Leading From the Inside Out℠ Explained: It Starts With Knowing Yourself
Over my career, I’ve navigated seven mergers and acquisitions from both sides of the table, including as a communications executive on a Fortune 100 deal team. Despite good intentions, even the strongest leaders can be tested. This series focuses on the behaviors and human dynamics that matter most in these moments.
In my work with leaders, one thing comes up often. The same habits that helped them get where they are can also be the ones holding them back.
That’s because your strength tends to also be your deficit.
We all develop patterns in how we think, decide, and react. The longer we live with them, the more automatic they feel and the harder they are to see. That's how they become blind spots, and the people around us usually see them before we do. And as with most things in life, we can’t change what we don’t know about.
Leading From the Inside Out (“Inside Out”) wasn't created in a vacuum. It was shaped by input from business sponsors and the leaders I coach. Their feedback kept pointing to the same three needs: a shorter duration, a personalized approach, and a less expensive option than a full coaching engagement. Those three benefits are the foundation of the program.
How It Works
Inside Out is a confidential, one-on-one coaching experience grounded in the Enneagram. It takes approximately four to five hours of the leader's time.
It starts with a pre-meeting so the leader and I can get to know each other. The leader then completes an online Enneagram assessment and receives a personalized 4-5 page report.
Our first session runs 90 minutes and walks through the results and what they mean for how the leader shows up at work. The next two coaching sessions connect those results to how the leader makes decisions, communicates, and works with others. The leader brings whatever is most on their mind, and we work through it using the Enneagram as the lens. What we discuss stays between us.
Added bonus? When 4+ leaders from the same organization take part, the sponsor also receives a summary of group themes, with no individual details shared. This can be especially useful in setting future leadership goals and shaping the profile of the leadership team the organization wants to build.
Shorter Duration
This program isn't meant to replace a longer coaching engagement. When a leader is building a specific competency or working through an action plan set with the business sponsor, a full engagement is still the better fit.
But those engagements often run six to eight months or more, and many senior leaders don't have that kind of time. A shorter format gives them focused time on what's top of mind right now, based on where they are in their career. It allows them to get very deep, very quickly.
Personalized
Unlike most behavioral assessments that measure how you act, the Enneagram starts with why. It looks at the core motivations and fears that drive how leaders think, act, and respond under pressure.
The report covers leadership and working style, contributions at their best, how they show up under sustained stress, strengths that can become overextensions, how they show up on a team, growth recommendations, and reflection questions. It all comes back to how the leader shows up in business, how they influence others, and where their blind spots may be. For many clients, this is the most eye-opening part of the program.
As I've seen time and again with clients, the higher you go, the louder and quieter it gets. Louder because there are more priorities, expectations, and challenges. Quieter because your circle of trust gets smaller. Leaders welcome a private conversation with a trusted, unbiased source.
A side note on development training for teams. It’s beneficial but to a point. Group training is homogenized by design. It has to serve many people at once. But as many leaders have told me, when they sit around a table together, they rarely share what's truly on their minds or what they're struggling with.
Less Expensive
The current economy has put pressure on nearly every organization. Sponsors told me they value leadership development and like what this program includes, but some needed an option that fits today's budgets. This program lets them keep investing in their leaders at a lower cost.
Why Now Matters
During significant change, it can be tempting to put leadership development on hold. Over the long term, that choice can cost more than it saves.
Change is when leaders need support the most. It's also when you most need your best leaders to stay engaged and help the organization move through it productively.
To no surprise, it all flows downward. We may not see our own patterns, but our teams see their behaviors every day. How a leader shows up during change shapes how everyone around them handles it. This is the time to lean in.
Offered at $3,200 per person (a price point also validated with leaders), Inside Out offers a shorter, personalized, and more affordable way to invest in your leaders. Sample reports and program materials are available for sponsors who would like a closer look at what to expect.
Onwards!
About The Author
Chris Chaia is the founder of Onwards Consulting, an executive coaching and strategic marketing consulting firm, serving leaders and organizations navigating growth and change. She is also the architect and publisher of The Business of Coaching 2025, a global research study on the practices, habits and behaviors of coaching entrepreneurs.
