Every sales call I run eventually hits the same sentence: “We’re covered.”

It usually comes about ten minutes in, right after I ask how payments work today. The prospect isn’t being dismissive. They have a provider, it works most days, and switching sounds like a project nobody has time for. For a while I treated that as the end of the conversation. Now I treat it as the start of the real one, because “covered” almost never means “efficient.” It means “it runs.”

The trouble is that the cost of running is spread across so many line items that nobody adds it up. Take a hypothetical distributor with about forty staff. The finance lead pays a percentage on every transaction, a monthly platform fee on top, and a separate charge for the gateway that sits behind it. Collections land in one system, payouts go out of another, and once a month someone exports both into spreadsheets and matches them by hand. Each piece looks reasonable on its own. Together they cost real money and a few days of someone’s month.

None of that shows up on the provider’s invoice as a single number, so the prospect has never seen it as a total. That’s the gap I try to close.

So I stopped asking, “Are you happy with your current setup?” Almost everyone says yes to that. Now I ask questions that make them do the arithmetic:

  • What do you pay in total for collecting and paying out money in a normal month, including every fee you can find?
  • How many systems does a single invoice touch between being sent and being reconciled?
  • Who on your team spends time fixing mismatches, and roughly how many hours a month is that?
  • When something goes wrong with a payment, how long does it take to find out why?

Most people can answer the first two in under a minute. The last two take longer, and that pause is useful. It tells me where the silo actually hurts.

The word I use for the category matters here too. If I say “the modern alternative to” a competitor’s name, I’ve made the call about someone else, and the prospect will hear a pitch. I now describe the job in plain terms: collecting money, paying it out, and matching both to the books. “Digital payments” is a neutral category, and buyers can hold it up against their own situation without feeling sold to. It also keeps the focus on their workflow instead of on my competitor’s brand, which is what they were already comparing against.

The deeper point is that silos are rarely a single bad tool. Each system can be fine in isolation. The cost lives in the gaps between them, and in most companies nobody owns those gaps. The finance lead inherits them, the operations manager works around them, and the vendor never sees them because each vendor only sees its own part. That’s why “covered” can be true for every tool and false for the business.

If you hear “we’re covered,” don’t argue. Reply with one question: “Covered for what, and what does it cost you each month?” Then listen. If they can’t answer, you’ve found the conversation worth having. If they can, write the number down, and send it back to them in their own words a few days later. Nobody wants to be told their setup is broken. Most people will happily look at a number they already gave you.