Addressing sensitive issues at work can be one of the most challenging parts of leadership. These moments require you to communicate with honesty so that the message is clear, but also with respect so that the relationship remains intact. Leaning too far in one direction can cause problems, too much honesty without care can feel harsh, and too much politeness without truth can lead to avoidance.
The key is to approach these conversations with the intent to solve a problem, not to win an argument. This means preparing both your message and your mindset. Clarity is important, but so is empathy. You want the other person to understand the issue and still feel valued and respected.
(more…)by Michelle Cummings
Most leaders don’t set out to avoid hard conversations. But when tension rises, it’s easy to sidestep the uncomfortable. Maybe we convince ourselves it’s not the right time. Maybe we worry about how someone will react. Or maybe we hope the issue will just fade on its own. But the truth is, avoidance is a choice – and it has a cost.
Every delayed decision, unspoken truth, or postponed conversation creates residue. What feels like short-term peace often leads to long-term strain. The small misalignment becomes a bigger disconnect. The minor performance issue becomes a culture problem. What we avoid doesn’t disappear. It compounds.
(more…)Many leaders put time and energy into preparing for a difficult conversation but overlook a critical final step – following up. Without follow-up, even the best intentions during the conversation can fade, leaving room for misunderstandings, uncertainty, or a return to old patterns.
Following up ensures that both parties are clear on what was discussed, what was decided, and what will happen next. It is an opportunity to reinforce agreements, answer lingering questions, and confirm that you are moving in the same direction. This step transforms a single conversation into meaningful, lasting progress.
(more…)Every organization is made up of interconnected parts: departments, teams, and individuals that depend on each other to succeed. As leaders, it is easy to focus on the needs of your immediate group without realizing how your actions ripple through the larger system. Sometimes those actions unintentionally create division or fuel misunderstanding between other parts of the organization.
For example, pushing for a tight deadline might meet your team’s goals but strain another department’s capacity. Sharing partial information may keep your group informed but leave others confused about priorities. These situations are rarely intentional, yet they can weaken trust and collaboration across the organization.
(more…)Courage is not the absence of fear, it’s the ability to act in spite of it. For leaders, courage is the spine that supports every other skill. Without it, difficult conversations are avoided, tough decisions get delayed, and opportunities slip away. But like any muscle, courage can be developed with intentional practice.
Leadership courage is built on four key skills: speaking up with honesty, making values-based decisions, taking responsibility for mistakes, and standing firm in the face of resistance. These aren’t abstract ideals; they are daily practices that separate leaders who inspire trust from those who merely manage tasks.
(more…)Being in the middle of an organization comes with unique challenges. You are accountable to senior leadership while also supporting the needs of your team. At times, those priorities align perfectly. Other times, they pull in opposite directions, leaving you feeling stretched and stuck.
Recognizing when you are caught in these “middle” dynamics is an important leadership skill. Without awareness, you can end up reacting to the loudest voice or the most urgent demand, rather than making balanced decisions that serve both sides effectively.
(more…)by Michelle Cummings
Every leader faces moments where silence feels safer. A meeting where the dominant opinion goes unchallenged. A decision that doesn’t align with the team’s values. A behavior that crosses a line. In those moments, speaking up is not easy – but it’s essential. That’s the heart of managerial courage: choosing principle over popularity, clarity over comfort.
Managerial courage is not about being loud, reactive, or confrontational. It’s about being steady, clear, and values-driven. It’s about knowing what matters most, and having the discipline to act even when the outcome feels uncertain. True courage is not the absence of fear. It’s moving forward despite it.
(more…)Tough conversations are part of leadership, but their outcome often depends on what happens before you sit down to talk. Walking into a sensitive discussion without preparation can lead to unclear messages, heightened emotions, and missed opportunities for resolution. Taking time to plan both what you want to say and how you want to say it can make all the difference.
Preparation starts with clarifying your purpose. Ask yourself, “What is the main point I need to communicate?” and “What outcome do I want from this conversation?” Having these answers in mind keeps you focused and prevents the discussion from drifting into unrelated issues.
(more…)Every role in an organization comes with unique pressures, priorities, and blind spots. Leaders at the top carry the weight of strategic vision and overall performance. Those in middle management balance the demands of senior leadership with the needs of their teams. Frontline employees handle the day-to-day work that keeps the organization moving, often without full visibility into the bigger picture.
Understanding these perspectives is critical for effective leadership. Without it, communication can break down, assumptions can build, and decisions can be made without fully considering their impact. Leaders who take time to learn the realities of different roles are better equipped to bridge gaps and align the entire organization.
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Tag: The Courageous Leader
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