Why you should follow the lead of Spotify, Bumble, and Twitter execs

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Is questioning the start line of innovation?

That’s a query I explored at size in my 2014 guide, A Extra Lovely Query, whereby I chronicled breakthroughs over the years that started with somebody asking a query. It seems game-changing questions led to the web, immediate images, Gatorade, the Worldwide Purple Cross, Netflix, and rather more. (For many who have an interest, some of these origin tales are briefly recounted here).

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But it surely was nonetheless stunning to study—as I did from Reid Hoffman’s new guide, Masters of Scale: Surprising Truths From the World’s Most Successful Entrepreneurs—what number of of immediately’s prime Silicon Valley entrepreneurs are inveterate questioners, pushed by curiosity. Whereas tech founders are generally stereotyped as hyper-driven individuals who scarcely pause to breathe, not to mention to replicate or query something, the Masters of Scale guide’s interwoven portraits of dozens of startup leaders (many however not all from the tech world) present that the course of of scaling a enterprise thought is rife with complexities, contradictions, and uncertainties. To navigate the problem, you should be a stressed learner and an individual who’s not afraid to query something—together with your personal vivid concepts.

The guide, primarily based on the Hoffman-hosted common podcast of the identical title, is coauthored by Hoffman with June Cohen and Deron Triff (who helped scale TED Talks earlier than launching the multimedia firm WaitWhat, producer of the Masters of Scale podcast). Disclosure: I consulted with the authors throughout the early phases of producing the Masters of Scale guide, which led me to do a deep dive into Hoffman’s recorded conversations with the featured entrepreneurs.


These conversations are primarily targeted on the sensible nuts and bolts of launching a brand new enterprise enterprise and enabling it to develop quickly—encompassing every little thing from how you can elevate enterprise capital funding to how you can rent the proper individuals. However what stands out most is the ardour behind the course of. These founders convey a real sense of marvel about the world because it presently exists and the potentialities to result in change.

As the guide reveals, entrepreneurialism all begins with “the huge thought,” and the concepts that drove so many of the Masters of Scale (hereafter MOS) startups got here out of the founders’ real-world experiences and frustrations. And people concepts tended to take form, at the least initially, as a query or set of questions. As in, Why does downside X exist? What if we tried doing Y to unravel it? As their companies launched and grew, the challenges—and the questions—tended to develop and turn out to be extra complicated.

What do some of these questions seem like? Under is a sampling of what the MOS founders requested themselves as they launched and grew their companies—a fast primer on the artwork of asking questions that spark innovation. Some of these questions could appear apparent in hindsight, however nobody else was asking them at the time.

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Whitney Wolfe Herd of Bumble

Reacting to her personal unsatisfying experiences with on-line courting providers (she’d beforehand labored on the courting app Tinder), Herd began with a easy diagnostic query: What’s damaged in on-line courting? She felt it simply wasn’t working for girls, who had little management over on-line interactions with males and generally ended up getting harassed. This led to Herd’s bold follow-up query: What if solely ladies might provoke the dialog? She then designed Bumble in order that with any potential match, ladies all the time obtained to make the first transfer. Herd’s two-step questioning strategy is basic: Begin by inquiring about a big, systemic downside, then proceed to a daring, imaginative what-if query that proposes a attainable answer.

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Daniel Ek of Spotify

Right here’s one other instance of an identical “one-two” questioning strategy. When he was younger, Ek had been a fan of Napster, however as a musician himself he understood why music piracy didn’t work as a enterprise mannequin. So his preliminary query was, Why hasn’t anybody made a model of Napster that works for each customers and artists? To try this you’d must design a web-based music streaming service that rewarded the content material producers; to that finish, Ek labored immediately with file corporations to strike offers with their artists. However he additionally needed to seize the fancy of customers, and as he set out to try this he was guided by this query: What if we might construct one thing that makes it really feel like you had all the world’s music in your laborious drive? To attain that, Ek had to make sure that Spotify supplied a large providing of music, delivered at near-immediate obtain speeds, and personalized to listener preferences.

