How to Communicate With Complicated People | Tim Newman Speaks

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Have you ever found yourself stuck in a conversation with a complicated coworker, wondering, “How do I actually communicate with this person to get things moving forward?” In today’s episode of Speaking with Confidence, I dive right into the core question: How can you effectively communicate with complicated people—especially when, let’s be honest, we’re all complicated in our own unique ways?


Hi, I’m Tim Newman, a recovering college professor turned communication coach, and I’m excited to guide you through practical strategies for navigating communication challenges at work. In today’s episode, I reference Ryan Leak’s insightful book, How to Work with Complicated People, which inspired much of the approach I share.


We kick things off with an all-too-familiar workplace scenario: a colleague agrees to a deadline with smiles and nods, only to send a passive aggressive note a few days later that derails the project. Your instinct may be to fire back or just give up, but I explain why that reaction rarely solves the underlying problem—because the real issue is how complicated humans communicate with each other.


Here’s what we covered:

• Why communicating with complicated people is a universal challenge
• The importance of translating your message for different audiences
• How workplace communication direction changes your approach (up, across, and down)
• Strategies for communicating up: focusing on outcomes and impact with leadership
• How to handle peer-to-peer conflict through respect, questions, and common ground
• Four keys for giving clear, motivating direction to your team
• The difference between tactical fixes and building a true communication system
• The foundational skill of knowing your audience and message, and why it’s essential for every workplace conversation

Whether you’re reporting to a boss, negotiating with coworkers, or leading a team, you’ll leave this episode with actionable techniques to stop the cycle of miscommunication and start showing up—every single time—with clarity and confidence. Remember, the goal isn’t perfection—it’s consistent progress.


Before I sign off, don’t forget to grab your free eBook, “The Top 21 Challenges for Public Speakers and How to Overcome Them,” at speakingwithconfidencepodcast.com, and check out our Formula for Public Speaking course. Thanks for listening and always remember: your voice has the power to change the world.


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