How a conversation with my absent father taught me about leadership and healthy confrontation

Many years after my parents’ divorce, my dad remarried. He left the States for an amazing job opportunity and went on to live in Kenya, Ethiopia, and Finland with his new wife and kids. Meanwhile, my mom, my stepbrother, and I struggled with a brief period of being unhoused and living on welfare. I often wondered what I had done to cause my father not to fight for me. I also worked very hard to make sure this didn’t happen with other people in my life. 



And so, I became a chameleon and did whatever I needed to fit in and be liked. In high school, that meant becoming a basketball player because “everyone loves basketball” and cussing because “that’s what the cool kids did.” At university, I gained a reputation because I was so desperate for affirmation.



It was through therapy that I recognized that my father’s gap in my life left me starving for affirmations, which is how I was able to rectify and undo many of my toxic or self-sabotaging behaviors.



But then, in my thirties, the pain of not having my father around returned. I found myself regularly breaking down in tears, questioning my self-worth, or yearning for the fatherly bond I was so certain I was missing.



And so, in the summer of 2019, I planned a trip to Ghana to confront my father.



When I opened up to some colleagues about this plan, someone suggested that instead of confronting him, I could ask for his story. My jaw clenched as I took sharp, quick breaths. “He doesn’t know my reasons,” I thought, in defensiveness. But their words planted a seed, which I discussed with my therapist. Together, we worked on how I would turn my “confrontation” into a “conversation” with my father. 



The day came in Ghana, and I asked my dad for one-on-one time. And then, I asked him what happened between us, and what his life was like growing up.



This conversation gave me access to a side of my father that I never knew about. I learned about his custody struggles, the interpersonal conflicts he had with my mother, and—more importantly—how his upbringing shaped his decisions. I discovered that his own father was hardly around. He also told me he went to boarding school at 14, leaving his entire family behind.



Ultimately, my dad decided that the best thing to do was to let me find him when I was ready.



I disagreed with my father’s decisions, and this conversation did not magically heal all our past wounds, or turn us into an aspirational father-son duo that plans camping trips together. However, I better understood his decisions. And, for the first time, I empathized with where he was coming from. In many ways, this conversation set me free and I chose to forgive him. For a long time, I’d felt personally responsible for my father not being around and I no longer carried around that burden. Surprisingly, this conversation also helped me show up as a better leader.



Previously, I avoided vulnerable conversations and I tried to minimize disagreements at work. For instance, if I could sense there was rising tension, I opted to change the subject, instead of allowing my team members to address their concerns.



Asking my dad to tell me why he wasn’t there for me proved to me that asking challenging questions can lead to productive outcomes. This made me seek out disagreements (the good kind) at work and challenge my employees to voice their honest opinions.



Strangely, it also made me more comfortable with sharing my vulnerabilities at work. I found myself sharing ways I messed up or failed at something which encouraged my team to be more open about their shortfalls.



To balance vulnerability without oversharing, I asked fellow CEOs in my community for feedback before taking certain topics to the whole team. I also reserved these important conversations for Zoom instead of email.



I also went out of my way to encourage my team to disagree with me. In the beginning, this was challenging, and I had to actively ask them questions like, “What went wrong?” and “What would you do differently?” When my team did disagree with me, I verbally rewarded them with statements like: “Thank you so much for disagreeing with me. This helped me achieve more.”



Recently, I wanted to host a LinkedIn Live over Zoom. My team pushed back and insisted that Streamyard was a better option, because of its multi-platform streaming capabilities. Thanks to my team’s pushback, we streamed on LinkedIn, Instagram, and Facebook and tripled the number of attendees tuning into the Live.



I was cultivating a culture of respectful disagreements at work without realizing it. My team was more collaborative than ever before. We were hitting our targets and coming up with creative solutions. More importantly, when I made a bad decision, my team was quick to point this out to me.



Asking my father for his story is one of the hardest things I have done. It is also one of the best things I have ever done. This conversation taught me that entering a discussion with empathy and a curious mind can transform our personal growth, productivity, and collaboration as humans and leaders.