Seven Steps for Turning a Difficult Situation into a Productive Conversation

We’ve all been there. Your coworker is not pulling his weight. Your significant other has been acting passive-aggressively. Your friend keeps letting you down on promises.

Relationships are hard. Good ones are also crucial to having a happy and productive life. So what do you do when you find yourself in one of these thorny situations?

Over the past few months, as part of our Leadership Fundamentals Course, I’ve been reading a lot about having difficult conversations and exercising varying methods and approaches to handling them. Here are seven tips I’ve learned to navigate these situations successfully.

1. Decide to Act

One of the biggest mistakes people make with difficult conversations is choosing not to have them. How many times have you convinced yourself not to address a problem because you didn’t want to go through the trouble of having the awkward conversation? Trust me, I’ve done it too. However, not addressing problems right away often leads to more problems piling up.

It’s also common for that one problem to turn into a behavior pattern, exponentially frustrating you each time it occurs. I’ve certainly been a victim of this as well. For example, is it really that annoying that your partner never closes the closet door? Probably not. But when it’s been bothering you every time they’ve done so over the past six months, it becomes death by one thousand paper cuts.

Don’t let the situation get to this state. When you sense an issue, address it in a timely manner.

2. Determine the End Goal

Before you approach a conversation of this nature, it is important to determine your end goal. Are you hoping for a change in behavior? Are you looking for someone to complete a single task? Figure out what you want to happen, and then work backward to determine how you might get to that end goal.

Determining the end goal first will also help you weed out bad end goals. For example, if your end goal is to “win” the argument, then you might need a little time to cool off and revisit it before you approach the other party.

3. Schedule the Conversation in Advance

People don’t like to feel like they are not in control. Don’t surprise someone into a crucial conversation. Instead, ask them to discuss the issue with you at a future time. This will give both of you time to prepare for the conversation.

Be careful not to schedule the conversation too far into the future, though, as this can be anxiety-inducing for your partner. Ideally, you want to schedule the conversation for later that day, or within the next few days.

When you approach your colleague to schedule this conversation, provide some context, but keep it concise. You could say something like:

Hi Kevin. I’d like to get together tomorrow to discuss the comment you made about my presentation. How does 3:00 pm sound?

If possible, schedule the conversation so it can happen in person. However, don’t let a lack of in-person availability stop you from having the conversation altogether. A video or phone call will suffice if getting together face-to-face in the next few days is not feasible.

4. Prepare for the Conversation

Have you ever had to give a presentation without having any time to prepare for it beforehand? It’s not a good feeling. Chances are you felt like you could have done a better job, if only you had time to prepare. Having a difficult conversation with someone is no different than presenting. Do not assume you can wing it.

I like to prepare for conversations of this nature by writing a sample script. I think through possible reactions I might get to each point and determine the best way to respond in each scenario. Throughout every step of this process, I am writing through the lens of my end goal. How do I need to pivot to make sure we get there?

I know I just told you to write a script, but I am not suggesting you read from a script when you have this conversation. The act of thinking through these scenarios and crafting your language will allow you to enter the conversation much more prepared than if you don’t. It will reduce the risk of having to pivot too much on your toes, since chances are, you’ve already considered the scenarios where you might find yourself.

5. Listen to Understand

The last tip was about preparing your talking points. This tip is about not jumping the gun on those talking points.

You need to listen to the other person. I mean really listen. You should not be listening, just waiting for a chance to jump in and spew out your talking points. You need to listen with the intent to understand how the other person is feeling, and where they are coming from.

You might learn something while listening that means you need to throw your original plan out the window. That’s okay.

Make sure the other person feels heard before you jump into strategizing solutions.

6. Determine Next Steps & Accountability

Always end the conversation by discussing accountability. What is the action item you’ve agreed upon? Who will do it? When will it occur? Make sure it is clear who is accountable, and that the other party will make it clear if the expectation has not been met in the future.

Determining next steps and accountability is crucial to ensure an unsavory behavior pattern does not continue. It’s easy to agree that a behavior is not desired. However, determining how to stop it and becoming comfortable enough to call your partner out on any slippage is key.

My favorite accountability steps are ones in which my partner and I agree to hold each other accountable. This resolution is more collaborative and ensures both parties leave the conversation feeling like a winner.

7. Follow Up

Don’t have the conversation and forget it ever happened.

Perhaps the conversation went so well that you never had to revisit the issue. However, it is still in your best interest to follow up after the resolution, to see how the other person is feeling. Is the solution you came up with together still working a month later? Is there anything about the conversation itself that could have gone better?

Getting feedback like this is a great way to learn more about your own interpersonal skills and find ways to improve them.