Ask a Chief of Staff: Live 1:1 and Group Coaching for Chiefs of Staff: Navigating the CEO Relationship
- Date
- 2025-10-23
- Host
- Personal
About this event
The CEO relationship can make a Chief of Staff role energizing, strategic, and high-impact — or frustratingly unclear. This session is built for Chiefs of Staff who want sharper judgment, stronger alignment, and a more effective day-to-day working partnership with the person they support most closely. About the Event This is a live coaching event focused on one of the most important and nuanced parts of the Chief of Staff role: navigating the CEO relationship. Rather than staying at the level of general advice, the session is designed to help attendees think through real dynamics, real decisions, and real moments of tension or ambiguity. Expect a mix of 1:1-style coaching and group learning. That means you will not only hear practical guidance directly relevant to your own work, but also benefit from the questions, examples, and patterns that come up for others in the room. The format is especially useful for Chiefs of Staff because so much of the role depends on judgment, context, trust, and communication. Those are hard to learn from templates alone. A live setting creates space to unpack the subtle issues that sit underneath execution problems: unclear decision rights, mismatched expectations, communication gaps, shifting priorities, and the challenge of staying strategic while managing the immediate. Whether you are early in the role or already operating at a high level, this event offers a chance to step back and get perspective on how you and your CEO work together. What to Expect The session will center on live coaching around the CEO-Chief of Staff partnership. You can expect discussion that is practical, direct, and rooted in the realities of the role rather than abstract leadership theory. Topics may include: Building trust and credibility with your CEO Clarifying expectations and scope in a role that often shifts Managing upward without creating friction Handling communication styles, feedback loops, and decision flow Knowing when to push, when to advise, and when to execute Creating alignment across priorities when everything feels urgent Because this is a coaching-oriented gathering, the value comes from interaction. You may hear a challenge that mirrors your own, learn a framing that helps you handle a difficult conversation, or leave with a more useful way to diagnose what is actually off in your working relationship. There is also a community dimension to the event. Chiefs of Staff often operate in roles that are highly visible but individually isolating. Being in a room with peers who understand the complexity of the work can be just as valuable as the formal coaching itself. Why Attend If you have ever thought, "I know I am solving the right problems, but I am not sure my CEO sees it the same way," this event is for you. The most effective Chiefs of Staff are not just organized operators — they are translators, prioritizers, sounding boards, and force multipliers. That requires a deliberate approach to the relationship at the center of the role. Attending can help you better understand where friction is coming from and what to do next. Sometimes the issue is not performance; it is cadence. Sometimes it is not trust; it is visibility. Sometimes it is not a strategy problem; it is a decision-making problem. Getting clearer on those distinctions can save months of unnecessary strain. You should leave with practical insight you can apply immediately, including better questions to ask, sharper ways to frame tradeoffs, and a stronger sense of how to create alignment with your CEO without losing your own judgment. This is also a chance to invest in yourself as a practitioner. Chiefs of Staff are frequently expected to create clarity for everyone else while having limited space to process their own challenges. A focused coaching session like this gives you that space. Practical Details This event takes place in person on Thursday, October 23 at 11:30 AM PDT. If you value live discussion, real-time coaching, and the ability to connect directly with peers, the in-person format is a meaningful part of the experience. The event is best approached as a working session rather than a passive talk. Come ready to listen closely, reflect on your current CEO dynamic, and capture ideas you can put into practice right away. A few helpful ways to prepare: Think about the biggest challenge in your CEO relationship right now Identify one conversation, decision, or pattern you want to improve Bring a notebook or a way to capture insights in the moment Be ready for honest, useful discussion with peers who understand the role If your work depends on influence, alignment, discretion, and strategic execution, improving how you work with your CEO will improve nearly everything else you do. This session is a focused opportunity to do exactly that.
Who should attend
This is for you if you want to become more effective in the relationship that shapes the rest of your work. - You are a **Chief of Staff** who wants clearer alignment, stronger trust, and better day-to-day partnership with your CEO. - You are **new to the role** and trying to understand how to set expectations, establish credibility, and avoid common missteps early. - You are an **experienced Chief of Staff** dealing with more complex challenges, such as evolving scope, shifting priorities, or unclear decision boundaries. - You are navigating a **difficult CEO dynamic** — communication friction, mismatched working styles, unclear ownership, or tension around influence and execution. - You want **practical coaching, not generic career advice**, and you learn best by hearing real questions, real examples, and tested ways to handle them. - You value being in community with **other operators who understand the role**, especially if you rarely get honest peer conversation about the realities of supporting a CEO closely. If your effectiveness depends on reading context well, managing upward thoughtfully, and turning ambiguity into action, you will get a lot out of this session.