Creative Solutions in Mediation: When Hotel Points Ended a Lawsuit

In most legal disputes, the path to resolution is paved with numbers. 

Settlement offers. Damages claimed. Attorney’s fees. It’s a negotiation about money – until it’s not.

Occasionally, a case breaks from the mold and reminds us what mediation is really about: discovering what matters most to the people involved.

Here’s the story of how 2 million hotel points – yes, hotel loyalty program points – resolved a long-running case in a way that litigation could not.

How Mediation Can Help Solve Your Dispute

A Pandemic-Era Stay That Turned into Years

The case involved a man who had checked into a hotel for an extended stay. 

Days turned into weeks, then months. Through a patchwork of outside resources and accumulated hotel points, he remained in the same room for years.

Eventually, the hotel – frustrated and facing business realities – initiated eviction proceedings. 

But what should have been a straightforward case quickly went off-course. Procedural errors by the defense caused delays. Time passed, the case dragged on, and the hotel guest stayed.

By the time the parties reached mediation, tensions were high. The hotel needed him out. He, in turn, had a growing list of demands, from new HVAC systems to changed locks and other unlikely requests.

Understanding what each party wants in a mediation

The Turning Point: ‘What Do You Really Want?’

Sometimes, there is a moment in mediation where the conversation changes. 

A pivotal moment of that nature happened in this case. Suddenly, rather than continuing to debate such things as pool access policies, the discussion shifted to one simple question: What do you really want?

The man’s answer surprised everyone: hotel points. Specifically, 1 million of them.

At first, it seemed unusual — but the hotel agreed on the condition that he would vacate by a specific date.

When he came back asking to stay later, the hotel stood firm on the proposed date — and he countered with a new request: 2 million hotel points in exchange for leaving by that date.

After some deliberation, they finally agreed. He signed the agreement, and the case closed with a settlement that no judge could have ordered, but that mediation made possible.

What resolved this case wasn’t a legal argument or a financial calculation. It was an insight into human priorities and a resulting settlement shaped around them.

For this individual, it wasn’t about money. It was about freedom in the form of hotel points. After being stuck for far too long, all he wanted to do was go places again.

Why mediation offers more flexibility than litigation

Why This Worked — and Why Courts Can’t Do It

A judge couldn’t have ordered a transfer of hotel points. 

Courts are limited by statutes and remedies rooted in law. Mediation, by contrast, allows room for creativity, especially when both sides are willing to think beyond cash.

What resolved this case wasn’t a legal argument or a financial calculation. It was an insight into human priorities and a resulting settlement shaped around them.

By uncovering this client’s true priority, the mediator helped the parties reach a win-win agreement.

If you’re looking for a creative solution to a dispute, mediation might be the way forward.  Schedule a consultation with Windsor PLC to learn more. 

Frequently Asked Questions About Creative Solutions in Mediation

Why is mediation better suited for creative solutions than litigation?

Mediation is a flexible, collaborative process where the parties – not a judge – decide the outcome. That means solutions can reflect human needs, business goals, or personal values in ways that courtroom judgments simply can’t. If both sides agree to an unconventional resolution, such as hotel points, services, apologies, or another remedy, it can become part of the deal.

Can you get this kind of creative result through litigation?

Not likely. Courts are designed to apply legal rules, not tailor solutions. A judge can’t award points or require a party to perform a service unless the law provides for it. Mediation opens the door to custom outcomes that courts don’t have the authority to craft.

What are the benefits of mediation over litigation?

Mediation is typically faster, confidential, more cost-effective, and less adversarial than going to court. But beyond efficiency, one of its greatest strengths is its flexibility. Mediation creates space for creative problem-solving — allowing people to prioritize what truly matters to them and shape an outcome that reflects those priorities. 

Jeffrey R. Windsor, Esq

On Behalf of Windsor PLC

Civil Litigation Attorney and Mediator

Jeffrey R. Windsor, Esq. is a civil litigation attorney and mediator. He established Windsor PLC in 2012 and has more than two decades of experience representing clients in complex legal matters.

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