The Box You're Starting In: How Your Enneagram Type Shapes Your Leadership
Have you ever wondered why, despite your best efforts to grow, you keep running into the same walls?
Or why certain challenges seem to follow you from company to company, team to team, relationship to relationship?
There's a reason for this—and it's not that you're broken or failing.
It's that you're probably operating from a 'box' you don't even realize you're in.
A box of patterns that may have served you as a child but are now unconsciously running your life.
But once you see these patterns, you can begin to shift them—and that's where transformation begins.
Imagine being able to see these patterns clearly for the first time. To understand why you react the way you do under pressure. Why certain leadership challenges keep repeating. Why some relationships feel effortless while others drain you completely.
Seeing these patterns allow you the choice to respond with intention rather than react from habit. Leading to a full range of perspectives, not just your default setting.
And once you are able to respond with intention outside of your default setting, you are free to make the moves that have the biggest impact on your company.
The Cost of Not Knowing Your Box
Every founder has blind spots. But what most don't realize is that these blind spots follow predictable patterns based on their personality type.
These patterns become the invisible ceiling on your leadership. They limit how effectively you:
- Build and motivate teams
- Make strategic decisions
- Handle conflict and stress
- Respond to challenges and setbacks
- Connect with others authentically
Left unexamined, these patterns don't just hold you back—they actively create the very problems you're working so hard to solve.
The founder who micromanages isn't just struggling to delegate; they're unconsciously creating a team that can't function without them.
The leader who avoids conflict isn't just preserving harmony; they're building a culture where important issues go unaddressed.
This is why knowing your type—your particular box—is so powerful. It reveals precisely how you're creating the limitations you experience.
The Enneagram: A Map to Your Box
The Enneagram is one of the most powerful frameworks for understanding these unconscious patterns. Unlike other personality assessments that tell you what you do, the Enneagram reveals why you do it.
Your Enneagram type isn't just a label—it's the lens through which you see the world, make decisions, and respond to stress by default.
And here's the key insight: Your greatest strength, when overused, becomes your greatest weakness.
But by knowing which box you’re starting in, you can begin to see how to transcend your default patterns so you can operate with full behavior flexibility and freedom.
The Nine Types: Which Box Are You Starting In?
Take a moment to see which of these patterns resonates most deeply with you:
Type 1: The Perfectionist - Driven by the belief you must be good and right to be worthy, with high standards and a relentless inner critic.
Type 2: The Giver - Believes you must give fully to others to be loved, often at the expense of your own needs.
Type 3: The Achiever - Defines worth through success and accomplishment, believing value comes from what you do rather than who you are.
Type 4: The Individualist - Seeks meaning and authenticity, often feeling like you don't quite fit in.
Type 5: The Investigator - Protects yourself by seeking intellectual mastery and self-sufficiency, preferring to observe rather than participate.
Type 6: The Loyalist - Craves certainty in an unpredictable world, remaining vigilant about potential threats and authority.
Type 7: The Enthusiast - Seeks pleasure and possibilities, avoiding pain by staying busy with new experiences.
Type 8: The Protector - Believes you must be strong and powerful to protect yourself and others, valuing directness and action over vulnerability.
Type 9: The Peacemaker - Desires harmony at all costs, often at the expense of your own needs and preferences.
Your Box and Your Leadership Blind Spots
Your type creates predictable leadership challenges:
- The Perfectionist creates a culture of criticism where team members fear making mistakes.
- The Giver burns out from taking on too much and struggles to make unpopular decisions.
- The Achiever builds high-performing teams but misses deeper connection and authentic engagement.
- The Individualist may foster creativity but create unnecessary drama when feeling misunderstood.
- The Investigator develops deep expertise but hoards information and struggles with collaboration.
- The Loyalist builds loyal teams but gets caught in worst-case scenarios and decision paralysis.
- The Enthusiast inspires with vision but makes it hard for the team to focus; starts many initiatives that never reach completion.
- The Protector drives results but intimidates others and resists showing vulnerability.
- The Peacemaker creates harmony but avoids necessary conflict and decisive action.
Any of these sound familiar? This is why awareness is the first step to transformation. You can't change patterns you don't see.
Breaking Free: The Paradox of Acceptance
Here's the fascinating truth I've observed working with successful founders:
The more you recognize and accept your patterns instead of fighting them, the more freedom you have to step outside of them.
You've already taken the first step. The fact that you're reading this means you're seeing your patterns with fresh eyes. And when you see the pattern, you gain power over it.
Instead of reacting the way you always have, you pause, choose differently, and shift the entire outcome.
Because the more self-awareness you gain, the more options become available to you.
But the goal isn't to abandon your type—it's to expand beyond it. To have access to all nine perspectives when needed.
The parts of ourselves we deny or resist tend to run the show from behind the scenes. But when you can say, "Ah, there's the Perfectionist/Achiever/Protector pattern showing up again," with no judgment, you've already created space to make a choice.
Because you are not your personality. You are the awareness watching your personality patterns play out.
From Limitation to Liberation
When you begin seeing and working with your patterns instead of being stuck within them, everything changes:
- Decision-making becomes clearer - You see options that were invisible before
- Team dynamics improve - You respond to challenges instead of reacting to triggers
- Your leadership expands - You access strengths from all nine types as needed
- Energy and creativity flow - You spend less energy fighting yourself
- Authentic connections deepen - You show up as your whole self, not just your patterns
If you want to explore this further, I recommend taking an Enneagram assessment (the Enneagram Group offers a good one) and reflecting on your results.
But the fastest way to step outside your box isn't by trying to do it alone. It's by having people who can see your blind spots and guide you past them.
This is why the most successful leaders surround themselves with coaches, peers, and systems that challenge them to grow in ways they can't yet see.
The feedback can be uncomfortable, but that discomfort is the growing edge where transformation happens.
Remember: The goal isn't to escape your personality. It's to expand it. To recognize when you're operating from a limited set of strategies, and to consciously choose a response aligned with what each situation truly needs.
When you can do that, you'll not only become a more versatile leader—you'll experience the freedom that comes from no longer being confined by patterns you didn't even know were optional.
I'd love to hear which type resonates with you and what insights this sparks about your leadership.
Hit reply and let me know.
With love,
- Dave Kashen
P.S. This is just scratching the surface. If there’s interest, in future newsletters, I can break down how each type can use their strengths to overcome their biggest leadership challenge. Stay tuned.
P.P.S. Ready to move faster and experience bigger breakthroughs? Request an invitation to join the IGE coaching program and community. You'll receive direct coaching from me and other IGE coaches to help you see your blindspots and break free from limiting patterns.
