How to approach difficult conversations with confidence

How difficult conversations can impact your team negatively

I feel like this is going to be another one of those calls where we walk away not having made any decisions.

This is what a team member said to my client, Jenny during their team meeting.

Jenny could feel the mood dampen.

Everyone was silent, digesting the comment and the obvious challenge on their end of the connection, maybe because they felt that too, or maybe because they didn’t know how to reply.

There were no raised voices. No slammed doors.

But often a difficult conversation doesn’t involve any of that.

A difficult conversation can look like a challenge from someone in your team. A cry for help, for attention. Jenny’s team member was feeling discouraged and needed reassurance. Needed Jenny to lead and create a different outcome. And the team was watching.

How we respond to that challenge is SO important.

Often, we’re not quite ready for the challenge, and we don’t address it. Jenny went on with the meeting and didn’t address the comment. In the following weeks she regretted it as she saw the team become quieter and team members become more withdrawn. Before she knew it, the whole team culture had shifted. It may sound like an exaggeration, but it’s really not. I see it so often in the teams I work with.

Avoiding difficult conversations or handling them badly can be the starting point for a lot of things going wrong in a team and an organisation.

Difficult conversations damage trust in a team

How we lead through a difficult conversation can impact upon our team’s trust in our leadership and in our ability to see their side of the story.

Difficult conversations undermine teamwork

Collaboration drops when difficult conversations are not dealt with well. People often generate a lot of negative energy that distracts your team from their shared purpose and goals. When people don’t feel seen or appreciated, they are more likely to focus on their own issues and goals.

Difficult conversations increase staff turnover

A lot of leaders are struggling with turnover at the moment, and you would be surprised how many of these turnover stories started with waiting for a conversation that didn’t happen or a conversation that was not managed well.

A difficult conversation is so often a turning point that can lead to positive change and impact, or to any of the things I’ve mentioned above. I know which one I’d prefer.

We don’t need to love difficult conversations, we just need to be prepared for them and lead people through to the other side of a conversation with confidence (and a touch of vulnerability).

How to have a difficult conversation with your team and achieve a positive outcome

I want to share with you the fundamentals you need to approach these conversations with confidence and to feel good about the outcome.

Plan the conversation

Even if it’s just a few minutes, take those minutes to think about the what and the how, and set a clear intention for the outcome you want from the conversation. You’ll be surprised what a difference that will make.

Be direct and specific

Don’t beat around the bush. Where these conversations often go wrong is when we try to protect people’s feelings, to prevent upsetting them or ‘rocking the boat’. But the lack of clarity does more damage. Clear is kind.

Treat the other person with respect

This is an opportunity to collaborate, not to dominate. Respect opens the door to genuine dialogue, to trying to find a way through things that works for you all, and that’s when real progress happens.

Listen to what is going on for them and empathise

Listening is one of the most underrated skills, and in difficult conversations, it is essential. When people feel heard, they’re more likely to engage openly and productively in conversation.

Manage your emotions

Emotions are very normal, but they can derail a difficult conversation if you let them drive the conversation. You can manage your emotions effectively by pausing, taking a deep breath, reframing the challenge and responding, rather than reacting. The great thing is that, when you manage your emotions, you can set the tone for the other person to do the same. Imagine what a difficult conversation could look like if emotions weren’t running the show.

I hope you find these helpful and put them into practice at the first opportunity.

All good things,

Juliet Robinson
Leadership and Change Specialist

Ways I can help you lead your team better:

Brush up your listening skills: Being an impactful leader requires excellent listening skills – easier said than done. They are about much more than hearing. Try some of the better listening skills in this FREE guide.

Get confidential expert guidance: Let me help you untangle the leadership knots you’re dealing with. You’ll be surprised by how much clearer you can get once you talk through things with expert help. You can book a one hour session with me here.

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