Okay, allow me to go out on a limb here and say that every true bona fide leader is a risk-taker at heart.  They have the gift of courage, the gift of taking healthy and appropriate chances, of fearlessly rolling the dice one more time (not literally, as in gambling) the gift of going out on a limb…I think you get my drift.

The cautious, careful and calculating  so called “leaders” are not usually out in front leading, but somewhere in the pack, reminding everyone of all the reasons why the current plan of attack won’t work and is doomed to failure.

Now that we have that settled, let me say that there are a variety of different kinds of risk-takers:


  1. Financial
  2. Strategic
  3. Physical
  4. Confrontational
  5. Emotional
  6. Career
  7. Big decisions

Some leaders are a combination of some of the categories above, and I’m sure there are other categories I haven’t thought of.

Let me drill down on just three of them:

 1.  The relational risk-taker is willing to stake a lot on a relationship to make things happen. He believes so strongly in what he sees in a person that he is willing to bet the farm even though he has no hard evidence and is going more on a gut instinct. The leader put his money on a person by hiring that person, giving that person responsibility beyond their experience or by allowing that person to make decisions that could be costly if they didn’t turn out well.

 2.  The confrontational risk-taker is first cousin to the relational risk-taker. This leader sees someone performing well below their potential or someone in clear violation of established values and is going to sit down and have the come-to-Jesus talk. The difficult conversation is about to happen. It can either make or break the future for this leader and his organization or church. The true risk-taking leader does not shy away from the tough confrontational interactions. He doesn’t relish them or look forward to them, but neither does he run from them.

 A friendship could be lost, an employee could leave, a gossip-spreading chain of emails could make life difficult for you and your future as a leader, but you are willing to take the risk.  You are more interested in speaking the truth than being popular. You are more motivated to deal honestly and openly with people rather than look the other way and ignore attitudes and behaviors that are in violation of your values and work standards. You are willing to be misunderstood and criticized (if need be) for your confrontational talk.

3.  The big decision risk-taker is willing to step out and take advantage of a once-in a-lifetime opportunity, knowing full well that it could be the best decision they ever made or the worse decision they ever made. There are churches and companies that are thriving today because the leadership took advantage of a paradigm- shifting opportunity that had some risks attached. There are other churches and organizations that are dying on the vine because they said “no” to such an opportunity to embrace a radical idea, move in a totally different direction, sell something, buy something.

 You and I have read about people and companies who saw an opportunity to try something new or different; go in an exciting, totally new, but risky, direction; take advantage of an offer being given; and yet, in all of this, having no guarantees whatsoever that it will turn out the way it was promised or perceived. These types of leaders operate with the philosophy of nothing ventured, nothing gained. They are thrilled with the prospect while the more careful and cautious types retreat into their comfort zone…their fear-zone. I have worked with both types.

 Here’s what I’ve learned. No matter what risk-taking decisions you move toward:

  1. Some will like your decision
  2. Some will not like your decision
  3. Some will not understand why you made the decision
  4. Some will understand why you made the decision, but still not like it
  5. Some won’t care what you decide
  6. Some will leave because of the decision you made

But that’s what true leaders do. They make decisions, they take reasonable and healthy risks without over-analyzing, procrastinating or being frozen with the fear of failure.  After all, not making a decision is, in and of itself, a decision–just not a good one!

“Twenty years from now you will be more disappointed by the things you didn’t do than the things you did do. So throw off the bowlines, Sail away from the safe harbor. Catch the trade winds in your sail. Explore. Dream. Discover.” Mark Twain

Jesus took some giant risks for you. Take a few for him!