The issues and conditions of employment has remained contentious and challenging to most industrial organizations especially in Africa. Compromise reached on matters under discussion between employer and workers in most cases does not promote industrial harmony within the organization. Mutual agreement between employers of labour, union leaders and their members is usually swept under the carpet. Coercion rather than persuasion is seen as instrument to bring about a settlement. The paper therefore present issues involved in collective bargaining in an industrial setting and challenges arising from non-implementation of terms of agreement. The hope for collective bargaining in industrial organizations could be brought about by matching structure of bargaining to the environment contexts as well as Organizational characteristics of the union and their workers. Regular and effective communication between trade unions and management is recommended among others things to prevent industrial and labour disputes.