What Leaders Need to Know About Coaching for Tough Conversations

Difficult conversations are a constant in the workplace. In this article, Tony Worgan, contributor to Coaching as a Leader, explores how leadership coaching helps managers navigate tough conversations, build a culture of feedback and create psychological safety so employees feel confident speaking up.

Q1. Why is the term ‘difficult conversations’ unhelpful in a coaching context?

Labelling workplace dialogue as ‘difficult’ can create resistance and anxiety before the conversation even begins. I prefer the term ‘courageous conversations,’ which reframes the encounter as a conscious, values-driven choice. Research by Vanessa M. Patrick and Henrik Hagtvedt shows that aligning language with personal identity fosters intentional, authentic behaviour, which is precisely what effective coaches should replicate.

Q2. Psychological safety vs psychological contracting: what’s the difference?

‘Psychological safety’ has recently become a catch-all phrase, often addressed through one-off workshops that can overlook deeper group dynamics and unconscious processes. The essential aspect of contracting is what Julie Hay and Charlotte Sills call ‘psychological contracting’. This process applies to individuals, groups, projects, appraisals and needs continuing review. It’s an agreement about how you will work together. It’s not a one-time checkbox but a continuous dialogue that adjusts to context, power dynamics and personal needs.

Q3. How can leaders use psychological contracting in challenging conversations?

Contracting begins with the self. Before any conversation, you must prepare. Acknowledge how you think and feel about the person. Ask “What am I hoping will change?” and “What’s in the other person’s control?”. Think about how you hold the person or group in mind. If you want someone to change their behavior, be clear in your own mind what you want to be different.

Effective leader coaches acknowledge a mutual understanding, preparing for a shared contract built on respect, clarity and a willingness to name what needs naming.

Q4. What are the best contracting questions for effective team communication?

To prepare for courageous and difficult conversations, consider the following questions:

• How do we relate to each other up to now?
• What are the real and hidden agendas?
• How will we respond to emotional triggers?
• What could sabotage our work together?
• How will success be recognized and celebrated?

These questions move the dialogue beyond tasks into relational and psychological territory, where the true change can occur. Contracting for courageous conversations invites all parties to name what needs to be named to make progress.

Q5. How do stroke patterns influence workplace culture and feedback?

Strokes (verbal and non-verbal units of recognition) are the emotional currency of workplace relationships. When leaders become conscious of stroke patterns (positive vs. negative, conditional vs. unconditional), they can foster inclusion and resilience. For example, “Your preparation for the strategy session was sharp and focused” (positive conditional) is far more developmentally useful than “You’re brilliant!” (positive unconditional) or “You’re sloppy” (negative unconditional). Coach leaders to be specific and purposeful in their strokes, avoiding sarcasm, deflection or hollow praise. Feedback should feed forward.

Q6. What should leaders do when conflict derails a courageous conversation?

When conflict spirals, it’s not failure. It’s feedback. A simple but powerful tool from non-violent communication is to name the derailment and invite a reset: “We’ve both become angry and I want us to have a productive conversation. Can we take a break and start again?” This helps promote emotional agility, reduces reactivity and restores the contact necessary for growth and trust.

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