To strengthen experimentation, at both the individual and organizational levels, consciously approach work and life with a hypothesis-testing mind-set. Attend seminars or executive education courses on topics outside your area of expertise; take apart a product or process that interests you; read books that purport to identify emerging trends. When... See more

“If I had a favorite question to ask, everyone would anticipate it,” Michael Dell told us. “Instead I like to ask things people don’t think I’m going to ask. This is a little cruel, but I kind of delight in coming up with questions that nobody has the answer to quite yet.”

Ask questions that both impose and eliminate constraints; this will help you see a problem or opportunity from a different angle.

Though innovative thinking may be innate to some, it can also be developed and strengthened through practice.

innovative entrepreneurs go out of their way to meet people with different kinds of ideas and perspectives to extend their own knowledge domains.

Innovators carefully, intentionally, and consistently look out for small behavioral details—in the activities of customers, suppliers, and other companies—in order to gain insights about new ways of doing things.

“Often the surprises that lead to new business ideas come from watching other people work and live their normal lives,” Cook explained. “You see something and ask, ‘Why do they do that? That doesn’t make sense.’”

Innovative entrepreneurs like to play devil’s advocate. “My learning process has always been about disagreeing with what I’m being told and taking the opposite position, and pushing others to really justify themselves,” Pierre Omidyar told us.

To question effectively, innovative entrepreneurs do the following:

Ask “Why?” and “Why not?” and “What if?”