Here’s an interesting situation: A client invites you to dinner. The evening is very pleasant; you talk sports, travel, the weather; but the client never says one word about business. As the meal ends you wonder if you should bring up the subject of your business relationship and ask if the client has any concerns he would like to address now. Should you or shouldn’t you?
The short answer is the person who does the inviting–in this case the client–is responsible for bringing up any business topics. You, as the person being invited, should follow the client’s lead and not introduce any of the business topics you were wondering if you should bring up.
It may be that the person who invited you simply wanted to get to know you better. After all, business is built on relationships. While business meals are a time when business is discussed, they also are an opportunity to build relationships—to become more comfortable with a person who may be instrumental in the success of your company.
So in your current predicament, let the client who invited you take the lead. If he wants to discuss business, then jump in. But if he doesn’t want to talk business, then it’s not up to you to bring it up.
When you are the person extending the invitation and you decide you want to discuss business during the meal, when is it appropriate to bring it up? The business lunch or breakfast tends to be a quicker meal, usually just one course. At a breakfast or lunch meeting the chitchat takes place before and during the ordering. But once the order has been placed, the time spent waiting for the food to arrive is the perfect opportunity to focus on the business at hand. The multi-course business dinner is a more drawn-out and sometimes more formal affair. In this case the host should wait until after the main course is completed before bringing up business. It’s hard to focus on business while you are eating. Once the eating is out of the way, it is easier to then focus on the business at hand.
Finally, even if the client has hosted you previously and technically it’s “your turn,” don’t offer to pay for the meal when the check arrives. The etiquette rule is: Whoever does the asking does the paying. If you do want to pay this time, the time to negotiate is at the time of the ask. “John, I’d enjoy going to dinner again, but this time I’d like to take you.”