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Leading with Courage: How Effective Leaders Have Difficult Yet Important Discussions

Effective leadership requires having difficult yet important discussions with employees. These types of conversations, often called "courageous conversations," can be challenging but are necessary for the continuous development of people and optimization of organizational performance. While uncomfortable, courageous discussions allow leaders to provide candid feedback, clarify expectations, address underperformance, and resolve issues in a constructive manner. When handled well, such conversations strengthen relationships, enhance accountability, and propel both individuals and teams forward.

Today we will explore how research on courageous leadership, feedback, and performance management informs best practices for having courageous conversations. Additionally, we will look at practical strategies and specific examples of how leaders across different industries can have difficult discussions productively and positively impact their organizations.

Courageous Leadership

Research on courageous leadership helps establish a foundation for having courageous conversations. According to Wooten and Crane (2003), courageous leadership requires having the moral courage "to raise dissent and to challenge others to rise above their self-interest and prejudice in addressing hard problems" (p. 352). Leaders must be willing to confront issues respectfully rather than avoid difficult topics that could create tension. Ibarra and Scoular (2020) add that courageous leaders address challenges directly through candid yet considerate discussions. They do not shy away from having tough conversations but handle them in a way that considers other perspectives and maintains positive working relationships.

Establish the Need for the Discussion

An important first step in having a courageous conversation is determining the legitimate need for the discussion and its intended purpose. Leaders should not call out issues impulsively but thoughtfully assess situations requiring an important yet difficult discussion. According to research by Lund Dean and Forray (2019), leaders need to evaluate whether performance could be enhanced, values are not being demonstrated, or potential harm could occur if a problem remains unaddressed. Once a real need is established, leaders must prepare by clarifying the objectives for the conversation and how they plan to discuss the topic constructively. Taking time to thoughtfully consider the necessity of the discussion and intended outcomes increases the likelihood of a productive conversation.

Communicate Concerns Respectfully

Once prepared, leaders should communicate any concerns respectfully during the conversation. Sinar et al. (2020) emphasize using specific behavioral examples when providing feedback rather than vague generalizations, which helps individuals understand how their actions can be improved. Leaders need to describe issues factually while avoiding personal attacks, as research shows this builds trust and maintains engaged dialogue. Ibarra (2015) also advises focusing discussions on addressing underlying problems rather than finger-pointing at people. For example, when an upcoming project is behind schedule, an effective leader would respectfully note key missed deadlines rather than accusing individuals of poor performance. Communication grounded in objective facts allows for a collaborative discussion focused on solving issues rather than assigning blame.

For example, consider a division director at a technology company who noticed several project managers were struggling to meet deadlines on key initiatives. Rather than calling out individuals, she respectfully brought up specific examples from recent project timelines where deadlines were missed without clear reasons provided. This allowed for an open discussion where the managers could explain challenges faced and work collaboratively on process improvements to hit future targets. Focusing on objective facts prevented defensiveness and enabled problem-solving.

Promote Active Listening

Research by Sinek (2014) stresses the importance of leaders actively listening during courageous conversations to understand different perspectives. Effective leaders should allow others to fully explain their views and experiences rather than dominating discussions. This involves making eye contact, refraining from multi-tasking, asking clarifying questions, restating what was heard to check for accuracy, and following up on any points needing more context. Demonstrating attentive listening makes others feel heard and encourages openness that leads to constructive dialogue.

Practical strategies for promoting active listening include:

  • Setting cell phones to "do not disturb" to give full focus to the conversation

  • Taking brief notes to remember key discussion points rather than recall everything from memory later

  • Periodically checking one's own understanding of another's perspective through reflective questions

For example, a CEO at a manufacturing firm arranged to have individual discussions with each member of her leadership team about new strategic priorities. She made a conscious effort to avoid distractions by silencing notifications on her devices. Throughout conversations, she took occasional notes but mostly listened closely, restating key points raised by team members and asking follow ups to ensure she fully comprehended their views before providing any feedback. This enhanced communication and gained valuable insights.

Agree on Clear Next Steps

Research from Harvard Business Review emphasizes that leaders must guide courageous conversations towards constructive outcomes and action rather than unresolved issues (Goffee & Jones, 2015). Making requests or providing feedback means little without specifying clear next steps. Agreeing on concise, measurable action items that address discussed problems ensures accountability. Leaders should set follow up dates to review progress and encourage continued progress discussions as needed. Taking the time during and after difficult conversations to outline action plans driven by expectations for behavior change or performance improvement helps maintain positive working relationships and forward momentum.

For instance, the director of nursing at a major hospital held feedback discussions with nurses identified as underperforming on key quality measures. Rather than leaving meetings with vague promises for future improvement, she worked collaboratively to establish explicit, timed goals such as reviewing a set number of patient charts weekly or retaking certification exams. Return meetings were scheduled in advance to review documentation demonstrating fulfillment of agreed upon next steps. Focusing discussions on clear accountable actions kept everyone invested in positive outcomes.


While uncomfortable, having courageous conversations is vital for leaders seeking to optimize organizational success. By thoughtfully establishing real needs for difficult discussions, communicating respectfully, promoting active listening, and agreeing on clear next steps, leaders can address challenges productively and move teams constructively forward. When handled well through research-guided best practices and specific example applications, courageous leadership enhances relationships, increases accountability, and ultimately strengthens both individual and company performance. Leaders across all industries who demonstrate courage in having tough yet important discussions will positively impact their organizations.



Jonathan H. Westover, PhD is Chief Academic & Learning Officer (HCI Academy); Chair/Professor, Organizational Leadership (UVU); OD Consultant (Human Capital Innovations). Read Jonathan Westover's executive profile here.



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