From Awkward to Awesome: How To Handle Tough Conversations (+ Free 1:1 Coaching)

Some conversations make me feel like I’m pulling teeth. 

Others are more like I’m walking on eggshells (only slightly less unpleasant), and some feel like being lodged between a rock and a hard place—with night quickly closing in.

As a leader, I’m sure you know exactly what I mean.

I've seen some of the most experienced leaders struggle with tough conversations in my 20 years at TTGG. 

I get it, they're not pleasant, but they're a necessary part of being a strong and influential leader. 

Why Are Some Conversations So Hard?

During one of my earliest team coaching sessions as a facilitator, one of the younger leaders described a tough conversation she’d recently had.

An employee was underperforming and needed to address the issue by giving constructive feedback. 

Understandably, she was worried: about damaging their relationship, being seen as the “bad guy,” and even the possibility that the conversation might escalate.

But what makes conversations like these so agonizingly difficult?

Cognitive Dissonance

Cognitive dissonance describes any kind of conflict between what you need to do and how you feel about doing it. 

Here’s something most leaders don’t already know: there’s a valid psychological reason that tough conversations are "tough.”

You can blame it on cognitive dissonance—but let me illustrate. Have you ever: 

• Wanted to be honest with a colleague but also needed to withhold confidential details?
• Needed to share bad news with a hard-working teammate who is still underperforming?
• Had to confront a coworker (whom you like) about a complaint from someone else?

How did those situations make you feel? Nervous? Guilty? Or like a sellout?

Cognitive dissonance describes any kind of conflict between what you need to do and how you feel about doing it. 

And sadly, it’s almost unavoidable when your role involves:

• Addressing problems that could spiral out of control
• Giving teammates guidance and feedback
• Supporting positive behavioral change, and
• Helping teammates reach their full potential.

…Basically, anything that relates to being an effective leader.

How To Handle Tough Conversations

It's one thing to understand why tough conversations are difficult; it's another to know how to handle them. 

This week, I’d like to share three tips to help you navigate unpleasant interactions with self-awareness, confidence, and professionalism.

Prepare Yourself

Sounds obvious, right? 

The truth is that you’d be surprised how many people don’t think their message through before diving into tough conversations.

Considering the other person’s perspective and potential reactions is important if you want to plan your approach and avoid getting caught off guard. How might they react? What concerns might they raise, and how would you react if these things happened?

Be Direct And Specific

A straight-to-the-point approach during tough conversations can really reduce the potential for misunderstandings and misinterpretations. 

The more direct and specific you can be in interactions like these, the easier it is for colleagues to understand your perspective. The last thing you want is to create more confusion or uncertainty, which can lead the other person to misinterpret any sugarcoating as insincerity.

Listen Actively

Active listening is one of the most important skills we try to teach in our communication and influence workshops. 

Listening actively means trying to understand the other person’s viewpoint by asking questions, summarizing, paraphrasing, and clarifying. 

This is a particularly useful tip if you’re actively trying to establish common ground or move towards a win-win solution.

Over to You

Handling tricky conversations isn’t as simple as I’ve made it sound, you’ve probably realized, because it requires a wide range of communication and influencing skills. 

That’s why I’m offering one free 1:1 coaching session as this week’s 20th Anniversary TTGG giveaway.

If you’re interested in finding out more about your communication strengths and weaknesses at a deeper level, this 1-hour session will be focused on:

• Exploring leadership situations that trigger cognitive dissonance for you
• Understanding your “go-to” communication styles in these contexts
• Identifying ways to strengthen how you handle tough conversations, and
• Learning actionable techniques for confidently handling them in the moment.

Whether you're struggling with delivering feedback, managing conflict, or addressing sensitive topics, it can help to take a closer look. Send me a DM with a description of the communication topic you’d like to focus on, and don’t forget to sign up at this link:

Sign up here

Looking forward to hearing from you! ??

— Govert