6 Simple Tips for Handling Difficult Conversations

PERSONAL DEVELOPMENT / Wednesday, January 16th, 2019


“I enjoy having a difficult conversation.”

Now that’s something you don’t hear people say.

The truth is, nobody likes difficult conversations. As much as 70% of people choose to ignore them. But this avoidance comes at a great cost.

A problem usually grows like a snowball rolling down the hill instead of dissolving magically on its own like we’d hoped by ignoring it. Bad feelings fester under the surface, frustrations leak out in other unproductive ways, and our relationships suffer as a result.

I see this happening all the time at work and in my personal life.

In my day job as Ms. HR, I’ve had to deal with a lot of conflicts that could have been averted if only someone had initiated a difficult conversation earlier. When negativity brews for too long, sometimes the damage is too great to ever recover from.

It’s the same in our personal relationships too. It can be scary to have an open and honest conversation with someone we love on a painful subject, so we leave it alone. I’ve seen relationships, friendships, and even families fall apart because it was easier to turn away than face up to difficult conversations. What a shame.

Difficult conversations suck, there’s no doubt about it. But from what I’ve seen, it’s better to have them than to look the other way and pretend the problems don’t exist. So if you can’t run from difficult conversations, what can you do?

You Can Become Better at Handling Difficult Conversations

Unless you commit to a life of solitude, you will inevitably come across a situation where you need to have a difficult conversation. But fear not, like most other things in life, you can learn and become better at this.

Trust me. I used to be terrible at having difficult conversations myself, but because of my line of work, I had to learn how to handle difficult conversations. I attended seminars on this topic, sought out advice from seasoned HR professionals, and read about the subject on my own. And then I practiced.

The biggest takeaway from my learning is that there are 6 simple things we can do to make difficult conversations both easier and more effective.  These 6 strategies have helped me become more adept at handling difficult conversations not only at work, but in my personal life as well.

Read on to find out what they are!

6 Simple Tips for Handling Difficult Conversations. Learn how to deal with the hard conversations that come up in your life. A guest post by the Budding Optimist

Mind the Time and the Place

Before you initiate any conversation that you know will likely stir up some negative emotions, you need to give some thought as to when and where this conversation should take place.

Don’t just blurt it out whenever you feel it’s convenient for you. The time and the place are crucial to the success of the conversation.

Let me ask you this: How would you feel at 5pm on a Wednesday afternoon when you just crawled through yet another traffic jam on your way home with your stomach growling ferociously, and the minute you walk through the door, your significant other says “honey, I lost some money investing in Crypto”?

Or it’s Friday right before lunch during the busiest time of the year for your team, and your boss calls you into his crowded office, closes the door and says “we need to talk about that error you made on the Leahmann project”?


That’s what I’d be feeling.

Difficult conversations are well…difficult. Don’t make them tougher by having them at a time when people are hungry, extremely stressed, or super tired. If you can, choose a neutral space where it’s bright and uncluttered, like a boardroom of a workplace, a coffee shop with some privacy, or even in a park if the weather is nice.

People are much more willing to listen and respond positively when they feel relaxed. Cornering them into a difficult conversation at a bad time and place will only make them more defensive and uncooperative. So do yourself a favour and be selective about your time and place.

That doesn’t mean you should wait and wait until the “perfect” time and place line up though, because it may never happen. Sometimes you just have to schedule a time and a place with the person for the conversation to take place. Instead of waiting for the right opportunity, create it!

Don’t Make It All Negative

Did you know there’s an ideal ratio of the number of positive comments to negative comments that leads to better team performance and happier marriages?

It makes sense. Nobody likes to hear a whole bunch of criticisms all at once. It dampens the mood, decreases morale, and can even cause further rift the relationship. But the tricky part is a difficult conversation by nature will contain some negative comments. After all, the reason for the conversation in the first place is there’s either something the other person did (or still doing) that requires change, or you’re delivering some kind of bad news. So how do you balance the negativity?

