Q As a manager, I sometimes have to give negative feedback and feel very uncomfortable with it. Consequently, I tend to hold back. How can I get better at this?
A Helping an employee improve is one of the great contributions you can make, and it's worth taking the time to learn to do it well.
The inner game
Start by managing your anxiety and dispelling any false notions you have about providing constructive criticism. Delve into the inner messages that you associate with it. Do you feel like you're accusing the employee of having done something "bad"? What if you are on the receiving end? If it's hard for you to accept feedback from your manager (or others), it'll likely be hard for you to believe that you're helping by offering feedback.
Notice your feelings. If you're angry, it'll be hard to be constructive. Moreover, you may be angry not because of the error, but because the employee put you in the situation of having to correct them. Or, if you're nervous, what are you afraid of? Ask yourself what is the worst that could happen. The employee could be angry or upset? If so, prepare by thinking about how you'll handle it.
Be realistic about how bad the situation is, and notice any tendency you may be feeling to dramatize things.
The outer game
Let's face it -- people usually know if they've messed up, so helping turn an error into a learning event is going to be more helpful than emphasizing the mistake. If they're truly unaware, then you'll need to start there.