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Look at the pattern from a safe position
Regularly spaced openings in a horizontal row are worth asking about. An isolated broken brick or ragged crack is a different observation. Neither pattern proves what is hidden behind the wall. Photograph the row in context so the assessor can see where it sits relative to the base, an opening or an adjoining roof.
Ask where water behind this brick is meant to go
On a designed drainage wall, flashing collects water and directs it toward outlets. The Brick Industry Association illustrates several arrangements for brick walls. Its details do not classify every chimney. A brick veneer around a framed enclosure differs from a solid masonry chimney, and roof step flashing serves another purpose at the roof surface.
Have the proposed sealant locations identified
If a painting estimate includes “caulk all gaps,” give the crew a marked photo and ask for confirmation of which joints are intended to stay open. If you see staining after a previous sealing job, document which openings were altered and when. Avoid probing, drilling or cutting the joints or the hidden flashing to investigate them yourself.