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Sharpend’s Step by Step Guide to Mastering the Enneagram

Welcome to Sharpend’s step-by-step guide to mastering the Enneagram in 6 months.

As a coach for 8+ years working with 100+ CEOs and founders. I’ve studied nearly every personality assessment and leadership framework available, and the Enneagram, when understood at a deep level is the most effective ways to expand your self-awareness and leadership range.

This guide is for anyone who wants to and spend 6-18 months of committed work understanding the Enneagram and enacting its teachings.

If you choose to go on this journey I guarantee the time and work you put in will make you a more joyful, authentic, and effective leader. I applaud you for committing to do this critical work.

Download a PDF version of “Step by Step Guide to Mastering the Enneagram.”

Go to the start of the guide.

About This Guide / What to Expect

What this guide is and is not:

This resource is a step-by-step guide that will take 6 to 18 months of self-study to complete.

When you complete all the steps in this guide you will have grown in profound ways as a leader and will be able to use the Enneagram as a powerful tool in your leadership toolbox. 

Three beliefs that underpin this guide:

  1. It’s better to master ONE self-awareness framework than to spread yourself thin by studying many different frameworks.

  2. There is an ideal sequence of steps to learn the Enneagram if depth is your goal. 

  3. There are different tiers of teachers out there who talk about the Enneagram and picking the right teachers and resources to invest in while dramatically improve the speed and depth at which you learn this framework.

To summarize:

This guide IS for leaders interested in a longer-term study of the Enneagram and committed to deeper growth.

This guide IS NOT for folks who want to read the high-level, greatest-hits descriptions of the nine types. 

Why study the Enneagram?

There are three reasons why the Enneagram stands above all other personality frameworks.

  1. The Enneagram is accurate. I’ve worked with 100+ CEOs, founders, and executives using the Enneagram either directly in our coaching work or in the background, and I can personally attest to what decades of research on the Enneagram shows—this framework is highly effective at matching core human psychological archetypes with the 9 nine Enneagram types. 

  2. The Enneagram is dynamic. The Enneagram emphasizes that each type behaves differently under different conditions (stress, one’s self-control/awareness, and more). In this way, the Enneagram helps us see that our psychology that makes up our default fears, motivations, and behaviors may be set, our behaviors and ability to grow and change within our type is incredibly dynamic.

  3. The Enneagram is in the zeitgeist. The Enneagram is used by many top CEOs (Ray Dalio, Tobias Lutke, Tim Ferris, and more) and leading companies (Shopify, Bridgewater, Stripe, and more).  The predominance of the framework makes it easier to learn (you’ll meet many other execs who are similarly using this tool in their personal growth work) and adds to its effectiveness as you’ll find more situations where you can easily talk about the Enneagram with peers and colleagues.

Thank You to My Teachers

This guide in many ways is an homage to the wonderful teachers who helped me learn and unlock the power of the Enneagram as a coach and in my life.

Every guide and resource I recommend are one’s either written or created by one of my teachers or recommended by one of these same individuals.

You will see these names again throughout the guide, but I want to thank Rasanath Das and the team at Upbuild Coaching, Russ Hudson (previously of the Enneagram Institute), Richard Rohr, and the Conscious Leadership Group each of whom has been instrumental in my understanding of this framework.

Sharpend Coaching’s Step-by-Step Guide to Mastering the Enneagram

Mastering the Enneagram and unlocking its potential requires the same time and commitment needed to learn any new and complex skill. 

This means you’ll need to commit upfront hours to expand your understanding of the framework, and then ongoing study and time to continue to use the framework and deepen your skill with it.

During this process, you will have inflection points—moments when different learnings click together and help you achieve breakthroughs. And, you will hit plateaus—periods when you’ve learned new information about yourself and this tool, but your ability to act on those insights is not there yet. 

As you embark on this process, it’s important to remember Gates’ Law: “It is easy to overestimate what we can achieve in the short-term and underestimate what we can achieve in the long-term.”  

If you stay with this process and complete this guide, I guarantee you will evolve as a leader and lasting change.

How to Use this Guide:

  1. This guide is a self-study checklist, made up of 9 activities and 5 readings that in total should take around 6 months to complete.

  2. Each checklist item (in both this online version of the guide and the downloadable PDF) is a link that will take you to a resource or activity to complete.

