Bossing a difficult conversation

Words by Janie Van Hool

That’s it… you’ve reached the end of your tether and you know you’ve got to have ‘the conversation’.

It’s time to reset the situation, or relationship and your aim is to get the other person – or people – to do something differently. But even thinking about tackling this conversation knots your stomach, raises your heart rate, and makes you want to run for the hills.

Where are you going to start? Lose your temper and tell them what’s what? Go silent until they approach you to ask what’s up? Dance around the issue and make lots of hints hoping they’ll get the message?

No – none of these options will help you to achieve your goal. But there are routes to success and here are some options to help you find your way through.

Firstly, ask yourself what you want to happen as a result of having the conversation. This will ensure that your messaging is clear and keep you on track if the other person tries to shift the conversation away from the core issue. 

Then think carefully about what you don’t want to happen! Knowing what you hope to avoid should help you keep your own emotions in check.

Secondly, 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 can be really tricky for us, because our instinct is to defend our position - to be right and to correct someone else’s point of view. Remember the mantra ‘what they say is their stuff… and what I hear is my stuff’. Try 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.

Thirdly, get their shoes on. Be curious and ask questions. 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.

Finally, 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.

If the conversation doesn’t go as you’d hoped, don’t lose heart. Celebrate yourself for taking it on and, critically, reflect on what you have learned about the situation, the other person (or people) and about yourself.

And if it does go well? Do the same. Developing expertise in conversations of any type is a learning journey. And well worth the effort.

Janie Van Hool is a prominent communication expert and the founder and director of VoicePresence. She specialises in leadership development programmes and executive coaching. She is also the acclaimed author of The Listening Shift: Transform your organization by listening to your people and helping your people listen to you.