Issue 22: Self-Management as a Chief of Staff
The most important person to manage you as a Chief of Staff? You.
Welcome back, aspiring and current Chiefs of Staff!
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This week’s issue is co-authored by John Quayle. John Quayle is a graphic designer turned operations specialist with over 13 years of experience in marketing, business operations, and entrepreneurship. He currently serves as the Chief of Staff for an AgTech industrial automation robotics company. In his previous tours of work, he has been a founder, a COO, and has spent time as a consultant.
How Can You Best Self Manage as a Chief of Staff?
As a Chief of Staff, your greatest manager will be you: It may seem a little counterintuitive, but it is the truth.
While your principal may be a strong leader and sets the priorities for your role, once the initial foundation of trust is built up, they may take a less hands on approach with you and assume that you have the capacity to manage on your own. And because Chiefs of Staff typically don't have peers in the organization or a commonly established career track, job and career management can easily be an afterthought. This is especially the case for any Chief of Staff that is in their second or third tour of duty.
That's why it's important for any Chief of Staff to become their own best manager, in both job and career.
If left as an afterthought, a Chief of Staff may find themselves in a reactionary tailspin; often accepting whatever processes that come their way, diving into projects that don't move the needle, having a serious lack of self-care and often willing to be a passenger out of fear.
💡The Importance of Managing Yourself
Ask any Chief of Staff how work is for them and they'll give you a wide array of answers: some will say that they love the challenge and variety of the role, while others will say that it can be overwhelming and stressful.
But one thing that all Chief of Staffs have in common is that if they do their job well, their principal will often be relatively hands off when managing their Chief of Staff, instead focusing their time on the things that only they can do, whether it be investor relations, raising money, finding first clients, etc. After all, a Chief of Staff is often hired to do exactly this: free up the principal’s time so that the principal can focus on their superpowers and continue to look at the big picture.
This can often lead to the "if it isn't broke, don't fix it" awkward management experience a Chief of Staff may live through. The principal leaves the Chief of Staff to their own devices because in their eyes, "My Chief of Staff has things under control and they'll figure it out". The Chief of Staff, however, may feel even more isolated on their island of one, clearly driving initiatives and projects, but unclear on what their upward mobility may look like or what career growth entails.
This is why Chiefs of Staff often need to be their own best managers.
This diligent process of self-management does two key things:
It allows us to be more effective at our job
It helps us understand our wants and needs better than anyone ever could
At the heart of it all, acting as your own manager will unveil your strengths, values, while showing you how you best fit in the overall puzzle at your company.
🖼️ Self-Management Frameworks for Success
Whether you're looking to improve your day-to-day work or plan for the next five years of your career, there are a few frameworks that you can adopt to build a process for self-management.
Short Term Week-to-Week Actions
📘 Bookend Admin Hours:
Schedule two 60-minute admin hours, one at the beginning of the week and one at the end.
Use these hours to review your weekly goals and projects, track your progress, and make adjustments as needed.
Note: These are 'anchor' hours and should not be skipped or moved. These are moments that help you understand if you're moving on the right path and to help you understand what is possible vs. what isn't. While it may be tempting to skip a week or two if progress isn’t notable on certain initiatives, it’s the diligent tracking over time that will help you see trends and patterns in your work.
🎤 Conduct Check-ins through Self Q&A
Schedule an additional (separate from admin hours) time each week to reflect on your work and ask yourself the following questions:
What were the best and worst parts of your week?
Are there resources that would help unblock or speed up your progress? If so, what are they and why those things?
How are you feeling? What has brought on stress or anxiety for you this week?
Note: Make sure you conduct your weekly check-ins when you won't be disturbed by incoming requests or the pressure of being around people. This could be after hours or a time blocked on your calendar where you remove all distractions (Slack notifications, etc.) and are in a truly DND mode..
Long Term Career Planning Actions
🪞Monthly Reflection
During the first week of each month, take some time to reflect on the previous month.
