ChatGPT Interview: How Working With My Son Led to Being Estranged For 7 Years

Legacy, Life, Lessons

There are many valuable “how to” or “coaching” articles on social media that provide insight to business owners and executives. ?My thoughts are not meant to be how to or avoid.? Charting my five-decade entrepreneurial journey, "Legacy, Life, Lessons" delves into what I wish to pass on, my personal experiences, and the transformative lessons that shaped my path.? I hope one finds value in them.

ChatGPT Interview:? How working with my son led to being estranged for 7 years

Recently, I inputted my career background and experience into ChatGPT and asked if interviewed what questions could I be asked that might have of importance to business owners and executives? ??

Five questions popped? up, the first being “what have been my greatest challenges in my 50-year career as an entrepreneur of many businesses and founder & CEO of a wealth management firm”.? Though there have been many challenges, some existential, no challenge was more confronting or devastating as an individual, CEO and father as working with and eventually asking my son to leave my firm.? And eventually realizing that I was totally responsible for this.

A couple of other family members had worked for me over the course of 40 years.? My wife worked full-time during the early stages of my businesses. But working long hours together during the day and then bringing work issues home just did not work out.? We mutually agreed she should “retire.” ?I was very close to my sister-in-law.? She worked for me for 10 years, but again, we reached a situation where I decided that she had to leave.? That was 20 years ago and we barely speak to each other even now.? You would think I would have learned that I was unable to work with family members.

Then, my son asked to join the company.? I had always dreamed of one of my sons taking over the company when I retired.? I remembered the 12 summers I worked with and reported to my father during my teen and college years.? While I am sure I was a challenge to my father many times,? he patiently taught me and made sure we worked well together. Those summers remain my most cherished memories.? I wanted to create those same memories for my son and relive those special years with my Dad.

I did not have a great record with working with family. My son and I had had a tense relationship for some years prior to his joining my company.? Due to this, I did not treat him like other colleagues: I was afraid to talk honestly with him for fear of angering and losing him.? Additionally, I did not want to show my son favoritism.? So, I decided he would initially ?report to a partner rather than me.? I felt that this would remove conflict amongst my partners and me and ?I could avoid work issues with him. ?It was a mistake. My son did not get honest and proper guidance. He chafed in his position. He grew impatient with advancement.? His job performance suffered. ??I was not there to patiently guide him on what it would take for him to succeed or even be a future CEO. ??With a firm our size, with talented partners and management, there was no guarantee he would ever be the CEO.?

He became resentful of management and me and started to cause issues for me with them. ?I blamed him for the problems. ?I could not understand why he could not give 100% and just get along like I did with my Dad so many years ago.? The last straw was him calling me up on vacation and screaming at me, making wild allegations about the COO.? I had had it.? I was angry and disappointed.

I met with him and my COO and released him.? While he received a generous exit package, the humiliation of being released from his father’s company and in the presence of the COO he disliked, the company he hoped to run someday, was devastating to him and our relationship.?

We did not speak for the next 7 years.? When we tried via texts, there was just rage and insults by both of us.? For me, these were years of anger, hurt, blame and questioning my skills as a father as well as a CEO.? There were many times I just cried.? I loved and missed my son.

Over the years separated, I finally realized that I was responsible for the situation that occurred to him.? My father faced the same challenges, but he took responsibility for our relationship.? I did not.? I blamed my son for him not working out.

We reconciled a couple of years ago.? We still work on our relationship.? I do not do it well all the time.? I am still angry and disappointed at times, but I get beyond this and continually strive to take responsibility for our relationship.? ??