By Matteo Cassese. I help brilliant overthinkers lead.
The brief I usually get from director level clients sounds like this: my career grew thanks to my hard skills, being the best at finance, the best at design, and now I need to step up because I will have an even larger team. Most of my job will be talking to people, and I need better communication skills.
In my experience what we call leadership is 80 percent communication. How do you get your team to do the job? You can’t just say, do this.
The leadership communication skills that decide what happens in a room are four strategies you can rehearse in a sentence: framing, directing attention, holding tension and saying the harder thing.
Why most lists of leadership communication skills are useless
Active listening, empathy, authenticity, clarity: all great qualities. Some people have these qualities by nature. I’m not one of them. For me good confidence communication is not innate. Otherwise I wouldn’t be able to teach it. Because if for me it was natural I would say: yeah, just be charismatic. Many of the traits of great communicators are non-transferable. Storytelling is transferable. Self-motivation is very hard to transfer, and it’s not a trait that you learn.
What can be taught is a strategy, something you do. I’m Italian, so in the United States I know I need to tone it down. In Italy nobody listens to you unless you’re very assertive, and that doesn’t work where everyone acts very politely. The same person, two continents, two different behaviors: that is a skill, and you’re constantly adapting your communication style to the person in front of you.
The four leadership communication skills that decide outcomes
How do we get out of our heads? The only way I know is to learn how to get into the audience’s head. The four strategies below all do that.
1. Framing: deciding what the thing is before you explain it
Framing is the use of specific words to influence a conversation. A frame is made of one or multiple words that assume meaning in the ears of the audience.
“Zero confidence strategy” is a frame I use often. “Confidence in chaos and conflict” is another one. This website has a button up on the right that says “Stuck?”. That’s another frame. I help “brilliant overthinkers,” that’s another frame.
Once you introduce a frame in a conversation, your interlocutors can’t help but have these words in their mind.
The brilliant linguist George Lakoff explains this brilliantly in the short book “Don’t Think of an Elephant!” Once you read the title of his book, you can’t help but have the image of a pachyderm in your mind. That’s the power of a frame.
In the worst sense you may have encountered framing in the form of spin. That’s where layoffs become rightsizing, a dangerous sounding oil spill turns into an innocent accidental discharge, where a strategic price hike becomes a forced inflationary alignment.
2. Directing attention: knowing exactly what you want the listener to hear and remember
Directing attention is picking, inside the sentence you’re about to say, the one word that carries the meaning and putting the weight there.
I put the emphasis on that word: a long pause before, a long pause after. We have a strong competitive advantage. You can say the same sentence in many different ways. Do you emphasize strong, competitive or advantage? The choice is yours.
My emphasis helps my audience digest what comes next: I’m going to explain our biggest competitive advantage. What is it? I can create anticipation, interest, curiosity before I reveal what it is. For instance “the customer relationship.” But why is it such an advantage? Now the list of advantages is eagerly awaited by my audience.
Communication is leaky by definition: directing attention helps the audience orientate in the sea of information thrown at them.
3. Holding tension: not resolving the discomfort too early
All communication is about change. If we don’t need to change the hearts, minds, opinions of those in front of us, we usually don’t communicate. Most communication is not really just about information: we are not taking the stage just to say “the exit is to the left.” We talk because there is something substantial that needs to change in our audience.
A mistake that a lot of inexperienced communicators make is to try and make it easy for the audience to go through the tension of change. Whenever change needs to happen, we want to announce this change and then help the audience go through the emotional journey of resisting this change before adopting it. We don’t want to defuse the conflict. We must lean into the resistance, opposition and discomfort of our audiences to help them change and see how we deal with the conflict of change. So holding the tension is fundamental in communication. Holding the tension is also fundamental in mindset.
Whenever you have a problem, you try to jump to the solution rather than stay with the discomfort. There’s always an eagerness when you have the solution, but you have to withhold the solution. When two people in the room disagree, say both positions back and do not resolve it in the first minute: this conflict, before it’s resolved, needs to blossom.
Transcend means to get over. The way I read Jung’s transcendent function: if you hold two conflicting ideas, a third way can emerge, on one condition, that you hold the tension. That is exactly what we do not do. So, for instance, are we taking the car or the plane? We are swimming.
4. Say hard things: stop avoiding them
Saying hard things means naming the problem while everyone else tiptoes around it.
We’re so worried about tension that often we take everything interesting out of our communication, and all that is left is information. “This is a window.” We can all agree, that’s just information. If I say this is a window and you see a door, what I see is different from what you see, then we have a conflict, and that is interesting. Somebody needs to raise their hand and say, we have a problem, and nobody wants to do that, because usually who raises their hand is made into a martyr.
If you measure your self-worth by the smiles and harmony you create around you, you’ll never begin communicating.
If these four read like things you already know and still don’t do, that gap is the work I call founder communication coaching.

