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How to Start a Difficult Conversation

The Doe Team

by The Doe Team

| December 21, 2021

Putting off a hard conversation? Here's your guide to beginning the conversations that keep you up at night.

The toughest part of having a difficult conversation is getting it started. This blog outlines four tips to not only get that conversation going but to increase your confidence and ease your anxiety.

If you’ve ever had to give upward feedback, come out to loved ones or end a relationship, then you know the particular challenge of starting a difficult conversation.

However anxiety inducing it may be, there are a few things that can help. The key to successfully starting a difficult conversation is to plan. 

While things never go exactly as expected, having a solid plan often helps keep you organized and focused on the desired outcome. This allows you to gain more control over a situation that is causing you stress. Planning for a difficult conversation isn’t any different.

Here are four solid ways to plan ahead for any of your tough discussions so you can speak with less fear and more confidence.


1. Set the Stage

You’ve seen the movies where someone gets dumped in a restaurant and a scene ensues. It’s crucial to the plot but hard to watch. The setting is usually inappropriate to the conversation, proving that time and place matter in your sensitive discussions.

When you’re planning your setting, consider the level of privacy that you (and your counterpart) want. If there are kids or roommates around, a walk or visit to a nearby park might be an option. If having people nearby makes you feel more comfortable, then your local coffee shop might have the perfect table.

Another aspect of setting is timing. Being considerate of the other person’s schedule goes a long way in setting up the conversation for success.

As you set the stage, it’s important to be conscious of the clues you may be leaving about the conversation. There’s a balance between giving too much or too little information. Both can leave your counterpart stressed out.

The setting you choose and the information you give are essential to creating a comfortable atmosphere. Having these details planned out will take away some of the stressors that can sneak up on you the day of the conversation.


2. Know Your “Why”

It seems obvious. Of course you know why you want to talk. But when the conversation rolls around, you may find yourself struggling to communicate amidst the stress and emotions surrounding the topic. Having a clear understanding of why you want to talk and what you hope to get from it can help you remain focused.

Once you’ve thought about your reasons for wanting to talk, as well as considering solutions, write it down. Just like other types of public speaking, having notes as a reference is an excellent way to stay on track.


3. Practice Your Delivery

Once you’ve worked out your why, the next important step is your delivery. If you’ve ever had a difficult conversation with a friend or colleague who made their point at least five times (or talked for an hour and didn’t seem to make a point at all), then you know how important being succinct and clear in a tough discussion is.

One of the ways you can keep this from happening is to take your “why” and figure out how to say it in the simplest way. Practicing aloud can help you work out awkward or uncomfortable topics and language. This will give your conversation the opportunity to be as seamless as you hope.

Knowing what you want to say and how to say it will also help you feel more confident going into the conversation because mulling over the same thing without practicing rarely yields the results you want.


4. Tips for Tact

Having tact in a difficult conversation is part of good communication. For example, being so direct that you’re insensitive is not the best approach in these types of conversations. “Hi, I’m breaking up with you,” or, “Good morning, we’re letting you go” is no way to start a discussion. Sensitive topics require a warm-up.

A great way to begin these conversations is by starting on a neutral-to-good note. This can look like expressing gratitude for a meeting or simply sharing that there have been some thoughts that you wanted to communicate.

Another tip is to speak with “I” statements. This is a classic tool to have in your communication toolbox. It steers the conversation into a place of accountability and avoids assigning blame. Backing someone into a corner is the fastest way to end what could be a healthy conflict resolution.

Consider choosing your opening and writing your “I” statements prior to the conversation. By planning your approach and beginning on a good note, you can help ease any tension, which will help later on as you dive into the tough stuff.


A Final Note

Difficult conversations will always present challenges, but they do get easier with practice, especially when there is thought and intention behind the approach. As you move forward in your everyday interactions, consider applying these tips when planning your difficult conversations.

Discourse shows up outside of social media and serious conversations. It is part of your everyday life. Subscribe below to read more about how discourse shows up in your life and why it’s important.


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