How to approach difficult conversations

  • 18 Mar 2022

Language matters and naming it ‘difficult’ is off-putting

By Janie Van Hool, author of The Listening Shift and the founder of Voice Presence

It’s impossible to grow your business without facing some difficult conversations. Dealing with colleagues or employees who don’t share your energy and commitment: managing customers and clients who don’t honour your payment terms or revisiting finance agreements with investors are just some of the conversation challenges faced by entrepreneurs and SMEs navigating ever-changing circumstances. Not many of us view engaging in such dialogue with much enthusiasm.

Part of the problem is in how we frame the conversation in the first place. Language matters and naming it ‘difficult’ is off-putting. Who would want to embark on something ‘difficult’ without the promise of a reward at the other end?

Difficult physical or intellectual challenges help us find out what we might be capable of. There’s an element of achievement and the promise of realising a goal. We plan and prepare for it, we rehearse, we seek help and we engage tried and tested strategies to raise our confidence. We celebrate the win, we learn from it and we build on that knowledge to take us forward to our next challenge. But a difficult conversation? Not much to strive for there, excepting the promise of having it done and maybe – just maybe – moving the situation in our favour.


Perhaps if we were to take this route of engaging strategically with difficult conversations, we might have similar cause to celebrate. Here are some pointers to start building your toolkit:

Be prepared

Spend time thinking about what outcome you want from the conversation – see if you can articulate what you want to happen. And then think about what you don’t want to happen. Knowing what you hope to avoid should help you keep your own emotions in check.

Know your own style

Do you tend to avoid difficult conversations? Do you roll over and agree at the first sign of challenge? Do you ‘go into battle’ determined to come out on top at all costs? Or do you see yourself as a negotiator, willing to compromise to protect all parties involved?

You may see yourself in all these styles – the situation and behaviours of the other party may shape your approach – but if you go into the conversation knowing how you may react, you can plan a more effective response.

Get to the point, and listen

When you get in front of the other party, acknowledge straight away that there is an issue you’d like to address and – here comes the big hurdle – commit to listening to their perspective first before trying to get your own side of the story across.

This is tricky, because our instinct is to defend our position: to be right and to correct someone else’s point of view. Discipline yourself not to be derailed by what you hear but allow yourself instead to listen to the full picture from their point of view before responding.


Put yourself in their shoes

Focus on asking questions that help you understand fully how things may appear from their perspective. See if you can imagine what emotions they might be feeling and what they might need from you in this intense moment.

Ask what would be helpful for them. It’s important to take every opportunity you can to acknowledge how they might be experiencing this situation. Have solutions to offer or discuss. Keep them safe – then they will be available to listen to you.

Learn from it

After the conversation is over, review it carefully. What worked for you? What are you pleased with? What might you do differently if you had the same conversation again and what might change when you are next facing such a conversation? Do this whatever the outcome as every review offers a learning opportunity.

The key to managing any difficult conversation is to commit to curiosity. If you engage in any conversation with a fixed mindset (e.g., this could get nasty; they won’t agree with me) then you will find it hard to achieve your aims while holding on to the relationship.


Be curious, not certain. You will learn something from what you hear, and you will win yourself the opportunity to be heard. And that’s not a difficult conversation; that’s a trust-winning, relationship-building triumph.

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