Hipmunk CEO Adam Goldstein’s template will quell workplace anxiety

Flight Templates are templated flights, or sets of questions, written by some of the world’s preeminent business leaders. With Flight Templates, Balloon users get unparalleled access to seasoned perspectives and proven business strategies across all areas of business, including leadership, product, marketing & sales, innovation, employee experience, culture, and more. This feature is part of a series on The Insight that profiles Balloon’s Flight Template authors.

When Adam Goldstein was leading and growing the travel price-comparison platform Hipmunk, he thought intense, persistent anxiety simply came with the CEO territory.

“I thought that was how it had to be if you're in a competitive industry and growing quickly,” Goldstein said. “And to a certain extent, yes, anxiety is part of the deal, but now I know it doesn’t have to be to that extreme degree.”

Experience with anxiety, Goldstein noted, is helpful in managing it: If you’ve been through intense times before and come out the other side still alive, it’s easier to have perspective and keep yourself from spiraling. But unlike Goldstein, not everyone has years of experience founding, leading, and managing huge companies like Hipmunk, which he co-founded with Reddit CEO Steve Huffman in 2010.

That’s why Goldstein distilled his philosophy on workplace anxiety into his new flight template, Reduce Team Anxiety.

“For leaders, reducing anxiety means simultaneously doing the best that you can with your best guess, while also acknowledging that not everything is within your control,” Goldstein said. “It's actually better to openly acknowledge the uncertainty than to pretend that it doesn't exist.”

For many people, talking openly about what keeps you up at night can feel too personal for work, but Goldstein emphasized that sometimes you need to address uncomfortable subjects head on, especially now that anxiety is at an all-time high. His flight template offers leaders a space to ask their teams vital questions that could cross boundaries in a high-intensity, public forum—but on Balloon, they’re an avenue to camaraderie, collaboration, and a renewed sense of calm.

“Anxieties around very rational concerns can easily become sources of irrational fear and panic, but writing them down can make them just pieces of information, and they can be treated in a much less charged way,” Goldstein said. “So flights are a perfect way to have everyone verbalize their anxieties together while also brainstorming some solutions.”

Concretizing your fears not only makes them less threatening but also helps teams emotionally, operationally, and financially prepare for worst-case scenarios.

“I actually think these, ‘What could go wrong?’ and ‘What do we need to figure out if that happens?’ kinds of questions can be really helpful,” Goldstein said. “The more explicitly that those things are shared within an organization, I think the better decisions leaders can make, and the less anxious everyone can be.”

Ultimately, though, Goldstein explained that assuaging anxiety comes down to mindset: Transparency, optimism with a dose of realism, and a persistent sense of adaptability are key.

“Leaders should have ideas, and they should be figuring out what the plan is, but that there are inevitably going to be lots of things that they just don't know,” Goldstein said. “And if they acknowledge that calmly and directly, they’re going to get much better results than if they pretend to know it all. Because no one ever knows it all—that’s why you’re a team.”

Check out Adam Goldstein's Flight Template Series

Entrepreneur, investor, author