Family Transformation

Connect52 transformed “my relationship” with my family, and I got a best friend in the process.
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Family Transformation

As the creator of Connect52 and as someone who is extremely passionate about transforming families, marriages and relationships of all sizes, shapes and kinds, I am frequently asked, “how did asking and answering questions with your family transform your family dynamic?”. It has been brought to my attention that people may not want to participate in Connect52 because they don’t believe transformation with “their family”, spouse or group is possible. I believe the assumption is that I must come from a “high functioning” family. It also is assumed that everyone in my family participates. Connect52 transformed “my relationship” with my family, and I got a best friend in the process.

52 questions ago, to anyone who asked I would have described my family as “dysfunctional”. Like a lot of families I know we love one another, I just don’t think we would consider each other  “best friends”. We get together around the obligatory holidays, major sporting events and in our case we attempt to get together annually for a family reunion. My parents recently celebrated their 50th wedding anniversary, I have five siblings, 2 brothers and 3 sisters, each of them having children of their own for a total of 16 nieces and nephews. The size of your family might not be the same, your parents may have gotten divorced, and maybe in your family you are best friends; and yet we all share one thing in common, we come from a family, no matter how dysfunctional it may seem.

The genesis of Connect52 started innocently when I returned back East alone, after one of the annual family reunion trips. For the first time in my life I felt truly alone. Obviously as the fourth child of six, I never felt alone growing up, and the majority of my adult life I had been accompanied by intimate relationships and friends. I had recently divorced for the second time and my job transplanted me on the East coast where I knew know one, worked in a warehouse all alone, and the nearest family member lived in Colorado. It was at this moment that I realized the potential value of the family connection. Now the question was, what could I do to create a new, better, stronger connection with these people that I didn’t really know anymore, didn’t consider friends but they are my family, the common denominator?

During that family reunion my father asked if I would be willing to share with my family the benefits I had experienced from my Mediation / Conflict Resolution practice. It was my Mediation education that created a realization as to the power of questions. I come from a family of “know-it-alls” and we tend to not ask a lot of questions as much as tell others what and how to do things. So the question I had was, how can I demonstrate to my know-it-all family the value of asking questions and listening intently for answers? So I shared with them a game I like to play called, Your Life in 30 Seconds. The game is played with anyone with whom you genuinely want to know better. Invite them to share their life story in 30 seconds; you do nothing but listen intently taking mental notes for follow up questions you might want to ask about certain portions of their life, as 30 seconds is not enough time to go in depth. The beauty of this game, is that most people are willing to play for 30 seconds, and if you will do nothing but ask the question, followed by sincere questions of interest, minutes will pass and they will walk away with a sense of feeling like their life is of interest and you will receive the gift of knowing and learning from another fascinating member of our human family.

It was this time alone; in a grocery store walking aisle to aisle not recognizing anyone and not being recognized, or in a restaurant where you silently observe as neighbors and friends gather to socialize or celebrate, standing in a room of people heads buried in their phones is when I really learned just how disconnected we are from our human family. Sure we have our family of friends, we even have hundreds of friends on social media, and my observation is that all too often we communicate with our virtual friends while in the presence of our friends and family. So it was during this time of social isolation that I gained a much greater appreciation for my friends, a new desire to reach out and connect with my human family and questioned why I wasn’t doing more to connect with my brothers, sisters and parents.

So I sent the following email to my family…

I don’t believe it will come as a shock to any of you that I don’t consider us the poster family for closeness. This is not a complaint as much as it is an observation. We can continue to go the way we have always gone and I am sure it will be just FINE. As a restaurant manager I considered a guest leaving who informed me that their experience was fine, to mean that they had a less than memorable experience.

I informed each of you  that I like to play a game with complete strangers in which I ask them to tell me their lives in 30 seconds. As all of you know I have had the opportunity through divorce  to meet and bring new people into my life. In this process I often describe my family members, your spouse and children… I must admit I am probably providing less than accurate information on all of you. So if interested I would like to play a game, a game that doesn’t particularly have an end. I would like to play a very slow, yet more detailed version of “tell me your life in 30 seconds”. 

