Asset condition monitoring is focused on assessing the condition of any asset for delivering the expected business outcome. Gap analysis for asset condition monitoring helps to identify risks and take corrective and preventive measures where the asset condition could be a problem. The goal is to reduce risks related to failure of the assets to perform according to the expected level. Australia has a vast land mass covered by overhead powerlines to meet the energy needs of a population that is located at geographically dispersed places over the country. Failure of the powerlines and the supporting poles not only lead to loss of supply, but also to huge loss of revenue. Bush fires can have catastrophic consequences such as loss of property, injury and death of people, in addition to a loss of forests which causes adverse impact on the environment and wild life. In 2009, Victorian bush fires in Australia killed 173 people, injured over 414 people, damaged 450,000 hectares of forest and vegetation and destroyed over 3,500 buildings and structures. Insurance estimates came to over Australian $1.5 billion. The total economic, environmental and social impact and the effect on quality of life of the people and wild life due to the disaster were estimated to be several times more than the insurance claims. Many of the bush fires in Australia are caused by powerline failures including failure of cables and poles. This paper discusses gap analysis for asset conditioning monitoring. It uses condition monitoring of power transmission lines and poles as an illustrative example for managing risks related to business objectives.