Why I Suck At Communicating


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Why I Suck At Communicating

Raise your hand if this sounds familiar:

You’re in a meeting, your friend's venting about their job, or you’re on a first date. The other person asks you a question. You give a response, they share their thoughts, and so on.

Back and forth you go, like a tennis match. Serve and return.

But it lacks depth. There’s no real understanding or connection being built.

That’s because most of us are absolutely awful at communication. We listen to respond rather than understand. And this ruins our relationships and impedes our success.

As legendary basketball coach Dean Jackson put it:

“Listening is an art that requires attention over talent, spirit over ego, others over self.”

The quality of your listening and communication ability directly impacts almost everything:

  • Sales ability

  • Leadership skills

  • Relationships

  • Overall life enjoyment

So why do we all suck so badly at simple talking and listening?

In this newsletter, we’ll uncover root causes for communication breakdowns and 5 critical frameworks to fix them. Master these and you’ll transform the way you build relationships and influence people.

Let’s dive in.

Why We’re So Bad At Talking

To mix sports metaphors, when I first started podcasting it felt like being thrown into the deep end.

I was forced into conversations with brilliant people – authors, entrepreneurs, philosophers.

At first, I relied on shallow questions begetting shallow responses. It was like verbal tennis - back and forth but no depth or connection.

This wasn’t entirely my fault...

From childhood, we’re conditioned to approach communication like a match rather than a dance. Two warring sides rather than a cooperative flow between two people.

We’re taught to avoid vulnerability or exposing too much. Play your cards close to your chest rather than putting your real self out there.

But real communication requires openness and honesty. Letting your guard down rather than sword fighting with words.

On top of this, several cognitive biases lead us astray. We filter information through our existing beliefs and leap to conclusions rather than carefully considering other viewpoints.

Biases + walls up + verbal jousting = communication breakdowns.

Luckily, frameworks beat frustration. With the right mental models, you can quickly level up your listening abilities.

Here are 5 of my favorites for avoiding assumptions, diving deeper into conversations, and filtering out the noise to zoom in on what really matters.

Framework #1 - Climb Down The Ladder

We all know communication involves speaking AND listening. But too often we just wait for our turn to talk rather than focusing intently on understanding the other person.

A model called the Ladder of Inference explains why.

As we take in information, we unconsciously:

  1. Select “data” that fits our existing beliefs

  2. Interpret what we select based on our biases

  3. Draw conclusions that fit our worldview

  4. Develop beliefs based on those conclusions

  5. Take actions aligned with those beliefs

Then the loop repeats – our actions impact the data we select next time, fueling our biases.

This all happens subconsciously without us noticing!

As you can imagine, these mental shortcuts wreak havoc on mutual understanding.

To “climb down” the ladder and empathize, pay attention to how your beliefs color incoming information. Observe your internal voice judging and reacting. Question your conclusions and assumptions.

Actively reprogramming your reactions takes effort. But it’s worth it.

Suspend disbelief and approach conversations with an open, curious mindset. You’ll be amazed what you discover.


Source: Designing Regenerative Cultures

Framework #2 - The Five Whys

When a topic piques your interest, resist the urge to settle for surface-level discussion. Go deeper by asking “Why?” 5 times.

For example:

You: Why do you feel unfulfilled at work? Them: Because my manager doesn’t support my goals.

You: Why don’t they support your goals? Them: They don’t align with upper management’s objectives.

You: Why aren’t they aligned? Them: The executives are prioritizing short-term profits over long-term vision.

You: Why are short-term profits being prioritized?

And so on...

Like peeling an onion, asking "Why" exposes layers of meaning and gets to the heart of issues. This builds understanding and rapport.

Sometimes you’ll hit a dead end answer, like “I don’t know” or “That’s just how it is." Other times you’ll strike gold.

Either way, it avoids superficial small talk and forges real connections.

