6. The Only Way to Start a Hard Conversation

Have you avoided a hard conversation recently? If so, I wouldn’t blame you. No one’s really any good at them. It’s one of those things you hope to be “not terrible” at. Even the best leaders struggle when confronted with opposing opinions, strong emotions, and high stakes (the best hard conversation definition from the book Crucial Conversations). To make things worse, these conversations are often “make or break”. You only get one chance to fire someone, to ask for a raise, to confront someone you care about regarding a sensitive issue. There’s no reset button if you screw up.

So naturally, we avoid these conversations. We do nothing. Not because we want to do nothing, but because it’s the safest thing to do. In turn, the situation festers, making it that much harder to address later as the stakes get higher.

To overcome this, you have to develop the tools to address these conversations early and tactfully, thus empowering yourself to be proactive about these difficult situations. What’s the best way to do this? Ensure that you keep the other persons mind open about having a challenging conversation. You want them to a) be willing to have the conversation and b) to be open to hearing your perspective. To achieve this, you need to have a clear idea of what you want, an understanding of why the other person would want what you want, and a script that communicates this neatly.

What do you want?

Before the conversation even starts, take a minute to reflect on the outcome you’re looking for. What are you hoping to accomplish? If you’re asking for a raise, talking to a spouse about finances, or confronting a coworker about shoddy work – what’s the range of outcomes you would be satisfied with?

If you don’t have a clear objective, you won’t be prepared for the natural curves in the conversation. Make your ask specific and be prepared to be open and honest (and potentially vulnerable) about where you’re coming from. Also consider the other person’s perspective. What push-back might they give you? What would prevent them with agreeing with what you’re asking for?

Why should the other person care what you want?

Why is what you’re asking for important? How does it affect the other person? How are they served through this conversation? In any hard conversation, it’s important to find common ground that both people can stand on. If you’re asking for a raise, it’s highly likely that you and your boss both want the thing that’s behind the request – your desire to feel adequately valued. That’s the common ground you share and serves as a good jumping off point for your conversation.

If you’re working through spousal disagreements around money, your common ground might be that you both want to be in a stable and healthy financial situation. If you’re talking with a disruptive coworker, your common ground might be that you both want to have a productive working relationship.

By understanding this approach, you’ll find that it also helps you to empathize with the other person’s perspective. If we all want the same thing, then the person disagreeing with me isn’t “out to get me”, they just feel differently about how to get that thing. It becomes a discussion about tactics and prioritization, not a discussion about values. You and the other person are actually on the same team.

Know exactly what you’re going to say

Equipped with a clear understanding of what you want and the common ground you’re working from, combine all of these elements into an opening statement. Your statement should be brief, clear, and communicate everything covered above.

The formula that everyone can use is:

1. I have something that I’d like to talk to you about
2. It affects you because it impacts something we both want
3. I’d like to have a dialogue/conversation about it
4. The outcome I’m hoping for is [outcome]

Here’s an example: “Hey [boss], I want to talk to you about my compensation. Recently, I’m worried that I’m not adequately compensated for [reasons]. It’s important to me that this is a place that values my contributions and compensates me accordingly. I’d like to talk about this openly and I’m hoping that you would consider [outcome].”

Is this perfect? No. There’s no perfectly smooth way to have one of these conversations. Your goal is to minimize cringe and awkwardness, not eliminate it. Practice your opening statement until it feels authentic to you and captures the heart of what you’re trying to say. It doesn’t have to be perfect, it just needs to get a conversation started.

Something important to keep in mind: you can’t force someone into talking to you if they don’t want to. If the other person doesn’t seem open to the conversation, don’t force it. Just because you want to talk, doesn’t mean the other person has to. Additionally, don’t pursue the conversation if the other person seems agitated or defensive – the worst thing you can do is start things off on the wrong foot.

One of the core differences between good leaders and great leaders is how they handle these kinds of interactions. Engaging in these conversations is an essential step, but so is learning to be a better listener and how to compromise. These skills take practice, so don’t be surprised if your first few attempts are rocky and painful. Again, there’s no such thing as an easy hard conversation.

Good luck out there.