Leveraging Leadership

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 Repor...

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 ne...

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. E...

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 Ch...

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...

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. Rem...

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...

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 Sta...

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...

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...

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...

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 merg...

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 s...

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 in...

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 fo...

Vivek Modi shares his journey from engineering in Africa to consulting at Ernst and Young and Roland Berger, and now to Chief of Staff for two CEOs at a fast-growing German startup. He compares consulting and Chief of Staff roles, breaks down how he builds trust with senior leaders, and offers practical advice on influencing without authority. Vivek also highlights the importance of clarifying res...

Emily shares a personal story about being made the interim leader of a digital marketing department as Chief of Staff, even though he knew nothing about digital marketing at the time. She talks about asking basic questions like "What does SEO stand for?" and dealing with colleagues who doubted her, including being called out during a team meeting. The episode highlights how not being a t...

Chanelle Pearson, Chief of Staff at the Victorian Chamber of Commerce and Industry, shares how her career moved from journalism to leading teams in advocacy, media, and events. She talks about launching the Chamber Change women’s leadership program, organizing the upcoming World Chambers Congress in Melbourne, and balancing her diverse responsibilities. Chanelle also offers advice for other Chiefs...

Emily answers a listener’s question about job titles in a growing 50-person company, giving advice on moving beyond generic VP roles and considering more specific titles like VP of Operations or Chief of Staff. She explains the importance of planning for future growth, staying flexible with titles, and being mindful of internal dynamics when making these decisions. She also shares cautionary tales...

"Any views expressed are the opinions of Mr. Williams and do not reflect the position or represent the U.S. Department of Defense. Mr. Williams' participation does not constitute any implied or actual endorsement of any nonfederal entity by the U.S. Government." Johnathan "JDUBB" Williams, Chief of Staff for the Joint Functional Component Command for Integrated Missile Def...

A Chief of Staff asks how to handle a team member who never submits their flash report, despite lots of reminders and training. Emily suggests letting the slacking team member feel the peer pressure in meetings, such as by leaving their section blank in the board report or calling on them in front of the group and holding an awkward silence. The episode covers practical escalation steps and emphas...

Jessica Porter shares her path from Executive Assistant to Executive Business Partner and acting Chief of Staff, working in both venture capital and private equity-backed companies. She talks about managing KPIs, handling turnarounds, being a conduit between PE firms and leadership teams, and leveraging AI to solve business problems. Jessica also highlights the importance of understanding investme...

Emily answers Nicole S.'s question about how to balance the tactical and strategic sides of the Chief of Staff role, sharing examples from both startup and large company experiences. She covers ways to prioritize, how to have conversations with your principal about trade-offs, and offers practical advice like delegating, automating, and asking if all tasks are necessary. Emily also explains w...

Steve Werner shares how he helps founders and companies run engaging sales events by building a story arc that keeps audiences interested. He gives practical tips for prepping investor pitch decks, including being clear about strengths and weaknesses, saying where you need help, and avoiding slides covered in text. The conversation covers how to sequence team stories in a pitch, build trust with i...

Cutting your Chief of Staff during a downturn is a big mistake—they act as a utility player who can fill gaps in HR, operations, sales, and more. Chiefs of Staff keep morale up after layoffs, help maintain strong communication, support the CEO’s decision-making, and are key to rebuilding when things improve. Emily compares them to the knight in chess: flexible, able to jump over obstacles, and unb...