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How to Have Difficult Conversations: Tips From A Physician Coach

Updated: Nov 25, 2023

By Tracey O'Connell, MD, Educator & Coach

Woman sitting down thinking about something
Wondering how to make having difficult conversation easier?

When people don't agree, there's either tension or a difficult conversation. Sometimes we think we can avoid a difficult conversation and the tension will go away on it's own. But, the tension won't go away without the difficult conversation. There will just be more tension. What to do to break the cycle?

There comes a time in everyone’s life when they need to figure out how to have difficult conversations. At its very core, if you find the idea of a specific conversation difficult, you’re experiencing a deep inner feeling of, Hey, I don't like that. Your inner self is trying to protect you from conflict, but this can sometimes be unconstructive, particularly if you’re navigating having a difficult conversation at work or with a loved one.

To counter that uncomfortable feeling, ask yourself, Why am I upset? What do I want to be different? Understanding the core reasons a conversation might feel difficult will help you approach it mindfully and in the most constructive way.

Any conversation can be difficult if you let it, and we physicians are not exempt from that, but avoiding tough conversations holds us back and it certainly doesn’t benefit the organizations we work with or the people we serve.

So it’s time to speak up! Here are my tips for difficult conversations.

How to prepare for a difficult conversation

1. Have a strategy

The first step in how to start a difficult conversation is knowing what you want to say. Often, we get caught up in our emotions, and that can cloud the way we communicate. Having a strategy before you go into a tough conversation gives you a set of talking points you know you need to cover.

Ask yourself, what do I want to say? Asking this question will help you pinpoint the exact outcomes you want to achieve from a difficult conversation.

2. Set an intention

My next tip for difficult conversations is setting an intention for the discussion. Once you know what you want to say, it’s important you understand why you want to say it. This will help you establish if the problem can be solved another way, for example, if there is a different underlying unmet need, or it can help you better explain your feelings and be heard.

3. Know your purpose or desire

What is the outcome you’re hoping for?⁣ If this conversation goes well, what will be the takeaway? Where will you be once your thoughts and feelings are communicated and heard?

Having clarity on your desired outcome or purpose for having the difficult conversation will help you frame the conversation and clearly communicate what it is you’re hoping for.

One of the tricky parts when it comes to a difficult conversation is getting across exactly what you would like to change, whether that be behavior, material, work-life balance, or otherwise. This step helps you understand and therefore effectively communicate your desired outcome so the other party knows what needs to be done.

4. Let go of expectations

Ultimately, we cannot control the outcome of any conversation, let alone a difficult conversation. We take a risk every time we open our mouths that the conversation may not go the way we hoped or planned. ⁣

This is vulnerability. It feels scary. ⁣Yet, it’s the only way to connect with others and not continue to abandon ourselves. ⁣Being vulnerable gets easier with practice. Much easier. Believe it or not, it becomes so healing and powerful and cathartic, that it becomes the new default. ⁣

Even though not every conversation will end the way you’d hoped, the rewards of honest, meaningful relationships are worth the discomfort of learning effective ways of communicating. ⁣

Once you learn how to express what you really think and feel, you’ll never go back - no kidding!⁣

My script for having a difficult conversation

Whether you’re wondering how to have difficult conversations at work or how to have difficult conversations with family, it helps to be prepared. This is my script for having tough conversations, while communicating effectively, but with kindness.

Be curious and neutral

Bring up the topic in a curious, neutral way. Often when faced with a difficult conversation, both sides tend to get defensive. Approaching the topic with curiosity helps by letting everyone know that the problem is simply a lack of understanding, not them. It avoids a confrontational tone from the get-go.

“I noticed that you…”

Listen intently

When having a difficult conversation, listen and reflect back what you hear them say. This ensures there’s zero misunderstanding. It’s important at this point of the conversation that you really listen. Give them space to speak, and don’t talk over them.

Your aim is to understand where they’re coming from just as much as it is they understand where you’re coming from. Listen, and try to view things from the other perspective.

“So, I hear... Is that right?”

You may want to ask clarifying questions. Remember to clarify without minimizing their point of view.

“How do you feel about that?”

“Could you share more details on that?”

Communicate your thoughts and feelings

Share the impact the behavior is having on you. The other party may be totally unaware of how they are affecting you. Including this in the conversation gets them on the same page, and it gives you a benchmark to watch their behavior. If nothing changes after this conversation, it’s fair for you to assume they aren’t taking your concerns seriously, but you need to give them that chance.

“When you…I feel…”

Communicate what you want

Then shift the dialogue to what you actually want, speaking honestly. Communicate your desired outcome clearly and directly.

One of the best tips for difficult conversations is to try and use ‘I’ statements, rather than ‘you’ statements that can come across as accusatory.

“My preference would be…”


“I would like…” or

“Would you be willing to…”

Propose an agreement

Finally, form an agreement.

“How does that sound to you?”

Remember, not all conversations will end the way you’d like and that’s perfectly OK. Sometimes, at this stage, you need to agree to disagree. This doesn’t mean you cosign the outcome, it just means you’re protecting your peace.

The key to earnest conversation

Real conversation requires openness and honesty and many people are too scared to speak up for what they know they want to say. So, they stay silent, at the expense of remaining misunderstood or underappreciated. ⁣This is why difficult conversations are so important.

Keeping silent can be helpful if you need to pause to collect your thoughts, but staying silent, not sharing your thoughts, needs, opinions, and feelings, can become a default setting if you never learned how to stand up for yourself or if someone ever belittled you. ⁣

Having a difficult conversation doesn’t have to be difficult! Some people go to their grave wishing they had only had the courage to have that one conversation...⁣

But you are capable and deserving! So, let’s power up and speak up!⁣

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