April 8, 2023




How To Master Uncomfortable Conversations

At a glance

Fast Summary

  • Difficult conversations are a necessary evil both in and out of the workplace. We can’t skip them, so instead, we must learn to navigate them positively.

  • To tackle uncomfortable conversations, we need to first use an integrative mindset, which allows us to adapt and remain neutral when faced with difficulty.

  • Acknowledging our own discomforts, managing our emotions, and adjusting our communication approach is key to handling difficult conversations with ease.

  • Next time you have a difficult conversation, focus on your goals and intentions.

  • When we master difficult conversations, we command respect from our peers, gain confidence, and, most importantly, get what we want.

Throughout my early career, I struggled to engage in difficult conversations, especially those that stretched my comfort zone, involved crucial feedback, or addressed poor performance either from myself or others.

The issue only worsened when I had to face my superiors—like many, I found myself mincing words or beating around the bush. And ultimately, I put these conversations off, avoiding them entirely.

Difficult conversations take many forms—personally, I struggled with those that involved critical feedback, but you may struggle addressing your boss or higher-ups in the workplace, partners, friends, and even family.

Many of us worry about disappointing the other person. Confronting someone knowing you might disappoint them is daunting, especially when you may be at fault. And more so, many struggle to engage with those they find ‘volatile:’ If your boss is known for a short temper and booming voice, in all likelihood, you’re less likely to approach them with a potential issue.

We don’t like disappointing people, and that’s perfectly normal.

Mastering difficult conversations is paramount for personal, professional, and organizational success. When encountered with conflict, many people find themselves at a loss for words, just as I did, but this doesn’t help you, and only aggravates the conflict.

Putting them off doesn’t help either. When we continually put off uncomfortable conversations, the problem swells and worsens over time.

However, when we master tough conversations, we’re more likely to resolve conflicts, improve personal performance and self-confidence, and, most importantly, get what we want.

To conquer my fears and master difficult, often uncomfortable, conversations, I used a combination of approaches and mindset shifts, building off what Forbes writer Lindy Bewster calls a growth and integrator mindset. 

The Power of The Integrator Mindset…

The integrator mindset is characterized by trust and adaptivity; it involves approaching potential issues with personal and organizational goals in mind.

The integrator mindset is rooted in principles of adaptivity: When we adopt this mindset, we see that there are “numerous ways to achieve success,” and adjust our approach accordingly.

So how does this mindset help you master difficult conversations?

When we approach potential conflict with an integrator mindset, we approach others non-confrontationally with specific goals in mind. Approaching others with confidence and tact is important—people respond more favorably to neutrality and to those they deem confident.

For example, perhaps a peer approaches you with an issue in your latest project. They’re angry—furious even—and blame you for the problem entirely. They use harsh language, asking you, “Why on Earth didn’t you do this the way I said?”

You wouldn’t respond positively, right? Maybe you had a reason for doing the project that way, and their inability to adapt and adjust their approach aggravated what could’ve otherwise been a minor tweak.

In this example, the peer didn’t use the integrator mindset.

Guess what? You can.

Embracing Discomfort and Difficult Emotions

It’s likely you’ll feel a certain degree of discomfort when approaching and maintaining difficult conversations.

When facing a potentially uncomfortable conversation, we become anxious, on edge, and sometimes angry—that’s why we put them off to begin with.

We can’t ignore these feelings in any context, especially this one. The other person with whom you’re conversing can sense you’re on edge and would be more likely to react unfavorably.

To navigate these, I started acknowledging my own discomfort. When we understand what we’re feeling and put a name to it, we take away its power.

When I began embracing discomfort, both personally and professionally, I was able to manage difficult conversations, and more often than not, achieve positive results.

Before difficult conversations, try deep breathing, pinpointing areas of emotional discomfort, and goal-setting. You’ll relieve your sense of ‘edge’ or ‘nervousness.’

Embracing the discomfort and acknowledging the other person’s concerns is paramount and directly relates to the integrator mindset.

