Moving from Chief of Staff to Principal: Lessons from a Leadership Transformation at Microsoft
Many people see the Chief of Staff role as a stepping stone. But few understand how much it can shape a leader.
Andrew Kisslo reflects on his time as Chief of Staff at Microsoft and what happened after he stepped out of the role. He explains how the job sharpened his leadership skills, changed how he sees organizations, and helped prepare him to lead teams himself.
His story shows that the biggest value of the Chief of Staff role often appears after you leave it.
Key Takeaways
Know why you want the role
The Chief of Staff job is not about prestige or proximity to power. It is about learning how leaders think, make decisions, and run a business.The role changes constantly
A Chief of Staff may act as a fixer, strategist, coordinator, or problem solver depending on what the organization needs at the time. The job rarely stays the same.Leadership lessons come through observation
Watching a strong leader up close teaches things that books cannot. Culture, decision making, and strategy become clearer when you see them in action.
Notable Quotes
“Before you even entertain the job, you have to know why you are going after it.”
“When you are in the job, you just have to get through it. The return on investment comes after.”
“A leader is often acting in the moment, and the Chief of Staff helps them prepare for what is coming next.”
Real-World Applications
Be clear about your learning goals
Before taking a new role, define what you want to learn.
Example:
A manager accepts a Chief of Staff role to learn budgeting and strategy. During the role, they ask to participate in financial planning meetings and strategic reviews.Study how leaders operate
Working closely with executives is a rare chance to observe leadership behavior.
Example:
A Chief of Staff watches how their executive handles tough board questions and later applies the same communication style when presenting to senior leaders.Seek outside feedback for career planning
Talking to experienced leaders can reveal blind spots.
Example:
Kisslo spoke with many COOs to understand what skills he lacked. Their feedback helped him pursue a role that gave him profit and loss responsibility.
The Chief of Staff role is demanding and often unclear. But it offers something rare: a front-row seat to leadership.
Andrew Kisslo’s experience shows that the real value of the role appears later, when the lessons learned behind the scenes start shaping how you lead yourself.
For many professionals, it becomes one of the most important steps in their leadership development.
Time Stamps:
00:57 Andrew's Career Journey to Chief of Staff
01:53 Understanding the Chief of Staff Role
02:03 Historical Context of Chief of Staff Positions
02:59 Early Influences and Mentorship
03:43 First Impressions and Aspirations
05:05 The Reality of the Chief of Staff Role
09:05 Navigating the Challenges and Archetypes
13:38 Lessons from a Phenomenal Leader
18:14 Transitioning Out of the Chief of Staff Role
25:16 Becoming a Principal and Hiring a Chief of Staff
32:44 Final Reflections and Advice
About The Author
Emily Sander is an ICF-certified leadership coach with more than 15 years of experience in the business world and the author of Hacking Executive Leadership. She’s been featured in several print publications, online articles, and podcasts, including CEO Today Magazine, Leading to Fulfillment, and Leadership Powered by Common Sense.
Emily has a passion for helping business leaders reach their full potential. Go here to read her story from seasoned executive to knowledgeable coach. If you want to send Emily a quick message, then visit her contact page here.