• Did you get the invoice?
    Don't assume your customer is intentionally blowing off your bill. The invoice might have gotten lost in the mail or landed on the wrong desk. The problem could also be with the actual bill. Maybe it's missing a purchase order number or has incorrect information, which is holding up payment. Many collection issues are caused by simple mix-ups, says Robert S. Bernstein, a business bankruptcy attorney in Pittsburgh.

  • Was there a problem with my product or service?
    Here's why it's key to have a contract spelling out the terms of a sale: Suppose your customer says she won't pay you because she ordered green widgets but received yellow ones instead. You can refer back to the signed agreement to see if she's right. If it's your mistake, take the widgets off the invoice until the order is fixed, but keep your customer on the hook for any other charges on that bill.

  • Why didn't you let me know you're behind?
    You don't want your customer to think his overdue invoice went unnoticed. "Everyone has their patsy list of bills that they can let ride longer," explains Tim Paulsen, of T.R. Paulsen & Associates, a collections consulting firm in Toronto. "They're playing cash management with your money." A collection call lets your customer know that you're aware his check is late and that he should think twice before putting your bill at the bottom of his pile.

  • How much are you short?
    Say a client owes you $9,000 and you tell him that you'll get off his back if he gives you $3,000 today with the rest due next month. Bad move. You'll collect more money quicker by asking how close he can get to paying off the full amount. Let him suggest a dollar figure and negotiate from there.

  • Who is the best person to talk to about this invoice?
    That sweet bookkeeper who takes your calls may not be the one who signs the checks. Ask to speak to the individual holding the purse strings, whether it's the accounting department manager, the chief financial officer, or the business owner.

  • When did you send the check?
    "The check is in the mail" is the most overused excuse in a debtor's playbook. Find out when your customer sent the check, how much it's for, and what the check number is. Later in the conversation, casually ask for the check number again, suggests Paulsen. If the person stumbles or rattles off a different number, there probably isn't a check in the mail. In your standard contract, stipulate that the client will have to pay any attorney or collections fees you incur if the matter is turned over to a third party. "Use that as leverage to get them to pay now," says Bernstein.

  • Should I be worried about the other invoices?
    If you run into payment problems once, there's a good chance it will happen again. You may not want to withhold an order if doing so will cripple your client's business--after all, you'll probably never see your money if he goes bankrupt. One solution: Ship new orders on a cash-on-delivery basis plus 10 percent of the amount that's outstanding.