1) Remember that the child is fundamentally working for his own self interests but his view is more personal and immediate than your own. The child should believe that you want him to prosper, be safe, and be at least as competent as, and sometimes superior to, his siblings and even to you. Convince the child that you are on his side; remember, it is your child's opinion that counts in this area, more than your own. Parents who are seen as the enemy sometimes have difficulty getting chores done, whether cleaning the bedroom or doing homework. Refusal to complete tasks is a powerful way to get you upset; the sense of power can be addictive for a child who is down on himself. Most of them will probably take an immediate "win" (making you angry) even if it entails a delayed cost (loss of privileges).
2) Tailor your expectations to fit your child's talents. Give him opportunity for recognition in his areas of strength even if they lie outside your own priorities. Every child is really good at something. Find those skills and highlight them. Robert Brooks uses the concept of "Islands of Competence"; put it to work. Discovering those islands may require that you (a) watch your child carefully, (b) ask him what he can do better than anyone else, or (3) review your own family history to learn about family talents that your child may share. Impulsive children often have difficulty with self-monitoring but even they build a sense of their relative standing in the home, a position that may be largely a function of their sense of their own physical, social, and practical competence.
3) Even disruptive behaviors can be adaptive in a different setting. The oppositional child who does things "his way and not yours" could be very successful over the longer run and outside the structure of school or your home. Many children who are oppositional with you at home will perform better than average on their first job. Oppositional behavior requires (a) that you set your priorities carefully in areas of health, safety, and morals, (b) you be more consistent than gravity with consequences in your priority areas, and (c) you make provision for your son or daughter to periodically "win" in areas that don't conflict with your priorities.
4) Be sure that you are absolutely impartial in the application of rules. Children can be sensitive to parents who don't apply rules consistently. Rules are different from privileges. "Consistent" does not mean the identical privileges for each child. Adjust privileges for age, social maturity, and for task completion whether cleaning bedroom, completing schoolwork, or cooperating with you. Be consistent with your rules for having different privileges.
5) Have the child monitor himself for strengths & gains. If he is too self-critical, teach him to challenge his outlook by suitable questions such as, "Are you really sure that's true?" or "What else could be happening?"
6) Emotionally sensitive children may need more praise as average children. Don't lie to them about their work but find ways to make each of them special or "first." DO NOT use negative language such as, "Even a dummy could do it better," or "Don't do this or that," or sarcasm, "I can't believe you finally got it right." Households with frequent negative commands and lots of shouting often have children who lie, steal, fight, destroy property, elope, and skip school.
7) Do not compare one child with siblings who are more academically competitive or temperamentally easier. Sibling rivalry can be a useful tool (see other postings under "The Red Queen"); however, sibling rivalry can be treacherous. If you are careless, there is some chance your discouraged child will decide to compete by becoming the "worst possible child ever." "Winning at being bad" is probably more interesting than winning at nothing.
8) Self esteem may have some influence on whether a child is willing to accept extra help. Feeling "different" includes having to go to the nurse or a tutor, to have special rules, and to go to doctors. Finding a friend with similar needs may be helpful.
9) Assign him helping roles with siblings, the neighbor's children, or with your own chores. Find him someone who needs protection; perhaps another child who is weaker, less capable in a topic that is strong for the child with low self esteem. Arenas for him to be helpful may include your church daycare, a preschool, or a scouting event.
10) Don't lecture! You have 1 and only 1 sentence in which to make your point. The child knows your lecture and likely gives it to himself when you let him alone. Lecturing forces him to defend himself which he may do by tearing off a piece of your own self esteem in retaliation. A 5 minute time out should suffice for nearly any infraction (use a timer); use a 3-count before imposing it. (Use the stairs for a time out and make it shorter for children who have a lot of trouble being alone.) Keep your voice firm without being sarcastic; give discipline in as private a manner as possible. Once you have given a time out, do not linger over it. Don't punish him once and have dad do it all over again. Don't compound punishments. Don't punish by taking away a reward he has just earned for a piece of good behavior. Stay calm. Excess emotionality lets your child know that he has "beat you" and he truly feels prouder for making you upset. If the child argues, set a time or place for a future discussion. At that time, paraphrase his disagreement so that he can hear his own arguments from your mouth. Trade roles with him to help him see your point. Give him a say in the nature of his discipline ... he may be harder on himself than you would be.
11) Find them a friend, perhaps a grandparent or an uncle, who is nice, consistent, and who has the power to speak up for them. Teachers and ministers sometimes can help with this role.
12) Low self esteem may be one reflection of a depressive disorder and should not be ignored. Seek professional help if these steps are not effective.