Your First 100 Days as CEO: The Risk & Insurance Checklist Nobody Hands You

Sep 1

5 min read

Insurance Checklist Nobody Hands You

You were hired to run the company, not to read its insurance policies. But in your first hundred days the arrangements you inherited are quietly your problem - and the gaps in them can become your personal problem faster than most new chief executives expect. Here is how to get on top of them without becoming an insurance expert.

A new chief executive inherits a great deal on day one: a strategy, a team, a set of commitments to customers and lenders, and a filing cabinet of insurance policies and contracts that someone else negotiated. The strategy and the team get all the attention. The insurance program rarely does - until a claim, a lender question or a board paper drags it into the light, usually at the worst possible moment.

The good news is that getting across it is not hard, and you do not need to become an insurance expert to do it. You need a deliberate first hundred days and the right questions. This is the checklist we wish every incoming chief executive was handed on their first morning.

Days 1–15 - Find out what you actually have

You cannot manage what you cannot see, and most new leaders are surprised by how hard it is to get a clear picture of their own insurance program. Start with the basics and ask for them in writing:

The policy schedule: which lines of cover the business actually holds, the limits on each, the excesses, and the renewal dates. Public liability, professional indemnity, contract works, plant and equipment, motor, workers compensation, cyber and management liability are the usual suspects, but the interesting question is what is missing.
The broker relationship: who your current broker is, when the program was last marketed to insurers, and when the next renewal falls. A program that has quietly rolled over for years without being tested is a common, and expensive, finding.
The claims history: the last three years of claims. Nothing tells you more about where a business actually hurts than what it has had to claim for, and how those claims were handled.
The internal owner: who inside the business is responsible for insurance and renewals. If the honest answer is "no one, really," that is itself worth knowing in week one.

Ask for a single-page summary of the program. If nobody can produce one quickly, you have learned something important before you have read a single policy.

Days 15–45 - The exposures that will not wait

Most of the program can wait for the next renewal to be improved. A few exposures cannot, because they attach to you and to the business the moment you take the role.

Your own neck, directors’ and officers’ cover. As a director and officer you are now personally exposed to claims arising from how the company is run, and your house is on the line in a way it was not last month. Confirm that a directors’ and officers’ (D&O) policy exists, that the limit is realistic for the size of the business, and that the cover responds to your predecessors’ decisions as well as your own. The gaps that catch new leaders out are inadequate limits, missing run-off cover for the outgoing board, and prior-acts exclusions. This is worth a dedicated conversation early.

Live projects and contract works. In construction, property and development, every current project should be insured in the way its contract requires, no more, no less. New leaders regularly discover confusion over who is carrying the contract works and liability cover on a given job: the principal, the head contractor or a subcontractor. Ask for proof that each active project is covered to its contractual obligations. An uninsured gap on a project already under way is not a renewal problem; it is a today problem.

The contracts crossing your desk. The insurance and indemnity clauses in the head contracts, subcontracts and leases you sign in your first weeks can quietly transfer enormous risk onto the company, -risk your policies may not actually cover. Before you sign anything significant, have someone who understands both the contract and the insurance check that the two line up. It is far cheaper to fix a clause before signing than to argue about it after a loss.

The statutory must-haves. Workers compensation in every state you operate in, compulsory motor cover, and any licence-required insurances are non-negotiable. Confirm they are current and correctly cover your actual footprint, especially if the business has expanded interstate.

Days 45–100 - Does the program fit the company you now run?

The program you inherited was built for the company as it was, not as it is today or as you intend it to be. With the urgent items handled, use the balance of your first hundred days to test fit:

Limits against reality. Do the sums insured and liability limits match current turnover, asset values and the size of the projects you now take on? Under-insurance is the silent risk, everything looks fine on the certificate until a large claim is scaled back because the declared values were years out of date.
Gaps and overlaps. Are there exposures with no cover at all - cyber, management liability, the true scope of your professional indemnity, and are you paying twice for anything through overlapping policies?
Growth and change. If you plan acquisitions, new services or new jurisdictions, your risk profile is about to change. A program that fits today may not fit the company you are building. Better to flag it now than at the next renewal.
What the claims are telling you. Recurring claims of a particular type are a signal about the underlying business, not just an insurance matter. They are worth a conversation with your operational leaders.

The question behind all of them: is your broker a specialist?

A generalist broker and a specialist look identical on a certificate of currency. They look very different at renewal, and even more different at claim time. As you work through the checklist, form a view on whether your current adviser genuinely understands your industry, your contracts, your projects, your board-level exposures, or simply renews what was there before. A broker who can read a head contract and tell you whether your cover matches its requirements is worth a great deal more than one who cannot. If you are not sure, that is reason enough to seek a second opinion.

The hundred-day mindset

You do not need to become an insurance expert in your first hundred days. You need to see what you have, deal with the handful of exposures that cannot wait, test whether the program fits the company you now run, and make sure a competent, specialist adviser owns the answers going forward. Do that, and one of the quieter risks of stepping into a new leadership role stops being a blind spot and becomes just another thing you have under control.

Your First 100 Days as CEOThe risk & insurance checklist — at a glanceDAY 1DAY 15DAY 45DAY 100DAYS 1–15Find what you have– Policy schedule, limits & excesses– Broker details & renewal dates– Three years of claims history– Who owns insurance internallyGet it all on a single page.DAYS 15–45Handle what can’t wait– Confirm D&O — limits & run-off– Live projects insured to contract– Check clauses before you sign– Verify statutory coversThe exposures that attach to you now.DAYS 45–100Test the fit– Limits vs current values– Hunt for gaps & overlaps– Plan for growth & change– Read the claims historyDoes it fit the company you now run?