Start with the reason for pruning.
Branches rubbing a roof, dead limbs and a crowded young canopy call for different work. Explain the result you want rather than asking for a blanket percentage of the tree to be removed. A provider should identify the branches, pruning objective and appropriate timing before cutting.
Ask how the proposed work will retain the tree’s natural form. Avoid treating a drastic reduction as routine maintenance; discuss alternatives with an arborist.
Live oaks need a timing conversation.
Texas oak-wilt guidance advises avoiding pruning or wounding oaks from February through June when possible and immediately painting oak pruning wounds. Have the provider explain how that guidance applies to your tree and any urgent damaged branches.
Source: Texas Oak Wilt pruning guidance. See our live oak planning guide.
Make cleanup part of the agreement.
Confirm where vehicles and equipment can go, what gets hauled away and whether small debris will be raked from beds or lawn. Tell the provider about lighting cables, irrigation, delicate planting and any access shared with a neighbor.