How to Have Hard Conversations With Elegance

In a world where everything takes place online, teaching, shopping, talking with friends, work, doctors’ visits, and so on, we are losing one of the most important values of our civilization. The ability to communicate. The upcoming generation is full of individuals who don’t know how to have a meaningful conversation or follow widely accepted conversational etiquette, such as maintaining consistent eye contact. Much less do they know how to have hard conversations.

2024 study by Preply showed that when the 2,212 respondents ranked their self-confidence in their communication skills, confidence decreased across generations. Leaving our Generation Z at a staggering 3.55, whereas Baby Boomers are at 3.88. So, to begin fixing this issue, here are 7 ways to have hard conversations with elegance!

The Golden Rule:

Treat others as you would like to be treated.

The golden and most important rule! Put yourself in the other person’s shoes and understand where they are coming from. Coming in guns blazing, pointing your finger at the other person, will likely not serve you as well as if you try to best understand their perspective as much as possible.

Prepare ahead.

If possible, reflect on how you would like the conversation to go before it happens. Take the time to think about how best to approach the topic in conflict with the specific person in question. Consider planning the points you would like to raise, along with possible resolutions or apologies. Additionally, be intentional about choosing the right time and place for the conversation when you are planning ahead. For example, during the holidays or when severe health issues arise is likely not the right time to deliver bad news.

Do it face-to-face rather than over the phone.

This is a non-negotiable. Having these difficult conversations face-to-face rather than over the phone can often eliminate misunderstandings about tone or emotions. It shows that you are intentionally taking responsibility for what you are talking about rather than hiding behind a screen. Overall, it builds trust in the relationship and leads to better conflict resolution.

Begin with praise and honest appreciation.

Start the conversation with something that person does well. Compliment one aspect of how they handled an issue, one assignment they completed exceptionally, an action they took, and so on. Be genuine when you do this! Then proceed with the sandwich method: after beginning with praise, deliver constructive criticism or bad news, and eventually close with something else good.

Choose your words slowly and intentionally.

Choose your words very intentionally and take your time as needed to accurately convey your thoughts. It’s okay to have an awkward amount of silence! Better this than say something you don’t mean just for the sake of keeping the conversation flowing.

Come from a place of calm collaboration.

Wait until you are calm to have hard conversations. Avoid jumping into those conversations when you are experiencing an overwhelming emotion, such as anger, which will likely cloud your judgment and lead you to handle the situation in a way you will regret. Be collaborative when talking about the issue; it should be a dialogue, not a monologue.

Listen actively to what the other person is saying.

Remain as objective as possible, trying your best to understand the words actively coming out of their mouth rather than jumping to conclusions about what they may mean. Additionally, while they are talking, truly listen to what they are saying rather than simply planning out your next point in your head.

Hope is not lost.

Although our generation has seen a steady decline in communication skills, hope is not lost! These are all habits that can be formed over time with intentional implementation. You won’t handle hard conversations perfectly at first, if at all, because we’re all human. But these tips will help you approach them with intention and grace, so both people can walk away feeling heard rather than frustrated.

How to Win Friends and Influence People by Dale Carnegie is a wonderful book for more in-depth ways to approach communication with people. Many of my communication practices are built on what I have learned from this book, and I believe it offers many lessons for improvement, especially for young professionals, so I highly recommend reading it. I hope these 7 ways to have hard conversations with elegance made you feel more confident that you can handle your next difficult conversation with grace!

With Love,

Isabella XO

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