There really isn’t any one right way of doing this, but there sure is a wrong way. “Where’s my money?” is usually not a good start and for the most part doesn’t lead to desired results. So what to do?

If, like me you’re a one-woman (or one-man) show you have the luxury of being your own boss. Definitely a perk. You provide services, bill your client and get paid in a timely manner – right? Sure, in an ideal world that is exactly how things go –  but well we all know that we don’t live in, much less do business, in an ideal world.

OK, so someone owes you money and they are past due the comfort zone timeframe. Time for a dialogue.  It’s been my experience that this is the most critical component to how the rest of this relationship will go. Either you will be able to generate good feelings all around where trust & integrity is not only salvaged but also nurtured or you will go down a darker path where a mutual dislike is born and you may (or may not) get your money or do future business with this client. Generally speaking, I like to avoid the darker path because there is nothing worse than having a client you dread doing work for due to what it will take to get paid by them.

It’s difficult for many to separate themselves from likable, face-time service provider to no nonsense accounting department. While it is an awkward task to take on, I assure you, ignoring it won’t make it go away. A good rule of thumb is to address someone in a manner that you would want to be addressed even if you were (in a sense) being scolded. Don’t talk down to someone but rather raise awareness and set the stage for a candid forum. After all, they may have simply forgotten to pay you or not received your bill. But if it’s financial difficulty or dissatisfaction with your services, this is where you have the chance to clear the air, make amends or set up a payment plan. This open scenario usually garners the best results and has the side effect of generating good buzz. I know I am always happy to recommend people/businesses who are capable of having a civil conversation about a billing dispute over anyone that spills out “well, we did the work & this is our policy..” rhetoric.

Additionally, you can and should use any personal rapport that you have developed with your client to ease into the subject. However, NEVER let that personal rapport forgive a slacker because you “like” them. There is friendship and there is business – and there is even friendship in business. Just remember never to exploit it or let it exploit you.

I have had clients that do business with friends and then don’t know how to get paid by them. What usually comes into play here is that they feel sorry for the friend, or feel they can’t possibly “ask” their friend to pay them. Well, that is no friendship. Besides creating awkward feelings in the relationship and enabling irresponsible behavior – it’s just bad business. Remember, friend or otherwise, talk to them. There is no shame in expecting to get paid.

So go ahead, be your own boss & do fabulous work. Make your own schedule and above all, don’t forget to gracefully demand what is due.