Lessons in Leverage from COS 25
Three takeaways for leading better from the second seat
Last week, I attended COS 25, the Global Chief of Staff Dialogue organized by the Chief of Staff Association and hosted at Microsoft’s HQ in Seattle. The event brought together a global community of Chiefs of Staff to sharpen our thinking, strengthen our networks and reflect on the second seat.
Each day, I walked away with the same word in my head: leverage.
The kind that moves the needle without needing attention, quietly orchestrates progress, and multiplies the impact of the principal, the team and the organization.
Jeff Buckeye, the Chief of Staff to the President of Microsoft Americas, described the room as a “collective wisdom.” That stuck with me because chiefs are enablers, challengers and space-holders. Everything we do is in service of alignment and momentum.
We are the leverage point.
Here are three takeaways from COS 25 that sharpened my thinking about that role and how I plan to use it.
1. Think Like a CEO
At COS 25, Harvard Professor Das Narayandas introduced the concept of a “dual advantage”: when companies centralize and analyze their data, they unlock exponential gains by doing two things: reducing costs and making the customer the hero. That’s the dual advantage.
That second part stuck with me because the real job of a principal is to build an organization that makes the customer feel like the hero of their own story.
But that doesn’t happen by accident. It happens through smart, aligned decisions. And every principal is making those decisions across two games:
Corporate strategy: which markets to play in
Competitive strategy: how to win once you’re there
As Chief of Staff, your job is to support both. That starts with clarity about what makes your organization different, what matters to your customers and how every decision aligns with both.
Data is how you get that clarity. Whether it lives in a dashboard or a meeting recap, centralized data gives you leverage. It helps you spot friction before it becomes drag. It keeps the focus on what matters most. And it helps your principal move faster with fewer blind spots.
Thinking like a CEO means seeing the full picture and keeping it clear for the one who must act on it.
Strategy moves fast when the signals are clear. Make sure your principal has them.
2. Know Your Orientation
One of the sharpest questions raised at COS 25 was this: Is your orientation to the principal, the team or the organization?
It’s a deceptively simple question (because the answer is yes). You need all three. But where you start matters.
For me, it starts with the principal. That’s where trust is built. Where you earn access to the information, context and instincts that drive the business. Supporting the principal means being a true right hand, someone who knows what they’re thinking and is already several steps ahead. It’s about anticipation and obstacle removal so they can focus on what only they can do.
Supporting the team means being a sounding board. It means listening first, then helping align priorities and clear the path to execution. Sometimes, it’s about momentum, and sometimes, it’s about clarity. Either way, you're the person who helps them move forward.
Supporting the organization means staying grounded in the mission and executing it with real discipline. It’s not just strategy, it’s alignment to values in action. And it’s your job to make sure decisions reflect that.
Your orientation shapes everything, what you pay attention to, how you communicate and where you spend your time. The most effective Chiefs move between these three planes fluidly, always solving for what the moment needs most.
Your orientation isn’t static—it’s strategic. And when you shift it with purpose, you create leverage.
3. Lead Yourself First
Dr. Michael Gervais presented us with a challenge: What’s possible for you? Are you living honestly enough?
He wasn’t talking about ambition. He was talking about purpose. About mindset. About growth.
He also made one thing clear: growth comes from investing in growth.
You can’t stumble into self-leadership. You commit to it. You make time. You build practices. You orient toward growth on purpose.
When you know what matters to you (and you’re honest enough to live it) you stop needing approval. Purpose quiets the noise. It frees you from chasing every shiny object or explaining your value. You’re no longer trying to impress anyone. You’re here to do the work.
That kind of clarity isn’t for show. The internal structure holds you steady when the pace is fast, or the situation is unclear. It’s what keeps you useful when no one’s looking. And it lets you lead from the second seat with calm, conviction and consistency.
You can’t support a principal well if you’re misaligned with yourself. Presence, discipline and influence all flow from purpose and purpose has to be cultivated.
Growth doesn’t just happen. You have to invest in it on purpose.
A Final Word on Leverage
COS 25 wasn’t about frameworks or titles. It was about clarity how we think, where we focus, and what drives us.
Leverage isn’t about power or attention. It’s about knowing where to apply pressure, when to hold space and how to make movement possible.
That’s the role of a Chief of Staff. You’re not the lever, you’re the fulcrum. Your job is to support and stabilize so your principal, your team and your organization can move with more force and less friction.
The second seat isn’t about you. It’s about what you help others unlock.
That’s the job. And I left Seattle more equipped to do it. Turns out, a room of Chiefs really is a wisdom!
Thank you to the Chief of Staff Association and Microsoft for creating the space, and to Trent and Jeff for leading it with clarity and intent. It was a privilege to be in the room.