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5 Ways to Coach Like Sherlock Holmes

I was recently reading a blog by one of the leading experts in the private investigation industry. No, I’m not planning to hire a detective! And yes, it’s important to read about all sorts of fields outside of your own profession.

I came across a list of Sherlock Holmes’ Investigation Strategies and I was inspired.

You see, Sherlock Holmes is one of the most famous fictional detectives on the planet for a reason. He was – and is – every criminal’s worst nightmare. And he’s as popular today as he was over 130 years ago when he first appeared in a novel by Arthur Conan Doyle.

I’ve been a fan of Holmes since I was a little boy. I read all the books by the time I was 13. And as a kid, I loved watching the black and white movies where he was played by Sir Basil Rathbone.

To this day, I enjoy watching Jonny Lee Miller in the TV show, Elementary. I’m enthralled by his modern portrayal by Benedict Cumberbatch, in Sherlock. (Honestly, I could have skipped the movies where he was played by Robert Downey Jr. And I’m secretly waiting for the movie Holmes and Watson, latter this year, where Holmes will be played by Will Ferrell!)

So I’ve taken 5 of Holmes’ top strategies of detection and broken down how they are actually high-level coaching skills.

#1. Define the Mystery

Too many coaches love solving problems. They love giving information. And they love answering their clients’ questions.

What’s wrong with that? you ask.

Nothing. Unless you want to be an extraordinary, high-level coach.

And in that case, you need to understand the distinction of A Puzzle vs A Mystery.

You can solve a puzzle when you have enough information, or when you have the right information.

But more information doesn’t help with a mystery. Mysteries require courage, risk-taking and the ability to be ok with discomfort.

Puzzles have clear answers. But mysteries are messy.

Puzzles can be solved. But your solutions can actually make a mystery worse.

In order to solve a puzzle, you need to know exactly what the puzzle is. In order to solve a mystery, you need patience, humor, curiosity – and a willingness to think differently.

You are a coach, not a consultant. Your clients don’t have too little information—they have too much. They need curiosity and patience and new perspectives. Slow them down. Don’t speed them up.

Be more like Sherlock Holmes and dedicate a lot of time to “define the mystery” that needs to be solved for your clients.

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#2. Approach Each Mystery with a Blank Mind

Too many coaches are more concerned about being seen as smart or avoiding looking ignorant than helping their client.

A powerful coach is willing to ask ‘dumb’ or ‘obvious’ questions. They readily admit what they don’t know and they are quick to celebrate their mistakes because they don’t need to look good.

Be genuinely curious with your clients. Ask “interested” questions vs “interesting” questions.

An interested question is focused on them. (e.g. “Tell me more about that…”)

An interesting question is focused on you, and often starts with the word, “I.” (e.g. “Here’s what I think … How about you?”)

Having a blank mind means that you’re willing to use provocative and “obvious” questions. It means that you listen for what’s not said. It means that you listen for the question behind the question.

Despite being a man of immense knowledge, Sherlock Holmes approached each case a blank mind, with absolutely no theories formed. He never relied on patterns. He never developed the lazy habit of relying on patterns and assuming an outcome with little information.

Be more like Sherlock Holmes and approach each client with a blank mind. (The more experienced you are, the harder this becomes!)

#3. Become Remarkably Curious

In “A Scandal in Bohemia,” Holmes instructs Dr. Watson on the difference between seeing and observing. Holmes says to Watson:

“You see, but you do not observe. The distinction is clear. For example, you have frequently seen the steps which lead up from the hall to this room.”


“How often?”

“Well, some hundreds of times.”

“Then how many are there?”

“How many? I don’t know.”

“Quite so! You have not observed. And yet you have seen. That is just my point. Now, I know that there are seventeen steps because I have both seen and observed.”

To understand the story behind each mystery, you must be able to listen for the context of the story, beyond the content.

Draw out your client’s secret desires and their deepest fears, so you can find out what they really, really, really want.

Get curious about how they think—and where their motivation and their energy come from.

Be more like Sherlock Holmes and observe what is really going on—what your clients need vs what they say they want.

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#4. Listen Deeply

The word “Listen” and the word “Silent” have the same letters for a reason.

Sherlock Holmes had an obsession with understanding people and he listened to anyone. He disguised himself as an out-of-work horse groom to get the boys in the stables to open up. And he would sometimes visit a public place to simply listen.

Silence is probably the #1 most underrated skill of a great coach.

Encourage your clients to talk. When they start speaking, stay silent.

One of my favorite “questions” is, “Tell me your story…”

And then I say nothing. I listen, deeply.

Be more like Sherlock Holmes – say less and listen more.

#5. Be Fully Present

In her book Mastermind: How To Think Like Sherlock Holmes, Maria Konnikova suggests that Sherlock is able to distinguish the vital facts from the incidental facts because he’s become an expert at mindfulness.

Mindfulness is staying in the present moment and learning to concentrate. It’s focusing your mind so that it can avoid distractions or anything that might get it off track.

But mindfulness is also about forcing your mind to take a step back. This is sometimes a tough thing to do because it seems counterintuitive to walk away from a problem that you want to solve.

In ‘The Adventure of the Bruce-Partington Plans,’ Watson observes:

One of the most remarkable characteristics of Sherlock Holmes was his power of throwing his brain out of action and switching all his thoughts on to lighter things whenever he had convinced himself that he could no longer work to advantage.”

Here’s Watson on Holmes’ violin playing from A Study in Scarlet:

Leaning back in his arm-chair of an evening, he would close his eyes and scrape carelessly at the fiddle which was thrown across his knee. Sometimes the chords were sonorous and melancholy. Occasionally they were fantastic and cheerful. Clearly, they reflected the thoughts which possessed him, but whether the music aided those thoughts, or whether the playing was simply the result of a whim or fancy, was more than I could determine.

Taking time out actually helps Sherlock think in a range of ways:

  • Distancing – leave the problem alone for a while
  • Meditation – clears the mind
  • Distraction – from physical needs
  • Creativity – enables creative process

Be more like Sherlock Holmes – be fully present to your clients. Or be fully present to switching off your thoughts to play. And help your clients do the same.

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Love. Rich

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