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35 ChatGPT Prompts for Insurance Underwriters: Assess Risk Faster and Write Better Policies

#ai #chatgpt #productivity #finance

Insurance underwriting demands precision, speed, and deep domain knowledge — from evaluating complex risk exposures to communicating decisions clearly to brokers and clients. AI can act as your always-available research partner, helping you draft coverage rationale, analyze loss histories, and stay current on emerging risk classes. These 35 prompts are designed to fit directly into your daily underwriting workflow.

1. Risk Assessment and Analysis 

I am underwriting a commercial property risk for a 50,000 sq ft manufacturing facility that produces industrial coatings. Key details: sprinklered building, 15-year loss history with two fire losses totaling $400,000, ISO Building Class 5, located in a flood zone AE. Identify the top five risk factors I should evaluate before quoting and suggest any additional information I should request from the broker.
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Analyze the following liability exposure for a mid-sized landscaping company with 30 employees, $3.2M in annual revenue, operating in three states. They perform tree removal, pesticide application, and snow plowing. List the primary liability hazards, explain which are most likely to generate large losses, and recommend coverage enhancements I should consider.
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I am reviewing a submission for a professional liability (E&O) policy for a boutique IT consulting firm. They provide cloud migration and cybersecurity advisory services to healthcare clients. Draft a list of underwriting questions I should ask to properly assess their professional exposure.
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Explain the key differences in risk profile between a frame-constructed residential rental portfolio of 20 single-family homes and a single masonry apartment building with 40 units. Which presents a more favorable property risk from an underwriting perspective and why?
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I need to evaluate a workers' compensation submission for a home healthcare agency with 120 part-time aides. Their three-year experience mod is 1.18. Summarize the factors that likely contributed to an above-unity experience mod and outline the loss control measures I should require or encourage before binding.
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2. Coverage Analysis and Policy Drafting 

Draft a coverage rationale memo for a commercial general liability policy being issued to a food truck operator with $500,000 in annual sales. Explain the coverages included, key exclusions that apply, and why a $1M/$2M limit is appropriate for this risk class.
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A broker is requesting manuscript endorsement language to add professional liability coverage to a commercial package policy for a small engineering firm. Draft suggested endorsement language that outlines the insuring agreement, key exclusions, and conditions, clearly noting this is a draft for legal review.
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Explain in plain language the difference between an occurrence-based and a claims-made commercial general liability policy. Write this explanation as if I am sending it to a commercial broker who needs to explain it to a small business client.
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I am building a coverage checklist template for new restaurant submissions. List the core coverages, optional coverages, and common exclusions relevant to full-service restaurant risks. Format this as a structured checklist I can use during each submission review.
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Review the following policy condition language and identify any ambiguities or coverage gaps that could create disputes at claim time: [paste condition language here]. Suggest revised wording that is clearer and more protective for the insurer without materially restricting coverage.
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3. Pricing and Premium Calculation Support 

Walk me through the manual rating steps for a Business Owners Policy (BOP) for a small retail gift shop: $250,000 building value, $80,000 contents, $750,000 annual revenue, no prior losses. List each rating factor I should apply and explain how each affects the final premium.
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I am comparing two competing submissions for a directors and officers (D&O) policy for a private company with $15M in revenue. Company A has no prior D&O claims and strong governance. Company B had a shareholder dispute settled two years ago. Explain how I should differentiate pricing between the two and what additional underwriting information I need.
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Explain how loss development factors and loss trending are used in commercial lines pricing. Provide a simple numerical example using a hypothetical general liability account with three years of loss data.
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I need to justify a 22% rate increase on a renewal commercial auto account with a deteriorating loss ratio. Draft a renewal pricing rationale letter I can share with the producing broker that explains the increase clearly and professionally.
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A large commercial account is asking for a multi-year rate lock on their property program. What underwriting and pricing considerations should I evaluate before agreeing to a multi-year deal? List the key risk factors and protective measures I should include in any agreement.
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4. Broker and Client Communication 