The solution is simple: for every negative comment, you have to inject at least 6 positive comments. Before you jump up and say “wow that’s a lot of work”, let me show you some common phrases that are positive. This should give you an idea of what you can say during your conversation to balance the ratio.

I agree with your point.

I can understand how you feel.

I like that idea.

I appreciate you trying.

I hear what you’re saying.

Start out your conversation on a positive note by letting the person know a few good things you noticed about them or you value them as a colleague/friend/family member. Then you can talk about the thing(s) they need to improve on. Likely you’re going to have some back-and-forth exchange of thoughts in this conversation and during this exchange, you can pepper in more positive phrases to keep the overall tone of the conversation positive.    

Remember the goal of the difficult conversation is to achieve understanding. Your intention isn’t to make someone feel horrible. While you need to communicate clearly what needs to change, don’t forget a few words of encouragements here and there.

Be Prepared

Unlike small talk, a difficult conversation is not something you can just “wing it”.

A lot of things can go wrong when emotions get in the way. You can easily get wrapped up in the heat of the moment and lose sight of the original intent of the conversation.

Before you know it, a conversation that started out on a good course can quickly derail and end up somewhere totally unexpected. Misunderstandings occur. Feelings get Hurt. And sometimes, a difficult conversation gone wrong can leave you with more than just a bad taste in your mouth. A friend of mine once lost her job over a difficult conversation she initiated in the spur of the moment that turned ugly.

When a conversation has a lot of potential for tension to explode, you can’t have it on a whim and hope for the best. In order to give the difficult conversation the best chance at success, you need to prepare for it.

First you have to prioritize your most important messages. What points do you want to get across the most? Stick to one or two points to make sure they really stand out.

Then think about how the person will likely respond. Chances are you know this person wellthey’re somebody you’ve been working with for a while, perhaps a friend you’ve known for a long time, or someone in your family. You know how they’ll likely react.

Even if you don’t know the person well enough to make an accurate prediction, you can make some guesses based on the nature of the message you’re going to convey. How would people normally react to what you’re about to say?

Once you have an idea of what the possible reactions may be, plan out how you will respond to each scenario. This way, you already have a decision in your head as to what you will do next when “x” or “y” happens. This will give you an opportunity to think ahead about ways to “save” the conversation if things go wrong.

Practice what you’re going to say in front of the mirror. Pay attention to your body language. Are you sending a completely different message with your expressions and gestures? Depending on the sensitivity of the topic, you might even want to practice the conversation with someone else.

Although you can never truly know how the conversation will unfold until you’re actually in the conversation, going into it with a plan will greatly increase your chance of success.

Don’t Just Talk. Listen.

When you’re having a difficult conversation, it’s easy to fall into the trap of rambling on, interrupting in the middle of a sentence, and ignoring what the other person is saying. You’re eager to get your point across. You want them to see things from your point of view. But don’t forget communication is a two-way street.

If you want someone to see things from your point of view, you have to be willing to listen to their point of view.

And I don’t mean the kind of half-hearted listening where you’re just waiting for the other person to stop talking so you can start again. I mean really listening to what the person has to say with your entire focus. Because when you show you’re truly listening, the other person is much more likely to listen to you.  

Remember the goal of your conversation is to establish understanding. You’re not giving a public speech. So keep your message clear and concise, and then stop and listen to what the other person has to say.

When you’re in the middle of a difficult conversation, practice active listening. Pay attention to not only their words, but the tone of their voice and their body language as well. What are they telling you about how the person is feeling? Does the person appear defensive, hurt, or confused? These details will help you appropriately respond and keep the conversation on a good course.

If Communication Isn’t Happening, Continue Another Time

Have you ever seen or been in an argument where both sides are talking but they’re not communicating? It happens often when emotions get in the way and people stop listening.

