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How to create a magical 3 day (or 3 hour) deep dive

A Deep Dive is a great coaching tool. It’s a powerful experience you can create for clients—live or virtual.  

You can run a Deep Dive as an intake session with a new client. You can run a Deep Dive as private intensive, with a small group of clients—or a corporate leadership team. And you can run a Deep Dive as a stand-alone, paid experience for clients not yet ready for deep coaching. 

You can lead a 3 day, in-person, Deep Dive at a retreat center, a hotel, or out in nature. And you can run a Deep Dive as a virtual experience, over Zoom, for 3 hours.

If you haven’t done so yet, it’s probably time to add a Deep Dive experience to your coaching menu. Let me teach you how… 

How to create a Deep Dive

However much time you choose to spend on the experience, you will break it up into three equal parts. 

You could spend as much as an entire day on each, if you’re running a 3 day experience. And you could spend as little as an hour on each.

Part 1: The Past
Part 2: The Future
Part 3: The Present

Part 1: The Past

Ask your client, “Tell me your story…” They’ll laugh and say, “You mean from the beginning?!” Reply with a single word, “Yes!”

Tell them, “Seriously. Tell me your story. What did you love to do when you were 6 years old?” 

Have your client tell their entire story in a way they’ve never done before.

As you listen, identify and draw out themes from their life. 

Have them feel deeply, deeply heard… 

If they are more visual, get them to draw pictures to illustrate their story. If they are more kinesthetic, have them act out or sing parts of their story.

Use the AI transcription app called “Otter” on your phone, to transcribe every word they say, so they leave each session with a full transcript.

Have them handwrite some of their answers. Writing draws powerful left-right brain connections and will slow down their thinking, to create the space for insight.

Here is a range of provocative questions. You can set some as advance prep work, or overnight/lunchtime assignments:

  • What did you love to do when you were 6 years old? 
  • What’s the secret connection with what you love most about your career?
  • What are you proudest of—in your professional life and in your personal life? 
  • What are your most painful memories? 
  • How did they become a gift, later in life?
  • What are the common themes in your struggles—from childhood until now? 
  • What big leaps catapulted your success?
  • What energizes you? What drains you? 
  • What have been your glass ceilings—the invisible blocks that have held you back the most?
  • What movie most closely matches your life? 
  • What actor would play you in the movie of your life?!
  • What’s held you back the most over your life? 
  • What’s your single biggest secret regret?
  • Who do you unconsciously model the most—your mother, your father, a caregiver? 
  • What’s the worst part of that?
  • How do you usually hold yourself back the most?
  • What are your top 3 personal success stories? 
  • What are your top 3 professional success stories? 
  • What are you really, really proud of? (Remember: it’s not bragging if you’ve done it!) 
  • Tell me about the moments you had the courage to live true to yourself. 
  • How about those times when you realized you were living a life others expected of you? 
  • Tell me about a time when you worked too hard. 
  • Tell me about a time when you were too scared to express your feelings. 
  • Which friends do you wish you’d stayed in touch with?
  • What ways have you not let yourself be truly happy?
  • What’s your greatest regret? 

Money, time and leadership

Now things are going to get real. Tell your client to bring their bank statements and their calendar to the Deep Dive—or to make sure that they can access them electronically during your session…  


  • How much revenue did you make, each month, for the past 12 months? 
  • How much profit did you make each month? 
  • What did you spend the most money on—in your business? 
  • What did you spend the most on—in your personal life? 
  • What do you regret spending money on over the past 12 months? 
  • What do you most regret spending money, over your life? 
  • What have your best investments been, over the past 12 months? 
  • How much did you spend on travel, experiences, learning, luxury, coaching, training, fun, your most important relationships? 
  • What are you hiding from your partner about money?
  • What are you hiding from your partner about money?
  • Where did you give the most money, over the past 12 months? Where would you like to give more?


Over the past 90 days:

  • How did you spend your time? 
  • What are your top 5 life values and how much time did you spend on each?
  • How much time did you spend working on your big mission? 
  • How much time did you spend building your business—doing things that will generate money in the future? 
  • How much time did you spend selling—doing things that will generate money now? 
  • What are the 3 most important activities in your business—and how much time did you spend on each?
  • How much time off did you take? Why wasn’t it higher? Why wasn’t it lower? 
  • How much time did you spend with people you love the most? 
  • How much time did you spend doing things that nurture your spirit? 
  • How much time did you spend moving your body or exercising? 
  • How much time did you spend with friends? 
  • How much time did you spend serving others
  • How much time did you spend doing things just for you? 


