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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Transcript
Tim Newman [00:00:09]:
Welcome back to Speaking with Confidence, the podcast that helps you build soft skills that lead to real results. Communication, storytelling, public speaking, and showing up with confidence in every conversation that counts. I'm Tim Newman, a recovering college professor turned communication coach, and I'm thrilled to guide you on a journey to becoming a powerful communicator. If you haven't read Ryan Leak's book, How to Work with Complicated People, I highly suggest it. I must warn you, though, that it's not a book about how to manipulate or coerce people to think or act like you. Instead, it serves as a guide or reminder for you to look inward at yourself. Because we are all complex individuals. Today I.

Tim Newman [00:00:51]:
I want to talk about how to communicate with complicated people. Keep in mind, we're all complicated. Let's say you're in a meeting and a peer agrees to a deadline. They nod, they smile, they say, I'm on it. Then three days later, you get the email. It's a passive aggressive note about unrealistic expectations and competing priorities. They just silently derailed the project and you're left feeling angry, defensive, and completely stuck. This is the trap.

Tim Newman [00:01:26]:
Your instinct is to fire back, to defend your position or maybe just give up on them entirely. And that instinct is wrong. The problem isn't necessarily that they're a bad person, is that communication between complicated people is inherently broken. We're all imperfect humans trying to get our messy points across to other imperfect humans. The data proves it. In a Gallup poll, a staggering 93% of people felt their workplace communication was not accurate, timely, or open. Think about that. 93%.

Tim Newman [00:02:04]:
So that means only 7% felt it worked well. That means nearly everyone you know is struggling with this exact same problem. But what if you could stop the cycle? Instead of talking at them and hoping they finally understand? What if you started translating for them? The secret isn't changing them, it's changing your approach based on one critical direction. Our default communication mode is usually just broadcasting. We have an idea, we explain it from our perspective, and we get frustrated when it doesn't land. We assume that because the words make sense to us, they should make sense to everyone else. That's like speaking English to someone who only understands French and just talking louder and or slower when they don't respond. This is where the concept of direction becomes your most powerful tool.

Tim Newman [00:03:04]:
Every single professional communication has a direction. You are almost always communing in one of three ways. Up to your supervisors and leaders, across to your peers and teammates, or down to your subordinates or anyone you're Directing. The only other way that we communicate is out to our customers or constituents. But we're only going to focus on these three today. Each of these directions comes with a completely different set of priorities, pressures and perspectives. The message might be the same, but the way you package it has to change dramatically. Think of it this way.

Tim Newman [00:03:44]:
When you communicate up, you're talking to someone who is thinking about strategy, revenue and the big picture. When you communicate across, you're talking to an equal who is worried about their own workload, reputation and goals. And when you communicate down, you're talking to someone who needs clarity, direction and motivation. Your one size fits all approach fails because you're using the same language for three entirely different conversations. Translation isn't about manipulation, it's about precision. It's the deliberate act of encoding your message so it can be decoded correctly on the other end. And it starts with the most high stakes direction. Communicating up.

Tim Newman [00:04:29]:
When you're talking to your boss or your boss's boss, you have to understand the world operates at a different altitude. They are not typically focused on the granular, step by step process you use to complete a task. They are focused on outcomes, impact and strategy. They speak the language of results, not effort. There's a great quote from Ryan Lee's book that nails this. He says communicating effectively with C suite executives requires that you frame your information or request in the context of what your leadership is aiming for and cares about. And you have to do it in using terms and concepts that make sense to them. Your communication with them needs to fit within their strategic, high level perspective.

Tim Newman [00:05:16]:
So let's break that down into an actionable technique. The most common mistake people make when communicating up is presenting operational details. You walk in and say, we had a server issue. So I spent 6 hours re indexing the database, which required coordinating with the infrastructure team. And then I had to run a series of diagnostic scripts. Their eyes glaze over. Heck me even saying that my eyes glaze over, but you've just given them noise. The translation is to convert your effort into their strategic impact.

Tim Newman [00:05:52]:
The same update translated sounds like this. The same update translated sounds like this. We identified a potential risk to system stability that could have impacted customer transactions. I led the resolution and the fixes, safeguarded our revenue stream for this quarter with no downtime. See the difference? You took the technical problem and connected it directly to a business outcome. They care about revenue and stability. You didn't just tell them what you did, you told them why it mattered to them. This translation doesn't just convey information.

