Mastering Challenging Conversations: Insights from Speaking Coach Matthew Matheson

Mastering Challenging Conversations: Insights from Speaking Coach Matthew Matheson

Are you tired of those nerve-wracking, tough conversations that seem to catch you off guard? You’re not alone. As a CTO or senior technical leader, you're often thrust into challenging dialogues without a script, and those moments can be daunting. Whether it's delivering tough feedback, presenting to stakeholders, or navigating team conflicts, mastering communication is key. That’s why I recently sat down with Matthew Matheson, a renowned speaking coach who specializes in helping tech leaders like you become better communicators.

In our latest podcast episode, Matthew shares practical strategies and insights on how you can elevate your communication skills and handle tough conversations with confidence. And guess what? You can watch the full episode right here! 

Video interview

You can watch the video on YouTube or below:

Why Communication Matters More Than Ever

Let’s face it—being a great technical leader isn’t just about coding skills or understanding complex architectures. It’s also about how effectively you can communicate your ideas, motivate your team, and manage difficult conversations. As Matthew points out:

“The biggest problem tech leaders face isn’t the technology; it’s the human element. If you can’t communicate your message clearly and confidently, you’re missing out on the chance to truly lead.”

Matthew hits the nail on the head here. Think about the last time you had a challenging conversation at work. Maybe it was with a team member who wasn’t meeting expectations, or perhaps you had to justify a technical decision to non-technical stakeholders. How did it go? If it felt awkward, rushed, or unproductive, you’re not alone.

The Challenges of Tough Conversations

In our chat, Matthew dives deep into the nature of tough conversations and why they seem to escalate out of control so quickly. He highlights a common scenario:

“The biggest challenge is when conversations meant to be formal and planned turn ad-hoc and spontaneous. Suddenly, you’re on the spot, unprepared, and it feels like a minefield.”

Does that sound familiar? You walk into a meeting expecting to discuss project timelines, and suddenly you’re dealing with an unexpected conflict or performance issue. It’s these moments that often leave us flustered, feeling like we’ve lost control of the narrative.

But Matthew’s insights don’t just stop at identifying the problem. He offers concrete steps to regain control, even in the most spontaneous situations.

Matthew’s Top Tips for Navigating Difficult Conversations

So, what can you do when you’re thrown into one of these high-stakes conversations? Here are some of Matthew’s top strategies:

1. See Every Conversation as Feedback

Matthew suggests that every message, whether it’s a compliment, criticism, or neutral comment, can be seen as feedback. He encourages leaders to filter these interactions through a lens of curiosity rather than judgment.

“When you see every message as feedback, you remove the emotional charge. You’re no longer reacting—you’re responding with intention.”

2. Use Nonviolent Communication (NVC) Techniques

Matthew introduced the concept of Nonviolent Communication (NVC), a powerful framework developed by Marshall Rosenberg. It’s all about turning reactive, judgmental communication into mindful, empathetic dialogue.

“NVC helps us break the judgment cycle. Instead of escalating conflicts, we learn to express needs and make requests clearly, without blame or defensiveness.”

For example, instead of saying, “You’re not meeting your deadlines,” you might say, “I noticed the project is behind schedule, and I’m concerned about how this impacts our team’s goals. Can we discuss what’s causing the delay and how we can address it together?”

3. Shift from Parent-Child Dynamics to Adult-Adult Conversations

Matthew also explores the PAC (Parent-Adult-Child) model of communication. Often, in high-pressure situations, we slip into critical or defensive roles, which only fuels conflict. Matthew encourages leaders to stay in the “Adult” state—objective, calm, and solution-focused.

“When you enter a conversation in ‘Adult’ mode, you set the tone for a productive dialogue. You’re not scolding or placating; you’re engaging in a respectful exchange.”

How to Benchmark Your Communication Skills

One of the most common questions Matthew gets is, “How do I know if I’m a good communicator?” His answer is simple: feedback. Both external and internal feedback are crucial for understanding where you stand.

“External feedback is about how others respond to you. Are your ideas well received? Do people engage with you positively? Internal feedback, on the other hand, is about self-reflection—how did you feel during the conversation? Did you manage your emotions well?”

By regularly seeking feedback and reflecting on your own experiences, you can start to identify patterns in your communication style. Are you often rushed? Do you avoid eye contact? Use this information to set intentions for improvement.

Quick Wins for Better Communication

If all of this sounds like a lot, don’t worry—you don’t have to transform overnight. Matthew emphasizes the importance of small, actionable steps that you can start implementing today. Here are some quick wins:

1. Set Intentions Before Meetings

Before every meeting, set a simple intention. It could be as basic as “I’m going to listen more than I speak,” or “I’ll keep my responses neutral.” These small shifts can significantly impact how you engage with others.

2. Embrace the Power of Silence

Silence can be your best friend in a tough conversation. It gives you a moment to collect your thoughts and prevents you from reacting impulsively. As Matthew notes:

“Silence is power. It shows that you’re in control and thoughtful about your responses.”

3. Practice, Practice, Practice

Don’t wait for the big presentation or the high-stakes meeting to start working on your communication skills. Use everyday interactions as practice grounds. Whether it’s a daily stand-up or a quick one-on-one, treat every conversation as an opportunity to improve.

Final Thoughts

Challenging conversations are an inevitable part of leadership, but they don’t have to be a source of anxiety. With the right tools and mindset, you can turn these moments into opportunities for connection, collaboration, and growth.

Matthew Matheson’s insights offer a fresh perspective on how you, as a tech leader, can navigate the human side of your role with confidence and clarity. So go ahead, watch the full episode, take notes, and start implementing these strategies in your daily interactions. Your next tough conversation could be your best one yet.

For more insights from Matthew, you can connect with him on LinkedIn or his website where you can find more articles, podcast episodes, etc. 

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Michal Juhas

Michal Juhas