic in that regard. Sometimes there is an instinct to want to hire junior people to execute and get the work done. But as a manager, I always try to find that balance of, yes, hiring younger junior people to get the work done, but also give them space to think and learn and surface ideas. Because they’re probably going to have better ones.

SG: Using the 2007 construct, there’s digital native, right? Then there’s the emergent generation almost being meme native. They’re conversant in this language, they understand how these things connect together seamlessly and then break apart. How an image or a JPEG or a TikTok or a NFT tells a story. I’ll never fully learn that. I can read it and I could study it and I could do it but it will never be native to me. The cool thing about working in this industry and working in comms, is that if you’re paying attention, there’s always a new thing to learn. And it’s super fun to learn it. To learn from people who can do this, obviously, one of the reasons why I respect you so much is because of all the stuff I learned from you. Trying to continue that and trying to constantly learn from each other is a great path. Hopefully it leads us to a place where we can also teach that to the folks who make the buying decisions around how comms is used.

CP: It’s an interesting point around the languages. I really take on the identity of the companies I work for, as you know. Embracing Twitter as a method of communication, my writing became more crisp. Embracing Vine as a method of communication, I understood the power of visual storytelling and how much you can convey in six seconds. At a minimum, trying out these new platforms and trying to create with them, even just participating in them as a consumer or a viewer, is really important. It teaches you that your announcement blog post does not need to be 1200 words. Especially for an early product, it can probably be two tweets or maybe even one tweet.

That’s another area where I think younger people are more open to trying new things. Even if they download an app that they only use for a week and then the app just dies, they’re going to learn something from that. That’s part of the reason I like working in this space. You work with companies and it pushes you towards these new products and you get a sense of what you like, and what you don’t. You also get a sense of how today’s innovators are thinking about the world. If you start to pick up on what’s been new in the last year, you can get a sense of where things are going to go. Using innovation as a barometer for where the world is moving is really interesting. Young people just have way more unique ways of communicating. You could probably announce a product with a clever meme. And that’s it.

SG: Why are you not on 10 boards? With a few exceptions, why are companies not bringing on folks with this perspective? This seems to be a pretty important skill or a pretty important additive perspective that could be useful on a board. When does this happen?

CP: Increasingly, people in our world of communications are getting involved in early stage investing and advising. Those are really good indicators of companies understanding the operational value of having a savvy communications and brand aware person in their midst. I’d love to be on a board. What I have noticed in consulting, is that I do my best work when I’m not in the weeds. Sometimes stepping away for a week is where the best ideas come from. I would love to see a world where more companies are looking to communications people just to bring a different voice and perspective into a room. It’s not like you’re either a brand person or you’re business minded. They’re super connected and as the gap between those two sides of the coin gets smaller, hopefully we’ll start to see more people like us in positions of influence within companies.

Previous Studio Sessions:

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