Keep a running list of accomplishments that you’ve completed the month prior - your weekly reflections will come in handy and this is a good time to recognize any patterns or trends in you work (Example: Lily Konings’ hype doc)
🗓️ Set Goals for the New Month
These goals can be self growth oriented, company initiative oriented, or personally oriented. Make them specific, measurable, achievable, relevant, and time-bound (how to set SMART goals).
Examples: Find and enroll in an online class to learn more about X skill, audit Q2 company expenses for irregularities, increase website traffic by 15% by creating a new digital campaign.
🔭 Forward Looking Projection
Keep a living document that outlines your career path. This document should include your current skills, the skills you want to learn, and the challenges you want to face.
Also do a holistic check in on where your life stands and where you would like it to go. Using a template like Level 10 life to better understand what areas of your life you want to invest time in and know that these priorities may change over time.
Once you have understanding on skill sets and areas you’d like to build on, you can use this to brainstorm new ideas and opportunities in your Chief of Staff role.
🔎 Using Your Findings to Managing Your Principal
Upon completion of the previous frameworks, you can synthesize your findings into three main categories: requirements, asks, and future fit. These categories will provide you with key talking points that you can use in your check-ins with your principal as well as performance reviews:
Requirements: Short-term resources, skills, or decisions you’ll need to make progress on a project or task.
Requests: Medium-term asks that would help you become a better CoS for your principal and the company
Future Fit: Long-term petitions that help you align your future career ambitions & interests with the company.
For example, as part of the Future Fit discussion, you may be interested in learning SQL to better understand the analytical parts of your org. If you believe that this is the right skill set for you to learn, you may request a small personal development budget to take an online course or two, or you may lobby for an introductory project that would allow you to put your newly acquired skills to the test.
If you haven’t already set up a monthly or at least quarterly cadence to discuss career trajectory with your principal, it’s highly recommended to do so. Not only should your discussions include new initiatives for growth for yourself, you can also round out the conversation by building in guidance & feedback requests as well.
📈 Leveling Up as a Chief of Staff
Achieving self-management is a great accomplishment, but it's not enough to reach your full potential. You also need to be exposed to new insights, opinions, and tools. One of the hardest blindspots to overcome is the bucket of things you don’t even know you don’t know.
In a world where Chief of Staffs can feel isolated or unable to discuss key issues with coworkers, a community of peers can be essential for self-mastery.
The community at Ask a Chief of Staff has done the difficult work of assembling some of the brightest and most ambitious minds in the Chief of Staff field. If you're curious about how others have solved the problems you're facing, join and participate in the community. ➡️ Apply here ⬅️
However, if you're not ready or don't have the budget for that quite yet, don't hesitate to reach out to individuals for their insights, advice, and support. Virtual coffee meetings can go a long way in helping you achieve your goals. No matter what community you join or which individual you reach out to, you're not alone in the Chief of Staff world!
📣 In case you missed the announcement, Ask a Chief of Staff has reopened our waitlist and is accepting new members. We’ve also introduced a new “Aspiring Chief of Staff” membership tier for folks who are looking to focus on their job search and transition into a Chief of Staff role!
If you’re an aspiring, current, or former Chief of Staff, we’d love for you to join us in our Slack community to share best practices and knowledge with each other.
🎥 Upcoming Events and Workshops:
July 26th: IN PERSON EVENT - SF Chief of Staff Happy Hour (registration must be approved to attend)
July 27th: MIT Club of North California Event - Learn about the Chief of Staff role
August 3rd: Strategy and Storytelling with Data
August 10th: Networking Your Way to Your Next Job
As a reminder, events and workshops are free for all Ask a Chief of Staff community members (including our newest Aspiring Chief of Staff tier!) and the recordings will only be provided to members. There is a suggested ticket price on all workshops on but the first 25 registrants can waive your ticket price with code ASKACOSREADER.
Additional Chief of Staff Related Reads:
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👋🏼 Until the next issue,
Clara
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