How to Have Hard Conversations

Contributed by: Kristin Bower | HR Consultant

The things that are hardest to talk about are often the most important things to talk about. But, well, it’s hard so we tend to avoid it. We may worry that we won’t have the right words to express ourselves. And we might worry that the person who we need to have a conversation with will get mad, defensive, or have hurt feelings.  

The truth is that most of us dislike conflict. But do hard conversations have to equal conflict?  

Our workplaces and communities are becoming more diverse. As businesses strive to celebrate and embrace that diversity, our differences can sometimes sprout misunderstandings. Talking about things as they come up is far better than letting unresolved tensions and unhappiness grow. It’s not easy, but it’s better. In the long run it helps us to build meaningful relationships. 

We don’t like to be wrong or to be called out in a way where we feel ambushed. Set the tone for the conversation by starting with, “Hey, I have been thinking about something. Can we talk about it?” 

The words we use hold power. If you approach a conversation by saying “YOU did this, and it made me mad” you will likely put the person on the defensive. This shuts down a conversation before it can really begin. Try this instead, “I felt upset when I heard you say that.” It becomes more about the actions of the person than about the person. 

Depending on the nature of your conversation, a quiet and private location could feel like a safer place for someone to open up and share what’s going on for them. Or, it could feel unsafe if the person now feels cornered or separated. When in doubt, ask! “Should we talk here or somewhere else?” 

It can be helpful to remember that the other person is human. Consider that the other person has hopes, anxieties and vulnerabilities just like you; they likely want to feel respected and appreciated, too.  

Think about what you want to say and how you want to say it. In the words of Dr. Brene Brown, Research Professor at the University of Houston and author, “Clear is kind. Unclear is unkind.” When we take the time to plan our hard conversations, we have a better chance of expressing ourselves clearly and for the other person to receive and understand our message. 

Be curious about the other person. Why did they say or do what they did? Maybe there is something that you don’t realize that was behind their actions. Most people aren’t bad people, they are simply unaware that their words and actions had a negative impact. Recognize that we all make mistakes and help others to learn from those mistakes. 

A hard conversation, no matter how well you plan for it, will bring up emotions for you and the other person. Prepare yourself for the possibility that you might need to pause the conversation and continue it another time. You also might not be able to resolve differences.  

But what does success look like? It’s when we all take steps to understand each other better – that’s what will help us to bridge differences. 

A new server, Bonnie, needs help talking about the after-dinner drinks with a guest. They ask the bartender Arthur, who is not busy, to address the table. The bartender refuses. As the manager, Joan needs to follow up with Arthur to find out why he was not helpful and try to improve his response for next time. Arthur and Joan haven’t always had the best working relationship, so Joan fears that this will not be easy. However, Joan asks Arthur to chat after service and they agree to talk before Arthur heads home. 

Joan: “Bonnie asked for some help this evening when it came to speaking about the digestifs with one of the guests, but you declined to help. I’m curious what the barrier was?” 

Arthur: “I don’t know the whiskies well enough. How am I supposed to, since I can’t afford to drink this stuff? I’ve only had one of them before and we’ve never had a staff tasting or anything.  How am I supposed to sell something that I don’t know about? You’re making me out to be the bad guy here, you’re saying I’m a bad bartender, but it’s not fair to expect me to be a whisky expert.” 

Joan, taken aback, says:  “I do not think you are a bad bartender. On the contrary, I’m hoping you can support Bonnie with your expertise while she’s learning. It’s true that we haven’t done any formal tastings of the whiskies. I can understand why you felt unprepared to speak to that selection. We did do all that cognac training last week though… do you feel like you have enough other options in the meantime?” 

Arthur: “Yeah, I mean, I guess I could have had fun talking about cognac. But I guess I just wasn’t really in the mood to go to the table either, to be honest.” 

Joan: “Well, I understand that it’s not fun to approach a table when you feel unprepared. So, let’s make sure you know the whiskies better. I’ll connect with the bar manager to make sure he gives you a thorough tasting on them. But if I do my part and make sure you get the right training, will you do your part and help your teammates when they need your expertise?” 

Arthur: “Sounds like a fair deal. Thanks.”