ALL FIELD NOTES
Aug 5, 2026·6 MIN READ
Hiring & Disputes

10 essential questions to ask a contractor before hiring

Clear communication up front prevents expensive disputes later. Here are the 10 questions that tell you how a contractor actually works.

10 essential questions to ask a contractor before hiring

1. Are you licensed and insured for this specific trade?#

Never accept a verbal "yes." Ask for an active Certificate of Insurance (COI) sent directly from the broker showing general commercial liability and workers’ compensation coverage.

Contractor milestone verification review
Structured payment milestones ensure fair compensation for trades while protecting homeowner budgets.

2. What is the payment schedule and deposit requirement?#

  • Deposit: A reasonable initial deposit (typically 10–20%) to secure scheduling and order custom materials.
  • Milestones: Progress payments released upon completion and inspection of defined phases.
  • Holdback / Final payment: A final 10–15% held back until all punch-list items are finished.

Contractor hiring scorecard#

Evaluation CriteriaGreen Flag (Professional)Red Flag (High Risk)
Licensing & InsuranceActive COI provided directly from insurance brokerVerbal assurance only; no written proof
Payment Structure10–20% deposit; milestone payments; final holdbackLarge upfront payment (>30–50%) demanded
PermitsContractor pulls permits in business nameAsks homeowner to pull permit as owner-builder
Change OrdersWritten change order signed before extra work beginsSurprise additions tacked onto the final invoice
ModelQuoter

Start your contractor search with confidence. Model your project to establish a fair, itemized planning estimate and clear scope specifications.

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