The skill nobody lists
What if my objective is to leave my audience with a doubt? Not conviction, not a change of hearts, the doubt that they should pay more attention to what I have to say. A doubt is the beginning of a conflict, a conflict between what they thought before and a new idea growing in their minds.
Whenever there is conflict, communication is working: we try to make everything clean and sanitized, with no emotions and no conflict, but communication begins when people start discussing. When you say something and it lands completely flat, with no pushback, communication is not really working. Most of the time it even begins with a misunderstanding, and that misunderstanding can be the beginning of something great.
We repeat things three times because we expect people not to pay attention. My communication is only as good as what you receive.

Five questions for your next meeting
- What is the one thing you want them to repeat when they leave the room?
- Which word in your opening statement carries most meaning?
- What frames are you introducing and why?
- What is the problem you are avoiding naming?
- What did they say back, and what did you hear?
Questions leaders ask about leadership communication skills
What are the most important leadership communication skills?
The four leadership communication skills I would work on first: give the question back in your own words before you answer it. Pick the one word in your sentence that carries most meaning and put the weight there. When two people disagree, say both positions back and leave the question open. Name the problem the room is avoiding.
How do you improve leadership communication skills?
Improving leadership communication skills is a mindset shift that happens inside of us. Watch people with less knowledge but more ability to communicate: they are tailoring the message to the audience.
Why do senior leaders struggle to communicate?
I call them sharks with a floppy fin: a director or even C-suite who has done everything they can with their hard skills, and now their soft skills are holding them back. We always think we’re saying something of no consequence, because we are experts, because we know much more than what we say.
What is the difference between clarity and simplicity?
Clarity is using just enough words, just the right concepts, for you to understand. Simplicity is expressing ideas at the most understandable level of articulation. As simple as possible, but no simpler. Essential, not watered down.
How long does it take to improve?
In my coaching the breakthrough, the big change, usually happens in eight to twelve weeks. First you break the fear, the emotional component, and then you’re free to start communicating. The refinement takes three to six months. Then every day for the rest of your career.
Can leadership communication skills be coached?
While most communication coaches will help you work on how you communicate, I have no problem in helping you work on what you’re going to say. If we can figure out a message that is punchy and clear, how you say it is less important. Bring the meeting you’re dreading, and we start there.
What to do next. Before your next board meeting, all-hands or investor call, write the one sentence you want them to repeat when they leave the room, and find the word in it that carries most meaning. If you’ve done that and the audience still doesn’t move, I can help. I call it founder communication coaching.
What you should do next
Discover what’s holding you back from the inside out. Understand where you naturally have leverage and where it eludes you.
Take the free founder mindset course.
Tell me where you want to go. I’ll tell you how we get there.

About Matteo Cassese
Business coach, keynote speaker, and mythmaker, Matteo helps leaders thrive in chaos and conflict. Twenty years across tech, film and consulting, seven of them at Warner Bros., founding-team at Netflix Italy, and advisory work for Sony, LinkedIn and Heineken. His unique perspective as a queer nerd passionate about mythology and technology creates a safe space for leaders to be vulnerable and reach their full potential. Read more about Matteo.

