Learn to Ask the Tough Questions

Sometimes asking the right questions is more important than receiving the correct answers.

always the beautiful answer
who asks a more beautiful question
— e.e. cummings


New things inevitably bring out questions in us: What is genuinely new? How can we create new things? How can we effectively respond to the new things that affect us? How do we appreciate what new really is?

In The New New Thing, a book on Netscape founder Jim Clark, author Michael Lewis observed that Clark had paused when describing his work: “On the line that asked him to state his occupation, he did not know what to write. There was no name for what he did.” David Bowie had a similar reaction when giving a commencement address at the Berklee College of Music, in 1999: “As always on occasions like this, I really never know what to do — which is pretty much the way that I’ve handled my career as a musician-writer.” What is it about new things that stops both successful Silicon Valley entrepreneurs and rock stars in their tracks?

If we have learned anything about the end of the first phase of the Internet and the new economy, it is that we must be forceful questioners about what will be genuinely new and exciting in the second phase. Following the recent correction in the capital markets, we have witnessed a massive shift back to the future as defined by old-industry players. Many of the first-phase startups have exited, and even the strongest players — like and Yahoo! — are refocusing or scaling back. We’ve replaced long-term optimism with both the new and a focus on short-term profitability and a heightened assessment of operations and financial control. The need for short-term answers has replaced the tolerance for not knowing what to do — but always asking what to do next — that we developed during this recent period of rapid change.

But this too will change. As questioners, we are suspicious of single-factor analyses. The capital markets have changed, but technology is still evolving, and a driving curiosity in the new remains. The music industry is a case in point. Two years ago, the industry committed itself to a proprietary hardware and software encryption scheme for digital-music distribution, called the Secure Digital Music Initiative (SDMI). That initiative was the industry’s response to a bevy of new intermediaries like and Napster, which were intent on rewriting the rules for how music and the Internet would meet in the future. The new was confronting the old.

Napster now has over 50 million users worldwide, and despite continuing legal challenges, the technology for peer-to-peer file sharing that the company introduced is widely disseminated in key consumer markets worldwide. has over 117,000 artists posting music to its site, which is viewed by approximately 725,000 daily users. These numbers could be reasonably defined as new. The industry consortia SDMI, on the other hand, continues to work on releasing its content-protection scheme to its 200-odd corporate members. This is the difference between consumer- and producer-led markets.

One of the great questioners of the 20th century was Richard Feynman, who was awarded a Nobel Prize in physics in 1965, but who was more popularly known for his New York Times best-selling book, ‘Surely You’re Joking, Mr. Feynman’: Adventures of a Curious Character, and for his role in the Rogers Commission hearings on the 1986 Challenger accident. Frustrated by the commission’s bureaucracy and the evasive answers that were given by key witnesses, Feynman conducted a live, impromptu experiment that resolved a key point in the investigation: He dunked a piece of the rocket booster’s O-ring into a cup of ice water and showed that it lost all resiliency at low temperatures.


But the best part of this story was Feynman’s own reaction to his experience. In his last media interview, Feynman told a Boston Globe reporter that his work on the shuttle commission had so piqued his interest in the complexities of managing a large organization that if he were starting his professional life again, he might be tempted to study management rather than physics.

Feynman’s comment is testament to the complexities inherent in preparing ourselves for leading the next wave of innovation on the Internet and beyond. In both educational and corporate settings, we should be teaching more about questions than answers, and more about those things that will be genuinely new and exciting in the next phase of the Internet. And we should subject all claims to the new to the Feynman test: Dunk them first in a proverbial cup of ice water.

James Short ( is a visiting associate professor at the MIT Sloan School of Management and associate director of the school’s new Center for eBusiness. He is on leave from the London Business School, where he is both an associate professor of strategy and information management and a founding director of the School’s i:Lab digital research laboratory.