Look along the roof line for shingles that are curled, cracked, lifted or missing. Check gutters and the splash zone below downspouts for granules, the mineral grit that washes off shingles as they age. Look at valleys and around the chimney, vents and skylights for lifted or rust-marked metal. In heavy rain, water spilling over the front of a gutter usually points to a blockage rather than a roof fault, but it soaks the fascia either way. Green growth spreading across a slope is easier to deal with early, before the moss thickens and starts lifting shingle edges.
Inside, ceiling staining, damp insulation, frost on the underside of the deck in cold weather, or daylight through the roof boards all need looking at promptly. A stain can appear some distance from where water is entering, which is why tracing a leak is rarely as simple as it looks.