Navigating difficult conversations with confidence and grace
Do you find yourself having to face a difficult conversation that you know has to happen but you’re avoiding it?
I feel like I avoid difficult conversations every day, especially with my children 😆.
Tough conversations tend to put us in that fight or flight mode. In fight mode, we either blame/shame others, or defend ourselves. When we’re not thoughtful, it’s so easy, or dare I say it - natural, to lose our cool and say things we don’t mean. Or, and this is my go-to instinctive survival strategy, we avoid having a conversation altogether, stewing in anxiety.
It really helps to consider difficult conversations as opportunities to practice your leadership skills. We all want to learn and grow, and there is no better challenge to our egos than being vulnerable and authentic. The goal of such conversations isn’t to "win" the conversation, but to create more space for clarity, connection, and common ground.
We create true connection when we are willing to be humble and open (rather than robotic, shutting down our emotions and humanity), and come from a place of understanding rather than defending or pushing.
No matter how much you prepare, you can't control the outcome of the conversation - you’ll have to meet the other person where they are. But you can control how you empathize with the other person, and how you engage with them.
As you prepare for tough conversation, here are three things to keep in mind:
Show up with integrity – stay true to your values and how you want to show up.
Respect the other person’s perspective and humanity – acknowledge their perspective even if it’s very different than yours, showing that you’re willing to listen and understand them.
Focus on a common goal – guide the conversation toward a constructive outcome that you and the other person truly care about.
Here are some tips to help you approach any difficult conversation with grace:
1. Resist the temptation to go straight into problem-solving
Put yourself in a positive state before the meeting, breathe, calm your nervous system. Imagine a positive outcome for that meeting, and find a way to be optimistic even if you can’t imagine a positive outcome quite yet.
State your intention clearly and with positive energy . “Thanks for meeting today. My intention for this conversation is to understand in more detail what happened and for the two of us to come up with a plan to ensure we’re better prepared for the next client pitch. I know we can make this work.”
It’s the unspoken feelings that make conversations challenging. Take a moment to create a safe psychological space. You might start with a non-judgemental inquiry that builds emotional connection: “I wonder how you felt about what happened.”
2. Listen without interrupting
When the other person is speaking, focus on truly listening to where they’re coming from. What are their motivations and fears? Don’t correct, defend, or jump in. Let them finish their thoughts before responding. This builds mutual respect and trust.
3. Paraphrase what you’ve heard and validate their feelings
After they’ve spoken, reflect back what you understood, even if you don’t agree. You’re showing that you’re listening and validating their experience, for example: “I’m hearing that you felt your review wasn’t an accurate reflection of your performance, is that right? I can totally understand why that was so upsetting”
Everyone has the right to their feelings, and they’re never about you personally, even if it might seem that way. Feelings are a result of a person’s thoughts, assumptions, perceptions, judgements about themselves and others, their experiences, upbringing, values, culture, etc
4. Ask open-ended questions
Ask thoughtful, open-ended questions like: “Why do you think that? I really want to understand your perspective. Say more about that.”
5. Use “I” statements, not “you” statements
Speak from your own experience rather than making assumptions about theirs. Share how their actions impacted you instead of blaming. For example: don’t say “You are too pushy”, say “When you say X, I feel Y (confused/pushed/judged/sad/hurt).”
6. Take a break if necessary
If emotions become too intense, it’s okay to pause the conversation. Example: “I’ve just heard a lot and I think I need some time to process. Is it ok if we take a break and come back to this in half an hour?”
7. Agree on next steps
End the conversation by checking if there’s anything else to discuss, and agree on what the next steps will be. Maybe You need more data, or more time to review what was discussed.
Let’s practice grace under pressure, and show up as the leaders we aspire to be—especially when it’s hard.
If you’d like to dive deeper into mastering these skills, let’s explore it together in our next session. I’m here to support you every step of the way.
With love and courage 🩷
Ramona
