Sell by Listening: Mastering the Subtle Art of Shutting the #%$* Up

Courtesy of Kristina Flour of
“The quality of your life is reflected in the quality of questions you ask yourself”

The old sales adage is to lead with questions.

Rather than “show up and throw up”, success is often found in the ability to ask good questions.

However, I often observe sales professionals and marketers making the same mistake I saw among my medical school classmates; asking questions for the sake of asking questions.

Do you add more value by asking a question that shows how smart you are or to demonstrate that you “care about their problems”?

Maybe, but that’s not what converts a prospect in the pipeline into a sale or an optimized marketing campaign to have more conversions.

So what’s the variable we can change here to have better quality questions that give us more information to sell?


Like any student of the game does, I researched the topic and pulled the best practices from behavioral therapists and psychology to improve my ability to listen, or what I call-

The Subtle Art of Shutting the Hell Up

Ken Husted, a sales director I had the fortune to work with, has a great saying -

Listen with two ears and one mouth.

This article is in honor of this simple yet powerful advice many of us young leaders got to learn under Ken’s mentorship.

Amazing things started to happen when I actually put his words into action (or perhaps in this case, inaction).

Customers gave me more valuable information, executives I admire suddenly had more pearls of wisdom to share.

However, I also realized that just because I had my mouth shut didn’t mean I was listening.

As I discovered, being quiet while someone is speaking does not constitute real listening.

Committing to Compliment

Listening is a commitment and a compliment.

It’s a commitment to understanding how other people feel, their worldview, and how they fit their feelings into that view.

That entails putting aside your own prejudices and beliefs, your self-interest and anxieties, and start to see the world through their lens.

Listening is a compliment because it says “Hey, I care about what’s happening/happened to you and your perspective is important to me”.

Bill Clinton is said to have the ability to make anyone feel as though they’re the only thing that matters in that moment.

We all have rose colored glasses on in this world, but they’re different shades of red.

Listening comes in two forms: Real and Pseudo.

Real Listening

Real listening is based on the intention to do one of these four things:

  1. Understand someone
  2. Enjoy someone
  3. Learn something
  4. Get help or solace

Whether it’s helping someone express their thoughts, understanding a point of view, or learning, the key to listening is wanting and intending to do so.


Unfortunately, pseudo-listening parades around and masquerades as the real thing.

However, I quickly found that a lot of pseudo-listening does not have the intention of listening, but the intent to meet some other need of ours, such as:

  1. Making people think you’re interested so they will like you.
  2. Being alert to see if you’re in danger of being rejected.
  3. Listening to one specific piece of information and ignoring everything else.
  4. Buying time to prepare your next comment.
  5. Half-listening so someone will listen to you.
  6. Listening to find someone’s vulnerabilities.
  7. Looking for the weak points in an argument so you can always be right or listening to get ammunition for an attack.
  8. Checking to see how people are reacting, making sure you produce the desired effect.
  9. Half-listening because a good, kind, or nice person would.
  10. Half-listening because you don’t know how to get away without hurting or offending someone.

Blocking Our Ears

Mental blocks (aka cognitive biases) are a common cause to poor decision making. The same goes for listening.

There are twelve listening blocks that obstruct us from listening:

  1. COMPARING — You can’t listen if you’re comparing what they’re saying to what you said/are about to say.
  2. MIND-READING — Thinking about what the other person is thinking actually shows you distrust them. You hear them say “they’re happy” but really you think they’re not. The mind-reader spends less time paying attention to words and more time on intonations and subtle clues in order to see through to the truth.
  3. REHEARSING — No time to listen to the other person! Your attention is on preparation and crafting your next comment.
  4. FILTERING — This is one where cognitive biases lay mental blocks along with listening blocks. You only hear what you want to hear, and not all of it. Another way is to avoid hearing certain things.
  5. JUDGING — Negative labels carry enormous power (and cognitive biases). Can you really listen to someone if you think they’re not smart enough or [insert adjective] enough to say what they’re saying? A basic rule of listening is to make judgments AFTER you’ve heard and evaluated the content of the message.
  6. DREAMING — You’re half-listening because you’re thinking about the moment you close the sale and get hoisted up by leadership for helping the organization meet quota. This often happens when you feel bored or anxious.
  7. IDENTIFYING — You take everything the person says and relate it back to your own experience.
  8. ADVISING — You are a great problem solver, ready to help, and have suggestions. Just a few sentences and you searching for advice. In reality, you miss what’s important about how the person actually feels and a subtle clue to a greater pain.
  9. SPARRING — This block has you arguing and debating with people. You’re attention is finding things to disagree with (Presidential Debates anyone?). A subtype of sparring is using sarcastic remarks to put down or dismiss what the other person says. A second subtype is people who can’t stand compliments, e.g. “Oh I didn’t do anything special”.
  10. BEING RIGHT — You’ll go to any length to win. You twist words, raise your voice, make accusations, call up past sins. You can’t listen to criticism, can’t be corrected, and can’t take suggestions to change. Your convictions are unshakeable. Since you won’t take responsibility for past mistakes, you keep making them.
  11. DERAILING — You find ways to change the subject when you get bored or uncomfortable with a subject.
  12. PLACATING — “Right….Uh huh…..Yes ok….Yup…Yup.” This is not active listening. It’s just being nice and trying to hurry the conversation along.

Demonstrating the Subtle Art of Shutting Up

When people speak to you, they subconsciously look for clues to prove you are. You must:

  1. Maintain good eye contact
  2. Lean slightly forward
  3. Reinforce the speaker by nodding
  4. Paraphrase what you think they said in your own words
  5. Clarify by asking questions
  6. Actively move away from distractions
  7. Be committed to understanding what was said, even if you’re angry, annoyed, or in a rush.

BONUS SECTION! Listening for Executive Boards and Teams

When on a leadership board, it is often like a marriage. You spend a lot of time together, you actually show how you REALLY feel, and put up with a lot.

When you’re speaking:

  1. Explain your point of view briefly and succinctly.
  2. Avoid name calling and blaming. Don’t accuse and don’t focus on your colleague’s shortcomings.
  3. Talk in terms of yourself and your experience. Focus on what you want and what you feel.

When you are the listener:

  1. Give your full attention so that you can really understand your colleague’s feelings, opinions, and needs.
  2. Don’t disagree, argue, or correct anything they say.
  3. You can ask questions to clarify the issue, but not to debate and make counterpoints.

You Go, I go, Then You Go

How does this all come together?

The Speaker goes for five minutes, Listener summarizes under a minute (using paraphrasing), and Speaker can clarify anything the Listener left out or misunderstood.

Effective listening and the subtle art of shutting the hell up (both your mouth and your mind) slows down communication so that conflicts are less likely to escalate while promoting clarity about the needs and feelings of the other person.

Now, you can actually ask relevant, effective questions.

Happy selling.

Omar M. Khateeb is an unorthodox and innovative medical device marketing leader with a background in science and medicine.

He currently serves as Marketing Manager for Product and Platform Technologies at Restoration Robotics.

His interests reside in sales psychology, neuromarketing, and self-development practices.

Check out his virtual bookshelf here to find your next great read, and connect with him on LinkedIn, Twitter, or SnapChat.