The Icarus Syndrome is a well-known plight in business leadership (in case you don't know, it's the applied symptom to a leader that takes too higher risks because they feel invincible, but ultimately they fall fast and land hard). Of course this was a term bandied about a lot during the GFC, and rightly so.
My concern, however, is that many business leaders have overcorrected. I feel many are idly chugging along an endless plateau of "the safest option" which could be a costly trip for them and their organisation.
Always playing it safe is a manifestation of languid thinking fuelled by a preoccupation with survival in the "top job". It's widespread. What's ironic is that the leaders who make decisions based on survival are embarking on the one journey they're desperate to avoid; the one that ends in failure.
Whenever I meet someone who has survival as his or her dominant theme, I ask myself; do you not realise that you are breeding a complacent, passionless culture? Aren't you bored of always playing it safe? Did you really work so hard to reach this position so you could acquire the title and do little else?
At the root of the problem are people that wrap their personal identity up in their professional title (I myself was guilty of this very early on my career). These people let their role define who they are as a person, so their professional decision-making processes are unnecessarily weighted by a fear that if they get it wrong, the consequences will reflect negatively on them as a human being. The blurring of professional and personal reputations is a pointless exercise. To endure in business you must learn to compartmentalise.
Of course certain situations call for the safe play, but if it's your guiding principle then that's a real issue. Challenging the orthodox approach and making calculated risks is something leaders need to be prepared to do.
My approach to risk-taking is fourfold.
One, don't misunderstand or overestimate your own ability. You must have a strong sense of self, schooled by your experiences, wins and losses. The essence is to rely on your own counsel and test that judgment with people that you trust.
Two, which is linked to the first, is to manage the relationship with the Board. Be honest, open and earn their respect. Depending on your style and the people involved this will either evolve rapidly, or gradually. Sometimes there's a chemistry, other times not, but if there is a foundation of mutual respect and trust then they'll back you, lessening the blow if the direction or new idea proves ineffective.
My third point is that you don't need just the right mix of people, but people that are smarter than you, too. Seriously. If you're able to develop a collective of specialists all working within your vision architecture you're a third of the way there. I'd add to that delegation is also critical. The obvious person to handle a situation isn't necessarily the right one: titles can be misleading.
Finally, use your judgment to know if you need to have a contingency. Sometimes the smallest risks on paper can unfurl into the most significant. Be prepared.
Leadership and risk taking go together like night follows day. Taking one away from the other leaves an incomplete universe that will satisfy no one.