Checklist: Reviewing Risk Strategy Through a Claims Lens

Stress-testing your insurance program before a claim lands

Jul 10, 2025

Most risk strategies look solid until something actually happens. That’s when things break: policies don’t respond as expected, documentation’s incomplete, or no one’s sure who’s meant to do what.

This checklist flips the usual approach. Instead of building from policies upward, we work backwards from the moment of impact. Think of it as a pressure test: if a major claim landed today, how well would your strategy hold up?

1. Start at the end: walk through a hypothetical claim

Forget hypotheticals; get specific. Take a material loss scenario (fire, cyber attack, product recall, serious injury) and walk through it in detail.

✅ Have we simulated what a material claim might look like for each key policy?

✅ Have we set explicit, board-approved thresholds for what constitutes a “material” loss in each risk category (e.g., property, cyber, liability)—both in dollar terms and operational impact?

✅ Who’s likely to identify the incident first? Would they know what to do next?

✅ Do we have the right information flow in place to quickly trigger a claim?

Tip: Tabletop exercises reveal more than strategy documents ever will. Run one and watch where friction shows up.

2. Review policy wordings against real-world events

Now map your policy documents against your messy operating environment.

✅ Do the triggers and definitions reflect how we’d actually describe the event?

✅ Are our sums insured and policy limits regularly updated to reflect current asset values, revenue, and business scale?

Warning: Underinsurance is a leading cause of claim shortfall, especially for fast-growing businesses. If your cover hasn’t kept pace with your growth, even a successful claim could leave you exposed to significant out-of-pocket costs.

✅ Are there grey areas or vague triggers (e.g. “unforeseen,” “sudden,” “malicious”)?

✅ Have we tested exclusions using real examples from our business?

✅ Would indemnity periods, limits, and sublimits hold up under our current operations?

✅ Are we relying too much on extensions or endorsements to fill core coverage gaps?

E.g.: Would our cyber BI policy respond if a third-party SaaS outage took us offline? And how would we prove causation?

✅ Do we have a process in place to review and update our insurance program whenever there are material changes, such as new locations, product launches, acquisitions, or entry into new markets?

Tip: Many claims are denied or reduced because policies weren’t updated after business changes. Schedule policy reviews after any major operational shift—not just at annual renewal.

3. Map claim ownership and documentation gaps

Claims don’t fail because something went wrong, they fail because no one can prove what happened.

✅ Who owns the claims process internally (beyond initial notification)?

✅ Are we clear on who prepares claim files, liaises with adjusters, and controls messaging?

✅ Have we documented key workflows for evidence collection, incident logs, and financial loss tracking?

✅ Can we reconstruct timelines from systems, emails, and decision logs under pressure?

✅ Are we capturing costs that may be recoverable under claim preparation or loss mitigation clauses?

4. Challenge broker and insurer alignment

This is where many programs fall short—not due to bad intent, but because no one asked hard questions.

✅ Does our broker proactively test our policies against emerging risks and real scenarios?

✅ Have we had a claims-focused review? Or just a renewal meeting?

✅ Do we know who will represent us in a claim, and do we trust them?

✅ Are we relying on assumed market norms that don’t hold up when contested?

✅ Have we seen how similar claims played out across the market?

5. Test strategic fit and appetite alignment

Insurance should match your risk appetite, not misrepresent it.

✅ Does our program reflect our operational reality?

✅ Are there legacy covers in place that no longer match how we work?

✅ Have we adjusted for changes in scale, geography, tech infrastructure, or supply chain risk?

✅ Are emerging exposures (e.g. ESG litigation, regulatory change, digital dependencies) covered?

Final check: could we move at claims speed?

When a major incident occurs, speed and clarity of response can make or break your claim. Even the best policy won’t help if notification is delayed or evidence is lost. Claims are just as likely to fail on execution as on policy wording. Test both.

✅ Do key people know how to notify and escalate a claim right now?

✅ Is our notification process fast, documented, and easily actioned under stress?

✅ Do we have legal, PR, finance, and operational responses aligned in advance?

✅ Have we captured lessons from near misses, small claims, or industry events?

Wrap-up

Most businesses only see the cracks in their risk strategy after a claim. The smart ones reverse the lens early.

This checklist is designed for leaders who are accountable for their organisation’s resilience. Use it to uncover blind spots, challenge assumptions, and ensure your risk strategy holds up under real-world pressure.