CEOs of established businesses are nothing if not risk-averse. In their public statements, hiring choices, and marketing decisions, executives tend to toe the line. In many situations, that’s a good thing. Good leaders don’t put their people or their company’s reputation in danger without a reason. But when it comes to branding, taking risks is essential. A brand that seeks to blend in can’t stand out. CEOs who refuse to approve any art style or brand voice with actual flavor inadvertently put their company’s brand at even greater risk. The Right Kinds of Risk To be clear, many brand risks are bad ideas. The CEO of Overstock.com managed to tank his company’s share price by more than a third in two days by issuing an unprompted statement about his role in the Trump-Russia affair. Half-baked statements about political and social controversies rarely turn out well for brands. Creative risks don’t always work out as intended, either — that’s why they’re risks — but rarely do they arouse the sort of strong emotions that cause customers or investors to draw a line in the sand. At worst, creative risks fall flat. Typically, though, they get people to share. Unusual, artistic, and funny campaigns break through the noise in a way humdrum product ads simply do not. Changing the CEO’s Mind 1. Start small. Much as you might want to, a skeptical CEO isn’t about to rebuild his or her brand from the ground up. Ask to start small: HubSpot suggests social media as a perfect way to test the waters. Posting something fun on your profile page requires no investment or training, and it allows users to provide feedback instantly and directly. If your cover photo is a no-nonsense team photo or a shot of your building, change it up. Creative risks don’t need to be offensive. Create a meme around a cultural touchstone like “The Office” that’s relevant to your company. Create your own Schrute fact, or make up something Michael Scott might say. 2. Embrace quirks. Every company has things that make it unique. Whether it’s your CEO’s hairstyle, your team yoga sessions, or your office cat, play it up in your marketing materials. People connect with brands that come across as “human.” If your CEO can’t see that, get an outside opinion. Case Paper had been making dad jokes and whimsical sketches for years, but it didn’t see how that culture could possibly sell paper. B2B agency Renegade convinced it to own its style in an “On the Case” campaign featuring bright colors and jokes about dinosaurs and the space-time continuum. 3. Be inclusive. Everyone wants to feel like part of the fun. Remind your CEO that customers are a lot less likely to push back when they’re invited to join in. Enter a hotel lobby these days, and you’re likely to find it empty. Upscale hotel chain The Standard tried to buck that trend with The Lobby, a chat app for its guests. Using geosensing and anonymized user profiles, The Lobby gets people out of their rooms to talk with each other. Event marketing is a natural ally of this strategy. Invite people to an event that gets them out of their comfort zones. Whether it’s a social event, an avante-garde film, or a tasting session for a new product flavor, invite customers to try something new with you. 4. Show them the data. If you can’t reason your way into a new type of campaign for your company, gather data to bolster your case. Citi Bank’s “Live Richly” campaign featured ads with lines like “He who dies with the most toys is still dead.” Such a sentence might seem to cut against what bank customers are trying to do — build wealth — but it sure connected with Citi’s customers. What made Citi’s confident that it would? Fallon, a marketing agency the bank enlisted, presented data showing that “balance seekers,” or the people skeptical of “get rich quick” culture, constituted nearly half of its customer base. Risk-averse leaders love numbers. Although nobody can know how a campaign will be received in the real world, CEOs know data is their best tool for predicting the future. 5. Check out the competition. Another bank, Northstar Bank, unveiled a campaign a few years ago that, on the surface, could not have had less to do with banking. To communicate its mix of big-bank resources and small-bank relationships, Balcom built ads that spliced together different animals. The way Balcom sold the bank on the strategy was to show Northstar Bank’s leaders what its competitors’ marketing materials looked like. While everyone else was touting APRs and posting photos of people working on laptops, Northstar Bank stood out with content that looked decidedly non-banklike. You can’t blame executives for trying to protect their brand. But you can show them that “protection” isn’t a winning strategy in a sea of sameness. Test the waters first, but don’t be afraid to dive in.