The Top Comms Mistakes Startups Make — And How To Avoid Them
PR & Marketing

The Top Comms Mistakes Startups Make — And How To Avoid Them

After two decades of comms experience with companies like Eventbrite, Yahoo, Mattel and Nike, Terra Carmichael shares four common PR mistakes and her techniques for sidestepping them.

When it comes to public relations, startups are often focused on what they can do to win coverage and secure that big story to help make a splash in a noisy space. So much energy is poured into landing the interview or getting that speaking gig, that it’s easy to under-index on the part that comes next: what you’re actually going to say.

Terra Carmichael’s decades of experience in communications have shown her that from the smallest startups and greenest founders to the largest companies and most seasoned executives, most PR blunders are actually strikingly similar — and completely avoidable. Instead of chasing those glowing puff pieces or coveted cover stories, the current VP of Communications at Eventbrite argues that leaders should be putting more thought into what not to do.

Because no matter what you're building, following Carmichael’s expert advice on finding and pitching the right journalists is only half the battle. You still need a game plan for navigating the interview itself. And from botched messages to those embarrassing yet unintentional gaffes, there are all too many ways for an interview to go off the rails.

Luckily, after working with companies such as Yahoo, Mattel, Nike and Trulia, Carmichael has a good sense of what to look out for and avoid. At First Round’s Founders Summit, she boiled it down to the four most common comms mistakes companies make, sharing her practical tips and techniques for sidestepping them.


“Fake it till you make it” has long been a popular operating philosophy, especially among first-time founders or early startup teams finding their way to traction. But the truth has never been more important. And faking it publicly can have dire consequences.

“It’s not hard to see why this phrase has staying power,” says Carmichael. “There’s seemingly a lot of benefits to ‘faking it’. As a founder or executive, everyone seems to be watching: your team, your investors, the public. There’s a lot of pressure out there, whether it’s raising money, generating buzz or proving yourself as a leader. You’re expected to be inspirational and visionary, even when you don’t always feel that way or when the product isn’t quite there yet.”

So while faking it may seem like a great shortcut to willing things into existence, there are some real dangers lurking. “It’s easy to stretch it too far, flying too close to the sun while you’re waiting for reality to catch up to the hype. And faking it in a public setting carries some significant risks,” says Carmichael. “The very obvious and sad example of this is Theranos. It was a seemingly wildly successful startup, getting enviable press and at one point being valued at $10 billion. Now, in one of the most rapid, public meltdowns we’ve seen in startup land, the company is teetering on the edge of bankruptcy and executives are facing jail time.”

But faking it needn't rise to the level of criminality to become a problem. “There are loads of subtle and innocuous ways that people fake it and get carried away,” Carmichael observes.

Here are two of Carmichael’s tips to avoid getting swept away in exaggeration:

Connect it back. Stay grounded in your company’s mission, vision, and values. “This may seem like big company speak, but it doesn’t have to be a daunting exercise. It can just be a few lines that can help center you and tie everything together. What it’s really about is being true to what your company stands for, and what your team is passionate about,” says Carmichael. “For example, if one of your values is centered around teamwork and collaboration, then you would work that into everything you do, whether it’s in evaluating future team members, rewarding behavior at work, making business decisions or talking about your achievements to the press.”

Be deliberate. As an executive or spokesperson, you want to be intentional about how you speak and what you speak about. “For me, it really comes down to one question: Who are you to your core? Think about topics that you can authentically speak to with passion instead of speaking about things that you wish you were passionate about. You also should think about your style — when do you show up at your best? It’s possible that showing up at your best isn’t necessarily how you wished you came across,” says Carmichael. “For example, not all CEOs are funny, but many try to be when they are on stage because they think that’s what people want. The problem is that it ends up looking inauthentic and is often painful to watch. The reality is that when you are speaking, people want you to succeed. No one likes to see failure (at least not decent people), so show up as your true self, and you’ll win.”

For help with that, there are a couple of exercises Carmichael recommends. One is just a simple audit. “Ask your team or trusted colleagues to give you real feedback on where you crush it, and where you fall down. You’d be surprised what people will share with you when you simply ask and give them permission to tell you when things aren’t working,” she says.

