Issue 37: Strategies to Handle Pressure and Prioritize Effectively as a Chief of Staff
When everything is urgent, doesn’t that mean nothing is urgent?
Welcome back, aspiring and current Chiefs of Staff 👋🏼
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We are pleased to have John Quayle return as this week's guest author! You may remember his previous guest authored issues about Self Management and Writing a Chief of Staff Resume. 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 Does a Chief of Staff Prioritize their Work?
Ever come across the adage, “If everything's a priority, then nothing is”? As a Chief of Staff, it's a phrase that hits home more often than not. No matter the company's scale or scope, our plates are perpetually piled high with tasks. From constant interruptions to ongoing projects reaching their deadlines, the workload seems never-ending.
And depending on the kind of principal that we report to, the workload can swiftly spiral out of control. A query here, a demand there, and suddenly, we’re drowning in tasks, struggling to discern priorities. This scenario is par for the course for Chiefs of Staff, whether they're new to the role or seasoned veterans with experience across multiple organizations.
So, how do we crack the code of prioritization? If you've ever felt the pressure of this conundrum, you're in good company. Fear not, because we're here to steer you through the maze and demystify the process.
🎯 Defining Goals for Your Success
Before we jump into the mechanics of prioritization, it's crucial to grasp how Chief of Staff roles are structured to support principals. In smaller setups, Chiefs of Staff might find themselves involved executing initiatives across multiple departments and with various stakeholders. Conversely, in larger organizations, our responsibilities may be more delineated, emphasizing communication and collaboration with a broader range of key players.
In either scenario, as part of your Chief of Staff onboarding, your principal should have shared the position’s goals for the upcoming year (or sometimes your first 90 days since things can change quickly at startups), broken down into quarterly and annual targets. If these goals weren’t outlined upon your arrival, you likely will need to collaborate with your principal during your first month to define them. This exercise, whether received upfront or developed collaboratively, serves to align you and your principal with the major objectives and guiding principles for the forthcoming quarter or year, providing a clear understanding of how your role intertwines with their overarching objectives. This process will also allow you to establish key pillars outlining the company’s, department’s, and your own role’s ultimate goals.
Some examples of what your goals might look like include:
Collaborating with your Chief Revenue Officer (CRO) to establish a new sales division dedicated to our latest product.
Planning the company's Q3 annual offsite retreat.
Spearheading the hiring and onboarding process for the next five engineering professionals in alignment with our hiring roadmap by Q2.
Overhauling communication standards and procedures for engaging with external investors.
It’s important to acknowledge that if you haven’t been provided with such documentation or haven't collaboratively crafted it, take it upon yourself to block time with your principal over the next few weeks to create a similar roadmap for the rest of 2024 and on a rolling quarterly basis. This proactive step ensures alignment, clarity, and effective task prioritization in line with organizational objectives.
If you're still unsure about how to begin, consider utilizing the First 90 Days template by Katie Larabee (part of the AaCoS resource library that’s free for members!) as a starting point. Additionally, don't forget to onboard yourself effectively within 30 days by following the invaluable guide from Regina Gerbeaux.
🌀 Making Sense of the Chaos
With objectives, goals, and guiding principles established, it’s time to tackle the day-to-day whirlwind that comes with the Chief of Staff role. Each week (or month) brings a fresh array of tasks and assignments, some in line with our quarterly objectives, while others veer off in new directions.
To navigate this complexity, we lean on repeatable processes to dictate priorities and timing. An invaluable tool in this regard is the Eisenhower Matrix, an industry-standard framework that categorizes tasks based on their urgency and importance. Within the matrix, tasks are divided into four quadrants, balancing urgency and importance. Each assignment falls into one of these categories: urgent, not urgent, important, or not important.
For tasks that are both important and urgent, prioritize immediate action.
If a task is important but not urgent, schedule it in your calendar for future attention.
Tasks that are urgent but not important should be addressed within 24 hours.
For tasks that are neither important nor urgent, plan to address them within the next few days.
Further complementing the matrix, you can streamline your workflow by completing a brief 30-second form for each new project. This form aids in categorizing projects into the appropriate quadrant. Whether a task comes through email, a meeting, or a call, take a moment to ask yourself:
Date: What is the deadline for this project or the timeframe for response?