  3. We recommend you complete each step in the order provided as the sequence is intentionally designed to help you learn the framework in a way that most quickly leads to new insights and personal breakthroughs.

  4. Some steps will be short. Others are long. The timeline I suggest will give you (assuming you are a busy executive) ample time to complete all the steps in the guide. 

Months 0-6: 

Learn Your Type, Your Operating System, and Your Path to Lasting Growth

Goals:

  • Learn the core principles that underpin the Enneagram framework.

  • Discover your type.

  • Unpack the core fears and motivations of your type that underpin your personal operating system.

Activity Checklist:

Months 7-18 (and beyond):

Deepen Your Knowledge and Expand Your Range

Goals:

  • Crystalize your knowledge about your type and personal operating system.

  • Take action based on this knowledge to proactively expand your range.

Activity Checklist:

<more resources coming soon>

Resources

Resource #1: The Enneagram and Levels of Consciousness (video, 15 minutes)

Listen to “The Enneagram and Levels of Consciousness” by Upbuild Coaching here.

Resource #2: Read “Three Principles to Master the Enneagram” (article, 5 minutes)

The Enneagram is a framework that once mastered allows you to take the immense variance of human psychology and behavior and pattern-match people into accurate and actionable archetypes.

Here are the three core principles of the Enneagram that unlock deeper insights when using the tool.

Principle #1:

Self-awareness is the key that unlocks personal growth.  

Self-awaress of our strengths, weaknesses, triggers, and patterns under stress, allows us to catch and counteract negative behaviors that we typically do reactively and subconsciously. 

Principle #2:

The Enneagram leads to “nuanced” self-awareness. 

One of the traps that comes from studying the Enneagram at a skin-deep level is that it’s difficult to understand why we often act in contradictory ways. 

For example, I was recently working with a CEO who is known for being incredibly adaptable and calm. However, with their co-founder they are stubborn and reactive. 

What explains this?

The Enneagram helps us see how these two different behaviors stem from the same core fears. In this example, the leader is heart-felt and ambitious. They care about efficiency and are triggered by inefficiency. Their ability to adapt to challenging situations, stems from their innate sense of wanting to be efficient and adaptable, which is the same desire that leads to them being triggered by their co-founder with whom, navigating change together feels inefficient and overwhelming.

 Principle #3:

Your personal operating system is made up of four key components:

  1. Zones of Genius (aka strengths)

  2. Weaknesses (almost always connected to your strengths)

  3. Triggers

  4. Patterns under stress

These four items are what you should focus on building nuanced self-awareness around.

Resource #3: “Typing, Mistyping, and Wings.” (podcast, 15 minutes)

Listen to this short podcast from Upbuild’s Enneagram podcast series on typing, mistyping, and wings, here.

Resource #4: “15 Commitments of Conscious Leadership and Your Enneagram Type.” (article, 20 minutes)

Read this blog post from Conscious Leadership Group founder, Diana Chapmam, on the nine Enneagram types, and what commitments/actions you can take to grow as a leader depending on your type.

Resource #5 Deep Dive on Your Type (video/audio, 3 hours)

Two of the best online teachers of the Enneagram are Richard Rohr (the famous Friar and one of the modern pioneers who brought this framework to millions of people) and Upbuild. One of Richard Rohr’s seminars on the 9 types was videotaped and is now available on YouTube.

Todos:

  • Find your type below and watch Richard Rohr’s video (~1 hour) and Upbuild’s podcast episode (~30 minutes) about your type.

  • Do the same for your wing or a second type that you are interested in learning more about.

  • Optionally, do this for 1-2 more types you want to learn more about.

Links to videos and audio series:

Type 1:

Type 2:

Type 3:

Type 4:

Type 5:

Type 6:

Type 7:

Type 8:

Type 9:

Activities

Activity #1: “Where Am I in My Leadership Development Arc?” (journaling, 30 minutes)

To begin your journey in mastering the Enneagram, please complete the following self-reflection activity.

Spend 30 minutes journaling answers to the following four prompts.

  1. Where am I in my leadership development arc? 

  2. How would I explain my zones of genius, weaknesses, and triggers as I understand them today? 

  3. How effective am I at noticing when I am triggered or reacting to stress?

  4. What tools, actions, and processes have helped me expand my range as a leader and get to where I am today? Be specific, for example, “working with a coach for 12 months,” or “working on a high-performing team under a top-tier boss who regularly gave me feedback,” etc. 


