Image for blog Uncomfortable conversations and how to have them with two couches

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Have you ever taken a dive into the vast and bizarre world of phobias? If you do, you may discover that your lifelong apprehension of knees is actually shared by others, and is called genuphobia. If you can only count to seven before a feeling of dread overtakes you, you have octophobia. And if you feel anxiety when having uncomfortable conversations, then you are in the majority.

The fear of conflict is a common, and even valid, fear. After all, uncomfortable conversations are usually synonymous with high-stakes conversations, or conversations of significant emotional weight. Where there is great risk, there is typically a corresponding fear. So why pursue these conversations at all?

Consider this: If uncomfortable conversations imply large emotional consequences, this can be intimidating—or incredibly exciting. If the consequence in question is, say, a pay-raise at work, then you are only a conversation away from a better quality of life.

In fact, a large amount of the things we want, like better careers or better relationships, are only a conversation away. By mastering the art of the embracing difficult conversations, you possess the power to change your life in dramatic ways.

Regardless of the benefit in question, high-stakes conversations can be scary. But, remember that a successful conversation is not had in the absence of fear; it is in spite of it.

Here are a few tips to help you negotiate an uncomfortable conversation, and ultimately reap the lasting benefits.


Tips for Uncomfortable Conversations


  1. It’s all about the gains.

Everyone, at one point or another, has been in a plank for too long, or straining through their 50th push-up, and had their friend jeer, “No pain, no gain.” Though this phrase is historically poorly timed, the principal is true.

It’s obvious that getting in shape requires discomfort, so why is it so hard to identify this principal in our relationships or careers?

Uncomfortable conversations become more manageable when they are understood as necessary steps for growth.

To maximize your odds of a successful conversation, try visualizing the desired product of an uncomfortable conversation before having it. By doing so, you can more easily identify that five minutes of discomfort is well-worth the negotiated price of a new motorcycle, or a misunderstanding resolved!


  1. Leave the bush out of this.

In critical conversations, beating around the bush will only hedge in opportunity.

Sugarcoating or snow-blowing is a surefire way to convolute a critical conversation, create unnecessary, awkward tension, and ultimately move you away from your objective.

If you’ve mustered up the courage to have an uncomfortable conversation, you may as well follow-through with direct and concise requests.

Just like any endeavor or skill worth pursuing, the key is practice. Rehearse your asks in advance, and try to limit them to as few words as possible for maximum clarity.

If requests are made confidently, they are more likely to be met with corresponding respect.


  1. Use your imagination.

What we are about to suggest may anger and upset you.

Like uncomfortable conversations, role-playing requires minutes of discomfort, yes, but yields effective preparation.

Before you start having high-school drama club flashbacks, take it from our friends at Harvard: “…role-play[ing] as a training tool helps students change behaviors and use best practices in real-world settings.”[1]

Though role-plays can be performed alone, it is ideal to include a partner.

Fill your friend in on the situation, and encourage to them to throw you some curveballs. The more prepared you are to respond to a variety of situations, the more likely you are to succeed.

Uncomfortable conversations are difficult, sometimes awkward, and always worthwhile. By recognizing and accepting their necessity, being direct with your requests, and role-playing these uncomfortable conversations, you can catalyze growth in every element of your life.

Just speak-up.


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[1] Elmore, L. B., Ed.D. (n.d.). Role play. Retrieved April 15, 2021, from