What is one mistake you made when selecting insurance coverage that you wish you could have avoided? What lesson did you learn and what advice would you give to someone in a similar situation?

I made the mistake of considering insurance as something done after-the-fact to cover liabilities that arose from running our contracted services instead of viewing it as an active part of my financial strategy, from the beginning, I did not increase my professional liability coverage at the same time I increased the complexity of our enterprise contracts. When we contracted at a baseline level of coverage for liability, we assumed that would always be enough. As we grew from small teams of contractors to managing large amounts of engineering dollars , the difference between our policy limits and the contract's indemnity obligations became a very large, unaddressed risk. The biggest lesson learned is that insurance should be analyzed against the largest contract you have, not your average size contract. As you grow engineering teams or move into regulated environments, the standard coverage often has exclusions to coverage, leaving you at risk if an event occurs that would create the potential for you to file a claim as a result of that delivertory failure. Therefore, my recommendation is to do a full gap analysis each time the manner in which you provide services and/or take on clients that have a much higher risk profile than what you are used to should do a full gap analysis. This should include not just the cost of the coverage, but all of the different ways a potential event could lead to a claim. We now perform a pre-flight check for insurance prior to signing any major contract, so that we are certain we have the proper coverage in accordance with the specific liability environment of that project. Building a business is balancing risk-taking and risk avoidance. You don't want to think of insurance as a burden; you want to think of it as a support system that provides you with the confidence to take the calculated risks required to achieve true innovation and growth. That's the type of peace of mind necessary to concentrate on delivery instead of worrying about "What will happen if something goes wrong?"

One mistake I made when I first started my insurance agency was not paying attention to the deductible on the incident response section of a cyber policy. And yes, I am one of the insiders. I should have known better. I assumed "incident response included" meant all the forensics and IT recovery work would be fully covered from the first euro. After a real cyber incident I found out the hard way that my policy had a €5,000 deductible on incident response costs. That meant I had to pay for all the forensic work and system recovery out of pocket before the insurer would contribute. The technical help was there. The financial shock was mine. Never overlook the deductible on incident response. Check your cyber policy to see whether there is a separate deductible for forensics, crisis management and IT recovery. Most modern cyber policies go beyond just coverage. They are designed more like a service, offering free value added benefits like risk management tools, cyber hygiene assessments, employee awareness training and access to incident response specialists. And they often have no deductible on incident response, so you get immediate expert help without an unexpected financial hit. When shopping for a cyber policy or at renewal, ask your broker one direct question "From the moment an incident is discovered, what do I pay out of pocket before the insurer starts to pay?" If they cannot answer that clearly, push for a policy where incident response has no deductible. If it happened to me, it can happen to you.

Purchasing minimum coverage is a mistake. When you purchase coverage, especially as a new driver, you are often tempted to look for the cheapest option. If you have an old beater car that isn't worth much, liability-only coverage is a good option, but make sure your liability limits actually protect you. If you go with the state-required minimum coverage, you could easily be liable for twice the coverage you have, putting your assets at risk. Thankfully, I was never in a crash when I had minimum coverage, so I didn't have to learn the hard way. But now that I know more, I would never opt for minimum coverage. Adding adequate real-world liability coverage doesn't cost much more and is totally worth it.

Early on, I made the mistake of accepting a standard business insurance policy from a general broker without checking whether the coverage matched how we actually operate. We ended up paying for blanket coverage, including areas that did not apply to a mostly remote team with minimal sensitive customer data. The lesson was that insurance should be based on your real risk profile, not a generic template. My advice is to document how your business works, what data you handle, and where your true exposure sits, then take that to a broker or insurer that specializes in your industry. That extra step helps you focus coverage where it matters and avoid paying for protection you do not need.

I mistakenly underestimated the need for comprehensive liability insurance, particularly concerning digital content and advertisements. I focused mainly on general liability and errors & omissions coverage, believing these were adequate for our straightforward operations. However, I overlooked the complex liabilities in affiliate marketing, including risks like copyright infringement.

A common mistake in choosing insurance is underestimating the necessary liability coverage. Businesses often prioritize cost savings over adequate protection, leading to financial vulnerability during unexpected events. For instance, a business that opted for minimal general liability insurance faced significant out-of-pocket costs when a customer was injured at a promotional event, exceeding their coverage. The key lesson is to thoroughly assess current and potential future risks when selecting insurance.

One mistake I see over and over again and one I thought before I worked in insurance is buying based on price instead of espouse. I often hear "I don't need that much coverage". We often suggest if you can afford it to go higher on liability coverages, It is often not that much more. It can save you in the long run. It is a whole lot more affordable to pay a few dollars more a month, rather than several hundred thousand in property damage and medical bills.

A common mistake is choosing the cheapest policy without closely reviewing exclusions and coverage limits, which can leave key risks uncovered. The lesson is that price alone does not equal adequate protection; the policy language and limits matter. Before buying, read the sections that define covered events, exclusions, and claim procedures so you understand what is and is not protected. Ask an agent or broker to explain any unclear clauses and get written confirmation about coverage for risks tied to your contracts, and review your coverage annually as your business changes.

The biggest insurance mistake I made was choosing the cheapest comprehensive coverage for my company vehicle without reading the exclusions carefully. As a business owner running Software House, I assumed all comprehensive policies were essentially the same and picked the one with the lowest monthly premium. That decision cost me significantly more than the savings were worth. When my car was damaged in a parking lot incident, I discovered that my policy had a surprisingly high excess and did not cover certain types of cosmetic damage that I assumed were standard. The repair bill came to about $3,200 and my policy only covered $1,800 after the excess. If I had chosen the mid-tier option that cost just $40 more per month, the entire repair would have been covered with a much lower excess. The lesson I learned was that the cheapest premium almost always comes with trade-offs hidden in the fine print. Now I approach insurance the same way I approach vendor contracts at Software House. I read every exclusion, I ask the provider to walk me through specific scenarios, and I calculate the total potential cost rather than just the monthly payment. My advice to anyone selecting insurance coverage is to ask yourself one question before signing: what is the most expensive thing that could realistically go wrong, and would this policy actually cover it? If the answer is no or maybe, you are not saving money. You are gambling. The peace of mind that comes from knowing you are genuinely protected is worth far more than the small monthly savings from cutting corners on coverage.

My biggest mistake was underinsuring my home by choosing a lower premium without confirming the actual coverage limits. I learned that adequate coverage matters more than the cheapest rate and that being underinsured creates real financial risk. I now focus on the four main types of homeowners coverage, personal property, liability, dwelling, and additional living expenses, and make sure limits align with the events I could face. My advice is to note what events and complications you currently face, compare policies for loss and damage protections that some insurers include and others do not, and adjust your coverage accordingly.