How to have a difficult conversation (and feel good about the outcome)!

women having a conversation

Article by Dr Lucy Ryan

You know you need to have a difficult conversation with a friend or a colleague. But how to do you it so that you both walk away with your heads held high and still talking to each other?

If this is a topic that makes you feel apprehensive, you’re not alone! In my twenty years as a leadership coach, this is the one topic that results in clammy hands and high levels of anxiety, and everyone has stories of feedback going wrong – whether being on the giving or receiving end. And that’s because there are big, hairy emotions involved, fear of getting it wrong, anxiety of it being career limiting or distress of not being liked. All of us have spent wakeful nights churning the conversation around in our heads, with the outcome of avoidance or procrastination, until the issue gets worse and out of hand.

So here are five ways to prepare for, and hold, that conversation you’ve been avoiding, and feel good that you’ve tackled a difficult conversation and given feedback in a compassionate and confident way.

Prepare your mindset

Your mindset towards this conversation is crucial, so think about this question: What outcome do you want for you, for them and for the relationship? Once you’ve written this down, you can then work out how you will need to behave to achieve these outcomes.

What you’re doing here is ensuring you’re approaching this conversation with flexibility, rather than a rigid “I’m right” mindset. 

Start with facts

Facts are respectful. They can’t be argued with, and they lay the groundwork for a successful conversation. So, if you’ve been interrupted in a meeting, start here, and be clear and concise.

Tell your story

But facts alone are not enough. It’s the facts plus your conclusion that makes this a two-way discussion. Use ‘I’ to show this is your story, not someone else’s and share what the facts make you think and feel.  For example, “at the meeting this morning, you interrupted me twice even though we talked about this last week. It makes me think that I haven’t been clear enough about the impact of your behaviour on me and leaves me feeling undermined and frustrated.”

You’re opening the door here to an honest, mutual conversation, not just presenting a slam-dunk version of the facts. They might have a different story!

Keep exploring

What do you think? What else matters here? How can we resolve this? These three questions will help you frame a mutual conversation. Avoid what I call the ‘Tug of Tell’ and remember, you’re trying to get the best outcome for you and for them, not just win a battle of wits. Encourage the other person to express their facts, stories and feelings. Listen and be willing to reshape your story as you learn more facts.

Manage the ‘roadbumps’

In any difficult conversation, there are moments when it might take an adverse turn. You’ll recognise this – a look, a sigh, a turn of phrase (I remember when my teenagers used to sigh and say ‘whatever Mum’). Remember this is just a sign that the other person feels unsafe to talk openly and requires a blend of confidence, humility, and skill from you not to react in a similar vein. Be the bigger person!

When you see that flash of anger, defensiveness, or blame, stay curious. What’s causing this response? Think of the conversation as a dance and you need to step out, to step back in again. Remain calm, breathe, listen and ask another question, “You sound annoyed, I’d like to hear more…”.

After all your hard work, end this conversation with a mutually positive agreement. And if you’re asking yourself if you really need to do all of this for a brief conversation or piece of feedback, the simple answer, is yes! These conversations will get easier with practice, and I guarantee there’s a huge payback. You’ll go into each new exchange feeling prepared, acting with compassion and confident that you can achieve a positive outcome.

About the author

Lucy RyanIn the last twenty years, renowned leadership coach Dr Lucy Ryan has coached and developed over 10,000 leaders across 29 countries. She knows what works for leaders, what they want to understand, and what gets them results.

Dr Ryan specialises in blending the academic with relevant practice. With a masters in Positive Psychology, and PhD in Management and Leadership, she ensures her clients get the latest in thinking, combined with ideas for positive application, for themselves, their teams, and their organization. Lucy’s latest book, Lunchtime Learning for Leaders (Kogan Page, 2021), summarises the 16 critical topics leaders commonly face, offering highly accessible reflections and solutions. 

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