Another way to achieve this is to develop an executive brand profile for key spokespeople. Carmichael worked with Helena Maus of Bite Communications to build one for an executive she was advising, using an interview to determine where the leader’s authentic self could be brought in. Afterwards, they came up with three to four topics or platforms that were very clear, deliberate and clearly mapped back to the business. “These defined themes help focus you and ensure greater success. It’s like the squirt gun game at state fairs — if you point them all at the same target and focus your efforts, you’ll get there faster,” Carmichael explains. “Once the profile has been created, you can work from there to start seeking press, social engagement or speaking opportunities to advance your public persona and brand around these specific topics. But more importantly, this exercise is also a tool to filter out opportunities that don’t further your work or benefit your business. Not everything is worth your precious time.”


When you’ve discovered your authentic self, it’s easy to feel ready for primetime and eager to share your message with the world. But as Carmichael cautions, there is a hidden danger here: Saying too much.

According to Carmichael, there are many factors that lead people down the path of talking too much or speaking too transparently in interviews: sometimes it’s ego, the fear of being misunderstood, nerves or just wanting people to like you. Whatever the reason, it’s easy to slip up and slide into sharing too much. And it’s not always a matter of getting carried away or being too chatty, but rather sitting down for interviews that you shouldn’t be doing in the first place.

“Some folks have an intense ambition to get their message or their side of the story out there. But that can cloud your judgement when it comes to leveraging press,” says Carmichael. “For a non-tech and more sensational example, I always like to point to Mark Sanford, the former governor of South Carolina. You might not remember, but he was caught in an affair with an Argentine woman, and it was this really big fiasco. But then Michael Jackson passed away unexpectedly. And that was just such a big moment, probably one of those few times in history when people remember where they were when they found out. And while tragic, from a PR perspective, for Sanford this really was an enormous opportunity to allow the news cycle on his affair to fade while mainstream media were consumed by something else. Jon Stewart even commented on this topic, joking that ‘God killed Michael Jackson to save his ass.’ But instead Sanford jumped back in the spotlight and did a lengthy interview with the Associated Press, calling his mistress his soulmate. This is an example of someone who felt misunderstood and had a blinding need to get his version of the story out there. Obviously, this backfired. Going silent wouldn’t have changed the outcome for him, but the additional attention on the issue did him no favors.”

For Carmichael, it all comes down to knowing when to stop talking. Here’s what you need to watch out for to make sure you’re not sharing unnecessarily:

Don’t fill up the silence. “One of the oldest tricks in the book that trained reporters use is silence,” says Carmichael. “You'll finish your answer or message, and they'll just sit and look at you, baiting you into saying more. Or they’ll quietly write in their notebooks, with their silence swallowing the room. And executives often feel this need to fill it right? It gets awkward and uncomfortable. So they just keep talking, digging themselves in further and further, creating more opportunities for a reporter to pounce on something that they really didn’t even mean to say. That’s because when you’ve run out of messaging and are just winging it, you often end up sharing more than you intended to, in a less than polished way.”

Know your message, deliver it and then put a period on it.

Remember your role. “It’s important to remember that while it’s easy to be friendly with reporters (after all, most are very nice people), you have a job to do — and so do they,” Carmichael cautions. “It helps to remember your different roles. While not adversarial necessarily, you aren’t on the same team. Most journalists aren’t out to get you, but they certainly aren’t an extension of your comms team. They're not there to do your PR for you, so don't expect that. Their job is to find a story, and sometimes what you want to tell and what they want to hear don't match up. Essentially, they are looking for the juice and the headline, especially in today’s clickbait driven world. So that might not align to your goals, and it’s important to be mindful of that and make smart decisions about what to participate in and what to pass on.”

Define the rules of engagement: As any trained comms person knows, there are certain terms you can use to navigate the conversation with reporters to maximize the chances of getting what you want. For example, you can frame a conversation as “off the record,” which means you can can influence a story by providing context without having your fingerprints on the story, if that is the best course. There are other handshake agreements that you can use with reporters when you already have a relationship with them, such as giving information “on background” or “exclusively” that can help you both achieve your goals.

