Leveraging Leadership

Emily answers a listener’s question about feeling stuck to a script during presentations. She explains how to focus on key points instead of memorizing every word, suggests adding emotion and attitude to messages, and demonstrates this technique with a “baseball is boring” exercise using different emotions like anger and sadness. Emily gives practical tips to build real confidence by practicing with main ideas, knowing the audience...

Erika Aquino, an angel investor with 26 portfolio companies across five countries, and her Chief of Staff Patricia de Leon, share how they work together to find and support women and minority founders in sustainability, wellness, education, and future of work. They talk about Patricia’s role as the first filter for deals, relationship building, and special projects like producing a TV show on female founders. Erika also opens up ab...

This episode covers practical ways for a Chief of Staff to reduce decision fatigue for their principal and executive team, like removing low-value tasks from their plate and organizing clear, concise email options for faster decisions. Emily shares real examples, such as giving decision options in an “A, B, C” format and using thresholds for approvals, to keep leaders focused on high-impact choices. The discussion also highlights w...

Dr. Keith Dorsey talks about his book, "The Boardroom Journey: Practical Guidance for Women to Secure a Seat at the Table," explaining what corporate boards do, why diversity matters, and how anyone - no matter their career stage - can start planning for a board role. He shares actionable advice on building skills across different business areas, networking intentionally (even mentioning how a janitor helped someone land ...

A Chief of Staff struggles to make three different presentations - an internal all hands update, a customer pitch, and a board meeting - feel meaningful and tailored for each audience. Emily suggests using common core info but adding exclusive details for each group, plus using questions from past meetings to anticipate concerns and adjust content. Real examples include noticing trends in employee questions about pay raises or offi...

Tracy Van Grack and Michael Patino talk about working with a Chief of Staff, sharing real stories from startup and established companies, including how early-stage teams can build a culture of communications even with limited resources. They cover the difference between hiring internal or external communications experts, using examples like tech startups handling crisis PR and the importance of authentic messaging. The episode also...

Chief of Staff can be a lonely job, even when you're surrounded by people. Emily shares real ways to handle this, like joining Chief of Staff networks, leaning on trusted coworkers or friends outside the company, and working with a coach. She also talks about knowing when to just acknowledge the loneliness and when to actively address it.

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Episodes featuring founders of the following Chief of Staff comm...

Frank Noyola shares how he went from turning down the Chief of Staff role at Quest Global to shaping it into a job focused on strategy, team building, and supporting a rapidly evolving CMO/Chief Strategy Officer. He talks about building a small team to handle operations, collaborating with the only other Chief of Staff at the company, and making sure the position stays a “driver” role instead of just administrative support. Frank a...

Emily, Ed, and Rory break down how to use a Flash Report to keep leadership teams aligned and focused on key business metrics. They give a real example of a Flash Report, show how it highlights things like cash, sales, and training completion rates, and explain why keeping it simple matters. The episode covers choosing the right KPIs, what to include in the written updates, and how the Flash Report improves transparency and better ...

Tarra Stubbins shares her journey from dropping out of high school to travel with rock bands as a personal assistant—including wild hotel room requests from Mick Jagger—to founding the Take It Easy Group, where she now provides Chief of Staff and executive support to high-profile clients. She talks about handling unusual demands like putting a toothbrush in a hotel dishwasher, building a strong network, and helping CEOs, athletes, ...

Emily shares practical delegation tips like breaking up complex tasks such as invoice processing into smaller, easier pieces, moving teammates upstream in a process, and letting others help with basic steps like data collection. She explains how small steps—like making quick guides, recording simple training videos, or copying others on emails—can add up, lighten your load, and help others grow. Emily also stresses that if delegati...

Scott Amenta, founder of Chief of Staff Network, shares key findings from their recent AI report, including that 84% of surveyed companies are already piloting AI tools and that change management and ethical concerns are major barriers. He talks about the new role of the Chief of Staff in AI adoption, working closely with CEOs and CTOs, and highlights the launch of several new programs like the Chief of AI Fellowship and Launchpad ...

Emily shares a story about someone who gave their boss a basic org chart when asked about their department’s future, but missed the bigger picture the boss wanted. She explains how to shift from being just a task-doer to a strategic leader by connecting department changes to the company’s new vision, outlining system upgrades, communication plans, and several org chart options that align with that vision. Emily encourages thinking ...

Remi Guarini, a three-time Chief of Staff, shares how she moved from fashion operations at Maison Kitsune to working at Capital Factory, and then to helping launch Neon, an early-stage venture capital firm. She talks about learning on the fly, juggling investor and operations duties, building strong relationships, and how her role evolved to include everything from audits to portfolio support. Remi also gives practical advice for t...

This episode covers how a Chief of Staff can address two teams stuck in a blame game at a biotech startup. Emily shares examples like holding one-on-one meetings with managers and team members, presenting anonymized feedback, setting clear expectations for team behavior, and publicly reinforcing new team norms. He explains how to reset the group dynamic so everyone understands the new way forward and knows “pointing fingers” is no ...

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 ...

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 ...

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 relations...

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...