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To Move Quickly and Solve the Right Problems, Leaders Need to Ask Better Questions Asking better questions doesn't just drive innovations, it can also build expertise in your team by setting an important expectation.

By Linda Lacina


How Success Happens is a podcast featuring polar explorers, authors, ultra marathoners, artists and more to better understand what connects dreaming and doing. Host Linda Lacina guides these chats so anyone can understand the traits that underpin achievement and what fuels the decisions to push us forward. Listen below or click here to read more shownotes.

Heidi Zak founded ThirdLove to change how women buy bras. Today, the company has more than a million customers and has mastered features like half-sizes and letting online shoppers try before they buy. The company has even developed an app that's aggregated more than 150 million data points from real women to ensure what few other bra companies could: a better fit.

But things weren't always so rosy. When ThirdLove's online site first launched, the sales didn't follow. In fact, some days didn't see a single customer order. Women didn't know about ThirdLove, and weren't used to the idea of buying bras online.

Related: Inventor, Entrepreneur and Inspiration for the Movie 'Joy' Joy Mangano Shares How to Be Successful

This tough moment taught Zak an important lesson about the importance of asking the right questions and solving the right problem.

While another team might have assumed that customers didn't like the site or even the product, Zak didn't make that assumption. To fix sales, she called an urgent all-hands meeting where her entire 12-member team questioned every aspect of the business -- from Facebook ads and messaging to customer behavior.

Related: Hear How This Woman Coached Herself Through a Near-Death Experience to Become a One-Person Fitness Brand

This process, plus a consumer survey, got the team to an important realization: to build sales, they'd need to build trust first. Women weren't used to buying bras online and didn't know what to expect from ThirdLove, a new company they'd never heard of.

To that end, ThirdLove launched a program that let women try on a bra without buying it first -- even letting them take off the tags and put it in the wash. The program removed any risk for buyers and boosted sales. Zak sees it as a turning point in the company.

Asking better questions doesn't just drive innovations, though, it can build expertise in your team by setting an important expectation. Zak pushes her team for answers that are clear, succinct and easy to understand. Such answers reveal how much -- or how little -- someone actually knows about the topic.

"There's a complexity in every business decision," says Zak. "The best members of a team have spent the appropriate amount of time and research to understand how to answer a complex question."

Related: Podcast: When PowerPoints Weren't Working, This Powerful Exec Passed Out Comic Books Instead

Leaders need to dig deeper anytime someone's answer has them wondering "Is that right?" or "Is that really true?" Zak says. She believes it's also a leader's responsibility to push harder when an answer seems unfocused or rambling. "There's no such thing as asking too many questions," says Zak.

Pushing for clear answers can give you the solid recommendations you need to truly move quickly.

Listen to this week's podcast and learn more about how better questions have fueled ThirdLove's growth and what that process has taught her.

To subscribe to this podcast, find us on the following platforms: SoundCloud, Stitcher, iTunes, Google Play.

Thank you to our sponsor:

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Linda Lacina

Entrepreneur Staff

Linda Lacina is the former managing editor at Her work has appeared in the Wall Street Journal, Smart Money, Dow Jones MarketWatch and Family Circle. Email her at Follow her at @lindalacina on Twitter. 

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