Activity #2: Book an Enneagram 101 Workshop (in-depth study, 2-day workshop)

Sign up for an Enneagram 101 Workshop with Upbuild here.

Given that the goal of this guide is to help you master the Enneagram, it’s important that you don’t just rely on podcasts and books to learn the subject.

Upbuild is in my view far and away the best modern-day teacher of the nine types and how to learn and use this framework at a deep level. They have had countless CEOs, founders, executives, and more attend these Enneagram 101 Workshops.

The secondary benefit of attending a workshop is that you will go from self-study to group-based study, with all the benefits for learning (accountability, rapport with teachers, etc.) that come with that change.

I further recommend Upbuild’s course because as former monks, the partners at Upbuild deliver this work from a place of compassion not capitalism. They are dedicated to teaching the Enneagram in a deep way and charge far less than other similar companies charge for lesser workshops.

The one downside is that Upbuild only runs the 101 course once or twice a year.

If the timing to attend Upbuild’s 101 workshop doesn’t work out you have a few other options to complete this step.

  1. You can request and download a recording of Upbuild’s Enneagram 101 workshop here.

    1. This is not as effective (given what I shared above) but still a powerful way to continue your study.

  2. You can attend a similar workshop offered by a different organization. 

    1. My next best recommendation if Upbuild’s course doesn’t work for you is to take a course via the Enneagram Institute which you can find listed here.

    2. Finally, check out the courses offered by Russ Hudson one of the two original founders of the Enneagram Institute, which you can find here. Russ offers both on-demand and in-person workshops.

Activity #3: Book a Typing Session with an Enneagram Coach (live coaching, 1.5 hours)

  • You can book a typing session with Sharpend by scheduling a coaching session with him here.

  • You can book a typing session with an Upbuild coach by reaching out to the Upbuild team here.

Sharpend is offering a highly discounted rate for these sessions as part of this guide. Similarly, Upbuild offers typing sessions on a low-cost, sliding scale for leaders.

Activity #4: The RHETI Enneagram Assessment (activity, 1.5 hours)

To complete this activity do the following:

Part 1: Completing the Assessment

  • Please complete the RHETI Enneagram assessment here. The test costs $20 and takes ~30 minutes to complete. 

  • Answer questions based on what has been generally true for you throughout your life vs what is true right now ( don’t overstress your answers–the assessment is a first step in discovering your type).

NOTE the assessment is ~80% accurate so don’t take your top score as dogma on your type. The test is directionally correct and helps point to the types you should read more about. 

Part 2: Review Your Result

  • Read the descriptions of the THREE types you scored highest on. HIGHLIGHT any specific statements that either strongly resonate with you or don’t resonate at all. 

  • The goal is to find language that accurately captures some of the nuances of how you operate, including strengths, weaknesses, patterns under stress, and triggers. 

Activity #5: “Guessing My Type.” (journal, 30 minutes)

At this point, you’ve signed up (and maybe completed) an Enneagram 101 Workshop, you’ve had a typing session with a coach, you’ve completed the RHETI Enneagram assessment and hopefully have a decent understanding of the core framework of the Enneagram. 

Through these steps, you likely have a strong belief of what your type is.

Please complete the following prompt (30 minutes) to make a choice about what you think your type is and why.

  1. I believe my type is _______.

  2. One core fear that underpins my behaviors including both strengths and weaknesses is _______.

  3. One thing I love about being a type ____ is? (this can be a strength or simply something you love about your type. For example, as a type 4, I am intuitive and care about depth and creativity, which makes me appreciate the beauty of the world.)

  4. One thing that is hard and painful about being a type ____ is? (this can be a weakness or a reflection of a painful flaw of yours. For example, as a type 4, I feel everything and can dwell on negative emotions. This can be both painful and distracting from the truth.)

Activity #6: My Personal Operating System (activity, 1 hour)

One of the most powerful and actionable ways to use the knowledge that is distilled from studying the Enneagram is to get clear on your unique zones of genius, weaknesses, patterns under stress, and triggers. 

I call these four aspects that capture your leadership style and behaviors your “Personal Operating System.”

Todo:

  1. Make a copy of this Google document titled “My Personal Operating System.” 

  2. Add your name to the document and save it somewhere where you can easily return to it. 

  3. Add TWO succinct and clear self-descriptions under each of the four categories–zones of genius, weaknesses (connected to strengths), patterns under stress, and triggers.