You’ll feel uncomfortable at first, but it’ll be incredibly influential to your professional and personal growth over time.

Simple Communication Strategies (Verbal & Nonverbal)

First things first, the most important strategy you can implement is preparation. “Failure to prepare is preparing to fail,” after all, right? Preparation goes hand-in-hand with emotional regulation and the integrator mindset.

To prepare, consider your desired outcome and think about the necessary information. Ask yourself your goal, and consider your audience: How will they react to this information?

Harvard University’s professional development publication notes the following tips on verbal communication when engaging in uncomfortable conversations:

  • Use clear, concise language

  • Repeat information only when it's necessary

  • Focus on your tone: The volume at which you’re speaking, the language you use, and your intonation (the tone and manner in which you’re speaking)

Nonverbal communication strategies build trust and rapport between you and the other person, and involve how you stand, use hand movements, and express yourself.

As I said, people are more receptive to those who they deem open and honest, and studies show that nonverbal cues are between 65 and 93% more impactful than the words we use.

The following strategies will work wonders for you:

  • Maintaining eye contact

  • Using gestures to punctuate your words and sentences

  • Standing up straight and with confidence

  • Monitoring facial expressions and remaining neutral

  • Providing the other person your full attention

When you build trust and rapport prior to and during a tough conversation, the other person is more likely to remain receptive to your message. When you start paying attention to your tone, language, and posture, those around you will take note.

Difficult People

I’ve met my fair share of difficult people, and oftentimes there’s no way around dealing with them. Bosses, family members, and co-workers can be real pains at times, but by focusing on accommodating them and adapting (there’s that word again), you can maintain positive interactions with them as you would anyone else!

In many ways, difficult people are much the same as those who ‘go with the flow.’

I use these strategies to manage my interactions with difficult people, and I highly recommend them:

  • Remain neutral and non-judgemental throughout the conversation, paying attention to your facial expressions

  • Reflect respect

  • Be curious and constructive. Approach the conversation as if it were a problem to solve and you’re optimizing for low emotion and maximum outcome

  • Ask neutral questions. Instead of saying “Why did you do this?” ask about their intentions

  • Don’t approach them defensively

  • Set personal limits and boundaries

  • Leave the conversation if things escalate

By combining the integrator leadership style, embracing difficult emotions, implementing scientifically proven effective communication skills, and using techniques to deal with difficult people, I’ve been able to significantly improve my personal and workplace conduct for the better.

Using the positive communication and adaptive strategies we’ve discussed, you too can master difficult conversations with difficult people.

This Week’s Practical Challenge

This week, I ask you to think back to a difficult conversation you’ve encountered and to consider how these strategies might’ve changed the outcome. Write down your answers to these questions, and take a moment to reflect on your actions.

  1. Recall what happened during the conversation:

    a. What was your initial objective? How did you approach the other person? Was your approach fruitful?

    b. Be brutally honest with yourself—if you’re thinking of a difficult conversation, it’s likely it didn’t end the way you initially hoped. Write down a brief overview of what happened, and why it didn’t end the way you’d intended.

  1. Consider the communication strategies you used.

    a. Which verbal communications strategies did you use: Did you respond neutrally and with confidence? Did you listen and pay attention while the other person was speaking?

    b. Which verbal strategies explained in this newsletter did you need to use?

    c. Did you utilize any nonverbal strategies? Which ones?

    d. Which nonverbal strategies did you forego?

  1. Finally, map out what would’ve happened had you implemented the techniques we discussed.

    a. Consider these techniques both in the context of the conversation and in the context of those you may have in the future.

    b. Which communications strategies and approaches feel most natural to you?

Take a look at what you’ve written, and use it to guide your next difficult conversation.

It’s time to put these into action and (finally) achieve your desired results both in and outside the workplace.


I’d love to hear from you:

Question 1: Which of these tricks do you think will be most difficult to integrate?

Question 2: What do you do to manage your own discomforts?

Tweet at me (@_alexbrogan) or respond to this email — I’ll try to respond to everyone.

Until next week,


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