Tim Newman [00:06:31]:
It builds immense credibility. It shows you understand the business, not just your job. And it's the fastest way to get your ideas heard and respected by leadership. But what about when the complicated person isn't above you, but right next to you? Communicating across, with or to peers is often the most emotionally charged. You share the same status, but you don't share the same goals, pressures or perspectives. And this is where passive aggressiveness, defensiveness and outright conflict fester. You can't pull rank and you can't just delegate. You need a different strategy, a three step system to de escalate and find common ground.

Tim Newman [00:07:19]:
Step one is non negotiable. You must start with respect. Even if you're furious, even if you feel completely disrespected by them. You have to model the behavior you want to see. You can control the tone of the conversation from the very first word. This isn't about being a pushover. It's about being strategic. You're lowering the temperature before the real negotiation even begins.

Tim Newman [00:07:48]:
Step two is where most people fail. You need to ask really good questions. And this is the opposite of lashing out. Instead of accusing them with why did you change the deadline without telling me? You ask a clarifying question. I saw the project timeline shifted. Can you help me understand what changed on your end so we can get it aligned? You see, a good question forces clarity. It forces them to articulate their position. And it often reveals that conflict isn't personal.

Tim Newman [00:08:19]:
It's usually a clash of priorities or even a simple misunderstanding. Your goal is uncover their why. This leads to step three. Notice where your worlds collide. In every peer conflict, there's almost always at least one shared objective. Your job is to find it. Maybe you both want the project to succeed, even if you disagree on the method. Maybe you both want to look competent in front of your boss.

Tim Newman [00:08:51]:
That point of collision, that shared interest, that's your anchor. And once you identify it, you can pivot the entire conversation from you versus me to us versus the problem. You stop negotiating from opposing sides and start collaborating from a position of mutual benefit. This three step course turns a potential collision into a coordinating maneuver. Now let's flip the script. When you're the one in charge, communicating down to your team requires a completely different translation. This isn't about collaboration between equals. It's about providing clear direction that inspires action and maintains momentum.

Tim Newman [00:09:37]:
The biggest mistake leaders make here is either micromanaging every detail or being so vague that the team has no idea what to do. Your translation needs to achieve clarity without Suffocation. Think of it as four keys to effective direction. The first key is to keep it real. Your team can smell corporate nonsense from a mile away. Be honest about the challenges. If the deadline is tight, say it's tight. If there are obstacles, acknowledge them.

Tim Newman [00:10:10]:
Authenticity builds trust far more effectively than false optimism. They need to know you're giving them the straight story. The second key is to keep it simple. You might understand the 27 interconnected steps required to launch a new product, but your team needs to know the next three actions they're responsible for. Complexity paralyzes simplicity and powers. Break down the big scary goal into digestible actionable chunks. Your main role is to be a clarifier, translating strategic complexity into operational simplicity. The third key is to keep it interesting.

Tim Newman [00:10:52]:
Nobody is inspired by a task list. Connect the work to a larger purpose. Explain how this project helps a client, advances a company's mission, or provides a specific skill they can add to their resume. You have to make them care about the why behind the what. And this is what turns a chore into a challenge. And fourth, perhaps the most important key is to keep it hopeful. You must express genuine confidence in their ability to execute and your direction with belief. A simple I know this is a challenge, but I have no doubt the team can pull it off is incredibly powerful.

Tim Newman [00:11:36]:
It combats imposter syndrome and builds morale. And when you combine these four keys, keeping it real simple, interesting and hopeful, you're not just assigning tasks, you're leading people. You're providing the translation they need to move from confusion to confident action. So we've covered the map. Translate up by speaking the language of strategy, across by using a three step de escalation process, and down with four keys to clear direction. These are powerful immediate tactics you can use the next time you face a complicated person who isn't you. But here's the thing. These are just tactics.

Tim Newman [00:12:21]:
They solve specific problems in specific directions. What you really need to stop the cycle of miscommunication for good is a system, a framework that lets you walk into any conversation with any person in any situation and know exactly how to structure your message so it lands that systematic approach. The foundation of all effective communication is knowing your audience and message. It's the core skill that makes translation possible. And it's the first principle we teach. Master that and you stop reacting to complicated people and start leading the conversation. That's all for today. Remember, we're looking for progress, not perfection.

Tim Newman [00:13:07]:
Be sure to visit speakingwithconfidencepodcast.com get your free eBook, the Top 21 Challenges for Public Speakers and How to Overcome Them. You can also register for the Formula for Public Speaking course. Always remember, your voice has the power to change the world. We'll talk to you next time. Take care.