Stick to the truth. Though the truth may not be as sexy as reality, Carmichael says it’s absolutely the way to go. “Don’t embellish or stretch the truth beyond recognition because you can always count on reporters to sniff out the facts, as they should. Beyond the ethical case for telling the truth, it’s also easier to remember,” she points out. “Sometimes startups are tempted to stretch too far when describing the nature of partnerships or integrations in order to leverage a larger brand or showcase momentum. But in addition to running the risk of being untruthful, you also could fall out of the good graces of existing or potential partners that could be useful to you in the future, so it’s a dangerous move.”

Eventbrite VP of Communications Terra Carmichael


With interviews, most worry about the questions they’ll get asked and how they’ll get tripped up. But according to Carmichael, you have more control over this than you may think. “When it comes to the press, you may not have much control on the final draft or on how the story turns out, but you have complete control of what you say and how you say it,” says Carmichael. “I always tell the executives I’m working with that navigating interviews is an art — there’s a way to master it, but it takes work.”

The goal of an interview isn’t to answer questions. It’s to deliver your messages.

Here are four techniques Carmichael recommends to guide the conversation where you want it to go:

Limit yourself to your top messages. When you land a new interview opportunity, immediately start thinking about the top three messages you want to get across. “You don’t want to have so many topics that you’re trying to cram in a single interview,” Carmichael says. “That’s just too much to remember and you’ll get caught up in trying to deliver what you’ve memorized or in worrying about leaving one point out, which will make you seem distracted or inauthentic. What it’s really about is whittling down what you want to say, distilling your company’s narrative or announcement into a few key points that you can anchor your answers on. And then under that you can fill in the color.”

Prepare for the tough ones. Of course, focusing on getting your points across doesn’t mean that you shouldn’t give any thought to what a reporter might ask. Do your homework by reading up on the journalist’s recent pieces to get a feel for his or her style. Start by making a list of the questions you fear most. That way you can head into any interview knowing the five worst things you could be asked and have at least an outline of how you’d tackle them. “These can include scrutinizing questions around your business model, competitive landscape, exit plans and timing. It’s also important to be real about any potentials skeletons that may be hiding in your closet, and prepare as if they are going to be revealed,” Carmichael advises.

Block and bridge. A go-to technique many successful spokespeople use for navigating interviews is what the industry calls blocking and bridging. “In a nutshell, you block by acknowledging and briefly answering the question that's been asked, and then you bridge to the message you actually want to deliver. Think of it as jumping off point to the information you want to shine a spotlight on,” Carmichael explains. “Once you have your top three messages outlined, you should see if can take any question and bring it back to your messaging.”

Here are two block-and-bridge starter statements to have in your back pocket:

  • “That’s an interesting observation...but the heart of the matter is really…”
  • “You raise a good point about a key issue in our industry today…How we like think about XYZ is…”

Avoid the negative. There are a number of techniques that reporters use to try to get you to go down a dark path or give a negative answer that makes a good headline, but isn’t good for your business. 
“If you're ever asked a loaded question or something framed as a negative statement, never repeat the negative. Doing so ends up putting you on your heels with connectives such as ‘but’ or ‘however.’ Using words like that make you sound defensive,” says Carmichael. “And it's just not worth it. Don’t play back the negative sentiment. Start fresh with your perspective.” Here are three statements you can use to redirect and take the conversation where you want to go could be:

  • “Another way of thinking about this is…”
  • “I think what you’re really asking is…”
  • “That speaks to a bigger point about…”

The same advice applies when you’re asked about a problem your company or industry is facing. Don’t reiterate the problem, but instead talk about a solution. As an example, Carmichael cites an interview where a Lenovo executive did a masterful job of of bridging as he’s faced with probing questions about their earnings on the air.

