lead / handling difficult conversations as a leadership discipline

TLDR
For teams who want to build confidence in having difficult or sensitive conversations. This programme focuses on the confidence, emotional intelligence and respectful communication needed to address issues early and maintain trust.

Most people don’t avoid difficult conversations because they lack technique. They avoid them because they lack the confidence to be clear without being harsh, honest without causing damage, and decisive without closing down the relationship. These fears are normal - they show up whether the conversation is with a direct report, a colleague, a senior stakeholder or the public.

This programme takes a confidence-first approach. It is delivered to a team to create shared norms, but the bulk of the work is individual. Each participant examines the conversations they personally find difficult, why they hesitate and how emotion shows up for them. From there, confidence emerges through rehearsal, emotional intelligence and a better understanding of what they are trying to achieve.

Empathy sits alongside confidence in a practical, not sentimental, sense - noticing how the other person is experiencing the conversation without abandoning your own position. When empathy and confidence coexist, people speak more plainly, listen more fully and preserve relationships without diluting meaning. What often gets described as “authenticity” is the result of this alignment: people say what they mean, mean what they say and do so with respect.

Marie Thake, Associate Trainer at Teamshaper
enquire

  • Participants will:

    • Identify the specific conversations they find difficult and understand the fears, beliefs and triggers that make them hesitate

    • Build confidence to initiate and hold difficult conversations with clarity and respect

    • Recognise and manage their own reactions under pressure

    • Use empathy to remain connected to the other person’s experience without losing their own point

    • Practise opening, navigating and closing real conversations involving performance, behaviour, disagreement or sensitive issues

    • Apply practical approaches to managing reactions, maintaining boundaries and preventing escalation across staff, peer, stakeholder and public-facing contexts

  • Teams and organisations will benefit from:

    • Increased confidence across the team to address issues early rather than defer, dilute or avoid them

    • Clearer, calmer and more respectful conversations that preserve working relationships and reduce friction

    • Improved emotional awareness and behavioural self-management in pressured interpersonal situations

    • Reduced escalation of unresolved issues that quietly undermine wellbeing, trust and performance

    • Practical confidence that transfers into everyday interactions across roles, hierarchies and audiences

  • 09:30 – Welcome and framing the day
    Why confidence matters more than technique.
    What makes certain conversations feel difficult.
    Team and individual objectives and expectations for the session.

    10:00 – Why we struggle with difficult conversations
    Exploring fears, beliefs and assumptions that create avoidance.
    Recognising personal triggers and discomfort cues.
    Linking confidence to clarity, purpose and preparation.

    11:00 – Break

    11:15 – Emotional intelligence and staying composed
    Reading our own reactions and state changes.
    Staying calm and respectful under pressure.
    Recognising how the other person may experience the conversation.

    12:00 – Communication habits that support confidence
    Listening without trying to fix or defend.
    Assertive language vs passive/aggressive responses.
    Using empathy to stay connected without losing your point.

    13:00 – Lunch

    13:45 – Preparing for the conversation
    Clarifying purpose, boundaries and the “why now”.
    Planning opening lines that feel natural, honest and respectful.
    Working with real scenarios (performance, behaviour, disagreement, discrimination).

    14:30 – Practising real conversations
    Paired or trio rehearsal using participants’ own examples.
    Coaching and feedback focusing on confidence, composure and clarity.

    15:30 – Break

    15:45 – Handling reactions and awkward behaviours
    Responding to defensiveness, upset or challenge.
    Resetting without losing direction or respect.
    Agreeing actions, follow-up and next steps.

    16:15 – Commitments and confident habits
    Personal commitments for conversations to be held after the workshop.
    Team norms for handling difficult conversations.
    Closing reflection and next steps.

    16:30 – Close

  • Core programme – Workshop
    A full-day highly interactive session delivered in person or virtually.

    The workshop is built around the team’s real difficult conversations and live communication challenges. It combines reflection, discussion and practical rehearsal to help participants build confidence, understand why they struggle, and develop a more composed and respectful approach that can be applied immediately in conversations with staff, colleagues, stakeholders or the public. The programme is adapted to whichever of these audiences is most relevant in the team’s specific context.

    Optional add-ons

    Team assessment (e.g. GC Index)
    A diagnostic that reveals how each leader contributes to team impact and decision-making. This insight is used to shape the workshop discussion and strengthen collective performance leadership.

    Follow-up session
    A short 2hr virtual session around a month later to review progress, share examples and refresh commitments.

    One-to-one coaching
    Individual coaching for selected leaders to refine their approach to objective-setting, feedback or moderation and to embed the learning in practice.

Lead - a Teamshaper training module