In this Section:

How To Talk To Anybody About Anything

“Wow! I would really like to meet that person but I don’t know what to say!”

From time to time, we see people we would like to befriend, connect with or just meet. Some are easy. It gets difficult when there’s a wealth gap or when our motives seem obvious – such as when the supermodel walks into the singles bar.

This three-article series will examine seven scenarios. The first will focus on starting the conversation. The second on how to keep the conversation going and finally, how do you wrap up and lay the groundwork for seeing them again?

Seven Scenarios

It’s easy to start conversations with the guy at the next desk. How about these scenarios:

  1. The Big Fish – These corporate executives know they are wealthy and powerful. People who talk with them usually want something because The Big Fish are, of course, great prospects.

  2. The Stunner – You’re single and you’re having a drink when an extremely attractive person sits down at the next table. Heads turn. “They’re way out of my league” flashes through your head. But when will this opportunity ever happen again? You’ve got to try.

  3. The Casualty – The economy has been rough. You recognize a person who has fallen from a great height. You’ve been out of touch. Many visual clues signal they are having a very difficult time. You want to help.

  4. The College Roommate – You attend your reunion. Across the room you see a former classmate. You were once great friends but haven’t spoken in decades. Didn’t they invent that social networking website?

  5. The Service Provider – You get your hair cut and grass mowed. The same person has been doing it for years but you’ve never really gotten to know them.

  6. The Sideline Parent – Your children play school sports. You attend every game and see other parents regularly. Their faces are familiar but you’ve never spoken.

  7. The Extremist – You hold moderate political beliefs. One of the people in your extended social circle holds extreme views. They are passionate and uncompromising. Thankfully, the election is over, but you want to move on and maintain or build on your relationship.


Conversation is an art and a one-size strategy doesn’t fit everyone. While it’s human nature to prejudge, here’s what’s probably going on in the background. They are:

  • Wary – Does this person want to profit at my expense?

  • Weary – I’ve heard every pick-up line. Which will they use?

  • Wise – They can think several steps ahead. They won’t be fooled.

Engaging everyone with respect and dignity is important. You establish your standing by how you approach others, especially in the initial conversation.

Your Strategies

  1. The Introduction – Look around the room. Who do you know that knows that person? Would they walk you over and introduce you socially?

  2. Friends in Common – The person you both know isn’t present. No problem. You walk over and state the obvious. “You don’t know me” followed by “I believe we have a friend in common.”

  3. The Compliment – They made the news recently. They are wearing a great piece of jewelry or a great tie. Their lapel pin or broach is distinctive. Who is offended by a sincere compliment?

  4. The Event-Related Observation – “These shrimp are wonderful! Have you tried one?” “The museum throws the best parties. Wouldn’t you agree?” or “The committee did a terrific job on décor.” The organization is the common bond that brought you together.

  5. The Neutral Question – People can sense when you want to talk with them. They may feel the same way. “Do you have the time?” or “Is this seat taken?” is simple and inoffensive.

  6. The Insightful Question – Assuming you know about the person’s career or role in the community, ask a question that gets him sharing his opinion. “Aren’t you glad the election is behind us?” or “I heard the President visited Hatboro last week. Did you see him?”

  7. The Waiting Game – Useful if something else is absorbing your attention. You are watching a football game on the wide screen. They are cheering. You wait until they remark on a great play or question the referee’s eyesight. When they speak, you give your opinion and follow-up with another question.

  8. The Volunteered Observation – You are sitting together and remark, “My wife and I are new around here. We just moved into the Generic Hills development. Do you live around here?” If they answer, you draw them out.

  9. The Information Request – It puts you on equal footing, useful if you are the more successful looking. “I’m trying to find (place). Do you know where it is?” They get to help. It makes them feel good. Asking for advice fits in the same category. Your friendly demeanor helps them relax.

  10. The Shared Memory – You’ve had a previous relationship but time has passed. You shared common experiences related to your current location. Mentioning the common bond may draw them out.

Matching Strategies to Scenarios

Your golf bag now has an assortment of clubs. Which ones are suitable for which scenarios?

The Big Fish

One successful person is meeting another. The introduction or friend in common is ideal. No connections? Try the compliment, ideally about news connected to the firm they run or their achievements in the community.

The Stunner

This isn’t business, it’s romance. Compliments are good but, obviously, only if in good taste. The Neutral Question or The Event-Related Observation can get the conversation started. The Waiting Game can work also unless a bolder competitor sits on their other side.

How Does This Sound? (Neutral Question + Event-Related Observation)

“Excuse me, is this seat taken? Thanks. I really enjoy coming to the Chamber’s Taste of the City each year. Have you tried the grilled shrimp? I have an extra one here. …”

The Casualty

A friend has fallen on hard times. You are a peer. The Information Request positions you as equals. The Neutral Question is similar. The Volunteered Observation could work.

How Does This Sound? (Neutral Question)

“Charlie, I’m so glad to see you. I haven’t been downtown for months and forgot about the construction. Do you know how to get to the freeway from here? I really appreciate the help. …”

The College Roommate

They’ve hit it big. You didn’t stay in touch. In fairness, neither did they. You are on an equal social footing. The Shared Memory can refresh common bonds. The Event-Related Observation gets you talking. Both The Insightful Question and The Compliment give them the opportunity to talk about their successes.

How Does This Sound? (Shared Memory)

“The chemistry building. Remember those sleepless nights we would spend cramming for exams? I still get a chill every time I see those classrooms. …”

The Service Provider

You’ve seen each other for years but don’t know each other. The Waiting Game hasn’t worked! The Volunteered Observation, The Request for Information and The Shared Memory put you on equal footing.

How Does This Sound? (Information Request)

“Charlie, we’ve known each other for years. I was wondering if you could give me some advice. Our ride-on mower has finally given out. What’s the best place to get another, someplace that provides good service if you ever need it?”

The Sideline Parent

You both want to provide for your children. You may not know each other, but your children might! The Friend in Common can reference flattering observations your child has made about their child. You might utilize The Compliment to recognize their child’s sports performance. The Volunteered Observation can draw them out about where they live.

How Does This Sound? (Compliment)

“You are Timmy’s parents, aren’t you? Our son Charlie told us the greatest story about this incredible shot Timmy made at basketball practice. You’ve got a real star there. You must be very proud. …”

The Extremist

You know their views and they aren’t your own. People are rarely focused on one issue. There should be common ground somewhere. The Shared Memory can draw them out about the local area. The Insightful Question can get them talking about an issue of your choosing.

How Does This Sound? (Insightful Question)

“Phil, I would like to ask your opinion. You’ve always been a strong supporter of limited federal government. I’m concerned about school taxes on the local level. They’re talking about building a new middle school. What’s wrong with the old one. …?”

You’ve got them talking! In part two, you'll learn how to keep the conversation going, gather information and position yourself as a person they want to know.

is president of Perceptive Business Solutions in New Hope, PA. His book "Captivating the Wealthy Investor" is available on He can be reached at [email protected].

More from InsuranceNewsNet