Personal Leadership
“He was like a brother to me,” he said, tears welling in his eyes as we sat in our weekly 1-on-1. His voice cracked as he described the accident that had taken his family member just days before. In that moment, spreadsheets and project timelines evaporated from relevance. What mattered was the human being sitting across from me, wrestling with a grief I could see but never truly understand.
Reflecting back on this moment taught me one of the most important lessons in my career: Great leadership transcends management. While good managers focus on deliverables and performance, exceptional leaders understand that the path to extraordinary results runs directly through human connection. It’s your ability to build deep, authentic trust with each person on your team that will make the difference.
In that raw moment with my grieving team member, I faced a delicate balance. It wasn’t my place to process his grief—I’m not a therapist. But it was absolutely my responsibility to ensure he knew his position was secure while he navigated his loss, and to gently guide him back to work when he was ready. This required something beyond management skills. It required trust that could only have been built through genuine personal connection.
Beyond Management
The cornerstone of this connection was the many 1-on-1s where I worked on creating a safe space for my team. Whenever a team member joined the biweekly call, they know without a shadow of a doubt that what was said in that meeting would stay in that meeting. Confidentiality isn’t just a nice-to-have; It’s the foundation that the trust is built on. Without it, you’ll never move beyond surface-level discussions about tasks and timelines.
I’ve found that safety is established not through declarations but through consistent actions. When a team member shares something personal and sees that it never becomes hallway conversation, they learn to trust. When they express a fear or insecurity and it doesn’t appear in their performance review, the walls begin to come down. Each protected confidence is proof that you have their back.
But here’s the truth that many leaders miss: vulnerability has to start with you.
I remember the day I had to tell my team about my biggest professional mistake. I had misconfigured an email service, inadvertently triggering hundreds of thousands of spam emails that flooded our customers’ inboxes—and worse, their customers’ inboxes too. The damage was significant and entirely preventable.
Sharing this story with new team members when they make their first meaningful mistake doesn’t only make them feel better—it fundamentally changes our relationship. By showing my own fallibility first, I create space for them to be human too. Not to excuse poor performance, but to establish that we can talk about failures honestly, learn from them, and move forward stronger.
The Balancing Act
I still struggle with this balance sometimes—just last month, I caught myself hesitating to share a relevant failure with a coaching client. I noticed I was worried about undermining my credibility, falling into the same trap of wanting to appear infallible. The moment I recognized this and opened up anyway, I could visibly see their posture change as they realized they weren’t alone in their challenges.
It struck me then that the courage to be vulnerable doesn’t get easier just because you’ve changed roles or gained experience. Whether you’re leading a team or coaching other leaders, that moment of choosing openness over protection still requires a deep breath and a leap of faith.
This kind of leadership walks a fine line. Again, you’re not a therapist, and pretending to be one is dangerous territory. When my team member was grieving, I didn’t attempt to process his trauma or suggest coping mechanisms. I think that the most important thing I did was simply acknowledging his pain. I sat with him in silence for almost a minute to let myself take in the gravity of what he had just shared.
When I was sure he understood that I felt his pain, I switched gently switched back into manager mode to make sure he knew his job was secure and that we would work together to create a flexible return plan after he took some time off to process the grief. Knowing when you’re approaching a boundary that requires professional support is as important as being willing to go deep with your team.
I used to resist getting personal, believing that professionalism required a certain distance. I watched other leaders maintain their authority through separation and thought that was the path to respect. I’ve come to see this early belief as one of my most significant professional misconceptions. The leaders who inspire extraordinary performance aren’t those who remain distant—they’re those who dare to see and be seen as complete human beings.
The Transformation
This trust isn’t only about dealing with hard times (or becoming friends). The magic that happens when you build this kind of trust is transformative. In the safety of a truly personal 1-on-1, people reveal their deepest professional dreams—ambitions they might never share in a standard career development discussion.
One simple example was when a team member confessed that while he excelled at his current role, his passion lay in product strategy. This insight allowed us to gradually shift his responsibilities, ultimately creating a new role that acted as a bridge between business and technology, that served both his aspirations and our business needs.
This alignment between personal passion and business needs isn’t just a nice outcome—it’s a strategic advantage. When people work in their zone of genius, they bring an energy that spreadsheets can’t measure but customers can feel. I’ve found that one deeply aligned team member often contributes more meaningful innovation than three who are merely competent but disengaged.
I’ve found myself returning to a simple practice that consistently unlocks these insights—asking open-ended questions that gently challenge existing beliefs. When I asked a team member, “Is it really true that you couldn’t lead that initiative?” I watched his perspective shift before my eyes. This is where leadership begins to look like coaching, helping people discover answers within themselves rather than simply directing their work.
Wrap Up
I’m not suggesting you can transform your leadership overnight. This journey toward trust-based leadership is both challenging and ongoing. I’ve worked with several coaches over the years who have helped me navigate my own barriers to connection. Having support in the form of an outside perspective has helped me see my blind spots and push through my comfort zones, making me a much better leader.
The difference between a good manager and a truly transformative leader often comes down to this willingness to get personal—to build the kind of trust that inspires people not just to do their jobs, but to bring their full, creative, passionate selves to work every day. The transformation begins with honest self-assessment, so I’ll leave you with this:
Think about your last five 1-on-1s. Did you learn something personal about your report that you didn’t know before? Something that helps you understand not just what they do, but who they are and what drives them? If not, what might be holding you back from creating that space? Your answer to this question might just be the first step toward becoming the leader your team truly needs.
