Leadership Lens: How to take the “difficult” out of difficult conversations

As leaders, we often avoid challenging conversations, labelling them as “difficult” and associating them with tension, discomfort, or potential conflict. Yet, these moments hold the greatest opportunities for growth, clarity, and stronger relationships. Avoiding such conversations can leave unresolved issues to linger and impact individual and team performance.

It’s a little bit like having an uncomfortable conversation with your child. You don’t want to have it, and they might not like it, but it’s important for them to learn and grow.

Effective leadership isn’t about sidestepping discomfort; it’s about facing it with courage, empathy, and intention. A conversation perceived as difficult is often just one that requires preparation, clarity, and mutual respect. It’s as much about mindset as it is about using a structured approach.

This year I was coaching Susan, a leader of a marketing team of an e-commerce platform. Susan is a collaborative leader who empowers her people and gets out of the way. But some of her team members weren’t performing, were poor communicators and absence was a big problem.

Susan was suffering from the ‘being too nice all the time’ syndrome. She realised that she is a relationship person and that truly putting her foot down and having difficult conversations was hard for her. But it’s exactly what she needed to do to get back on track.

If you take ‘difficult’ out of difficult conversations, what’s left is: ‘CONVERSATIONS’

By shifting our mindset that these are JUST CONVERSATIONS and equipping ourselves with strategies to plan and craft our messages, we can take the “difficult” out of these conversations.

Gallup Research shows addressing difficult conversations has a positive impact on individual performance, team cohesion and even employee engagement. Whereas not having these conversations can lead to unresolved issues which erodes trust, collaboration and team performance. High attrition is often the result.

It’s not a question of if you are having difficult conversations, it’s about how well and consistently you’re having them.

“Courage is what it takes to stand up and speak; courage is also what it takes to sit down and listen.” – Winston Churchill

A structured approach to having “difficult conversations”:

Preparation:

 Understand the issue, gather facts, and clarify your goals and purpose.

Empathy: 
Listen actively, acknowledge emotions, and build trust.
Action: 

 Use clear language, agree on solutions, and follow through.

Susan listed all the ‘difficult’ conversations she needed to have and prioritised them. She then planned for each conversation by preparing well, especially what she needed to get out of the conversation and having facts for feedback ready. She scheduled the meetings and was transparent about the agenda. She then started each conversation with a coaching approach and asked for self-feedback first. Taking everything into consideration she used an objective approach to move forward with a plan together with the team member. Her focus here was on accountability.

Susan said to me: “Jess, since I have been taking the word ‘difficult’ out of ‘difficult conversations’ and I am using a structured approach, I am simply having CONVERSATIONS”.

If you want your leaders to learn how to take ‘difficult’ out of ‘difficult conversations’, get in touch for a training workshop quote. Jessica@intactteams.com

About the Author

Jessica Schubert

Cultural Transformation & Leadership Expert

Teams, individuals and organisations face different challenges. My mission is to listen, understand and tailor learning solutions that fit your cultural and organisational goals. My steps to transform people, culture and businesses:

Conversation

Listen and understand your challenges

Consult

Suggest tailored learning solutions

Co-create

Include leaders in the design process

Coach

Deliver, facilitate and coach

Consider

Feedback and go back to conversation

With over 25 years of corporate experience and leading large teams across Europe and Asia Pacific, I understand all facets of leadership. I leverage my experience of dealing with power dynamics and organisational complexities and blend it with proven leadership models, coaching theories and adult learning principles.