How To Have A Difficult Conversation

When did you last have to start a difficult conversation with a peer, your boss or a client? Disagreeing with someone and potentially causing a conflict can be a scary and an anxiety provoking idea.

You know you ‘should’ have that conversation, but wouldn’t it be easier to avoid it or let it go? It wasn’t that important anyway (was it?)

You probably spend days or hours worrying about what to say, when to say it and what their reaction
might be. A great loss of time, energy and emotion.

I’m sure you’ve found many logical reasons (excuses) to not initiate the discussion. But that just leaves you
with a churning feeling of guilt and shame, because you know you lacked the courage to speak up.

You’ve not expressed to the other person your thoughts. So, they’ll either not realise that something was wrong or they’ll see you as easily walked over.

Even more importantly…

It sends a message to your self-esteem that your ideas, thoughts and needs aren’t important enough for you
to speak up for them.

And guess what…

That knocks your confidence even more and reinforces the habit of not being assertive.

In my research with successful career women about 70% say they weren’t naturally assertive
and they had to learn the skill. But 100% say assertiveness is essential to achieving career success.

Of my clients, over two-thirds are looking for support to develop voicing their thoughts and needs. To be able to disagree confidently with seniors and to have the strength to stick to their ideas.

No matter what behaviours you see around you it is possible to discuss difficult issues in a calm, rational and respectful way. You just need to learn how.

Here are some top tips to help you:

1. Check your mindset. Are you feeling angry, resentful, frustrated or hurt? If you go into a difficult conversation driven by your emotion it will cloud your thinking and the chances of conflict are a lot higher. Instead take the personal out of it and go into the conversation ready to listen and understand the other person.

2. Have a plan. If you have a loose idea on a structure for the interaction you’re more likely to cover your key points. If you worry you’ll get flustered or overwhelmed then write down those points too ensure you raise them.

3. Actively listen. As Stephen Covey (of The 7 Habits Of Successful People) says “seek first to understand before being understood”. This means actively listening and not just waiting for a gap to make your next point.

4. Slow down. Whether you’re giving or receiving bad news you both need time to reflect, ask questions and offer answers. Because these conversations are uncomfortable we tend to rush through them. By slowing down and respecting each others point of view it gives a chance for emotions to settle

5. Offer a solution, compromise or follow up. Wherever you can, offer a solution or a suggestion to support the other person or to help you change your performance. If you can’t agree on a compromise then book a follow up session after you’ve both had time to reflect.

So next time you get that feeling that you ‘should’ have a difficult conversation, you’re probably right, take action!

If you’d like to learn more about assertiveness and speaking up for yourself, book a call with me at

Jo x

#confidence #difficultconversation #confidencecoaching

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