Leading others comes with countless rewards, but it also presents challenges that can leave even experienced professionals feeling stuck. After nearly four decades working with leaders across various industries, I've noticed one issue that surfaces repeatedly in our coaching sessions: the tendency to avoid difficult conversations.
Whether you're a senior manager, business owner, or team leader, you've likely faced moments where you know a conversation needs to happen but find yourself putting it off. Perhaps it's addressing underperformance, delivering unwelcome news, or challenging a colleague's behaviour. These situations create a familiar knot in your stomach and that voice in your head saying "maybe tomorrow would be better."
The Real Cost of Conversational Avoidance
When we postpone challenging discussions, the consequences ripple through our teams and organisations. I've been there and Ive also worked with countless clients who came to me feeling overwhelmed by workplace tensions that could have been resolved months earlier with direct communication.
Performance issues compound when left unaddressed. What starts as a minor concern about meeting deadlines or quality standards can snowball into team frustration, missed targets, and damaged relationships. Meanwhile, the leader carries increasing stress, often losing sleep over situations that feel increasingly unmanageable.
Beyond immediate workplace impacts, avoiding tough conversations affects our leadership credibility. Team members notice when issues aren't addressed, and this silence can be interpreted as either weakness or indifference. Neither perception serves us well as leaders seeking to build trust and drive results.
Understanding Why We Hesitate
Through my coaching practice I've identified several common reasons why capable leaders struggle with difficult conversations. Fear of conflict ranks high on this list. Many of us learned early in our careers that keeping the peace was valuable, but this can create patterns where we prioritise short-term harmony over long-term effectiveness.
Perfectionism plays a significant role too. We postpone conversations because we want to find the "perfect" words or wait for the "right" moment. This search for perfection becomes a form of procrastination that serves no one.
Some leaders worry about being liked or fear that direct feedback will damage relationships. This concern is particularly common among those who've been promoted from within teams where they previously worked as peers. The transition from colleague to leader requires recalibrating how we approach these relationships.
Imposter syndrome also contributes to conversational avoidance. When we doubt our own authority or expertise, addressing others' performance or behaviour feels presumptuous. We might think, "Who am I to give feedback when I'm still figuring things out myself?"
The Coaching Approach to Building Confidence
In our coaching sessions, we start by examining the beliefs underlying conversational avoidance. Often, clients hold assumptions about what might happen that aren't grounded in reality. We explore questions like: "What's the worst thing that could realistically occur?" and "What evidence supports your concerns about this conversation?"
We also work on reframing the purpose of difficult conversations. Rather than viewing them as confrontational or punitive, we help leaders see these discussions as opportunities to provide clarity, support team members' growth, and strengthen working relationships. This shift in perspective can be transformational.
Preparation becomes crucial for building confidence. We develop frameworks for structuring conversations that feel authentic to each leader's communication style. This isn't about scripting every word, but rather having a clear sense of objectives, key points, and desired outcomes.
Practical Strategies for Moving Forward
One technique I share with clients is the 24-hour rule. When you identify a conversation that needs to happen, commit to scheduling it within 24 hours. You don't need to have the conversation immediately, but getting it in your diary prevents indefinite postponement.
We also practice what I call "conversation bridges" – phrases that help navigate from casual chat to more serious discussion. an approach that feels natural while signalling the shift in conversation tone.
Starting with curiosity rather than conclusions proves helpful too. Instead of beginning with statements about what someone has done wrong, we might ask, "I've noticed some changes, What's your perspective on how things have been going?" This opens dialogue rather than triggering defensiveness.
Building Your Conversational Muscle
Like any leadership skill, having difficult conversations becomes easier with practice. Each successful conversation provides evidence that these interactions can be productive rather than destructive.
Role-playing different scenarios helps too. In coaching sessions, we prepare leaders to stay calm and focused regardless of the reaction they encounter. This preparation reduces anxiety and increases the likelihood of positive outcomes.
We also work on post-conversation follow-up. Often, the discussion itself is just the beginning. We help leaders plan how they'll monitor progress, provide ongoing support, and maintain accountability without becoming micromanagers.
Creating Sustainable Change
The goal isn't just to have one difficult conversation successfully, but to build a leadership style where direct communication feels natural and comfortable. This requires addressing any underlying beliefs about conflict, authority, or relationships that might be holding you back.
Many clients find that their ability to have challenging conversations improves dramatically once they experience positive outcomes from being direct and honest. Team members often express appreciation for clarity and feedback, even when the content isn't entirely positive. People generally prefer knowing where they stand to wondering about their performance or status.
Your Next Steps
If you recognise yourself in these patterns of conversational avoidance, know that you're not alone and that change is absolutely possible. Start by identifying one conversation you've been postponing and consider what's really holding you back from having it.
Remember that leadership growth often happens outside our comfort zones. The conversations that feel most challenging to initiate are frequently the ones that create the most positive change for our teams and organisations.
Building confidence in difficult conversations is a journey, each leader's path looks different, and the strategies that work best depend on your unique situation, personality, and organisational context. With the right support and approach, you can develop this crucial leadership capability and create more open, productive relationships with your team members.