The Skills to Be a Hero and Initiate the Next Conversation

By Alana Gerson

Engaging in conversation and learning about the life of someone you meet on the plane, at an event or in a tour group is a skill and activity I learned to enjoy as a child from my mother. You never know who you are going to meet and how either of you might influence each other’s lives.  It was that mindset towards networking that gave me much success professionally and personally while living in New York City for five and half years.

When I moved to Boston last year, I knew two people, the walk to and from work and that I wanted to build a new community for myself. Starting over in a new city is uncomfortable and completely different compared to when I was 22 and a bit naive. I wanted to tighten up those networking skills and came across the book The Fine Art of Small Talk. In her book, Debra Fine simplifies the skills and tools to make small talk less intimidating.

Below are techniques and pointers from her book and my personal experience to help guide you.


Get comfortable with showing your pearly whites

On your commute to work or stroll around town make eye contact with at least three people and smile at them. Even though this is Boston, it’s not NYC and most people will smile back. Practice every day until it feels natural.

Strategies to Navigating the Standing Room

I like to mosey around the food and drink tables because it is easier to spark a conversation with a single person than a group. Usually I have tried all the snacks and can either recommend or comment on a snack to the person initiating a conversation over a common interest.

The 8-Person Dinner Table

How many times have you been at a dinner table at a wedding, fundraiser or corporate event and knew maybe one person at the table? Be everyone’s savior by acting as the host. Introduce yourself to each person at the table as they sit down and take the lead to make introductions as new guests arrive. Not only do you feel the achievement of climbing Mt. Everest but you also put everyone else at the table at ease while creating a warm environment ready for conversation.

Big Takeaways

  1. Make eye contact with the approachable person who is not actively engaged with something or someone
  2. Handshake during an introduction
  3. Be fully engaged in the current conversation
  4. Act as a host and introduce people to each other
  5. Hand out your business card and if you have the moment (and a pen) write down the date and event on it
  6. Remember, your best friend was once a stranger

Alana’s Final Note:

One thing I know for sure is, if someone dares to leave their house and attend an event it is safe to say that they are interested in meeting new people and would be relieved to have someone else initiate the conversation. As Debra Fine says “most people there are scared to death to talk to you…but the probability of rejection is actually quite small.” So be their savior and you will be rewarded with stature, respect and rapport just for starting a conversation.

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