People naturally want to play it safe because it feels better in the short term. To break through this tendency, bombard it with tough and thoughtful questions. Hold other people accountable to do the same. Then hold them accountable for strategizing and executing.

Make it uncomfortable

Questioning everything could help you to spot problems and create a culture of understanding and action. What does this business look like in five years?  What are our customers worrying about today? What will concern them tomorrow? Where are we failing to communicate? Are we capitalizing on all our strengths? What opportunities are we missing?

Question everything

The dangers of playing it safe appear so gradually that they rarely get noticed.It is like a slow leak in a tire, you only notice it when you are stuck. You don't have an idea of how it happened.

Playing it safe: a silent killer

People try desperately to hang on to antiquated ways of doing business because of a false sense of security. They believe that they can maintain their old ideas indefinitely, even if all evidence shows the contrary.

Hanging onto old ideas

Last year Dina, a CEO I'd been working with, felt that leaders on her team were playing it too safe. They weren't finding and pursuing new growth opportunities and it was crippling the organization. She kicked off her October management team meeting, which I was attending, by reading the following passage from my book: The dangers of taking too much risk are very clear.

Question everything

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