Andrew Kisslo talks about his journey from marketing roles to Chief of Staff at Microsoft, sharing what it was like working in the role during a period of massive growth and change. He describes the different Chief of Staff archetypes, the importance of authenticity in leadership, and the process behind hiring his own Chief of Staff at SAP. Andrew also explains the career value of the Chief of Staff experience and offers practical advice on finding the right fit for both principals and Chiefs of Staff.

Free Resources:

• Strategic Planning Checklist
• Chief of Staff Skills Assessment Checklist
• A Day in the Life of a Chief of Staff
• Chief of Staff Toolkit

Get in Touch With Emily:

• Connect on LinkedIn
• Follow on YouTube
• Learn more about coaching
• Sign up for the newsletter
• Clarity Call with Emily

Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

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

Part 2 focuses on the practical steps and real-life challenges of carrying out layoffs, like coordinating with HR and IT, preparing benefit info, and setting up conversations with those affected. Emily shares personal experiences, including handling difficult reactions and making sure Chiefs of Staff help with both the announcements and the follow-up communication to support everyone involved. The episode also covers how to manage the work left behind and how to help teams refocus after a layoff round.

Links Mentioned:

• Emily’s Email
• Connect or Message Emily Sander on LinkedIn
• Clarity Call with Emily

Free Resources:

• Strategic Planning Checklist
• Chief of Staff Skills Assessment Checklist
• A Day in the Life of a Chief of Staff
• Chief of Staff Toolkit

Get in Touch With Emily:

• Connect on LinkedIn
• Follow on YouTube
• Learn more about coaching
• Sign up for the newsletter
• Clarity Call with Emily

Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

Time Stamps:

00:52 Preparing for Layoffs
02:38 Coordinating with HR and IT
03:54 Conducting Layoff Conversations
06:20 Handling Reactions and Follow-ups
07:25 Logistics and Safety Considerations
09:54 Post-Layoff Communication
14:42 Final Thoughts and Support

Jennifer Baron shares her 18-year journey working alongside her principal, Justin, starting as a temp cleaning a file room and eventually becoming Chief of Staff for a private equity firm. She talks about helping manage company growth, supporting multiple portfolio companies, and even working on a historic castle restoration in Scotland. Jennifer also offers practical advice for building a trusted Chief of Staff-principal relationship and setting healthy boundaries.

Links Mentioned:

• Jennifer Barron’s private equity firm: Duart Mull
• Connect with Jennifer Baron on LinkedIn

Free Resources:

• Strategic Planning Checklist
• Chief of Staff Skills Assessment Checklist
• A Day in the Life of a Chief of Staff
• Chief of Staff Toolkit

Get in Touch With Emily:

• Connect on LinkedIn
• Follow on YouTube
• Learn more about coaching
• Sign up for the newsletter
• Clarity Call with Emily

Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

Time Stamps:

00:31 Discovering Family History
01:54 Jennifer's Career Beginnings
03:43 Meeting Justin and Early Career at Endeavor
05:23 Becoming Chief of Staff
10:03 Private Equity and Company Growth
16:30 Current Role and Responsibilities
19:08 Role of a Chief of Staff in PE Firms
20:43 Building Trust and Dependability
24:44 Evolving Together Over 18 Years
27:41 Adventures in Scotland: A Team-Building Experience
30:55 Advice for Aspiring Chiefs of Staff