Business insurance gap check: what would an audit, a lawsuit or a fire find?
Most small-business owners bought their insurance on the day they signed the lease and haven't looked since. Twelve questions, about three minutes, and you'll know which coverages are missing, which are required by New York rather than optional, and what your landlord or GC is quietly assuming you have.
Answer twelve questions about your business, your people, your lease and your vehicles and get a 0–100 score with the likely gaps ranked by what they could cost, each with the question to ask. It checks the New York requirements that carry penalties on their own (workers' compensation from the first employee, DBL/PFL after 30 days) as well as what leases, general contractors and the Dram Shop Act expose you to. Runs in your browser; educational, not a quote.
This is the walk-through I do with a business owner who brings me a folder of policies. It doesn't ask for revenue or payroll figures; it asks the twelve questions that decide whether the program has holes, in the order those holes tend to hurt: the coverages New York fines you for not having, the ones your lease or GC assumes, the ones that keep the doors open after a loss, and the ones specific to what you do.
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Your browser has scripts turned off, so the interactive version can't run here. The twelve questions are listed below; answer them on paper and send me your notes, or call (518) 902-8822.
How the check works
Each answer feeds a ledger of nine coverage areas: workers' compensation, DBL and Paid Family Leave, general liability, contracts and certificates, property and business income, vehicles, liquor liability, professional liability, and cyber. The findings are ranked by how often each gap ends a business, not by premium size, which is why a missing workers' comp policy outranks a missing cyber policy. Every likely gap comes with the question to ask, in the words an underwriter understands.
The questions skip what doesn't apply: a solo owner isn't asked about DBL, an office isn't asked about liquor. "Not sure" is treated as a finding in itself, because a policy nobody has read is a gap with a premium attached.
The New York rules behind the check
| Rule | What it says | Where it comes from |
|---|---|---|
| Workers' compensation from the first employee | Nearly every New York employer must carry workers' compensation from the first employee, full- or part-time, family included. The Board can fine an uninsured employer up to $2,000 for every 10 days without coverage, and a stop-work order can follow. | Workers' Compensation Law §§10, 50, 52; WCB penalty schedule |
| DBL and Paid Family Leave | Disability benefits (DBL) and Paid Family Leave coverage are required once you've had one or more employees for 30 days, taking effect four weeks after the 30th day. DBL pays 50% of wages up to $170 a week; PFL is employee-funded at 0.432% of wages in 2026. | Workers' Compensation Law Article 9 (§§201–242) |
| Who counts as an employee | In construction, a worker is presumed an employee unless all three parts of the Fair Play Act test are met (free from control, work outside the usual business, independently established business). Paying cash or calling someone a subcontractor doesn't change it. | Labor Law §861-c (Construction Industry Fair Play Act) |
| Certificates of insurance | A certificate of insurance only confirms coverage exists; it can't add to or change the policy, and no one may demand one that says otherwise. Penalties for false certificates run $1,000 to $2,000 per violation. | Insurance Law §§501–503 |
| Liquor liability | Anyone who unlawfully sells alcohol to a visibly intoxicated or underage person can be liable for injuries that person later causes. A general liability policy excludes it; liquor liability is a separate policy or endorsement. | General Obligations Law §11-101 (Dram Shop Act) |
| Business vehicles | The 25/50/10 minimums and $50,000 no-fault apply to business-owned vehicles too, and a personal auto policy usually excludes deliveries and commercial use. | Vehicle and Traffic Law §311; Insurance Law §3420(f) |
| Salons and appearance-enhancement businesses | To be licensed by the Department of State, an appearance-enhancement business must carry at least $25,000 per person and $75,000 aggregate liability coverage. | General Business Law Article 27 and 19 NYCRR Part 160 |
| Customer data | Any business holding New Yorkers' private information must keep reasonable safeguards and notify affected people of a breach; cyber insurance is not required, but the breach costs are yours. | General Business Law §§899-aa, 899-bb (SHIELD Act) |
Quoted from the New York State Senate's consolidated laws, the Workers' Compensation Board and the Department of State, linked under Sources below, as of September 2026.
The twelve questions
- What kind of business is it? Restaurant or bar, contractor, retail, salon, office or professional, home services, trucking, other.
- Who works in the business besides you? No one, 1099 only, W-2 employees, both.