  • Which mentors have helped you the most? 
  • Who was the best leader you ever had? 
  • Who was the worst? 
  • What was the best/worst lesson they taught you?
  • What are the top 3 leadership lessons you have learned?
  • What are the top 3 leadership mistakes you have made in the past 6 months? (If you’re not making mistakes, you’re not growing). 
  • Over the past 6 months, what did you focus on most—and how’s that working for you: 
    • status or results?
    • popularity or truth?
    • security or risk?
    • perfection or productivity?


If you really want to go deep, have your client take one or more of these fascinating assessments, in advance of the Deep Dive. Use them to look back over their life, to see what has helped them fly and what has held them back the most:

  1. Kolbe – measure your instinctive approach to problem solving
  2. The Enneagram – reveal the unconscious traps you fall into, when you’re not paying attention
  3. StrengthsFinder – forget about fixing your weaknesses, figure out your key strengths, so you can double down on them
  4. The 4 Tendencies – assess how you get people—including yourself—to do what you want 
  5. The 5 Love Languages – discover the main ways you express and receive love
  6. The 6 Human Needs – discover how you prioritize the fundamental human needs
  7. Wealth Dynamics – assess how you best create wealth 


Have your client read: How will you measure your life? by Clayton Christensen

Part 2: The Future

Day 2, or session 2, of your Deep Dive is about creating the future.
Here are some of the most powerful questions to help your client:

  • What would you like to accomplish—that looks pretty impossible, right now—but if it was achieved would change everything?
  • Imagine we meet up 3 years from today, and you are looking back over those 3 years. You say, “Wow! I’ve just had the best 3 years of my life.” Tell me about them…
  • How will you NOT achieve what you want, in the next 3 years? (We always know, in advance, how we tend to fail at things. Let’s identify that now, so we can handle it).
  • What would you love to create over the next 25 years?
  • What’s your Breakthrough Goal? That’s the one thing on your list, that if you focused on it—to the exclusion of everything else—it would be most likely that you’d accomplish everything else, anyway?
  • What are you willing to sacrifice to achieve your goals? What are you not willing to sacrifice? 
  • What are the biggest obstacles in the way of you getting what you want? 
  • How do you usually prevent yourself from getting what you say you want?
  • What fascinates you and energizes you? 
  • If your great aunt died and left you enough money so you never had to work another day in your life, what would you spend your time doing?
  • What would you love to accomplish that currently looks impossible?
  • Make a list of 100 things you’d like to accomplish or experience before you leave this planet. [Pay real attention to the final 30 answers. These will be the crazy sounding ones, that don’t seem to make sense. The ones that come out after all the logical, realistic answers].
  • What scares you the most? [Fear is often a mask for desire].
  • If you could laugh more and have more fun in your life, what would you do? 
  • Too many people use money and status as measures for success. Make an “I’m Successful when… List”  to identify all the things that truly make you happy.


Have your client read: Bold: How to Go Big, Create Wealth and Impact the World by Peter Diamandis

Part 3: The Present

Here’s the funny thing… The past and the future don’t actually exist! 

All we ever have is this present moment. 

So, use Day 3 or session 3, to get your client completely present to this moment.

  • What are you tolerating in your life or business? What bores you?
  • What’s missing from your life or business? And how do you keep it out? 
  • What are you doing that drains you but would energize someone else?
  • What’s working? What are you confident about?
  • What’s your Zone of Genius? Wear are the 1-3 things that fascinate you and energize you the most?
  • What’s your single biggest insight from our time together?
  • What would you like to do about that?
  • What’s the TINIEST next step you’ll take after our Deep Dive is over?


Here’s how to really make your Deep Dive extraordinary:

  1. Less is more. Your client should leave more exhausted than you! Resist the temptation to do too much. This is about them doing the work. 
  2. Less is more. Especially if you run this as a 3-day Intensive. Resist the temptation to cram in too much. Create lots of time for breaks and reflection. 
  3. Less is more. Here’s an example schedule… Morning session 10am-12pm. Send them off for 2 hour lunch breaks. Have them take walks in nature, if at all possible. Afternoon session 2pm-4pm. Take them out to an early dinner one evening.

Enjoy diving deep with your clients. Let me know how it goes when you run your own Deep Dive. 

By the way, do you want to write powerful articles? Write them to ONE person. Jon is a great coach and a member of my program, Project Kairos. I wrote this entire article for him!

Love. Rich 


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