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Jenn Hyman of Hire the Runway

For these questioning the place to search for an issue that may spark an ideal query, the reply is . . . wherever. Hyman occurred to be wanting in her garments closet, the place it appeared nearly every little thing was outdated and outdated. Which prompted this query: Why is it that now we have a closet that’s a museum to who we as soon as had been? In pondering that query, she got here up with this second one: What if the closet had been a residing, continuously altering factor? The way in which to virtually and affordably do that may be to lease, not purchase, the garments in your closet. Hyman’s on-line website made it simple to lease the newest, most trendy attire, and the thought made sense not just for cost-conscious clients, but additionally for clothes suppliers—who now had a complete new market obtainable to them.


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Ev Williams of Twitter and Medium

As Hoffman explains in the guide, Williams has been pursuing some model of the identical query for years, as he has had a hand in launching first Blogger, then Twitter, and then Medium. The overriding query: What’s stopping individuals from sharing ideas on-line? Williams’s makes an attempt to reply which have taken the kind of running a blog, tweeting, or longer-form on-line writing. The important thing takeaway right here is that if you take possession of a sufficiently big query, and adapt it to totally different markets or conditions, it could actually spawn a number of solutions and alternatives over the years.

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Sara Blakely of Spanx

Blakely invented Spanx by questioning the approach ladies’s pantyhose had been designed; particularly, she famously reduce off the ft of her personal pantyhose and subsequently launched a billion-dollar firm round that creation. However the query featured beneath is one which Blakely started asking after she launched her firm, as she was beginning to scale it and wished to encourage creativity in her workers. Blakely’s query was: If nobody confirmed you how you can do your job, how would you do it? That query continues to information the approach she manages the individuals who work for her—encouraging them to study, experiment, and carry their very own concepts into the combine.

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Danny Meyer of Union Sq. Hospitality

The famed restaurateur shared the identical concern as many different MOS in the guide: How does one keep a robust firm tradition whereas rising quickly? However that’s a secular, relatively uninspiring query. It gained new drive when, at the suggestion of guide Erika Andersen, Meyer flipped that query to this one: How can we use development to advance our tradition? As Meyer realized, tradition can’t actually be “maintained” anyway—it’s a residing drive that’s certain to vary. However Meyer might leverage the firm’s development to speculate extra in tradition—by creating extra incentives for workers and placing extra assets into clearly articulating and spreading cultural values all through the group. The lesson: Questions can turn out to be extra highly effective when you flip them the wrong way up or flip them sideways, notably if you can flip an abnormal query right into a extra provocative or inspiring one.

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Caterina Faux and Stewart Butterfield of Flickr

One of the surprises in the Masters of Scale guide is seeing what number of success tales had been born out of failure. Simply earlier than launching the groundbreaking photo-sharing app Flickr, Faux and Butterfield had been making an attempt to get a web-based online game off the floor, with no luck. That they had burned via funding and had been about to surrender after they requested themselves: Is there any approach we cannot exit of enterprise? In his guide, Hoffman refers to this as the query that “has launched a thousand pivots.” You hit a wall and then ask what can we nonetheless do with what now we have? Faux and Butterfield had a online game nobody wished, however buried inside that recreation was a function that allowed you to pull, tag, and share pictures. They killed the recreation and targeted on that function, which turned Flickr.

For these looking for their very own lovely query to pursue, listed below are a pair of remaining suggestions from Hoffman (who helped launch LinkedIn and PayPal, and now could be an investor at Greylock Companions). He says too many would-be entrepreneurs are targeted on the query, What’s the subsequent huge factor? If you lack a crystal ball, that’s a troublesome query to reply. A greater query tries to get at one thing solely you can reply and that you care deeply about: What’s my imaginative and prescient for the future, and how can I start to appreciate that imaginative and prescient?

One remaining query that may be helpful: If you suppose you’ve discovered your huge thought and need to know what others actually give it some thought, Hoffman recommends sharing the thought and then asking: What’s flawed with this concept? Don’t ask for encouragement—ask for criticism. “You need individuals to problem and poke holes in your thought,” Hoffman says. “It’s higher to search out these holes earlier than you carry that concept into the world.”