Stepping Stool Coaching – Step Up Your Conversations To Reach New Heights


By Guest Blogger: Kathy Boyle President of Chapin Hill Family Advisors.

We want the best for our children…

As a first-generation business owner, you likely spent hours and hours of sweat, tears, frustration and exhaustion to grow your enterprise to where it is today.

As parents, we want to help our children and make life easier for them whenever possible.

This desire can carry over to the business, and we believe by giving the business to our children, we are giving them a gift.

Before you operate on the assumption you are providing a gift of a turnkey business, income, structure, clients or customers, perhaps real estate and more, take a moment to pause.

Are you giving your children the room and permission to communicate their true thoughts and feelings? Have you asked them for feedback?

Are you non-judgmental in hearing what they have to say?

Are you open to hearing that perhaps they wish to sell the business or take it in a new direction?

The business is like a baby to many founders so these messages can be hard to hear.

Open conversations….

Recently, I met with a gal to discuss a start-up which was in her area of expertise.

We were connected via our shared connections in the animal rescue world so she had no idea of my core business.

When I explained that most of my time is spent working with family owned businesses on creating succession plans, she shared her story.

Her mom is in her late 60’s and is actively trying to bring her daughter into the business, which supplies a service to the legal industry. It is a very successful enterprise but this gal’s passion and career is writing about health, beauty and wellness.

I asked her how she felt about taking over her mother’s enterprise. Her reply was that she feared that turning it down would be a huge financial mistake.

However, her real love is the world she lives in, freelancing about all types of health and wellness products and venues. This area happens to be difficult to get back into if you step out of it so her concern was that if she chose her mother’s business and decided to bail, she could not pick up her former career.

The daughter was afraid to broach the subject with her mother as she recognized her mother viewed this as a huge gift. Taking over her mom’s business would create a path to financial independence without worrying about which magazine was paying her for freelance articles each month. She lives in NYC so the lifestyle is expensive and it is tempting to take this on.

On top of her anxiety over bringing up the subject to her mother, she was also frustrated as her mom stated she wanted her daughter to add value and create systems yet was resisting changes. The daughter was spending two to three days of her week working in her mother’s business and felt that her contributions were not being valued. This is another common problem we see in family businesses.

Life coaches and professionals…

These situations are exactly where a life coach who specializes in family business communication can be a huge help to the family. One of our life coaches calls these “difficult conversations” as they are loaded with emotional content.

A trained professional can allow both sides to communicate freely yet without the conversation degrading into a fight or anger building up on either or both sides.

Allowing your children (or grandchildren) a safe space to tell you how they really feel is the best way to find out if you are bestowing a gift or passing on an unwanted asset.

Children are never exact replicas of either parent and have their own skill sets as well as passions and dreams.

While it may be very hard to hear, sometimes selling the business outright and providing funding for each child to either live a great lifestyle supplemented by investment returns or allowing them to found a business in a completely different arena may be the best possible outcome.

This can be really hard to fathom for an entrepreneur who loves what he or she does.

After spending a lifetime navigating their industry’s unique rhythms, parents only want to see his or her children run with the business and have an easier life than they did as they sacrificed to build the enterprise.

If you truly want what is best for your children, let them tell you it may not be a gift!

Leah Zimmerman is an Intergenerational Resolving Conflict Expert and Family Business Advisor who makes hard conversations easy. She blends her background in education, theater, personal development and spirituality to create transformational conversations for individuals, teams and families. Find Leah on Linkedin at to learn more.