Don’t be intentionally obtuse. While the goal may be to deliver messages instead of answering questions, you don’t want to come across as intentionally frustrating or evasive. It can’t be purely about pushing your own agenda and you don’t want to be too transparent or obvious in your pivots. “You certainly don’t want to create one of those viral clips where the interviewee or politician doggedly refuses to answer the question and gets called out on it,” says Carmichael. “Just like in everyday relationships, there’s a give and take that you need to balance in a way that is respectful and amicable.”


When it comes to strategic communications, it’s very easy to get wrapped up in dealing with reporters or crafting your external message. But in Carmichael’s experience, another major mistake leaders and companies often make is that they forget that their most important audience is already inside their building.

“I’ve long believed that internal comms is often overlooked,” says Carmichael. “Too many executives either don't make the time, or think about it as an afterthought or nice-to-have. But in my view, employees really should be your number one audience, especially as you scale. It’s absolutely critical that you communicate with them authentically and often."

What’s more is that this is a captive, highly invested group that can actually help your external PR efforts. When testing your message or story, make sure it resonates on the inside first. “Your employees are often your toughest critics,” says Carmichael. “They will call bullshit on you faster than anyone else. So if your story is not resonating with them, it's probably not going to resonate on the outside. Use them, and tap into the vested interest that they have in your company to help you tell your story better.”

But workshopping PR messaging isn’t the main reason to communicate inside. The industry is peppered with studies and data around the importance of employee engagement, highlighting that perks and benefits don’t necessarily mean your employees are engaged or believe in your mission. Rather, a culture that is built on accountability, authenticity, clear goals and strong two-way communication is what goes a long way to keeping your team engaged.

Carmichael recently invested in dedicated internal comms resources at Eventbrite and the team has been trying new ways to communicate to employees (lovingly called Britelings) more frequently — all based on a few tried and true learnings. Here’s how she’s going deeper on internal comms:

  • Leave it to the pros. “After five years at Eventbrite, I finally hired someone who knew much more than I did and specialized in internal and employee comms,” says Carmichael. “We’ve seen a big difference, especially among leaders and mid-level managers who appreciate the efforts to help cascade communications throughout the organization.”
  • Read all about it. “I’m a big believer in teaching leaders to fish. That’s why we’ve rolled out a weekly(ish) email for leaders at Eventbrite that summarizes all the things they need to be thinking about in terms of managing and messaging to their team. We break it down into a few sections: things to know, things to do, things to share,” says Carmichael. “It sounds simple, but let’s be real, leaders are an important and expensive investment, so you want to use their time wisely. Giving them the tools such as cliff notes and summaries of important matters not only helps them be better communicators, but it also enables a timely cascade of communications throughout the organization.”
  • Find micro-moments to connect. Aside from company-wide touchpoints, it’s also important to create moments to connect in small groups. “We've recently started a weekly coffee break with our CEO, Julia Hartz, where six people get to sign up to informally discuss a specific topic with her,” says Carmichael. “Not only does this give employees valuable face time with her, but it's also been fantastic for Julia because it’s a new way for her to talk to a broader cross-section of the team and get their thoughts on topics that are top-of-mind for her. She’s also able to get a pulse on how people of all levels of the organization are feeling and any concerns or issues that they bring up themselves.”
Just doing an all-hands or a town hall meeting once a month doesn't cut it anymore. Employees need to feel a deeper connection to you and the business.


Whether you’re bringing in a comms leader or you’re a founder of a small startup that wants to go it alone, the bottom line is that if you’ve put in the time cultivating your media network and getting in front of reporters, you should invest even more effort in learning how to talk to them and how to get your message across. Success comes down to understanding that, while communications and press can drive a business forward, they really need to be managed well. Navigate these testy waters by grounding yourself in your authentic truth, being laser focused on your story and your message, and most of all, by prioritizing your internal team.

“A lot of founders and executives at companies think that they've got their story nailed because they have mastered their pitch with investors, employees or even their parents and friends, but the press is a totally different animal,” says Carmichael. “You’ve got to be humble and put in the work, even if you don’t think you need it. You’re likely not as good as you think you are, and there’s always room for improvement.”