A guide to approaching difficult conversations

Whether we like it or not, difficult conversations are an inherent part of our everyday lives – Janine Schindler addresses the art of approaching them below

CREDIT: This is an edited version of an article that originally appeared on Forbes

One of the key challenges individuals face when engaging in tricky discussions is maintaining objectivity. It is human nature to anticipate negative outcomes or assume the worst in others, especially when the topic is sensitive. However, by adopting a mindset of empathy and open-mindedness, we can transform these challenging conversations into opportunities for growth, understanding and resolution.

The first step in planning for a conversation is to identify the goal and desired outcome. Knowing your goal can help you keep the discussion on track and stay objective.

Empathy is also a powerful tool for a positive outcome because it enables us to step into the shoes of the other person, understand their perspective and acknowledge their emotions. By doing so, we can create a safe space for authentic dialogue. Instead of assuming the worst, we can seek to understand the underlying motivations, fears or concerns that may be driving the other person’s behaviour.

Embrace empathy

A few years ago, one of Schindler’s clients—let’s call her Rachel—had to address a team member’s consistent underperformance. Initially, Rachel harboured negative assumptions about the team member’s laziness and lack of commitment. However, through our coaching sessions, she learned to approach the conversation with empathy.

As a result, Rachel discovered that the team member was dealing with personal challenges outside of work, causing their performance to suffer. By understanding and offering support, Rachel not only resolved the issue but also built a stronger bond with her team member.

In this conversation, she learned that open-mindedness is also essential when faced with difficult conversations. Keeping an open mind allows us to suspend judgment, question our own assumptions and genuinely listen to the other person’s perspective. By approaching these conversations without preconceived notions, we create space for alternative viewpoints and collaborative problem-solving.

It is very easy to fall into the trap of approaching a conversation already feeling defensive—with your armour up, ready for a fight. Unfortunately, starting a conversation in this way can be a self-fulfilling prophecy. If you approach a person with defensive body language and anticipate harsh words, then your conversation partner will probably pick up on that vibe and most likely put on their own defensive gear quickly. When both people are closed off and defensive, the conversation will not be a pleasant one.

My friend Sarah once had to address an incident where a team member had missed a critical deadline. Frustrated and assuming incompetence, she confronted the culprit and demanded to know what had happened. The co-worker was surprised and, perceiving a verbal attack, turned defensive. He began gruffly explaining, and too late, Sarah discovered that the team member had encountered unforeseen technical difficulties beyond his control that led to the delay.

After that, she had to work hard to rebuild trust and rapport with that person. She learned that she had to approach future conversations with curiosity and a genuine desire to understand. Had she given the team member the opportunity to explain, she might have been able to provide support and find a collaborative solution that prevented similar issues in the future.

Most leaders make these types of communication mistakes before mastering the art of approaching difficult conversations. We have also learned the importance of providing the other person with an opportunity to respond without jumping to conclusions or assuming negative intent.

Allowing the individual to share their perspective fosters a sense of psychological safety, encourages open communication and prevents misunderstandings. By actively listening and seeking clarification, we create an environment conducive to meaningful dialogue and resolution.

Mastering the art of approaching difficult conversations objectively is a skill that can transform both our personal and professional relationships. By embracing empathy, cultivating open-mindedness and providing space for response, we can navigate these challenging conversations with grace and effectiveness. Difficult conversations, when approached with the right mindset, offer opportunities for growth, strengthened relationships and improved outcomes.