A new roof does not automatically mean new gutters. Nor does a line saying “existing gutters retained” explain everything that will happen around them. Treat the roof, gutters, downpipes and fascia as connected parts with separately described work.
AI-generated illustration, not a drainage design.
Ask what will stay and what will move
For each component, ask whether it will be left in place, temporarily removed and refitted, repaired or replaced. Add who is responsible for the work and whether another trade needs to attend.
This is especially useful when a homeowner has assumed the price includes a refreshed roofline, but the quote only covers the roof cladding. Settle that difference while the proposal can still be revised.
Describe existing problems before pricing
Tell the contractor about overflow or staining you have observed, including where and when it occurs. Do not assume a new roof will resolve an existing drainage concern. Ask whether the proposed scope includes investigating it or whether that needs a separate assessment.
If a gutter is to be retained, ask what condition was observed and what remains unknown. “Retained” describes the proposed work; it is not a statement that the component is new or guaranteed to last as long as the new roof.
Confirm the finish and close-out
Where components will be replaced, confirm the specified product, finish and connection to the remaining work. Ask how any unexpected damage found during removal will be reported before additional work is authorised.
At handover, record outstanding items and keep any maintenance information supplied. See roof completion documents for organising those records. Full Tree's residential roofing page is a starting point for discussing the overall project rather than a single line in the quote.