Webinar report: The ‘joy’ of difficult conversations

However, there’s much to like about a successful outcome of a challenging dialogue: the resolution of a conflict, a fractious relationship made harmonious, the sense of a burden lifted.

As a specialist in helping people develop workplace relationships and non-technical skills, Joanna Gaudoin, founder of ClientWise (formerly Inside Out Image) brought the joy of difficult conversations to her final 2025 webinar with CLL. 

Know your conflict modes

Difficult conversations come in many varieties. In the workplace, for example, money (the organisation’s budgets and our own remuneration), targets, agreements, timelines, behaviours and our personal progression are common topics of tricky interactions. It helps, then, to be aware of the four common conflict modes:

• Collaborating - high on assertiveness, high on cooperation. Aim for this when working with peers with similar knowledge of an issue to yours, but with whom you disagree;
• Accommodating - high on cooperation, low on assertiveness. A good mode to adopt when your knowledge is not as deep as other peoples, but you have a view worthy of consideration; 
• Competing - high on assertiveness, low on cooperation. Limit this to crises and when time for cooperation and collaboration is severely limited; and
• Avoiding - low on cooperation, low on assertiveness. While generally unhelpful, there are times when a conversation is best avoided temporarily, such as moments of high emotion.

Casting its shadow over our conflict modes is, of course, the concept of compromise. Often, a watered-down solution can be accepted by all parties, however sometimes there’s no workable middle ground.

This is when you need to buy yourself time to manage your immediate emotions and plan your conversation. Consider the circumstances, how you’re feeling and why. Then, decide what outcome you want from the situation. This will ensure your reaction is rational.

It’ll also avert the consequences of avoiding a difficult conversation. These include unchecked resentment, wasted energy and the perpetuation of negative patterns, as this model, previously shared by Joanna, shows:

My beliefs shape my behaviour – which influences other people’s behaviour – which reinforces my behaviour

Understand your interlocutor

When preparing for a difficult conversation, assess where the other person sits on the introversion/extroversion spectrum and how task focused vs relationally focused they are. We rarely see people at the extreme ends of these scales, however understanding them through this lens helps us negotiate with them. Plan your approach based on whether they are:

• Dominant – a task-focused extrovert;
• Analytical – a task-focused introvert;
• Inspiring – a relationally-focused extrovert; or
• Stable – a relationally-focused introvert.

Have three conversations in mind

At the core of a difficult conversation are three sub-topics that drive our objectives and a set of considerations that we should keep in mind. Our three sub-conversations are based around:

• What happened. Set out the facts. What makes the conversation difficult? What was the timeline? Who are the people involved?
• How you feel. Separate your feelings from the facts but acknowledge them. Are they based on your relationship with the person or the situation itself? And;
• Impact on your identity. Has the issue in question contradicted your view of yourself?

Our key considerations meanwhile are:

• Relationship status. The better the relationship, the easier the conversation becomes. There’s credit in the bank and a level of trust that ensures you’ll have the person’s ear;
• Feelings. Show empathy but never make assumptions about what the other person is feeling. This can lead you to take the conversation in the wrong direction;
• Your contribution. What, if any, was your contribution to the situation? What was its impact – and was it intended or inadvertent? Are you absorbing blame unnecessarily, leaving yourself open to undue criticism? Conversely, could colleagues accuse you of shirking accountability?

Use your difficult conversations toolkit

Maximise your chances of success from a difficult conversation with these ten techniques and behaviours.

1. Stay calm. Powerful emotions usually subside after a while, so buying yourself time before engaging in a difficult conversation is priority number one.
2. Avoid blaming people. Be objective, not subjective. For example, say, “When this happened, it made me feel frustrated,” not, “You created this problem.”
3. Separate opinion from fact. Distinguish what you believe from what you know to be true. Your views may be different to others. Facts keep everyone on the same page.
4. Focus on what matters most. If your relationship with the other person is challenging, you may have several problems with them. Trying to solve all of them will dilute your efforts to resolve the most pressing issues.
5. Know what you do and don’t know. Separate what you know from what you’re assuming. Fill your knowledge gaps by asking questions, listening actively and making the other person feel heard.
6. Acknowledge feelings. Show empathy and make a conscious effort understand the other person’s feelings.
7. Paraphrase. As well as showing that you’re listening, paraphrasing helps you fully understand the other person.
8. Be upfront with bad news. If you’re giving unwelcome news, deliver it early and in a straightforward manner.
9. State assumptions. Always validate your assumptions to keep your conversation on track.
10. Postpone if you need to. Don’t feel you must resolve a conflict in a single conversation. If you need to postpone or schedule further conversations, do so while explaining why.

And finally, focus on a great outcome

Never forget why you’re having a difficult conversation. Keep your outcome in mind and remember, many a difficult conversation has transformed a poor working relationship into an excellent one. 

See more from Joanna

For more great relationship-building tips from Joanna, check out her book, Getting On: Making work work. It’s discounted to £13.00 on Amazon for CLL delegates (usual print price £14.99) using code CLL254 until Sunday 7 December 2025. 

Join us in 2026 for more webinars with Joanna covering relationship building skills in the modern workplace. We’ll post details soon and look forward to seeing you again next year.