Why are we getting together? Do you desire to build a genuine, warm connection, or are you suggesting we “throw ideas around” so you can try to sell me something right away?

Is this about more than business? There are times that a conversation becomes something more important than business. (Those practicing a faith may consider these “divine appointments.”) If I have a hard-and-fast rule only to have coffee if it might further my career, I may miss an opportunity to encourage someone or learn something.

Might we become good friends, or at least friendly business associates? Sometimes a real friendship grows out of a networking opportunity.

Would it be mutually helpful for our futures? In a different mindset than a quick sale, will our connection possibly help us both grow in career opportunities? For example, for at least three of my VA clients, we met weeks in advance of any money changing hands for my serving as a VA.

Can we plan a reasonable agenda for our meeting? I probably don’t have time for several “Let’s grab coffee” meetings a week. Can we have at least a general purpose for a meeting? Sometimes it IS valid just to have coffee with each other because we are people that “should know each other.” However, if you go out for coffee a lot to procrastinate on getting real work done, I need you to respect my time.

Can the meeting happen in some other way? A phone call or Zoom meeting may accomplish the same thing in less time than lingering over coffee.

Do we currently work or do business together? The original article noted the “difference” between small and large clients and the attention they would get. That is not a wrong approach necessarily, but can be a slippery A “small” client or work associate now may be connected to larger opportunities later. I should not base a meeting decision simply on how important I think you might be. That is shallow. At the same time, if you are a colleague or mentor, I may give you priority in schedule over a first time acquaintance.

Have we had coffee before? How valuable have our previous meetings been? Are we helping one another move the needle in our careers, or do we mainly have gripe sessions?

Are you suddenly more interested in me because I could help your new business or you need a job? I get a little skeptical when a light acquaintance suddenly shows a keen interest in me, especially if I am aware they are selling something new or need work.

Am I the best one to help you? If you need encouragement or resources, I might be able to help. However, if you are seeking in-depth coaching or even counseling, maybe I should introduce you to someone who is more equipped to help you at the level you need. (This guideline is also helpful if I feel a relationship might become too personal.)

I can’t answer the question of whether I should have coffee with you in the same way every time. These questions can help me decide. I hope they help you, too. Maybe someday, we can discuss them over coffee.