How to drum up the courage to make an audacious request

When you are asking for a raise or promotion, or funding for your business, it can feel as fraught as getting ready to plummet headlong into an unknown abyss. But as Kayt Sukel, author of The Art of Risk: The New Science of Courage, Caution, and Chance, told Fast Company, even the biggest risk-takers do a tremendous amount of work to prepare for high-stakes situations.

“These folks aren’t just walking out in the middle of the street and saying, ‘Hey, I think I’m going to jump out of a plane today.’ . . . They engage in a lot of planning, they have a lot of background, and they know all the ins and outs of situations before they face them,” Sukel explained. The most successful aren’t always the bravest, they just put a lot of time into understanding the situation and their objectives and anticipating any challenges they might face.

That said, gathering the courage to make an ask is a tall order for many of us. Especially if you’re battling social anxiety. So we asked the experts to tell us what it takes to soothe the jitters, find your voice, and get what you want.

“It’s important to remember that you’ve already done the hardest part: You’ve stepped outside your comfort zone and have taken an enormous risk to execute on your vision,” says Karina Sobieski, partner for human capital at SoftBank. “That’s why it’s crucial that you remember this vision and stick to the long game when taking a big leap or making a big ask. Your vision is your true north; it’s what separates you from others and what will draw others to you.”

Sobieski maintains that having the desire to ask for more means that you already have courage. “If you’re wary about taking that next step, remember that whether you fail or succeed, you’re already ahead because of the learnings that you will gain.”

When asking for capital, she says, trust your intuition, but also do your homework. “Surround yourself with advisers, ask them hard questions, and listen carefully to what you hear back. It’s okay not to have all the answers, but it should never be because you weren’t brave enough to ask the hard questions—or you didn’t care to listen carefully to others,” she says.

As part of the session she conducted at Unusual Academy, an experiential boot camp for seed-stage entrepreneurs, Sobieski taught entrepreneurs how to translate vision into execution. “No matter how many pieces of advice you seek along the way, at the end of the day you’re going to just have to have the courage to find your own way and not be afraid of failing,” she says.

Fear of rejection can keep you on the sidelines of your professional life, says Josh Grau, a lecturer at Stanford Graduate School of Business and in the Northwestern Medill Integrated Marketing Communications Program.

That hesitation can be even more intense if you’re an entrepreneur just starting out or lower on the totem pole inside your organization, says Grau. “But even the most experienced, senior people can fumble when it comes to getting others to buy into something new.” So what’s the secret to pitching with confidence and transforming how people think, feel, and act about a new idea? “One word: story,” he says.

Studies have proven the persuasive power of storytelling. However, in our work lives, advocating for ideas typically means making arguments based on data, facts, and figures alone, at the expense of telling a compelling story, Grau points out.

“Across two courses I teach—one in the executive education arm of Stanford’s Graduate School of Business called “The Innovation Playbook,” the other as part of the Unusual Academy—the goal is to bring the story out of witness protection.”

Grau believes that in order to move your audience intellectually and emotionally, you need to use convincing data and wrap it in a compelling narrative. “A story allows you to take the listener on a journey, evoking empathy, and providing a fresh perspective, which can engender confidence in both you and your idea,” he explains. “Whether you’ve thought up a killer new product you know people will love, developed a new process that will make your team work efficiently, or want to make a case for a promotion or raise,” Grau says, “a story helps transform a good idea into a great innovation.”