Tell Me About Your Highlight of the Year

Ideas for cocktail conversation.

Are you looking forward to the meetings and holiday parties scheduled in December?

As you celebrate the close of a productive year, consider what you will talk about with your colleagues, clients, contacts and friends.

Try this perennial question:

     What was the highlight of the year for you?

If it is a business-related event, add this prompt to confirm your genuine interest in learning about them and a project they completed with a client:

What is something you did for a client, that would not have happened, if you were not involved?

In our culture, it often is unseemly to brag.

Leaders and coaches say, “There is no ‘I‘ in team.”

Turn that upside down.

In order to better connect with someone, you give them this opportunity to brag and show off how they uniquely contributed to a client’s success.

This approach yields valuable insights about this person:

    • What sort of clients do they work with
    • What kinds of problems do they solve
    • What types of solutions do they bring to the table

Then, having heard their brief narrative, you may dig deeper.

No matter what they’ve said, continue with:

That sounds hard. How did you do that?

This question opens the door for additional details and for you to get a fuller picture of their work, their industry, their clients and so on.

What if it’s a social gathering?

The highlight question works the same way. Here’s what your acquaintance might mention:

    • They achieved a personal or chronological milestone
    • They visited a distant place
    • They started or finished a pet project

In this case, the follow-up question, How did you do that, may be inappropriate.

Instead, perhaps focus on the emotion the person felt, their sense of accomplishment or the people with whom they shared the experience.

There’s always a highlight, whether professionalor personal.

This Month’s Tip

Be prepared when your contact likes the highlight question so much they repeat it back to you. Review your list of successful projects; select a few that are the most indicative of the clients you work with, the problems you solve and the skills you bring to these situations. Consider anecdotes and events of a more personal nature as well.


Plan ahead for your holiday cocktail chatter. Let’s brainstorm a few questions and your own responses. Contact me at, set an appointment here or call me at 212.677.5770. Talking about a highlight with your contact can lead you both to celebrate the holiday season on a high note.

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