What’s the cheapest, most effective way to protect your business from a cyber disaster, insurance denial, or legal attack? 

Write stuff down. 

Seriously. If you're making decisions about IT security, risk, or compliance—and especially when you're turning down recommendations—documenting the rationale is the single most powerful, affordable insurance policy you’re not using. 

Insurance Claims Get Denied Without Documentation 

Cyber insurers don’t want to pay claims. They’ll look for any reason to push the burden back on you. And one of the most common reasons? Lack of documentation. 

If your IT provider recommended a change, and you didn’t approve it, the carrier wants to know why. Was it because of budget? Competing priorities? Implementation risk? If there's no record, their assumption is simple: you were careless. 

But when you’ve captured your decision—and your reasoning—you give them no room to deny the claim. You show you were informed. You acted within your capacity and risk tolerance. You were running your business like a responsible executive. 

Lawyers Will Tear Apart Your Decisions. You Need to Show the Whole Picture. 

In the aftermath of a breach or incident, legal teams will go hunting. They’ll look through every system, every contract, every conversation. And when they find gaps in your technology or controls, they’ll ask: “Why wasn’t this done?” 

If you don’t have an answer, they’ll write one for you—and it won’t be generous. 

But if you do have a trail of thoughtful decisions, those gaps become justified choices: 

  • A recommendation wasn’t adopted because there was no budget this quarter. 
  • A tool wasn’t deployed because your team was in the middle of a major migration. 
  • A security fix was delayed because you chose to prioritize another, more urgent concern. 

In legal terms, this can mean the difference between negligence and prudence. 

AND Every “No” Needs a “Why” 

This isn’t about saying yes to everything. Most businesses can’t. What matters is that every “no”—or “not now”—has a clear “why.” 

Think of this like a journal of leadership decisions. You’re building a library of evidence showing how your company approached cybersecurity and technology with intention, not neglect. 

Because when something happens (and something always does), having these records makes your story believable, defendable, and trustworthy. 

This Isn’t Expensive. In Fact, It’s the Most Affordable Risk Strategy You Have. 

Here’s what’s wild: this level of protection doesn’t require a new product, tool, or investment. It requires discipline and documentation. 

Start with a simple practice: every time your IT team or MSP makes a recommendation, create a quick note. Who made the recommendation, what it was, and why you chose to act—or not act—on it. That’s it. 

When you collect those notes and organize them into a running log, you’ve built an evidence packet. One that shows insurance carriers, legal teams, and any third party that you did your job. You paid attention. You acted responsibly. 

This is how liability gets reduced—without overinvesting in tech you may not need yet. 

Remember: Document Everything. Produce Evidence. Sleep Better. 

You’re making judgment calls all the time. The only mistake is failing to record them. The solution? 

Document everything. Keep a running log of IT and cybersecurity decisions. And if you don’t have time to build a system, use one that makes it easy. 

There are now affordable tools that help you do exactly this—creating your own low-cost, high-impact insurance policy that protects your decisions and your reputation. 

It’s not about spending more. It’s about proving you made the right calls with the information you had—and doing it in a way that holds up when it matters most.