Big Apples and Oranges: Navigating NYC and Chicago’s Different Business Meeting Cultures

Big Apples and Oranges: Navigating NYC and Chicago’s Different Business Meeting Cultures

Setting business appointments is an important early step in developing relationships with prospects and new customers. When engaging in global business, we all know the importance of relating to the business culture and cultural norms during these first impressions. It may come as a surprise that it’s just as important for a Chicagoan to recognize the differences in New York City business culture (and vice-versa).

Business culture is different in New York City than in Chicago.  Most people instinctively feel the difference just walking down the street.  Here are some key distinctions all businesspeople should know about setting meetings in both cities—and tips to make your appointment-setting a success.

By the Numbers

My firm Insight to Action conducted a small survey among business people who regularly schedule meetings with business customers and prospects in each city, asking them to focus on the city where they most often schedule meetings.  The findings, while directional due to small sample size, bear out these observations.

It tends to be more difficult to set and keep meetings with New Yorkers. By comparison, Chicago business culture is much less likely to move a meeting once it is scheduled. For example, in Chicago, there was 80% agreement that “Most of the time, customers/prospects try to keep an in-person meeting after it is scheduled and avoid rescheduling.”  In contrast, 50% agree that this is rarely the case in New York.

Big Apples and Oranges: Navigating NYC and Chicago’s Different Business Meeting Cultures

In addition, Chicago respondents report that “rarely or never” is an in-person meeting canceled the same day. Most or some of the time one is given several days notice if a meeting has to be rescheduled. By contrast, in New York, 50% of respondents say that an in-person meeting is canceled “some of the time” on the same day, and 75% say they are rarely given several days notice.

Big Apples and Oranges: Navigating NYC and Chicago’s Different Business Meeting Cultures

Big Apples and Oranges: Navigating NYC and Chicago’s Different Business Meeting Cultures

Additionally, New York respondents appear to require longer lead times to schedule in-person meetings, an average of nine days, as compared to seven in Chicago.  While it’s undoubtedly true that there are also differences by industry and age range, we believe these business culture differences are real and should be considered.

Tales from the Front

These norms can be very challenging for firms that are not based in New York City. Representatives might fly in for meetings, only to find them cancelled.  Colleen Fahey, US Managing Director, Sixieme Son, Audio Branding and Sound Design, regularly sets meetings in NYC. She adds:

“The thing that I notice about New York is that when you get to a meeting, you are very often told something like, ‘We’re running late,’  or ‘I’m double booked.’ They convey a ‘hurry up’ message that can throw you off balance.  ‘My time is so important’ -- gets communicated continuously.  Sometimes it feels aggressive, but I don't think it's meant that way.  Still, if you've planned an agenda that’s exactly half an hour, you'd better be flexible enough to finish your business in 12 minutes.”

Compare this to what another source says about setting appointments in Chicago:

“In Chicago, it’s a lot easier. We may bring a lunch if we are trying to meet with a group to encourage them to attend.”

Despite these challenges, New York business people can also be more spontaneous, accepting a same-day lunch invitation, or readily moving a meeting time back by an hour. Just last Wednesday, while in New York, my associate moved a meeting forward, giving only about one hour notice.  The change was not an issue for the customer.  

But Chicagoans are less spontaneous to changes in the plan, often finding changes to be disruptive and unwelcome. Last Friday, I shifted a Chicago meeting 30 minutes forward, and the person I was meeting was less than pleased.

One firm recognizes the need to honor New York’s business culture and finds a way to avoid a disappointing business trip:

 “We work with media people in all the major markets. In New York, it’s very tough to get appointments or meetings, so we remove the barriers.  For example, we have a full-time person following up to ‘ping’ them several times to remind them of the meeting, or we’ll send a car to pick them up an and bring them to the event.  In New York, they are always looking to maximize their time.”

What’s a Business Person to Do?

Knowing these business cultural differences between the two cities lets business people alter their approach to setting meetings. Here are some tips for managing the differences:

  • Take advantage of normal business hours. New Yorkers may start work as late as 9:30. Suggest meeting for coffee before their day starts, around 8:30-9:00. Chicagoans usually start earlier and might work through lunch at the office. ‘Lunch and learn’ presentations work well in this market. Also, in Chicago, the Wharton Club has had great success starting events at 5:00 to allow people to attend and still go home by 7:00.
  • In New York, remind the person the afternoon before or morning of the appointment . Email to confirm or send a text message, and even say, “I’m bringing treats.”
  • For advance meetings, give New York customers a few extra days to plan.
  • Try to avoid moving meetings with Chicago customers, although New York clients may be more open to it.

When you’re setting appointments in the Big Apple or the Windy City, use these tips and increase your success in each city. I’d love to hear your thoughts on other practices that work, and/or observations about the cities.

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    As a native New Yorker living in Chicago, I can honestly say this is spot on. New York business people seem to always be able to pivot on a dime (if you know New Yorkers..everyone is ALWAYS on the "Go") versus Chicago Business people who once they have settled on a time seldom deviates. I like to think Chicago is like this because here in the Midwest it all boils down to "your word is your bond" which for a Midwesterner it is a sense of personal pride to practice this mantra.

  • A great example of the Chicago culture is occurring today. The client who organized the meeting has an emergency doctor's appointment but found others to back her up. Other priorities have appeared on people's schedules--but instead of canceling they just shortened the meeting duration. Great for me, because I've rescheduled my team's work hours, hired a car service and put the Paris team through fire drill. It would be tough to hear the meeting was cancelled. Props to the considerate clients.

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