Framework #3 – Frame The Conversation

Teachers use an instructional design technique called “affective framing” to plan lessons. The idea is tying course content to student values and motivations increases engagement and information retention.

We can apply this idea to communication.

Start conversations by clearly stating:

  • What piqued your interest in the topic

  • What you're curious or concerned about

  • What you hope to learn or accomplish

This frames the dialogue and provides guardrails to prevent drifting off course.

It also shows you’re genuinely invested in the discussion, not just exchanging platitudes. This encourages vulnerability and honest sharing from the other party.

Regularly reconnect with your original motivation if the conversation runs long. This maintains focus and attention span.


My arena where I practice (The Success Story Podcast)

Framework #4 - Cut Through The Noise

Beyond poor listening, we fail at explaining our own thoughts clearly. Every discussion has:

  • Signal – The core message/idea you want to convey

  • Noise – Anything confusing, distracting or diluting the signal

Noise mucks up communication. You lose people’s attention and interest.

To cut through noise:

  • Boil down concepts to a simple essence

  • Use clear language – avoid jargon

  • Ask focused, one-point questions

  • Repeat back understandings to verify accuracy

This prevents misunderstandings and endless back-and-forth clarification.

Framework #5 - Pareto To Priorities

The Pareto Principle states 80% of outcomes result from 20% of activities. AKA the “vital few” dictate the “trivial many.”

This applies to conversations. We waste time endlessly debating trivial details at the cost of discussing critical issues.

Prioritize the 20% producing the most value:

  • Complex decisions needing clarity

  • “Undiscussable” issues causing tension

  • Different perspectives requiring empathy

As NYC ad legend Rory Sutherland said, “Allocate your best minutes to the thorniest problems.”

Address the hardest, most important topics first. Everything else becomes easier or redundant.



The Power Of Listening

Improving communication and listening skills generates tremendous benefits:

Strengthens Relationships

My closest friends are people who intently listen, ask thoughtful questions, and share openly. Vulnerability builds bonds.

When someone truly listens to you, you can’t help but feel valued and respected. This draws others like a magnet.

In fact, many key business contacts began as conversations where I simply listened with care. Listening comes before understanding, understanding before trust, trust before collaboration.

Boosts Leadership Ability

Leaders who listen effectively unlock new ideas and earn others’ buy-in. Who wants to follow a leader with all the answers rather than one committed to understanding them?

Former Secretary of State Dean Rusk summed it up: "The best way to persuade people is with your ears, by listening."

Improves Sales Results

Clients want to feel heard and understood. Master communicators uncover real needs rather than relying on persuasion gimmicks.

As legendary sales trainer JW Owens said, “If you listen well enough, the prospect will tell you exactly how to sell them.”

Enhances Life Enjoyment

Having great conversations fills life with meaning. Moments of genuine understanding remain etched in memory forever.

As author Stephen Covey wrote, “Most people do not listen with the intent to understand; they listen with the intent to reply."

Choose differently. Listen to connect vs simply respond.

Action Steps

Start improving your listening today with these steps:

  1. Observe your reactions during conversations. Notice judging statements and hasty assumptions.

  2. Suspend reactive conclusions. Approach discussions with openness.

  3. Ask "Why" 5 times when intriguing topics arise. Peel the onion.

  4. Frame conversations by stating your motivation and desired outcome upfront.

  5. Identify the signal amidst the noise. Prioritize the 20% accounting for 80% of value.

Master these frameworks and watch your influence & communication skills skyrocket.

Wrapping Up

The next time you’re talking with someone, catch yourself mid-sentence. Stop, take a breath, and simply listen.

Give them space. Seek understanding over argument. Find common ground.

I guarantee you’ll both walk away better for it.

As the saying goes, we have two ears and one mouth for a reason.

Or in other words, seek first to understand rather than be understood.

If you enjoyed this article, I’d love to hear from you.

Email me at scott@scottdclary.com or tweet at me @ScottDClary and I’ll do my best to get back to everyone!


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