- Do you carry New York workers' compensation?
- Do you carry New York DBL and Paid Family Leave?
- Do you have general liability coverage? On its own or in a BOP.
- Does a lease, GC or client contract require insurance, and does your policy match it?
- What business property would you have to replace after a fire or theft, and is it insured?
- Could the business survive a two-month closure?
- How are vehicles used in the business?
- Do you sell or serve alcohol?
- Could a mistake in your work cost a client money or hurt someone without physical damage?
- Do you take card payments or keep customer data?
What it can't tell you
It can't read your policies, so it can't catch a classification that excludes your real work, a designated-premises limitation, an assault-and-battery exclusion on a bar policy, or an additional-insured endorsement that's the wrong form for your GC. Those turn up in a real review. Bring the declarations pages, the lease and any contract with an insurance clause, and that review takes about an hour; certificates go out the same day once coverage is in force.
This check is educational. It's based only on your answers, not on your policies or contracts, and it isn't a quote, a coverage determination or legal advice. Requirements described are New York's as of 2026; your lease, contracts, licences and lenders may require more. Answers stay in your browser and nothing is sent unless you choose to send it.
- Is workers' compensation coverage required? (NY Workers' Compensation Board)
- Violations of the Workers' Compensation Law — penalties (NY WCB) — up to $2,000 per 10 days without coverage
- Construction Industry Fair Play Act and the independent-contractor test (NY WCB)
- Disability and Paid Family Leave coverage requirements (NY WCB) — required after employing one or more people for 30 days
- Paid Family Leave 2026 updates (NY WCB) — employee contribution 0.432% of wages
- Workers' compensation and disability requirements for permits, licenses and contracts (NY WCB) — C-105.2, DB-120.1, CE-200
- Insurance Law §502 — certificates of insurance (NY Senate) — a certificate cannot amend or extend the policy
- Appearance-enhancement business insurance requirements (NY Department of State) — $25,000 per person / $75,000 aggregate liability
- General Obligations Law §11-101, the Dram Shop Act (NY Senate)
- Minimum auto insurance requirements (NY DFS) — 25/50/10 applies to business-owned vehicles too
- SHIELD Act — data security and breach notification (NY Attorney General)
Common questions
Short answers to what people ask before they call.
Which business coverages does New York actually require?
Two, for anyone with employees: workers' compensation from the first employee, part-time included, and statutory disability plus Paid Family Leave (DBL/PFL) once you've employed at least one person for 30 days. Vehicles owned by the business need at least the state's 25/50/10 auto minimum. Everything else, general liability, property, liquor liability, professional liability, cyber, is required by your lease, your general contractor, your licensing body or your lender rather than by statute. Salons and spas are an exception: the Department of State requires $25,000 per person / $75,000 aggregate liability to hold an appearance-enhancement licence.
I only use 1099 workers. Do I still need workers' comp?
Often, yes. New York decides employee status by the facts of the relationship, not the tax form, and for construction the Fair Play Act presumes every worker is an employee unless a three-part test is met. If a 1099 worker is injured and found to be your employee, you owe the claim and the penalty. At audit, the payroll of any subcontractor who can't show their own certificate is charged to your policy.
My landlord asked for a certificate naming them as additional insured. Isn't that just paperwork?
The certificate is paperwork; the endorsement behind it isn't. A certificate can't add coverage that isn't in the policy, and New York Insurance Law §502 prohibits certificates that say otherwise. If your policy doesn't actually carry the additional-insured endorsement, the waiver of subrogation or the limits the lease requires, you're in breach of the lease and uncovered for the landlord's claim at the same time.
Is a business owners policy (BOP) enough?
For a lot of storefront and office businesses, a BOP covers general liability, property and business income in one package and is the efficient way to buy them. It doesn't include workers' comp, DBL/PFL, commercial auto, liquor liability or professional liability, and it has eligibility limits by size and class. The check treats a BOP as general liability plus property and then asks about the rest separately.
Where do my answers go?
Nowhere unless you choose. The check runs in your browser and remembers your answers on your own device. Only "Send results" attaches the summary to a message to me, and only after you add your name and number and press send.
Get a quote for your business
Tell me what you do, where, and roughly what payroll looks like. Quotes come from the private carriers I represent, usually within days.