Grow Your Wealth

Everything You Need to Know About Negotiating

From negotiating bills to rent, Cleo's resident financial advisor Anna Yen tells you everything you need to know


Negotiation is as much art as science – it’s not just asking for what you want; it’s about achieving goals using personal skills and a bit of psychology. 

And it’s not just for salesmen and corporate bigwigs, either. Everyone can learn how to negotiate medical bills, interest rates, monthly rent and utilities, and more. 

Here’s how to phrase your negotiations to be most effective and reach your goals. 

Ask to talk to the right person

The first step in a successful negotiation is working with someone with the power to grant your requests. Of course, who this is varies. 

If you’re trying to lower your rent, you should talk to the property manager or landlord. 

When negotiating medical bills, double-check whether the bill comes from your doctor or insurer. 

And when calling customer service at cable, utility, and credit card companies, inform the front-line rep you’re considering canceling. Often, you’ll be transferred to a supervisor or department with the power to negotiate you into staying. 

Woman on phone

Stay calm, patient, and polite

Unless you’re dealing with your landlord, most customer-facing roles don’t set prices or put unexpected charges on your bills. They’re just paid to clean up messes and help customers – and yelling makes them want to help you less. 

Express all concerns and requests in a calm voice, even if you escalate to a supervisor. Remain patient and understanding (yes, even when they put you on hold to “talk to their manager”). Most importantly, don’t yell, curse, or accuse the rep of screwing you over. 

Learn to be firm and kind

Staying calm doesn’t mean you have to be a pushover. 

Keep your tone respectful and polite and use “please” and “thank you.” Stress that you know this problem isn’t the rep’s fault. Provide proof of any claims of errors when possible.

Use this language while remaining firm. State your facts and goals quietly – e.g., “I’d like to negotiate my hospital bill” or “My budget for a new car is X.” 

If the rep can’t help you, request to speak to a supervisor. You might even sprinkle in apologies for taking their time.  

Ask what they can do for you

One of the first rules of negotiating: ask open-ended questions that encourage positive, in-depth answers. Phrase your intent as “What can you do for me?” instead of yelling about being overcharged by monocle-wearing crooks. 

For example:

“What can you do to lower my interest rate?”

“How can I qualify for a cheaper car insurance premium?”

“What kind of promotions are you offering right now?”

Lay it on thick

Sprinkling in a few details may help you connect with your negotiator on a personal level. 

Maybe you’ve lost a job, had a baby, or recently moved. 

Perhaps your landlord hiked your rent by $500, or might as well have after inflation gobbled your paycheck. 

Explain why you’re looking for assistance, and you may get more than you ever dreamed. 

Highlight your strengths as a customer

Businesses, landlords, and hospitals share a common bug: they like low-maintenance accounts. That means customers who pay on time, make a good income, and/or stay for the long haul. 

Wield this knowledge confidently during negotiations. 

You can’t receive an APR reduction because everyone’s rates are rising? Remind your creditor of your excellent credit history. 

Rents going up property-wide? Mention that you’ve always been a courteous tenant – oh, and weren’t you hoping to sign a new one-year lease?

In general, the more attractive you appear on paper, the more likely you’ll get a deal.

Wave those dollar signs

In a financial negotiation, each side has competing interests: you want to save money, and they want to make money. Fortunately, you can easily remind your negotiating opposite of your financial value by:

- Offering to pay cash upfront in exchange for a discount or debt reduction

- Extending your service with 12-month leases or contracts to solidify your commitment

- Suggesting payment plans for overdue debts or when negotiating medical bills – something is better than nothing.

Suggest that you’re willing to walk away

Another negotiation tactic is to mention that you’ve found an alternative that fits your budget better elsewhere. 

Maybe that’s a loan with a lower interest rate or a better deal on a new car across town. 

If you’re a current customer, note that you’ve considered switching because of better service or lower prices. (Even if you don’t want to leave.) 

Of course, this tactic doesn’t always work – such as when you’re negotiating a hospital bill you’ve already incurred. 

Learn how to negotiate medical and hospital bills

While these phrases and tactics can work anywhere, medical bills are a bit different.  Hospitals and insurance companies are constantly negotiating medical bills with each other. Patients may leave money on the (operating) table by not engaging in their own negotiations.  

Know who’s billing you

Hospitals, insurers, pharmacies, ambulance contractors, independent billing departments – each of these service providers charges a price. (Unfortunately and all too often, to you.) To avoid mix-ups, carefully track where your bills originate. It’s no use negotiating medical bills with a pharmaceutical rep, or vice versa. 

Compare your bill and explanation of benefits 

After receiving medical care, you’ll receive a flurry of medical paperwork, bills, and your insurance provider’s explanation of benefits (EOB). Your EOB explains your services received, hospital charges, insurance coverage, and out-of-pocket costs. 

Be sure to keep your EOB to compare to any medical bills you receive. Cross-check this information to ensure your insurance company is covering what you’re owed, and that your doctor’s office hasn’t accidentally double-charged you. 

Request an itemized receipt

One unfortunate-yet-exploitable loophole of U.S. healthcare: requesting an itemized receipt from your hospital and/or insurance company can result in your charges being reduced or waived entirely.

Sometimes, that’s because the billing department erases errors like double charges or incorrect billing codes. Other times, they simply reduce charges that would have otherwise been negotiated by insurance. 

Whatever the exact cause, requesting an itemized bill can have a big impact. 

Take advantage of available resources

It’s difficult to negotiate prices when you’re sick or in recovery, but you don’t have to negotiate alone. 

Patient advocates, like those found at patientadvocate.org or npaf.org, can champion your right to not be overburdened with medical debt on your behalf. 

They can also help you find hospital, nonprofit, or government assistance programs to provide essential financial relief. 

Don’t “Haggle It” alone

If you’re not sure where to start, Cleo’s new Haggle It tool can generate a unique negotiation letter just for you. 

Powered by ChatGPT and artificial intelligence, Haggle It helps you create custom, professional negotiation letters in minutes. 

Bonus: it’s suuuuuper easy to use. Just describe what you need help negotiating and answer a few quick questions. Then, Haggle It will deliver a personalized letter to help you secure the deals and breaks you deserve. 

Plus, for every person who uses Haggle It, Cleo will donate $1 to Operate Hope to expand financial literacy and economic empowerment. 

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