The Leadership Skill Most Leaders Fear...And Why It Builds Trust
As a leader, I’ve sat in countless meetings, pored over data dashboards, and attended professional development sessions that were meant to sharpen decision-making yet some of the most transformative moments in my leadership journey have come not from any spreadsheet or training but from the difficult conversations I once dreaded having with staff.
There’s a common misconception that tough conversations are simply necessary evils. Something to survive, manage, or minimize. What I’ve come to understand is that when approached with the right mindset and preparation, these conversations become powerful leadership tools. They don’t just resolve tension. They illuminate blind spots, clarify direction, and often lead to the very breakthroughs schools need to thrive [1].
I learned early on that walking into a difficult conversation unprepared almost always leads to defensiveness, confusion, or worse; miscommunication. Taking time to prepare changes everything. It forces me to get clear on what I truly want to communicate and why it matters. It makes me pause to consider how the other person might be experiencing the issue, and how I can remain calm, empathetic, and constructive, no matter how the conversation unfolds [2].
Preparation is not about scripting every word. It’s about building awareness. Before a recent conversation with a counselor struggling to meet expectations, I spent time reflecting on what I hoped to achieve. I reviewed examples of impact on students, thought through questions that would invite reflection rather than blame, and considered what support might be helpful. That mental work didn’t just make the meeting go smoother, it helped me lead with clarity and care [3].
I’ve had moments when I thought I had the full picture of a problem; only to be proven wrong during a difficult conversation. Staff members are the ones doing the work on the ground. They see and experience things I might miss from my office or in scheduled observations. I remember one instance when I approached a team leader to discuss resistance to a new system. What I thought was reluctance to change turned out to be deep frustration with a logistical flaw that made collaborative planning impossible. That insight didn’t just resolve the tension, it helped us adjust the system to work better for everyone [4]. Without the conversation, that problem would’ve persisted unnoticed.
It’s easy to lead when everything is going smoothly. But true leadership shows up in how we handle the uncomfortable. Over time, I’ve seen how consistently showing up for hard conversations without avoidance or deflection builds trust [5]. When staff see that I don’t hide from challenges, they’re more willing to engage with me honestly. They know I’ll listen, even when it’s hard. They also know that expectations matter and won’t be left unspoken. That kind of culture doesn’t happen overnight, but it starts with one conversation at a time. It also sets an example. Staff begin to engage differently with each other, modeling that same kind of courage and transparency in their teams and classrooms. That ripple effect can shift an entire school climate [6].
Many improvements started with a conversation that didn’t feel good in the moment. One I remember vividly involved a long-tenured staff member who expressed frustration over inconsistent practices. At first, I felt defensive. But I chose to listen, and what followed was a months-long collaborative effort to design a unified policy. That conversation became the catalyst for a change that improved equity and clarity for our everyone [7]. Difficult conversations, when prepared for and approached with care, can do more than resolve conflict. They move us from vague frustration to clear, shared action [8].
To make this process intentional, I started using a simple preparation checklist. Here’s what I reflect on before going into any high-stakes conversation:
What is the core issue I want to address, and why does it matter?
What do I want the other person to understand or take away?
What perspective might they bring that I haven’t considered?
What emotional tone do I want to set, and how will I manage mine?
What outcomes or next steps do I hope to walk away with?
This checklist helps me show up as a leader who is thoughtful, not reactive. It helps me listen better, speak more clearly, and follow through more consistently. I mentioned parts of this process earlier in the article, but having these five points (see list above) that makes preparation a consistent part of my leadership routine [9].
If you’re avoiding a difficult conversation, I understand. I’ve been there, but here’s what I’ve learned: the very conversations we fear often hold the keys to the clarity, innovation, and growth we’re chasing. Prepare for them. Walk into them with courage and empathy. You might be surprised by how much clearer your decisions become and how much stronger your building culture grows when you do.
Leadership isn’t just about having the answers. It’s about having the conversations that lead us to better ones.
References
Patterson, K., Grenny, J., McMillan, R., & Switzler, A. (2012). Crucial Conversations: Tools for Talking When Stakes Are High. McGraw-Hill.
Goleman, D. (1995). Emotional Intelligence. Bantam Books.
Knight, J. (2011). Instructional Coaching: A Partnership Approach to Improving Instruction. Corwin Press.
Fullan, M. (2014). The Principal: Three Keys to Maximizing Impact. Jossey-Bass.
Covey, S. M. R. (2006). The Speed of Trust: The One Thing That Changes Everything. Free Press.
Brown, B. (2018). Dare to Lead: Brave Work. Tough Conversations. Whole Hearts. Random House.
DuFour, R., DuFour, R., Eaker, R., & Many, T. (2010). Learning by Doing: A Handbook for Professional Learning Communities at Work. Solution Tree Press.
Aguilar, E. (2013). The Art of Coaching: Effective Strategies for School Transformation. Jossey-Bass.
Stone, D., Patton, B., & Heen, S. (2010). Difficult Conversations: How to Discuss What Matters Most. Penguin Books