Correct any moisture problems. Moisture may be coming from inside your home, or it may be the result of poorly performing eavestroughs and/or downspouts.
Remove the loose, peeling or flaking paint using a paint scraper. Be careful not to scratch, gouge or dent the surface below the paint. Remove peeling paint from a large area using a power washer.
Treat any mildew with a solution of three parts water to one part household bleach. Wear gloves and eye protection. Leave the solution on for 20 minutes, then rinse thoroughly with water.
Scrub the surface thoroughly with a stiff brush and water to remove any dirt, chalky residue or treated mildew. Rinse thoroughly with water. Allow to dry.
Sand all bare spots if the surface is wood. This will help the primer and paint layers to adhere.
Prime the surface, using an exterior primer recommended for the surface you are painting. Check the weather report prior to getting out the paintbrush or roller; do not prime if there is a chance of rain or if the temperature will be under 50 degrees Fahrenheit. Use a paintbrush for smaller areas and a roller for larger areas. Use a higher nap roller for rough surfaces. Paint larger surfaces in three foot by three foot sections. Roll paint on in a "W" shape, then roll paint into the empty areas.
Clean all brushes and/or rollers. Use mineral spirits if priming with an oil-based product. Store or dispose of primer according to the instructions on the can.