Are you one of those people? You shy away from hard conversations, especially in the workplace?

I have found that conversations around behavior and money are the hardest.

From negotiating pay, to raises and even gifts or bonuses, it’s a real tongue-tied moment for some.

Yes, it is a tired cliche’ which we hear about, that when we are involved with other humans, money can destroy relationships. But in business, it should be an open and shut case.

Over the years I have had to learn how to ask nicely, react gently, then sometimes just demand payment. Many, many years ago, I was providing news for a fledgling (read: wannabe) network in the state of Montana. I had to really dig for news and interview people with a certain background, which became a volunteering gig because the “CEO” never paid me. I did the work, billed the “network”, and was ghosted (before it was even a thing). When I asked nicely, I was met with disdain, when I began to demand my pay, $3,000 if I remember correctly, the CEO told me he was going to call the police on me for disturbing his meal. I clearly had a lot to learn about how and when to bill people. One time I was ignored by a client who I produced news for for 3 years. I learned then to demand the pay. It really can be infuriating when you’re a sole proprietor.

Here’s the key, you have to be willing to walk away from the client and the pay. Detaching from what might have been and connecting to what reality is — is the sweet spot.

Since I pay the people who work for my company at the end of each month, I decided to bill in advance over 15 years ago. That way I would have the money banked for payday. That has worked well, except in a few cases. The obstacle exists when someone doesn’t read the fine print in your contract. (Note: if you don’t do contracts, start!)

I have found the problem lies in the other party not actually having the cash to begin with.

Just last month I gently asked for money from a new client. I had just moved my office so there was a hold on my mail. Then some of the mail was sent back to the sender because the forward didn’t go through yet. I very gently asked the new client if they received the payment back to them because of the hold. It’s a whole Oprah Show, to explain this, but needless to say, they accidentally released some correspondence not meant for my eyes, so I knew the money was not there to begin with. Spoiler: I ended up getting paid, but I was not attached to the money, so I had let the client go in my mind. When I answered the email not meant for me, they turfed me! I believe I acted in good faith. They simply had a problem with me asking for what was ours. We had delivered their service, so what was the actual problem?

And then as I recovered from that one, it happened again. Was your check lost, did you forget to pay, or do you even have the money? A tired phrase, but an important one if delivered well.

Here’s the thing, I made space for all of that again. And I released the money into the ether, knowing I may never see it.

It’s important to note, in nearly 18 years of business, this has maybe happened 5 times. People are somehow astonished when you ask to be paid for your services. And that astonishes me.