There are no rules exactly however my idea is to ask one question a week  and each of us can respond to the group.

With everyone having busy lives I think that a question a week is plenty and if we answer 52 questions a year we might just get to know each other, more than the strangers we are now. Follow up questions to answers are appropriate. I don’t want to be a control freak and I also don’t want this to be an assignment or burden. If you have questions that you would like asked of the group, by all means…

Question 1: Inspired by David Letterman – What are the Top 10 Highlights of your life?

So that it is how it all began… I knew that I would know some of the highlights of each of their lives but I was more interested in learning what I didn’t know. Who knew, that my sister considered her years of high school water polo as a highlight of her life, sandwiched between motherhood and years spent in Argentina. I was hooked, I was fascinated and I wanted to know more. Interestingly, the effect of asking my family member questions about their lives left me feeling more connected.

The truth is… neither of my brothers have ever answered a question. My older brother claims he doesn’t like computers but he seems pretty savvy with the smartphone found in his pocket. My younger brother suggested that I ask multiple choice or easy survey style questions and even after doing so, he failed to answer the questions. It could be easy to consider their participation as a failure however, the lack of participation is a form of participation and I assume they participate by reading the answers of others if for no other reason than they are often mentioned in the answers. I am also willing to recognize that many things are subject to timing. I have failed to participate any many activities that would benefit my life just do to timing. Maybe the time will come in which they realize how important their participation in this family bonding process is to the rest of us and how valuable it might be to their own life.

My parents don’t always participate in the answering of questions but I know they find the answers of their children to be enlightening as we often reminisce about the things we did that my parents had no clue about, or we open up about our feelings, experiences and dreams for life, a priceless journal of information.

One of my sisters said, “This has been a wonderful process. The best thing is that even though there have been weeks I have been unable to participate, I have still been able to catch up with the others that did participate. We all know how life has gone through our own eyes, but it is amazing how each of us going through the same experiences have seen them differently. It makes you realize we need to take a step back and look at things through another set of eyes.”

And then there is the youngest,my sister Melanie. She is 8 years my junior and 52 questions ago, a virtual stranger. She has actively participated in the process, helping me with unique questions and always answering with an openness, honesty and vulnerability that allowed us to start connecting on a level that I would have never thought possible. She started the Connect52 process with her in-laws and her husbands family and they are now in the process of planning a family reunion in which the whole family will get together for the first time in over 10 years. After 12 years of marriage, Melanie and her husband take turns asking a question each week and have discovered how much their is to learn about your spouse. 

With each question Melanie and I started speaking more frequently on the phone, about what question to ask or providing more detail to our answers. As our relationship transitioned from sister to friend, Melanie planned a trip to come and visit me. We celebrated her birthday, riding bikes in Central Park, walking the streets of NYC, taking in Wicked on Broadway and talking over dinner at Carnegie Deli. Now it is rare that a day passes that we don’t communicate via, text, email or our phone conversations. As I have come to know my sister, value who she is in the world, I have gained an abundance of love and a best friend. Recently I visited Melanie in Colorado and received the following card…

Family Transformation - BFF

Craig – 

I love you so much! I can’t thank you enough for being willing and wanting to come out to Pueblo to see me and watch my kiddos for me. You and your friendship mean the world to me. I don’t know what I would do if I couldn’t pick up the phone and talk to you. 

Love you forever!


I can’t imagine my life the way it was 52 questions ago, 52 weeks ago; 1 year ago… my sister wasn’t my best, I didn’t know my brothers, sister or parents as well as I do today. So now imagine, “what would your life look and feel like if you had a deeper connection with your family?” It is as simple as 1 question a week for 52 weeks and come next year you will have transformed your relationship with your family.

(Featured Image: Thomas; cc2)


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