Photo by mpires
I recently talked to someone at a very innovative large web company (under Frie-NDA) who described their official engineering motto as "Move fast and break stuff". I love that philosophy because it ties in to research showing that really successful people get there by trying a lot more approaches than average folks. They fail faster, cheaper and more often than ordinary people.
The key to making that work is that the cost of the total failures must be less than the value of the cumulative successes. This is a hard problem, because the default for most organizations is "managing to avoid blame". Their implicit motto is "Reward success and inaction, punish failure", which ends up making inaction the most appealing course. "Move fast and break stuff" encourages a different mentality, "Reward success and failure, punish inaction".
So how do you get that mindset in your organization? The most important step is to de-stigmatize failure. The web company I mentioned makes it clear to their engineers that they will not be punished if they break the site, even if it costs millions of dollars in lost revenue. I didn't get to dig deeper on that topic but I'd imagine there are some serious post-mortem procedures to understand why things go wrong and build tools to prevent a recurrence, like the Five Whys.