Communicating with Complicated: 7 Tips for 360-Degree Collaboration in the Workplace

In his new data-driven book How to Work with Complicated People, speaker and bestselling author Ryan Leak shares powerful collaboration strategies so that you can work effectively with nearly anyone. This blog post has been adapted from chapter 8. You can order your copy here.

There is often a gap between what’s coming out of our mouths and what’s going into their ears. We might assume we are great communicators and that everyone around us knows exactly what we mean, but that’s probably not true. Communication is always at least slightly broken because we are imperfect, complicated humans trying to get our points across to other imperfect, complicated humans.

In a 2021 poll by Gallup, only 7% of respondents strongly agreed that communication at their place of work was “accurate, timely and open.” That means the other 93% felt there was clear room for improvement in one or all of these areas.

Nowhere is this communication gap more evident—and potentially more dangerous—than when you’re working with complicated people. It’s challenging enough to avoid misunderstandings when the person on the other end of the call, email, direct message, conference table, or in-person convo is someone you see eye to eye with. It’s a whole new level of crazy when you’re dealing with someone who is challenging or difficult.

If you’re dealing with complicated individuals regularly, take a fresh look at your communication style. Who you’re talking to changes everything. Just think about how you’d say something as simple as “no” to a few different people. For example: your parents, your spouse, your kids or other children, that one neighbor you like, that other neighbor you don’t like, a police officer who just pulled you over… you get the picture. You’d change everything from your tone to your posture to your wording, depending on the person on the other end of your “no.”

Do You Know Who You’re Talking To?

When it comes to the “who” in the workplace, it’s helpful to think directionally. You have to consider whether you’re talking up, down, or across. That is, within the particular structure and hierarchy of your company, are you communicating to people who lead you, people you lead, or people who are on the same level as you? To put it another way, are you dealing with a complicated boss, a complicated direct report, or a complicated coworker?

Speaking “Up”

Let’s start with how you talk to your boss, directors, or C-suite executives. Even if they aren’t complicated personalities, the mere fact they have so much power over your workday, job role, and career trajectory is complicated. And if, on top of that, they are complicated . . . then you’ve got your work cut out for you.

1. LEARN TO SPEAK C-SUITE.

Communicating effectively with C-suite executives—such as CEOs, CFOs, COOs, and CIOs—and other high-level leadership 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 using terms and concepts that make sense to them. Your communication with them needs to fit within their strategic, high-level perspective.

One way to do this is by understanding and utilizing key business concepts that resonate with them. This goes beyond just memorizing technical terms such as ROI, KPI, scalability, stakeholder engagement, sustainability, risk management, and value proposition. It’s also about understanding why that language matters and framing your conversation to align with their goals. It’s about learning what matters to the people upstream, then finding strategies to get your message across.

2. STAY READY SO YOU DON’T HAVE TO GET READY.

When you think of preparing to communicate well, your thoughts might jump straight to PowerPoint decks and spreadsheets, but preparation has to start sooner and go deeper than that. Learn to pay attention to the breadcrumbs your leadership continually leaves behind that show you what they value the most. Then, when you’re having a conversation or making a presentation, you’ll naturally address the concerns and goals they care about the most.

Speaking “Across”

Next up: How do you communicate with a complicated peer?

1. START WITH RESPECT.

​​In the case of a peer, you’re respecting a few things, including their autonomy as a human being, expertise, experience, knowledge, and finally, their lane or area of responsibility.

That means you don’t try to control them or do their job for them, and you don’t treat them rudely, even if they kind of deserve it. You can make suggestions, especially if their difficult behavior is causing problems for you, but you can’t really force them to do anything they don’t want to do. You can’t swoop in and demand they conform to your ideals.

In your conversation, make sure respect is at the forefront. Rather than saying, “You’re wrong,” say, “I have a different perspective. Instead of, “You messed everything up,” try, “Could you explain your thinking here?”

2. ASK REALLY GOOD QUESTIONS.

Since you can’t control them, you need to convince them. But you won’t convince them until you connect with them, and you won’t connect with them until you truly listen to them. In that complicated process, questions are your secret weapon. What do you think about this idea? How do you see this problem? Have you ever gone through something like this before? What do you think our goals should be in this situation? What would you suggest here? What dangers do you see? If you get them talking, they’ll often talk themselves right into thinking more highly of you, and that’s always a win.

Speaking “Down”

Whether you’re an executive, a manager, or anyone else tasked with leading complicated people, the good news is that your downline communication, just like the other directions we’ve discussed, can be improved with a little intentionality.

1. KEEP IT REAL.

Don’t beat around the bush. Don’t spin or sugarcoat things. People have brains and feelings, and they deserve to be treated like it. Whether you’re talking about a difficult topic or talking to a difficult person, remember they are intelligent and aware, and treat them accordingly.

In early 2024, Nike was forced to lay off over 1,600 people from their workforce. In a memo sent to employees, CEO John Donahue wrote, “This is a painful reality and not one that I take lightly.” He added, “We are not currently performing at our best, and I ultimately hold myself and my leadership team accountable.” He kept it real. That’s horrible news to have to deliver, and there’s no easy way to do it. But there is a clear, respectful, humble way to do it, and that is always the best road to take.

2. KEEP IT SIMPLE.

When you’re navigating a thorny topic, don’t use so much jargon that it feels like lawyers put it together with a splash of ChatGPT. You don’t want people to walk away from the message saying, “So what did they just say?” Whether you’re dealing with a challenging topic, person, or both, clarity is your friend.

3. KEEP IT INTERESTING.

Do you know what makes things interesting to people? When they see how it matters to them. Rather than just launching into numbers and charts, tell stories. Show human impact. Connect with people on the level of their motivations. What do they need? What do they want? What are they afraid of? What are they excited about?

4. KEEP IT HOPEFUL.

Give them a light at the end of the tunnel, especially when you’re communicating change or asking them to do something they aren’t super excited about. Help them see that the current challenge or hardship won’t last forever and that their effort, sacrifice, and growth will be worth it.

Ready to master the skill of collaboration?

Ryan Leak’s How to Work with Complicated People prepares you to build bridges with almost anyone – even the most picky, prickly, problematic people in your workplace. Discover how to…

• Detox from unrealistic expectations and get comfortable with complicated
• Communicate effectively in complex environments
• Embrace healthy disagreement as a tool to discover better solutions
• See challenging individuals as human beings to understand rather than problems to solve
• Set boundaries that let people into your world without letting them run your world

Order your copy here today and prepare to revolutionize your workplace relationships!