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

This episode talks about how leaders, especially a Chief of Staff, should handle layoffs with respect and care. Emily shares real-life examples of leadership teams deciding who gets cut, the importance of considering all other options first, and how to communicate tough financial realities to staff. He also discusses making fair decisions on who to inform, and gives practical advice on what to say in all-hands meetings when layoffs are on the table.

Links Mentioned:

• 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:

00:42 The Importance of Handling Layoffs Well
01:12 Personal Experience with Layoffs
01:54 Philosophy on Layoffs
02:58 Deciding on Layoffs
04:29 Planning and Coordination
10:56 Communicating Layoff Plans
15:40 Final Thoughts and Leadership Responsibility

Marcelo Elliott, Chief of Staff and head of HR at La Tourangelle, shares how his combined role helps connect HR strategy directly to company goals. He talks about using AI to handle repetitive HR tasks, setting up ad hoc committees for grassroots improvement, and building effective communication across teams. Marcelo also gives practical examples, like launching sustainability initiatives and merging HR data with business planning, and recommends pistachio oil on ice cream as a personal favorite.

Links Mentioned:

• La Tourangelle Artisan Oil

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:

00:51 Background and Career Path
01:35 About La Tourangelle
02:36 Role of Chief of Staff and HR
04:08 Benefits of a Dual Role
07:44 Impact of AI in HR
12:55 Balancing Chief of Staff and HR Responsibilities
17:43 Talent Management Strategies
19:31 Communication and Leadership
24:45 Continuous Improvement and Empowerment
32:45 Practical Advice for Setting Up People Operations
36:00 Favorite Products and Conclusion

Emily answers a listener question from Tamsen in Minneapolis, who’s been asked to build a mini PMO function. She talks through concerns about returning to project management work, possible worries about people management, and how to clarify the scope with the CEO and COO. Emily suggests separating past experiences from the new opportunity and making sure the Chief of Staff role remains broad and strategic.

Links Mentioned:

• Emily Sander’s LinkedIn Profile
• 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.

Sara Lobkovich explains how to use OKRs (Objectives and Key Results) without the common pitfalls, like having too many goals or confusing milestones with actual key results. She gives practical examples, such as how "launch Project X by end of Q2" is a milestone, not a key result, and pushes for OKRs to focus on measurable outcomes that often feel out of your control. The conversation includes tips for Chiefs of Staff on implementing OKRs successfully, handling change management, and using retrospectives to learn from what worked—and what didn’t.

Links Mentioned:

• Sara Lobkovich’s Website
• Sara’s Book and Workbook

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:

00:13 Understanding OKRs: Objectives and Key Results
01:47 Common Challenges in Implementing OKRs
04:35 Defining Key Results and Milestones
08:09 The Importance of Clear Definitions and Terms
18:47 Implementing OKRs Successfully
22:24 Quantitative Assessment and OKR Creation
24:32 Timeframes and Cadence for OKRs
25:53 Levels of OKR Localization
28:58 Change Management and OKR Adjustments
32:41 Retrospectives and Continuous Learning
34:54 Cross-Functionality and OKRs
38:33 Addressing Resistance to OKRs
40:41 Sarah's Work and Expertise
42:54 Sarah's Book and Resources
43:15 Conclusion and Final Thoughts

A listener asks how to handle a CEO who overpromises big ideas in public, causing staff to lose trust when they don’t happen. Emily suggests privately discussing the real impact with the CEO, sharing clear examples like lost productivity after public announcements, and separating brainstorming from commitments. She also recommends giving the CEO practical talk tracks and focusing on themes like follow-through to help restore trust.

Links Mentioned:

• 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:

00:58 Understanding the CEO's Awareness
02:07 Communicating the Impact
05:02 Creating a Safe Space for Ideas
05:39 Distinguishing Conversations
06:54 Equipping with Talk Tracks
07:46 Frameworks for Discussion
10:48 Encouraging Follow Through