Maybe you know him. Meet Fearful Fred. He takes to risk like a cat takes to water. Fred is constantly undermining himself with a built-in fear of failure. Fearful Fred means well, but more than anyone on your team, he needs your support. 

Start by listening to him. Take Fred aside and encourage him to share his fears. Once you've identified his fears, try to help him determine why he has them. 

The next step is to help Fred tap into his desire to overcome his fears and succeed. As his leader, you must endeavor to help him harness that desire. 

As soon as Fred is ready to take the plunge, lead him in a project that will give him a win under his belt. To maximize Fred's chance of success, be sure to include the following elements: 

1. Strategy: 

Begin by planning a project together; including Fred increases his ownership and confidence; including yourself insures success. 

2. Structure: 

Once you have a plan, give Fred very specific guidelines to follow. Remember, Fred's problem is fear of failure. Make this first project like a follow-the-numbers painting. That takes the doubt out of the process for Fred. 

3. Safety: 

Be sure to pick a project that is easy, and for which the stakes are not too high. 

4. Security: 

Do as much with Fred on the project as you can. This will give him confidence and build your relationship with him. 

5. Success: 

If you begin with a project that you know is winnable, then you guarantee Fred a personal success. And nothing succeeds like success.