3 Tough But Transformative Coaching Conversations Every Leader Should Have

Let's be honest, some coaching conversations are just plain hard. Think about it: confronting underperformance, navigating sensitive topics, or even pushing your top talent to achieve even more – these discussions can feel difficult, right? You're trying to balance support with challenge, honesty with empathy, and sometimes it just feels… delicate.

We've all been there. Maybe you've put off a tough conversation, hoping the situation would resolve itself. Or perhaps you've carefully skirted around a sensitive issue, worried about saying the wrong thing.  

But here's the truth: some of the most impactful coaching moments, the ones that truly unlock growth and transformation, often come from the discussions we avoid. They're the conversations that stretch us as leaders and create space for real connection and development within our teams.

So, as we head into 2025, let's commit to leaning into these crucial conversations, rather than shying away from them. This article will support you in navigating these challenging but essential moments.

1. Addressing Underperformance That You Have Been Stepping Over

Let's dive into a topic we all wrestle with: addressing underperformance. It's never easy to tell someone they're not meeting expectations. We might avoid these conversations for a number of reasons: fear of conflict, wanting to be liked, or even just hoping the situation will magically improve on its own. But you, as an experienced leader, know that stepping over these issues only hurts the team and the individual in the long run. 

Unaddressed underperformance can breed resentment, lower team morale, and ultimately impact overall productivity. It also deprives the individual of the opportunity to grow and improve. Think about it: wouldn't you want to know if you weren't performing at your best? These conversations, while uncomfortable, are an act of leadership, an investment in both the individual's development and the overall success of your team.

Coaching Tip: Start by sharing specific examples of underperformance and frame the discussion around growth. Ask, “How can we work together to improve this?”

2. Giving Feedback to Top Performers with Waning Engagement

You've got those high-performing individuals on your team – the ones who consistently deliver, exceed expectations, and seem to effortlessly handle any challenge you throw their way. It's tempting to think, "They're doing great, I don't need to focus on them right now."  

But here's the truth: even your top performers need feedback. In fact, especially your top performers need feedback. Often, these high achievers don't receive regular coaching because they're already performing well. This lack of attention, however well-intentioned, can lead to stagnation, disengagement, and even burnout. They might start to feel unchallenged, undervalued, or like their contributions are being taken for granted.  

Remember, helping your top talent grow and develop is just as crucial as helping others improve. Their continued success directly impacts the overall success of your team and the organization.

Coaching Tip: Acknowledge their successes first, then challenge them with opportunities to stretch further. Ask, “What’s one area where you’d like to take things to the next level?”

3. Discussing Career Plateaus Before Your Team Member Leaves

As leaders, we've all seen it: a valuable team member starts to seem disengaged, their enthusiasm wanes, and their performance might even dip slightly. Often, this is a sign that they're feeling stuck, like they've hit a plateau in their career. And when someone feels stagnant, they naturally start to look elsewhere for growth opportunities.  

It's crucial, therefore, to proactively address these situations before your team member decides to leave. Losing a valuable employee is costly and disruptive, but more importantly, it represents a missed opportunity to invest in their development and retain their talent.  

These conversations, while sometimes uncomfortable, are essential for fostering a culture of growth and demonstrating your commitment to your team's long-term success.

Coaching Tip: Ask open-ended questions like, “Where do you see yourself growing, and how can I help you get there?”

All three of these coaching conversations we avoid are often the ones that matter most. By addressing these topics with honesty and care, you’ll build a stronger, more tenacious team that trusts your leadership.

Remember, the toughest talks often lead to the greatest breakthroughs.

Special note: If you are impacted in any way by the LA Fires, please reach out to us so that we can share resources and practices to support you during this time.

Leadership Practice

Review the three coaching conversations above and reflect on your current team members and who would benefit most from one of these coaching conversations then include it in an upcoming one-on-one meeting. Take time to prepare for the conversation so that you can be as present as possible to navigate the conversation and get a good result. 

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About Athena

Athena Williams, Founder and CEO of Tenacious Leadership Institute, has been supporting leaders worldwide to become more tenacious for over 20 years. She has found that tenacity is the key to sustained leadership success in today’s ever-changing world. Through her coaching and leadership development programs, she helps leaders expertly handle change, complexity and other challenges so they can quickly get better results for themselves, their teams and their organizations. Take the first step to becoming a tenacious leader by scheduling a call with us.