Start with how they answer the first question
Describe your job and ask which filing path it falls under and what that filing needs. A contractor who works in this city regularly answers immediately: full demolition permit, Alt-2, or outside a filing. One who says “we handle all the permits, don’t worry about it” and cannot tell you what the package contains has told you something useful.
This is the fastest and most revealing test you can run, and it costs one phone call. Registration and insurance are worth confirming in writing before work starts — a general contractor supervising construction or demolition in New York City is required to be registered with DOB, and demolition on buildings of four storeys or more brings additional safety endorsements — but paperwork tells you who is permitted to do the job, not who will run it well.
Ask what happens on day one
A contractor who has sequenced this work before can describe the first day without being prompted: what gets protected, which route the debris takes out, how the utilities are proved dead, and what has to be signed before anyone starts.
Vagueness here is the single best predictor of a job that slips. The sequence is where demolition either goes cleanly or goes wrong, and it is the part a quote never shows you.

Ask about asbestos in the first conversation
If your building predates April 1987 and the work needs a permit, an ACP-5 is required before that permit issues. Any competent contractor will raise this before you do.
Be wary of anyone who offers to "have a look under the tile" to see whether there is asbestos. Disturbing suspect material to identify it is precisely what the rule exists to prevent.
Ask where the debris goes, and whether you get documentation
C&D debris has to leave in covered loads, to a permitted transfer station, with documentation per load. Ask whether you will receive that documentation.
Also ask what they do with the things that are not C&D debris. Asbestos and lead-contaminated material, fluorescent tubes and ballasts, appliances, tyres, drums and fuel tanks all have to be separated and routed differently. A contractor who has not thought about this is planning to put it in the container and hope.
Ask who they coordinate
A demolition needs specialists around it: a DEP-certified asbestos investigator, a qualified fitter to prove a gas supply dead, an engineer where anything carrying load is coming out, a licensed abatement contractor if the report comes back positive.
Ask who arranges each of those and who holds the programme together while they run. The answer tells you whether your job will be managed as one sequence or handed between trades with you in the middle.

Compare quotes on the same assumptions
Before comparing numbers, check that every quote assumes the same debris route, the same reinstatement standard, the same treatment of the filing work, and the same answer on asbestos.
A low quote is usually a different scope rather than a better price, and the difference tends to appear halfway through the job when your options are worse.
Signals worth taking seriously
- They ask about the building’s age before they ask about the square footage.
- They ask how a truck gets to the door.
- They want to see the alteration agreement or the lease clause.
- They give you a firm price only after seeing the site.
- They tell you when something is not their work.
- They can explain what happens if the asbestos assessment comes back positive.



