As an executive coach, it’s imperative for me to understand a leader’s family dynamic and important life events, both personally and professionally, that have shaped who they are as individuals. I start each coaching engagement with a deep dive into a leader’s personal life to better understand their story and where they are coming from, to have more context for where they are going. We look at milestones that happen from the time they were born until present day.

Family Legacy

I’ll ask, “How did your parents meet?” or “What were your grandparents like?” and what happens quite often is that clients are not able to answer the most basic questions regarding their parents or families; they honestly don’t know.

Why Don’t We Know our Parents?

There is often some mystery surrounding our parents. Older people don’t always talk about themselves, and when they do, they may only share the happy times of their lives. Even when adult children are curious about their parents’ background and choices, life gets in the way – they are too busy with their own families and careers to ask. Or if they have the time, they just aren’t sure how to start the conversation.

But that’s changing today, thanks to new technology and services available to the public for the first time. With the popularity of home DNA kits and sites like which help you build your family tree and understand your genealogy, younger people are becoming more interested in their parents’ lives. Technology like journaling apps makes it even easier for younger generations who are used to telling their own stories through social media.

A survey by StoryTerrace, which pairs professional writers with people who want to document their lives in a book, shows about a third of Americans admire what their parents have achieved but don’t know how they did it. Their November 2019 survey reported in the Wall Street Journal shows one in five don’t know anything about their parents before they became parents, and 45% learn more about their parents from discovering photos and family possessions than from direct conversations with them.


My Own Story

This hits home for me because I never really knew my own mother. She went into a mental hospital when I was just 18 months old, and she was gone the vast majority of my life. She would be released for a few months at a time here and there, but by the time I turned 10 years old, she was committed permanently to a state mental hospital. When I turned 21, I chose to become her legal guardian and moved her to a nursing home so she could receive better care, but the damage of numerous electric shock treatments had been done.

By the time I was old enough to ask questions of my mom, she was no longer a reliable source. I was only able to gather piecemeal information about her life from family, and she passed away when I was 29 years old.

I know that my mom was an extremely talented artist who won a scholarship to study art in college but was not only disallowed from going to college by her father, he also pulled her out of high school, effectively squashing her dreams of continuing her artistic education. During her time, women were supposed to be focused on being a wife, not having a career. But my mom turned her artistic talent into becoming an entrepreneur and unleashed her creativity by owning a successful baking and confectionary store before the onset of her mental illness.

If I’m ever granted one wish, I’d probably choose to understand who my mother was. I would love the opportunity to be an observer of her life: to see the environment she grew up in (which was no doubt harsh due to my strict Italian grandfather), to understand her challenges more effectively, to watch her bake and decorate one of her popular wedding cakes, to know why she made the choices that she did and to hear everything that went unspoken in her life.

My curiosity stems from my psychology background but also as a daughter. I would like to better understand the perceptional lenses through which my mother looked at and experienced her life. Once we examine our generational legacy, we can often see the patterns that can be both powerful and dysfunctional.

Related: Your Generational Legacy: How to Break Destructive Patterns

Here are ten questions I wished I would have been able to ask my mom while she was alive:

  • When you were young, what did you dream of doing with your life? What was life like?
  • What do you remember most about your childhood? Both your favorite and worst memories.
  • What were your parents like? Did your perceptions of them change as you grew older, and how?
  • What are your most joyous moments?
  • What are your most painful moments?
  • What are you most proud of?
  • What are your regrets?
  • What are the most defining moments – both small and large of your life?
  • If you could go back and do things differently, would you and why?
  • What were your dreams for me?


Why Now?

I’ll never get the chance to ask my mom these questions, but you still have time to get the conversation started with your parents. And if not, you can answer them for your own children. The current Coronavirus crisis and the staggering increases in dementia are proof that we won’t always have access to our parents, so now is the time to make the time for this activity. Don’t wait for the perfect time to present itself, because it never will.

I remember a young client I had many years ago who was a very successful entrepreneur in the tech field. Tim (not his real name) was only 23 years old but sought me out for executive coaching because he wanted to learn how to be a better leader. Even though his company was worth millions, he still lived at home with his parents, focusing 100% on his career. As Tim was sharing stories of his mom cooking for him and his little brother bugging him to watch Monday Night Football with him, it dawned on me how important his family was to him. He teared up talking about them. But he never expressed that emotion to them.

So, I gave Tim some homework. He was to watch football with his brother and do something thoughtful and nice for his parents to show them how much he appreciated them. He ended up having a blast watching football and prepared a nice meal for his parents, got his mom flowers and told both his mom and dad how he owed his success to them and how much he loved them. In our next session, Tim was positively glowing about reconnecting with his family and how good it made him feel.

Just a couple of weeks later while on a business trip in Florida, Tim unexpectedly passed away in a tragic accident. His family found his JMA notebook with all of his homework assignments and notes from our coaching sessions. A few weeks later, I got a call from his mother to tell me what a difference I had made in her son’s life. Because of Tim’s recent outreach to his family, they felt he had said everything that he needed to before he died. She told me that he was meant to work with me to complete his short life’s journey.

Years later, I reflect on this family’s ability to have a small piece of closure around Tim’s death, and I think about how I wished I could have had the same with my own mom. That’s why now is the time to do this with your own family. We always think there will be more time, but there may not be. We all need to tell our stories… now.

Do you need help telling your story? A coach can jumpstart your journey to a better you.

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