Draft a declination letter to a retail broker explaining that we are unable to offer terms on a nightclub submission due to assault and battery exposure, prior liquor liability losses, and operating hours extending past 2 a.m. Keep the tone professional and constructive, and suggest alternative markets the broker might approach.
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Write a conditional offer letter for a commercial property submission where we are willing to quote subject to receipt of an updated appraisal, installation of a central station alarm, and confirmation that the roof was replaced within the last 10 years. The tone should be collaborative and encourage the broker to respond quickly.
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A broker is pushing back on our exclusion of habitational exposure from a commercial package policy for a building owner. Draft a clear, professional response explaining the underwriting rationale for the exclusion and offering to discuss stand-alone habitational options.
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Create a one-page underwriting appetite summary for a specialty contractor program targeting HVAC and plumbing contractors with revenues under $5M. Include target classes, coverage highlights, key underwriting criteria, and submission requirements. This will be shared with retail brokers.
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Draft follow-up email language I can use when a broker has not responded to my request for additional underwriting information on a pending submission. The email should be polite, specific about what is needed, and include a clear deadline to keep the submission moving.
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5. Loss Control and Risk Improvement 

I am reviewing a loss control report for a distribution warehouse with a history of forklift-related injuries. Summarize the most effective loss control interventions for forklift safety in warehouse environments and suggest five specific recommendations I should require the insured to implement as policy conditions.
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A restaurant account has had three slip-and-fall claims in two years. Draft a loss control improvement plan I can provide to the insured that addresses floor maintenance, employee training, incident documentation, and vendor management for wet floor situations.
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Explain how telematics data from a commercial fleet can be used to improve workers' compensation and commercial auto outcomes. Describe how I should weigh telematics adoption when underwriting a trucking account.
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I am preparing for an underwriting site visit to a metal fabrication shop. Create a pre-visit checklist of the key areas I should inspect and questions I should ask management to fully assess the property and casualty exposures.
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A construction contractor has requested a waiver of our requirement for a formal safety program. Draft a response that explains why the safety program requirement exists, outlines the minimum components an acceptable program must include, and offers to help them develop a basic program template.
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6. Regulatory Compliance and Market Knowledge 

Summarize the key NAIC model regulations that affect commercial lines underwriting practices, including guidelines on risk classification, adverse action notices, and use of credit information. Format this as a quick-reference summary for a commercial underwriter.
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Explain the current state of the commercial property insurance market in the United States as of 2025, including rate trends, capacity constraints in catastrophe-exposed regions, and how carrier appetites have shifted. What should I communicate to brokers about our appetite in CAT-exposed areas?
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I need to understand the regulatory requirements for issuing surplus lines policies in Texas, California, and Florida. Provide a comparison of the key differences in stamping requirements, tax obligations, and diligent search requirements across these three states.
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Draft a brief internal memo summarizing recent developments in cyber insurance underwriting standards, including changes in ransomware coverage terms, MFA requirements, and how carriers are approaching systemic risk. This memo is for a team of commercial underwriters.
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A submission involves a cannabis dispensary seeking general liability and property coverage. Summarize the key regulatory and underwriting challenges specific to cannabis risks, including federal vs. state law conflicts, banking limitations, and how these affect policy issuance and claims handling.
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7. Professional Development and Training 

Create a 30-day self-study plan for a junior commercial lines underwriter transitioning from personal lines. Include key topics to master, recommended study materials, and practical exercises they can do using real submissions under supervision.
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Explain the concept of adverse selection in insurance underwriting. Provide three real-world examples of how adverse selection can occur in commercial lines and describe the underwriting controls that help prevent it.
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I am mentoring a new underwriter who struggles with setting appropriate deductibles for commercial property accounts. Write a clear explanation of how deductibles function, how they affect pricing, and how to determine the right deductible level for different types of commercial property risks.
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Create five case study scenarios for training junior underwriters on commercial general liability submissions. Each scenario should include a business description, loss history, and a coverage question that requires the trainee to make an underwriting decision with a rationale.
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I want to improve my knowledge of construction defect liability as it applies to commercial general liability policies. Explain the key coverage issues, important case law concepts (e.g., the "your work" exclusion), and how underwriters typically approach construction risks to manage this exposure.
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Get All 35 Prompts in One Place

If these prompts were useful, I've compiled all 35 into a ready-to-use toolkit with bonus prompts and usage notes.

Get the complete AI Prompt Toolkit for this profession →

Works with ChatGPT, Claude, and DeepSeek.

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