Each person is so focused on expressing their own thoughts they might as well be talking to themselves. At that point, the line of communication shuts down, the conversation becomes frustrating, and tension can easily turn into conflict.

If that happens, you might as well end the conversation, let things cool down and continue at another time. It’s a waste of time and energy to keep the conversation going, and you might end up saying things you regret.

When emotions heat up to a point where it hinders communication, it’s better to just step back from it, give yourself and the other person the space to think things through, and then come back to it when you’re both in a better headspace.

But before you end the conversation, let the other person know why you think it’s a good idea to take a break from the discussion and that you plan to resume the conversation later. Never walk away in the middle of a conversation without any explanation. That’s a sign of disrespect and it will further fuel the fire.

Sometimes all you need is 10 minutes for both people to take some deep breaths and come back with a fresh mind. Usually when that happens, the conversation becomes much smoother and both sides feel good about it afterwards.

Follow Up

I know, difficult conversations are yucky. You just want to get it over with and never mention it again. But in order for the difficult conversation to have any lasting  impact, I’m afraid you’ll have to follow up.

I’m not saying you have to have a whole ‘nother in-depth conversation around the same topic. Sometimes you do, if the first one didn’t result in any progress. But most of the time, it’s a short conversation where you confirm you’re still on the same page about things. It’s also a great opportunity to tell them you noticed and appreciate their efforts.

It can be as simple as this:

“Hey Sheryl, I noticed you’ve been taking the lead on more assignments since I talked to you a  few weeks ago about how I felt our teamwork wasn’t where it needed to be. I want to say thank you for listening to my suggestions and I’m glad to be on your team. Are we still good to go with our plan to divide the upcoming project like what we agreed on last time?”

See that’s not so hard is it?

When you follow up, it sends the message that the topic of the difficult conversation is important to you. People will take it more seriously. If you just bring it up once and never speak about it again, it gives the impression you don’t care about it that much.

When people think you don’t care, their natural response is to not care. With time, things will likely go back to the way they were before you had that conversation. It’s not their fault, changes are hard enough to make and even harder to maintain. You shouldn’t expect any lasting improvement from just one conversation.

Don’t follow up too often though. Give people time to digest the conversation and make any changes they need to make. Nobody likes someone breathing down their neck.


Key Takeaways on Handling Difficult Conversations

Think you’re ready to tackle your next difficult conversation? Just remember these key takeaways:

  • The time and the place of the conversation can determine the outcome of the conversation. Avoid highly stressful times or when people are hungry. Whenever you can, pick a neutral and inviting space.
  • The ratio of positive to negative comments should be 6:1. Start the conversation on a positive note and pepper positive phrases throughout the conversation.
  • Don’t wing it! Prioritize what matters to you and anticipate how the person will react ahead of time. Think about what questions they will ask and how you will respond to keep the conversation on course.
  • Pay full attention to what the other person is saying, including their tone  of voice and body language. Show them you’re really listening.
  • If emotions are ricocheting off the walls and communication is getting lost in the noise, end the conversation and continue another time. Explain why it’s a good idea to talk later before you step away from the conversation.
  • Don’t drop the conversation one time and never speak of it again. Show the other person you’re serious about the topic by following up in a balanced way.

If you’re interested in learning more about how you can communicate in a way that cultivates better relationships, check out my post “The One Word You Need to Know for Better Communication Skills”.

I hope you understand by now that difficult conversations are a part of life. We will run into them at work, at home, or with our friendswherever relationships exist. If we can’t avoid them, we just have to become better at them. And with practice, we can all become better at handling difficult conversations.

Let’s practice together.



A Guest Post by Sabrina from the Budding Optimist

Author Bio:

Sabrina is a Leukemia survivor living with a rare lung condition as a result of her cancer treatments. Not one to let these health challenges stop her, she continues to travel, hike, play dodgeball, and write in her blog “The Budding Optimist” where she shares tips, stories, and ideas that inspire people to live a healthy and happy life.

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