Stakeholders: Who are the key individuals involved in this project that I need to collaborate with?
Time: How much time estimate do I allocate for completing this task? Is it a single-day endeavor or will it span multiple days?
Information: What specific materials or information do I require before proceeding with this assignment?
As Chief of Staff at Four Growers, I often encounter interruptions to my scheduled tasks, especially when urgent matters arise, such as repairing or shipping out replacement parts for robotic units. Minimizing downtime remains a top priority regardless of my workload. I need to be ready for unexpected situations and be flexible with my schedule to handle them.
If you need templates for your work, try using the prioritization matrix or project tracking spreadsheet. They're easy to use and helpful for staying organized.
By implementing these two crucial exercises, a Chief of Staff can effectively assess the urgency and importance of every project, task, or request that lands on their desk. If, after completing these exercises, you’re still unsure of the task’s placement in the matrix, we recommend continuing to ask questions to all involved until you’re able to find clarity.
Looking for more templates? Members of the Ask a Chief of Staff community get access to hundreds of templates like the ones above included in the price of membership! ➡️ Apply to join us here ⬅️
🐳 Adjusting for Pressure
In our pursuit to accomplish everything, we inevitably encounter the human aspect of business: managing expectations and pressure within our environments. While not always within our control, there will be instances where your Principal assigns tasks exceeding our available time in a day or week. It’s during these moments that your organizational skills and ability to prioritize shine.
Recognizing the potential for overwhelming pressures in your roles, we acknowledge the importance of having a few quick tricks up our sleeves to alleviate the strain.
When faced with such situations, there are two effective strategies to manage the emotions and expectations of key stakeholders:
Maintain a concise record of your daily and weekly tasks (& progress) within a project management tool. This log should encompass current projects as well as your future projects.
You might want to consider tools like Monday.com, Asana, or Notion - just to name a few popular ones.
Take a moment at the start and end of your workday to plan when and how you'll tackle each project for that day or the next.
We cannot recommend blocking this time on your calendar each day so that the time doesn’t get swallowed by yet another competing priority.
In action, this could involve a weekly sync meeting with your principal to review accomplishments from the past week and determine the top 1-2 priorities for the upcoming week. During my tenure of nearly three years at Four Growers, I’ve consistently held such meetings with my principal to ensure we reflect on past progress and plan for the future. I enforce a firm limit of two priority spots, giving the principal the autonomy to select projects within this boundary.
My own communication cadence with my principal looks like this for handling priorities:
Quarterly: We establish top priorities for the quarter and the next 12 months during our quarterly employee reviews.
Weekly: We meet on Fridays to review my workload, summarizing the week’s accomplishments and aligning priorities for the next week.
Mondays: We allocate two or three 30-minute meeting blocks to review each department objectives and priorities that I’m responsible for, covering areas such as Human Resources, Marketing, or Fundraising.
So, if your principal or a colleague assigns you a new task and insists it’s a priority, you can refer to your log to explain your workload and discuss what other tasks may need to be adjusted. You can also utilize the log in your one-on-one meetings to ensure alignment on projects and direction, providing transparency to all stakeholders about your workload and tasks.
Ultimately, mastering prioritization not only streamlines workflow but also ensures that tasks are aligned with organizational objectives. In essence, when a Chief of Staff excels at prioritization, their workload becomes more manageable, allowing them to focus on driving success for the entire organization.
🎥 Upcoming Events and Workshops:
March 5th: How to Measure the ROI of an Offsite
March 14th: Coffee and Co-Working at Industrious [IN-PERSON IN NYC, registration required]
March 14th: How to Delegate, Not Babysit
March 18th: Guided Breathwork Experience
March 21st: Generative AI 101
March 29th: Chief of Staff Virtual Coffee Mixer #2 hosted by Ask a Chief of Staff, Nova Chief of Staff, Ambient [FREE for all to attend]
As a reminder, events and workshops are free for all Ask a Chief of Staff community members.
Additional Chief of Staff Related Reads:
Playing Chess, Not Checkers: Intuit’s Brad Smith on the Value of a Chief of Staff Role
How to Implement Effective QBRs & OKRs
The Chief Factor: Use These Three Principles to Guide Your Networking (Plus a Bonus Framework)
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