Carve out about 30 minutes of time on a free day, such as a Saturday. You want to select a day when your child will be relaxed. Perhaps visit an ice cream parlor or a park.
Give your child a piece of paper and a pencil. Ask him to write down his strengths and weaknesses on the first page. On the back of the page, ask him to write down his personal goals.
Talk about the strengths and weaknesses together. Affirm the strong attributes your child has written down.
Evaluate the weaknesses he wrote down. Are they accurate? Is he too hard on himself? Instead of dwelling on the weaknesses, talk about how he might improve them. You also might consider turning the weaknesses into strengths. For example, if he wrote "Bad at spelling," you might say something such as the following: "Well, some of the greatest writers in the world have had trouble with spelling, and that is something that you can improve with practice."
Talk about your child's personal goals and evaluate them. This is a good opportunity to gently move your child in a direction that he can get excited about. Try to set small goals and one or two large goals together. Setting too many large goals can be overwhelming and will make your child feel defeated when he does not accomplish them. You might suggest that your child work on one goal for the week. For example, you might say something such as the following: "John, since you want to work on your spelling this week, why don't you make it your goal to learn your 10 spelling words perfectly by Friday morning. I will work with you."