  4. Re-read each of the statements you wrote and try to commit these to memory.


Activity #7 “Sharing My Learnings with a Friend” (activity, 1 hour)

It’s impossible to learn about ourselves in a vacuum. This activity invites you to share some of your self-learnings with a friend in order to better understand your personal operating system.

Todo:

  1. Schedule a 45-minute call with a friend.

  2. Tell your friend you have been doing a deep dive to learn about yourself and ask if they are open to having a call to discuss some of what you’ve learned.

  3. Prior to the call, ask them to write down an answer to the following:

    1. What is a unique strength (aka zone of genius) of mine?

    2. What is a weakness or blindspot of mine?

    3. What types of situations do you know trigger me?

  4. On your call, start by explaining to them the work you’ve been doing during the past few months as you’ve completed this guide.

  5. Share that you are excited to share your learnings with them and hear what they came up with from your prompt/request.

  6. Share that you are open to any and all thoughts they have and you see this as a learning environment.

  7. Start by listening. Ask them what they wrote down as your strengths, weaknesses, and triggers. Have them share one by one, and when they share each one, spend 5 minutes asking questions to understand what they wrote more fully.

  8. If anything they share resonates strongly with you, add it to your personal operating system.

  9. Now change roles. Share ONE strength, weakness, trigger and pattern under stress that you wrote in your personal operating system. Share them one by one and after sharing each ask if it makes sense and if they agree?


Activity #8: “My Commitment to Growth” (activity, 30 minutes)

Spend 30 minutes developing an answer to the following prompt:

“What is one behavior change I am committed to making, that I know will dramatically impact my effectiveness and joy?”

Write in the following format, “Over the next 6 months, I am committed to _______.”

Examples of commitments:

  • “I am committed to being direct and succinct when giving feedback to others.”

  • “I am committed to being patient and pausing before I respond to others.”

  • “I am committed to sharing my point of view vs withholding it.”

  • “I am committed to communicating my thoughts in writing to others before taking action.”

  • “I am committed to proactively taking actions vs waiting.”

  • Etc.

Fill in this “Personal Operating System” document.

Use the notes you took during your 1-1 Enneagram coaching session and any highlights you made when reviewing the results of your RHETI Assessment.


Activity 9: Celebrating Your Work (activity, 30 minutes)

Wow, you’ve reached the end of the critical first 6-months of this self-guided study. Kudos. Hoorah. And, well done.

This process was likely difficult on many levels. It’s time consuming. It requires dedication and consistency. And most importantly, when you finally start to see your true operating system and the fears that can cause you to turn into a painful and destructive version of yourself, it can be incredibly exposing and painful.

It’s important to celebrate the work you’ve done and the progress you’ve made.

Todo:

  1. Close your eyes and spend 5 minutes visualizing all you have done to reach this point. The courses you’ve completed, the actions you’ve taken, and the progress you’ve made. Focus on just the positive impacts this work has had and think about this work in a loving manner.

  2. Send an email to TWO friends or people close to you letting them know you’ve completed this process. Feel free to share any tidbits on why the work was valuable and why you are proud of having completed the work to date. Remember, this act of sharing is not only a way to connect with a friend, but also helps you in locking in key takeaways you’ve had from this journey to date.

Months 7 - 18 (and beyond)

Resources:

Resource #6: “The Wisdom of the Enneagram” (book, 1-hour)

The Wisdom of the Enneagram is the best book to read to go deep on the nine types, their psychology, and why they behave the ways that they do. Read the chapter about your type (and any other chapters you want to read).

Activities:

Activity #10: Update your Personal Operating System (activity, 1.5 hours)

Your personal operating system becomes most effective when it’s polished. This means distilling your self-awareness about how and why you operate into short and easy-to-communicate phrases.

Examples of a distilled statement include:

  • “I am a heart-based leader.”

  • “I am highly sensitive.”

  • “I am an idea factory.”

  • “I am a people-pleaser.”

  • “I have low emotional amplitude.”

The simplicity of the statement makes it easy to share and repeat, such that key people in your life whether those are business partners or life partners, get it and are able to understand you better.

Todo:

  1. Open your “Personal Operating System” document.

  2. Review everything you’ve written to date.

  3. Spend 30 minutes reviewing each statement and editing the statement to make it simpler and to best capture the nuanced truth about that specific strength, weakness, trigger, or pattern under stress.