On Leadership Struggles

There are two particular challenges in leadership that I find especially difficult to navigate.

First, I am deeply committed to fostering an environment where open communication flows both upward and downward across the organizational hierarchy. I believe one of the key indicators of organizational effectiveness is the speed at which leadership becomes aware of emerging issues. Despite my efforts to create a welcoming and psychologically safe space, I’ve come to accept that some colleagues may still choose not to engage directly with me. Whether due to perceived risks, past experiences, or personal reservations, barriers to communication will persist. As much as I strive to cultivate openness and trust, I recognize that I cannot compel others to speak up—it must be their choice.

The second challenge relates to the high expectations placed on leaders to be always “on”. I strive to lead with infusing virtues into every decision and interaction. However, on rare occasions, I make mistakes—perhaps an ill-timed joke, a delayed response, or a lapse in clarity. What I find particularly disheartening is that, for some colleagues, a single misstep can overshadow a long track record of positive actions. It can feel as though the standard is perfection, which is both unrealistic and emotionally taxing.

In response to these challenges, I’ve adopted a few key strategies:
1. Acknowledgment and Accountability: I take responsibility for my mistakes, whether I recognize them immediately or they are brought to my attention later. When I realize an error on my own, I make it a point to approach the individual involved, offer a sincere apology, and engage in a constructive conversation. Mistakes and missteps must be acknowledged.
2. Encouraging Courageous Dialogue: When a colleague who was previously hesitant chooses to speak with me, I make sure to acknowledge their courageous step. I understand that initiating these conversations can be difficult, and I want to reinforce that their voice matters.
3. Staying Curious and Open: Regardless of the situation, its crucial to remain curious and avoid defensiveness. Creating a culture of continuous learning and mutual respect is essential to building trust.

These strategies are far from perfect, and I find myself ruminating, especially when my misstep overshadows positive actions. Consultation with other leaders and supportive friends have been a lifesaver during those times.