By Dan Berman, Senior Partner, Leadership Development at Keystone Partners 

Learn how performance conversations develop essential leadership skills for succession planning. Discover communication strategies that identify future executives and build stronger leadership pipelines through empathetic coaching approaches.

Often a leader seeks coaching to navigate effective ways to communicate with a subordinate who is performing below expectations. This scenario is increasingly common in today’s workplace and it reveals a critical leadership development opportunity. The ability to navigate these sensitive conversations with empathy and skill is a defining characteristic of future leaders. For succession planning purposes, managers who can effectively handle performance challenges demonstrate the emotional intelligence and communication capabilities essential for senior leadership roles. 

Building Leadership Competencies Through Difficult Conversations 

Guidance is given to the leader so he/she can effectively engage with the employee in a compassionate and collaborative manner. This creates a safe space to allow for below-the-surface issues to rise. Among the issues potentially at play are employee burnout and disengagement. 

This approach represents a sophisticated leadership competency that distinguishes high potential managers from their peers. When identifying candidates for succession planning, the ability to conduct these conversations effectively signals readiness for increased responsibility and team leadership. 

The following questions can be asked to gain more clarity and understanding in support of an employee: 

• You’ve always been a high performer hitting and exceeding goals, meeting and beating deadlines and I’ve seen a shift – is everything ok? 

• Is your current workload working for you? 

• Are there any projects/aspects of your job that you find especially draining and unfulfilling? 

• Are there any projects or tasks that you may want to be more involved in? 

• Do you have all the resources you need to do your job effectively? 

• Do you feel that you’re getting enough recognition for your work? 

• How can I support you better in your job? 

• If there were one thing that you feel would significantly positively impact your work experience, what would it be? 

Creating Sustainable Solutions 

When leaders show up with empathy and compassion it allows them to uncovercore issues underlying sub-par performance. This leadership mindset creates a safe space to explore what may be going on below the surface and provides an opportunity to collaboratively seek solutions which yield positive outcomes for the employee, the team and the organization. 

For HR leaders, implementing this approach requires training managers to move beyond corrective action toward collaborative problem-solving. When developing leadership capabilities across your organization, prioritize managers who demonstrate these skills—they often represent your strongest succession candidates. 

The goal isn’t just performance recovery—it’s developing leaders who can create sustainable engagement while strengthening the overall leadership pipeline. These conversation skills become even more critical as leaders advance to senior roles where they’ll need to guide executives, board members, and other leaders through complex challenges. 

How Keystone Partners Develops These Critical Leadership Capabilities 

At Keystone Partners, we recognize that the ability to navigate difficult performance conversations is a cornerstone of effective leadership development. Our leadership coaching programs specifically focus on building the emotional intelligence and communication skills that distinguish future executives. 

Through our Emerging Leaders Program, we help high-potential managers develop these sophisticated conversation capabilities alongside other essential leadership competencies. We also work with organizations to identify managers who naturally demonstrate these skills—often revealing hidden succession candidates who may have been overlooked in traditional leadership assessments. 

Ready to strengthen your leadership pipeline by developing these critical conversation skills? Contact Keystone Partners to explore how our leadership development programs can help identify and cultivate future leaders within your organization.