How to lead a difficult conversation

As leaders we are going to run into moments that need bravery — where emotional or political stakes are high, there’s disagreement, and a feeling of risk for at least one person. It might be a one-on-one where you have to give difficult feedback to a direct report or a peer (or even a boss). It might be in a group setting, when you sense conflict or disagreement and suddenly find yourself second guessing what you might say.

Sometimes we initiate these conversations, other times we’re on the receiving end — to our horror!

Either way, if we see potential for disagreement and conflict, it’s human nature to fear the consequences of saying the wrong thing. Who wants to harm a relationship, get rejected or attacked?

The problem is if we let the fears dominate, we show up at our worst. Or we don’t show up at all…. We put off important conversations, we suffer in silence in a meeting, we (heart racing, mind in overdrive) misinterpret someone’s actions or intentions. Or we skate over our discomfort and bring our stress home to our loved ones and wreck our evenings.

One leader we were working with recently agonized about confronting a difficult colleague. Her colleague was assertive and self-confident — and intimidating. She kept putting off talking to him about how she felt he undermined her. But that was making things worse! She lost sleep, took the stress with her on vacation, delayed making important decisions… It was corroding her self confidence. It took patient work in a safe setting to slowly unpack her thoughts and arrange them in a way where she could lead a good conversation. But once she did, it was like she had been freed from a prison of her own making. She was lighter, happier — and even earned the respect of her colleague in the process.

Showing up as our best selves in this kind of difficult conversation — with intention, love, curiosity, a willingness to be vulnerable — is so challenging, and it requires real bravery as a leader. It means acknowledging our fears and choosing to put love above them.

But it’s worth it. Even to fumble through it.

In order to have a conversation with someone, you must reveal yourself.

James Baldwin

Leaders who are brave in communicating their way through difficult conversations are more influential, more effective — and are seen as more competent and trustworthy.

The good news is that anyone can learn to be braver in conversation.

Here are four major principles you can use, that we have seen work in practice, and grounded in research:

1 | Start with intention

Ask yourself: What is my intention?

When we enter a conversation in which there is possible conflict or disagreement, we experience a threat to our wellbeing — and that threat may hijack our reason. That’s why it’s so important to be grounded with an explicit intent. The simple act of asking yourself “what is my intention?” has a magical ability to ground you.

Aim that intention from a place of love and vulnerability, because that will tune you to be at your best. Any act of bravery, large or small, is born out of a love for something greater than our own egos, enabling us to be curious and vulnerable even when strong negative emotions are welling up in our bodies.

TIP: Label the emotions you may already be feeling, and then ask, what do you want, above all? Is your intention motivated by fear and ego, or by a cause that is selfless?

2 | Be curious

Ask yourself: Am I listening to understand?

In any challenging conversation, it can be tempting to assume we have the whole story. But there is never one truth. Not only does everyone have different inputs and observations, they also interpret things very differently based on their personal experiences and belief systems. So in any conversation there are multiple truths, multiple stories at play. The only way to make the conversation productive is to seek to understand those stories.

TIP: Ask questions! Remember that people don’t observe the same things or even share the same starting point of information. So don’t jump to conclusions before understanding the fact base.

3 | Go for clarity

Ask yourself: Am I getting to clarity?

As George Bernard Shaw put it, “The single biggest problem in communication is the illusion that it has taken place.” We think we’ve completed the communication when we’ve finished speaking. But a conversation is not just a two-way exchange of information — it’s a synthesis of meaning that results in a new mutual understanding. All parties walk away changed.

There are two common mistakes people make here.

First, we use ambiguous language to lower the risk of disagreement or vulnerability. But to quote Brené Brown, “Clear is kind, unclear is unkind.” In the long run, ambiguity hurts relationships more than directness.

Second, we fail to complete our communication by ensuring mutual understanding — we falsely assume what’s said is what’s heard. Repeating things back helps to avoid misinterpretation.

TIP: Repeat back what you believe you heard and understood — as in, “Here’s what I’m hearing and taking away…”. Only by stating that out loud can you verify understanding.

4 | Make a commitment

Ask yourself: What will I own?

In a brave conversation, we take responsibility for our contribution to a situation — and we commit to an action that will help move things forward to a shared goal. That commitment is an act of leadership, and it creates the energy to quite literally advance the conversation.

First, acknowledge that we always have a contribution to a situation — and that the acknowledgment is empowering. Second, take responsibility for following through, using the language of commitment and responsibility. An example of this might be: “I didn’t bring this feedback to you earlier because I was afraid it would hurt our relationship. In the future I will be more transparent and open with you in the moment instead of putting it off”. Avoid using words like “should”, “could”, or “need to”. “I will” signals responsibility and ownership.

TIP: Let go of a “blame frame” you could be holding onto — so that you can move from placing blame to learning and moving on.

These principles are easier to follow when you are the one initiating the difficult conversation. But we’re not always in the driver’s seat, and it can be uniquely challenging to be brave in an unplanned conversation. In those instances, lean into curiosity above all. Ask questions to better understand where the other party is coming from. Genuine curiosity can help defuse tension, theirs and yours, and allow for greater clarity and communication.

Lead bravely.