My family and I just returned from my favourite US city, Chicago, where we had a whirlwind 72 hours that will henceforth be referred to as “Dad’s 50th Birthday trip”, even though my birthday came and went a few days prior to our departure.

We hit all the stops from Navy Pier to Lincoln Park Zoo, from the Architectural Tour on the Chicago River to the John Hancock Tower Observatory, and even hit Soldier Field for a Bears pre-season game on Friday night. And of course we sampled some deep dish Chicago pizza.

But the part that I will not soon forget was the Cubs game at Wrigley Field, which we took in from the Skybox on Sheffield, one of the many places that have sprung up in recent years located across the street from the venue where the Cubs play their home games.

I had always said “some day I want to catch a game from one of those places”, so this trip became “some day”. The game was not memorable for what happened on the field, though, with the Tampa Rays winning 4-0. It was memorable because of the conversations I had with my 13-year-old daughter.

I attend many sporting events, mostly with my son, and only occasionally with her. She had not seen live baseball, and asked me to explain it to her. “Cool”, I thought, “this should be fun”.

The first thing that struck me was that the terminology can be quite confusing to those unfamiliar with the nuances. To her words like “throw” and “pitch” were interchangeable, and anyone who caught a ball was a “catcher”, as opposed to a fielder.

Just like family business, I thought, where succession planning and leadership can become confusing to different people in different positions and with different levels of “inside knowledge”.

As I explained the stuff about 4 balls for a walk, three strikes and you’re out, etc, it also dawned on me that everyone has a limited capacity to absorb new information in one sitting. After a few innings, the explanations became less frequent.

The next time we see a ball game on TV, I know that I will be able to explain a bit more to her, as what I helped her learn on Saturday has sunk in and formed a baseline (no pun intended), and we have something to build on, incrementally.

One step at a time is usually my favourite way to go about things, and when you are getting your family more involved in your business dealings, or getting them up to speed on how you are running your business and how and where the family fits into the picture, it is usually a good idea to go slowly and add more information with time.

The most important parallel that I felt was that spending time with the ones you love, helping them to learn and understand something that you know about and care about, is just about the most rewarding thing you can spend time on.

As a teenager, I played baseball, coached baseball, and umpired baseball. The Expos moving to Washington 10 years ago broke my heart, as I was a fan and had hoped to bring my kids to games. My son understands the game, and I have brought him to games at Fenway Park, Camden Yards, Philly, and DC, but I know that if we still had an MLB team here I would not have waited this long to explain the game to my daughter.

If you have a family business, don’t wait to explain things to the ones you love, start as soon as they show an interest. Go slowly, but then let them decide if and when they want to get involved further, and please don’t push them.

I know that my daughter learned quite a bit about baseball, but I am pretty sure she enjoyed the Katy Perry concert at the United Center on Thursday more than the Cubs game. And I was happy to be there with her too.

Steve Legler “gets” business families.
He understands the issues that families face, as well as how each family member sees things from their own viewpoint.
He specializes in helping business families navigate the difficult areas where the family and the business overlap, by listening to each person’s concerns and ideas.  He then helps the family work together to bridge gaps by building common goals, based on their shared values and vision.
His background in family business, his experience running his own family office, along with his education and training in coaching, facilitation, and mediation, make him uniquely suited to the role of advising business families and families of wealth.
He is the author of Shift your Family Business (2014), he received his MBA from the Richard  Ivey School of Business (UWO, 1991), is a CFA Charterholder (CFA Institute, 2002), a Family Enterprise Advisor (IFEA 2014), and has received the ACFBA and CFWA accreditations (Family Firm Institute 2014-2015).
He prides himself on his ability to help families create the harmony they need to support the legacy they want. To learn how, start by signing up for his monthly newsletter and weekly blogs here.