Issue 44: The Essential Playbook for Remote Chiefs of Staff
Tips for building a strong Chief of Staff & Principal relationship across time zones
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How Can Remote Chiefs of Staff Thrive Across Time Zones?
Being a Chief of Staff is already a challenging role, but it becomes even more complex when working remotely – especially if you and your Principal are in different time zones. However, with the right strategies and mindset, remote Chief of Staff & Principal relationships can thrive. Inspired by a recent question I received on LinkedIn, I asked several experienced and fully remote Chiefs of Staff to share their best practices for navigating this unique dynamic.
Thank you to the members of our very own Ask a Chief of Staff community for sharing so many insightful and actionable tips!
🧱 Building a Strong Foundation for the Chief of Staff & Principal Relationship
Building a strong foundation for a Chief of Staff & Principal relationship is essential for success, especially when working remotely. Experienced remote Chiefs of Staff agree that focusing on these key areas contribute to a solid partnership with their Principals, despite the challenges of distance and time differences.
💬 Frequent and Effective Communication
Establish a regular communication cadence, such as building communication into daily routines like a morning phone call during your Principal's commute to work.
Build in specific management meeting time and several 1:1 standing check-ins with the principal each week, while remaining flexible when needed.
Keep regular meetings sacrosanct, even when traveling or in different time zones. Some Chiefs of Staff find three, 30-minute meetings throughout the week works for them, while others have daily, non-negotiable check-ins.
Over communicate, especially in the beginning of the relationship, by providing more information in a concise way. For example, send a calendar primer for the next day (including meeting goals, objectives, key discussion points, and background on attendees), an update on what's been done thus far, and an outline of what you plan to do in the next day(s) and why.
🫱🏼🫲🏽 In-Person Time
Commit to in-person time. While all relationships will be different, quarterly or semi-annual face time can help Chiefs of Staff and their Principals stay in sync.
Alternate locations for in-person meetings. One Chief of Staff shared that when she first joined, her principal spent one week in New York, and then she spent a week in San Francisco, alternating so that both parties traveled equally.
Recognize that the frequency of in-person meetings depends on the relationship, but upfront face-to-face time is powerful for building trust and confidence in ways that cannot be easily replicated digitally.
🎯 Clarity and Alignment
Use the 1:3:1 decision method to give your principal an understanding of what solutions the Chief of Staff has considered to enable them to give a quick response.**
Follow up every verbal conversation with written text, such as a Slack message or email summarizing meeting takeaways, outstanding items, and the joint understanding of project statuses or issues. Using software like Ambient makes this easy and takes out the step of needing to manually write these up yourself.
Maintain a running document of your Principal’s to-do list and items you are bringing to your Principal for discussion or decision-making. Understand that if everything is a priority, then nothing is a priority so ruthlessly prioritizing is a must here as well.
Seek clarity by asking questions and leaning into your Principal’s thought process, especially in the beginning.
** Haven’t heard of the 1:3:1 decision method? This strategy involves the Chief of Staff:
1️⃣ Clearly defining the ONE problem you are solving together
3️⃣ Providing THREE viable solutions, with the recommended one first
1️⃣ Explaining the rationale for the ONE recommendation in a couple of bullet points
👥 Personal Connection
Carve out 10-15 minutes for non-work conversations. Allowing executives to share personal life and challenges helps build trust, compassion, and understanding. One Chief of Staff also suggests opening the door to personal sharing at least 1-2 times a week, as executives often don't have any avenue for this type of connection.
Spend time together outside of work. By alternating locations as already mentioned, the Principal and Chief of Staff can meet one another’s families and get to know each other not only professionally, but on a personal level as well. This helps provide context on each other and allows each person to bring their “full self” to work.
Share personal experiences and challenges. One Chief of Staff shared her experience with an executive who managed severe ADHD, which was critical for her to know. They were able to share their neurodivergent flavors to help them better understand each other and build compassion and understanding for how to work best together.
🔐 Trust and Autonomy
Be comfortable working independently and delegating "up" the tasks and decisions that are vital for your Principal to act on. This protects them from overload by issues or meetings that are not on the executive level.
Provide clear visibility into your work and priorities. Remote Chiefs of Staff agree that the worst thing you can do is leave your Principal wondering what you are working on, as this can lead to duplication of work or doubts about your effectiveness. Start the week with a message to your Principal, outlining key priorities, urgent items needing input, and closing the loop on those priorities throughout the week.
Be proactive in providing your Principal with answers and suggestions rather than just questions. This helps your Principal feel informed and in charge, while also being open to course correction when needed.
👁️ Cultural Awareness and Insights
Observe and report on the culture of different company offices to leverage your distance from your Principal's main location.
Provide candid observations and feedback to your Principal on employee sentiment, morale, and communication dynamics across the organization as your Principal’s “set of eyes and ears.”
Lead internal culture initiatives using insights from different locations to identify areas for improvement and foster a stronger, more inclusive company culture.
⏰ Managing Your Principal's Time and Workload
A proactive approach to managing your Principal’s time and workload is crucial for maintaining productivity, preventing burnout, and ultimately driving the organization's success. This is especially true in a remote work environment where the lines between work and personal life can easily blur.
📅 Meeting Management
Establish a meeting cadence with known times, agendas, and participants to ensure predictability and routine decision-making. Optimize meeting efficiency by facilitating productive discussions to make the most of your Principal’s time.
Set different, specific goals for each touchpoint with the Principal. For example, the first meeting of the week could focus on setting the tone and focus for the weekly leadership team meeting, the mid-week meeting could be a recalibration to stay focused on goals, and the end-of-week meeting could be a reflection on long-term topics like organizational design and culture development.
👫 Relationship with the Executive Assistant
Prioritize building a strong relationship with your Principal’s Executive Assistant (EA). Consistently check in with the EA and hold bi-monthly meetings to review the calendar and key documents for a unified line of communication. If your Principal doesn’t have an EA already, consider using a service like Athena to hire a virtual assistant to take on more administrative tasks that will help free up your time as well.
Consider the EA as a critical partner in managing your Principal’s time and workload. Collaborate closely with the EA to optimize your Principal's schedule, prioritize tasks, and ensure that the principal remains focused on high-level strategic priorities.
By focusing on frequent and effective communication, making time for in-person meetings, fostering personal connections, and strategically managing the Principal’s time and workload, remote Chiefs of Staff can build strong, successful partnerships with their Principals. With the right tools, techniques, and mindset, geography and time zones become minor obstacles in the face of a well-aligned, trust-based Chief of Staff & Principal relationship.
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📖 Additional Chief of Staff Related Reads:
Operating Leaders Also Deserve Executive Coaches
Making Decisions: How and why we need faster decisions in a startup
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