There is a word collectors probably say more often than we realize.

Yes.

Can I have until Friday? Yes. Can we split the payment? Yes. Can you hold off while I wait for a customer to pay me? Yes. Can we move this month’s payment to the end of the term? Sometimes, yes.

And in many cases, saying yes is exactly the right thing to do.

I’ve spent more than two decades in collections, and one thing I’ve learned is that rigid collections strategies rarely work well for long. Customers have cash flow problems. Jobs get delayed. Receivables come in late. Equipment breaks down. Insurance claims drag on. A large customer that was supposed to pay on the 15th suddenly tells your borrower the check will not arrive until the 30th. Things happen.

Particularly in commercial equipment finance, understanding what is happening inside a customer’s business can be just as important as knowing how many days past due the account is.

There is nothing wrong with flexibility. The problem begins when flexibility stops being a solution and becomes the expectation.

Every Exception Teaches the Customer Something

Suppose a customer has always paid reasonably well but suddenly misses a payment. You call, learn that one of the customer’s own receivables is delayed, and agree to give them another week. The customer pays exactly when promised. Great. The accommodation did exactly what it was supposed to do. It helped a customer through a temporary problem and got the account moving in the right direction.

Now change the story.

Friday arrives, and no payment comes in. You call again. The customer needs until Tuesday. Tuesday arrives. Still nothing. Now the customer can send half but needs another week for the rest. Meanwhile, another regular payment is getting closer.

At some point, you must ask a different question: Are we helping the customer solve a temporary problem, or are we simply making delinquency more comfortable?

That distinction matters.

Every exception teaches the customer something. Ideally, it teaches them that their finance company is willing to work with them when circumstances warrant it. But repeated exceptions can teach a very different lesson. The due date is flexible. The promise date is flexible. The consequence of missing the promise is flexible. And if the customer asks again, the answer will probably be yes again.

Eventually, the collector may no longer be managing the delinquency. The customer is managing the collector.

A Promise Has to Mean Something

Promises to pay are one of the most basic tools in collections, but their value is not really in the promise itself. Their value is in what happens next.

If a customer tells me payment will be made Friday, I now have information I did not have before. More importantly, the customer has made a commitment. If Friday comes and the payment arrives, that tells me something. If Friday comes and nothing happens, that tells me something too.

One broken promise does not necessarily mean a customer is intentionally avoiding payment. Circumstances change. The receivable they expected may not have arrived. A project may have been delayed again. Another unexpected expense may have appeared. But repeated broken promises are information.

Collectors sometimes make the mistake of treating each new promise as though the previous promises never existed. Friday becomes Tuesday. Tuesday becomes next Friday. Next Friday becomes “I’ll call you after I talk to my partner.” At some point, the history matters more than the latest explanation.

Good collectors listen to what customers tell them. Experienced collectors also compare what customers tell them with what those customers actually do.

The Goal Is Not to Win the Conversation

Collectors can also fall into the accommodation trap for another reason. Nobody wants every conversation to become a confrontation.

Especially in commercial finance, we are dealing with business relationships that may have existed for years. The customer may have other transactions with the company. Sales may value the relationship. The customer may genuinely be going through a difficult period and may eventually return to being perfectly performing. Pressure can build, sometimes self-imposed, to keep the conversation positive.

So we say yes. The customer is happy. The call ends well. Nobody yelled. Nobody threatened to surrender equipment. Nobody asked for an attorney. It feels productive.

But the goal of a collections conversation is not to make sure everybody feels good when the call ends. The goal is to move the account toward resolution. Sometimes those things happen together. Sometimes they do not.

A pleasant conversation that produces the fourth broken promise in six weeks is not necessarily more successful than a difficult conversation that finally establishes what the customer can realistically afford. Collectors must be comfortable with that distinction.

Flexibility Needs a Destination

This is where I think accommodations sometimes go wrong. We focus heavily on the immediate problem. The customer cannot make today’s payment. OK. What can they do?

That is certainly important, but another question matters just as much: What happens after that?

Suppose the regular payment is $5,000 and the customer can send only $2,500. Taking the $2,500 may absolutely make sense. But if another $5,000 payment is due in two weeks, what have we actually solved? The customer may soon owe $7,500 instead of $5,000.

That is why an accommodation should have a destination. How does this customer return to performing status? What changes between now and the next due date? Is there a large receivable coming in? Is a seasonal slowdown ending? Is an equipment problem being repaired? Is there a contract or project beginning that will restore cash flow? Or are we simply moving unpaid money from one date on the calendar to another?

Those are very different situations. A good accommodation creates a path back to performing status. A bad accommodation simply makes delinquency more comfortable.

“Yes” Can Still Have Conditions

Setting boundaries does not require collectors to become inflexible. In fact, I think the strongest accommodations are usually the ones with the clearest boundaries.

Yes, we can give you until Friday. I need the payment Friday.

Yes, we can accept the partial payment. Let’s also establish when the remaining balance will be paid.

Yes, we can review a modification request. I need the requested financial information before we can consider it.

Yes, we can work with you. But if the agreed payment is not received, we will need to discuss the next step.

That is not pressure for the sake of pressure. It is clarity. The customer knows what has been agreed upon, what is expected next and what happens if the agreement is not honored.

That last part is important. A deadline without a consequence is eventually just a suggestion.

Collectors do not need to make threats they cannot or will not carry out. In fact, they shouldn’t. But if we repeatedly tell customers that something needs to happen by a certain date and then nothing changes when it doesn’t happen, we weaken our own credibility. The next deadline becomes easier to ignore.

Sometimes the Best Answer Is No

This may be the hardest part. There are times when the customer has received enough flexibility. Enough extensions. Enough broken promises. Enough partial payments that never led anywhere. Enough explanations that sounded reasonable individually but, taken together, reveal a pattern.

At that point, saying no is not necessarily damaging the relationship. It may be the only way to define what the relationship actually is.

That does not mean immediately accelerating every account, demanding equipment back or sending everything to legal. It means recognizing that another accommodation needs to accomplish something different from the last one. Maybe additional financial information is required. Maybe management approval is needed. Maybe the customer needs to make a meaningful payment before another request is considered. Maybe it is time to discuss voluntary surrender, restructuring, liquidation or another resolution.

The specific answer will depend on the account. But simply repeating the same accommodation and hoping for a different result is not a strategy.

Flexibility Is Still a Strength

None of this is an argument for saying no more often just for the sake of saying no. Some of the best resolutions I have seen during my career happened because someone was willing to give a customer time. A few days can matter. A split payment can matter. A thoughtful modification can save an account. Working with a customer instead of immediately escalating can preserve both the business relationship and the recovery. That is what good collections should do.

But flexibility works best when it is intentional. There should be a reason for the accommodation, an expectation attached to it and some understanding of where the account goes next.

Otherwise, something subtle begins to happen. The exception becomes the precedent. The precedent becomes the expectation. And eventually the customer stops asking whether you can make another exception because both sides already know the answer.

That is the hidden cost of saying yes.

The word itself costs nothing. What matters is what your yes teaches the customer to expect the next time they ask. •

The Collector Chronicles by Ty Schwamberger is an exclusive series for Monitor that explores the challenges of business-to-business debt collections within the equipment finance industry.

Ty Schwamberger has worked in accounts receivable management for more than 23 years across various industries. He is well-versed in numerous collections and bankruptcy laws and believes great listening and negotiation skills are at the forefront when dealing with those experiencing financial challenges. Before joining Elevex Capital as head of collections in January 2025, he was assistant vice president of member solutions (collections) at a northeast Ohio credit union.