Why getting a human on the phone at your insurance company shouldn't take half a day

On this week's episode, we did our version of Festivus. We aired the grievances. Not about clients — clients are fine. The grievances were about the people on the other side of this business: the insurance carriers themselves, their phone trees, their underwriting departments, and especially their claims adjusters.

And here's the part that should worry you: if your insurance agent is frustrated trying to get a real human on the phone at your carrier, imagine what it's like for you. We're inside the industry. We have direct lines. We have agent portals. We have contacts. And we still spend a meaningful chunk of every workday on hold listening to bad jazz.

The phone tree that costs you half a day

You know the drill. You call your carrier with a quick question — change an address, add a vehicle, ask why the renewal premium jumped. The phone tree starts. Press 1 for billing. Press 2 for claims. Press 3 if you'd like to lose your mind.

Stephanie put it perfectly: "you sit there, you call, you press, go through the menu tree. You're 10 minutes in before you finally find the right one." And then half the time — "you get disconnected and you gotta do it all again."

What used to be a five-minute phone call is now a half-day project. And it's not because the carriers have gotten busier. It's because they've made a deliberate choice to push customer interactions through automated systems, portals, and chatbots — anything that doesn't involve a salaried human picking up a phone.

Health insurance is the worst of the worst

If you've ever tried to fight with a health insurance company about a claim that should have been covered, you already know this. But Dennis said it on the show and it's worth repeating:

And the math is rubbing salt in the wound. Health insurance premiums have shot up dramatically, while the coverage has gotten worse. Higher deductibles. More denials. Narrower networks. Price is going up, coverage is going down. That's never good.

We talked about this on the show in the context of why someone wouldn't just self-insure — and the answer is the obvious one. Even when the service is bad and the price is high, the alternative is far worse: "could you come out of pocket a hundred thousand dollars every year when you need these treatments? No." So you pay the premium, you take the bad service, and you hope nothing big happens.

Why your premium went up even though you didn't file a claim

This is the question we field most often, in every line of insurance. "My driving record is clean. My house didn't burn down. Nothing happened. Why am I paying more?"

The honest answer involves something most agents won't say out loud: your premium isn't really about you. It's about the carrier's whole book of business. Here's what Dennis said on the show:

What he means: the cost to rebuild a house has gone up. Lumber, drywall, labor, roofing materials — everything. The cost to repair a car has gone up because cars now have computerized everything, and a fender-bender that used to be $800 is now $4,200. Medical costs have gone up, which drives bodily injury liability claims. Litigation costs have gone up.

The carrier has a math problem. The dollars going out (to pay claims) have spiked. The dollars coming in (premiums) have to spike to match. Your individual premium goes up because the entire pool's claims are getting more expensive, not because you did anything wrong.

That doesn't make it feel less unfair. We get that. But it does mean shopping carriers periodically is the only real lever you have — different carriers reach different conclusions about which risks to be aggressive on, and you can sometimes find one that's hungry for your specific situation.

Claims adjusters: elusive creatures

Stephanie used to be a claims adjuster. She knows the inside of that job better than most. So when she says claims adjusters today are notoriously hard to reach — that's not an outsider's complaint. That's a former insider.

What Dennis said on the show, which we both nodded at:

Here's the dirty secret: most claims adjusters are now carrying caseloads that would have been considered impossible ten years ago. Carriers have downsized claims departments. They've outsourced. They've automated. The adjuster on your file is probably juggling 80–120 active claims at any given time. That's the structural reason they don't return calls — there literally aren't enough hours in the week.

But there's a workaround. Dennis hinted at it on the show: "there are certain words you can use with claims companies that they don't like — it's worked every time."

How to actually get a claim moving

If your adjuster has gone quiet, here's the playbook:

1. Get your agent involved. Carriers move differently when a producing agent — someone who sends them new business every month — is asking for a status update on behalf of a client. We have direct lines you don't.
2. Document everything in writing. Email beats phone for claims work. Email creates a paper trail. Phone calls evaporate. "I called you on Tuesday at 2pm and left a message" is much weaker than an email timestamp.
3. Ask for the supervisor. Not as a power move — just neutrally. "I haven't been able to reach my adjuster for five business days. Could you please connect me with their supervisor?" That sentence works.
4. Mention bad faith. Carefully. The phrase "this is starting to feel like bad faith claims handling" is a legal trigger word that gets a file moved to a senior adjuster fast. Don't throw it around if you don't mean it. But if your adjuster has genuinely ghosted you for weeks, it's accurate.
5. Use your state's Department of Insurance. You can file a complaint online with the Texas Department of Insurance (or whatever state's regulator) and the carrier is required to respond. This makes things happen.

AI is making it worse, not better

Both of us have strong opinions about this. The push toward AI customer service in insurance isn't about making your experience better — it's about reducing the carrier's labor cost. When the AI works for simple stuff (getting an ID card, paying a bill), great. When the AI doesn't work — and you're facing a real problem with your policy — you're more isolated than you used to be, not less.

That's the difference between an independent agency and a giant call center. When you call us, we don't just answer the question you asked — we listen for the thing you didn't know to ask about. The customer who calls about adding a vehicle is sometimes the same customer who didn't realize their umbrella coverage hasn't been updated since they had their second kid. A human agent catches that. An AI doesn't.

What you can actually control

You can't fix the industry. We can't either. But you can take a few moves that meaningfully change your experience:

• Work with an independent agent, not a captive one. The independent agent answers to you. The captive agent answers to their one carrier. Different incentives, different outcomes.
• Re-shop every two or three years. Not constantly — that creates issues with continuity. But every couple of years, get fresh quotes from a couple of different carriers. The market shifts. What was expensive in 2023 might be a bargain now.
• Keep your agent in the loop on life changes. New driver, new house, new kid, new business venture. Those are the moments when coverage gaps form. Tell us before the claim happens, not after.
• Read your declarations page once a year. Yes, really. It's two pages. Most people have never opened it. The named insured, the address, the coverage limits, the deductibles — that's the entire shape of your protection in five minutes of reading.

The insurance industry has earned a lot of the frustration it gets. We're not defending it. But the difference between "I hate insurance" and "I have a system that works for me" usually comes down to a few small decisions. Make them. The next time something goes wrong, you'll be glad you did.