Business, Pleasure and the Fine Line Between Them!

Most of us have had the experience of enjoying dinner or a day with family and friends who we may also consider to be potential sources of business or business collaboration!

Is there specific etiquette or possibly an unwritten set of rules that defines the appropriate ways to proceed?

Ways that help bridge the gap between business and pleasure without completely blurring the line or changing the dynamic in a negative way?

Of course there is!

Five Steps!

From the website attorneyatwork:

The keys are separation and permission. By that, I mean you need to separate the conversations into two distinct interactions. First are the innocuous exchanges about jobs and work, which are welcomed (even expected). Second are any forms of explicit business development, which involve getting permission to proceed.

These five simple steps will allow you to gracefully and reliably initiate business conversations with friends or social acquaintances — without risk to your personal relationship.

1. Show interest, whether it’s someone you know pretty well, or someone you know at least a little about what they do for a living, or someone you’ve just met at the event. For example, if they own a business, ask the standard, “How’s business?” If the person is not an owner, simply ask, “How’s work?”

2. Probe to identify “pain issues” with which you (or a colleague, if you’re not a solo) might be able to help. Demonstrate relevance by asking questions that show you have relevant knowledge about such problems. Most people, particularly those who already know you, will ask your opinion and may even solicit advice.

3. Keep things general. If the discussion shifts to particulars, don’t offer specific advice or possible solutions. Instead, acknowledge that you’ve helped others with similar problems, and suggest categories of solutions or types of approaches.

4. Cut off discussion of specifics by graciously acknowledging that you’re together for social reasons, and that you don’t wish to monopolize the discussion or your guest’s time. Be sure to say you are very interested in helping by talking more about ways to solve the problem.

5. Ask if they’re open to a next step. For example, ask, “Does it make sense for us to [have lunch, meet at your/their office, or connect by phone] to explore the problem some more?” Never offer a specific step without first confirming that they welcome any next step at all. If they do, explore possible dates, to be confirmed by telephone or email the next(business) day.

Bonus tip: Always honor your commitment and contact them the next day to get a specific appointment!


Written by Michael Haltman, President of Hallmark Abstract Service, New York.

HAS is a provider of title insurance in New York State for residential and commercial real estate transactions specializing in the areas of New York City, Long Island and Westchester.

Remember that you have the right to choose your own title company (click here to learn more)!

If you have any questions you can reach Michael by email at

Leave a Reply

Your email address will not be published. Required fields are marked *