How to Have Tough Conversations with Confidence

Do you ever find yourself putting off challenging conversations at work?

Sometimes, just thinking about a potentially difficult conversation has the power to fill us with anxiety. And that wave of dread often causes us to kick the can down the road, and avoid a conversation that really needs to happen.

But here’s the thing:  Conflict avoiders always wind up with more conflict. Putting off a challenging conversation pacifies the worry of the moment but exacerbates the overall angst over time.

People who cannot voice concerns are eternally fraught with worry; People who are unwilling to push back will feel constantly disempowered. It gnaws at you all the time.

It doesn’t have to be this way. Being able to navigate challenging conversations is a hallmark of exceptional formal and informal leaders.

Leaning in when you’re tempted to pull back takes practice.

Roberta Matuson’s new book, Can We Talk?, offers  a number of key tips :

  1. Start Small

If you struggle with difficult conversations and want to get better, focus on small wins first. This will boost your confidence.

Getting comfortable with low-stakes conversations could be speaking up when your restaurant order is incorrect, offering another point of view in a brainstorming meeting, or simply saying “no thank you” to plans you don’t want join (instead of making up a white lie).

Matuson suggests, “Start small, build your strength, and get a few wins under your belt. “

These small wins will emotionally prepare you for more difficult conversations later.  Over time, you will become less wary of temporary discomfort and more empowered to speak the truth.

  1. Don’t blindside the other person

If the conversation you need to have will have lasting implications (beyond a moment or two of discomfort for you), it’s important to prepare the other party for the conversation. The conversation should not come as a surprise.

Matuson notes, “In this day and age, they could be sitting at their dining room table with the kids running around. They could be driving. They could be sitting beside a colleague at happy hour. You don’t know.”

Ask the person you’d like to speak with if there’s a time the two of you could speak privately. This gives them the opportunity to come to the conversation with a level head, free of distractions.

  1. Use notes

I remember many years ago, the US President at the time was continually criticized for bringing notes to meetings with other foreign leaders. I didn’t understand the criticism. To me, it felt totally normal. Why wouldn’t you come prepared for high-stakes conversations? I’d rather have a President who brought notes than a President who tried to remember everything only to forget important details.

There is no shame in using notes. If you are preparing for a potentially difficult conversation, Matuson advises being transparent, saying something like, “This is an important conversation. I’ve been giving this a lot of thought and I’ve written down some notes.”

When you come prepared, you don’t need to worry about perfect memorization of the speech you rehearsed in the shower. Instead, you can authentically lean into the conversation.

Difficult conversations are a part of any impactful, purpose-driven career. Being able to navigate these conversations with kindness, truth, and authenticity is a learned skill. The more you do it, the better you become (and the less anxiety you will feel).