City Shift Finance: What challenge do leaders consistently underestimate until they experience it?
Ralph Kellogg Chief People Officer: I think many leaders underestimate the emotional and mental weight that comes with leadership.
It’s easy to look at a boss, mentor, or executive and assume they navigate challenges with confidence and certainty.
What people often don’t see are the internal pressures—the self-doubt, difficult decisions, and moments of uncertainty that accompany leadership. Leaders are frequently asked to make decisions with incomplete information while balancing competing priorities, managing expectations, maintaining productivity, and supporting their teams. The higher you rise, the more complex those responsibilities become. Leadership is often far less about having the answers and far more about navigating ambiguity while helping others feel confident in the path forward.
City Shift Finance: Where do organizations most often lose trust without realizing it?
Ralph Kellogg Chief People Officer: Organizations rarely lose trust through a single catastrophic event.
More often, trust erodes through small, everyday moments when leaders fail to follow through on commitments, communicate openly, or act consistently.
Employees pay attention to the details.
When promises go unfulfilled, communication becomes inconsistent, or leaders fail to address concerns, people begin to question whether they can rely on the organization. Over time, that uncertainty can lead to disengagement. Trust is built through countless small interactions, and when organizations overlook those moments, they risk weakening the very foundation that keeps employees connected, collaborative, and committed.
City Shift Finance: Which experiences shaped your leadership under pressure?
Ralph Kellogg Chief People Officer: Strong leaders create an environment where people can speak openly, raise concerns, and acknowledge mistakes without losing their dignity. They remain curious and adaptable while maintaining clear expectations. They understand that people may be carrying challenges that are invisible to everyone around them, and they respond with compassion while preserving accountability and focus. For me, courageous leadership means remaining grounded in your values when the situation becomes uncomfortable. It means giving others room to be human, extending that same grace to yourself, and continuing to move forward with humility, resilience, and integrity.
Pressure reveals whether a leader can remain honest, grounded, and accountable.
At a previous employer, I experienced a serious breach of trust after being encouraged to believe I could speak openly about a deeply personal matter. That experience showed me how profoundly trust, psychological safety, and dignity affect a person’s ability to contribute, build relationships, and feel respected within an organization. I also spent years struggling with my mental health before receiving a diagnosis, while continuing to carry leadership responsibilities and trying to convince myself and others that I was fine.
During that period, I sometimes became an obstacle to my own growth because I had not yet learned to acknowledge what I was carrying or ask for the support I needed. Those experiences changed how I understand leadership. Strategy, performance, and authority all matter, yet leadership is ultimately expressed through how people are treated, especially when circumstances become difficult. The lessons that shaped me most came through periods of uncertainty, isolation, self-doubt, and responsibility, when there was no easy answer and no opportunity to avoid the consequences of a decision.
When pressure is highest, leading well requires honesty, steadiness, empathy, and accountability. It means acknowledging uncertainty without allowing it to paralyze the team. It means asking difficult questions, listening carefully, making the strongest decision possible with the information available, and accepting responsibility for the outcome. Leadership under pressure also requires enough self-awareness to recognize when fear, ego, or personal assumptions are influencing judgment. A leader must remain open to feedback, learn from mistakes, and adjust when circumstances reveal that a different direction is necessary.
City Shift Finance: What is one issue facing nonprofit leaders today that deserves more attention?
Ralph Kellogg Chief People Officer: One issue that deserves far more attention is the growing tension between mission and sustainability.
Non-profit leaders are being asked to address increasingly complex community needs while navigating funding uncertainty, workforce shortages, increased regulatory requirements, and heightened expectations from boards, donors, and stakeholders. At the same time, nonprofit leaders carry the human weight of the work. They support employees experiencing burnout, make difficult decisions about limited resources, and remain accountable for delivering meaningful outcomes to the communities they serve. Unlike many sectors, the demand for services often grows faster than the resources available to meet it.
Balancing compassion with accountability, mission with sustainability, and leadership with personal well-being has become one of the defining challenges of nonprofit leadership today.
Chief Human Resources Officer at Lutheran Family Services
