Do you ever find yourself in over your head? If not, I would suggest you don’t spend enough time in the water. The truth is all leaders find themselves swimming in rough conditions from time-to-time. The difference between those who drown and those who become stronger swimmers is little more than a combination of attitude and preparation.

It was T.S. Eliot who said, “If you aren’t in over your head, how do you know how tall you are?” With all due respect to Mr. Eliot, it’s one thing to push past comfort zones and test your capabilities, but it’s quite another thing to survive to do so. Here’s the thing – good leaders take risks, but great leaders are prepared for the risks they take.

Being in over your head can lead to career-defining moments (good or bad). When leaders push personal, team, or organization boundaries one of two things is likely to happen: they’ll either exceed all expectations or fall short of them.

The difference between success and failure isn’t found in risk-taking alone but in the planning and execution surrounding the taking of the risk. There’s truth in the old military saying that “prior proper planning prevents poor performance.”

I recently went surfing in the frigid waters of the Pacific Northwest with my son in law. It was the first time I’d climbed on a surfboard in more than 30 years.  I crammed myself into the wetsuit (not a pretty sight) and paddled out to the waves. The truth is, my son in law surfed and I spent two hours trying not to drown.  He was prepared, experienced, and in shape. He challenged himself and I was just in over my head – literally and figuratively. He had a great time, and I just had a time of it.

My surfing experience was a great reminder that all the positive thinking in the world won’t overcome certain practical realities. I don’t regret surfing that day, but I do regret not being prepared for it. While I survived the experience, it was pure luck. Not everyone who takes a risk without proper preparation is so lucky. I’m not suggesting leaders don’t take risks, but simply that said risks be prudent ones.

The bigger issue for leaders is not the personal risk they take, but the risks they subject others to. While leaders have a responsibility to those they lead not to take unnecessary risk, they likewise have an absolute obligation to seek out and incur necessary risks. Many leaders take risks, but great leaders inculcate the planned execution of necessary risk as a cultural imperative. When calculated risk-taking becomes encouraged at all levels of the enterprise it’s an indicator of sound leadership and a healthy culture.

My message is simply this; rather than fear the rough waters, take the time and effort to prepare your team for them. Then and only then, go in search of the big waves. Surf’s up…