Issue 56: Managing Context Switching as a Chief of Staff

Ways to stay organized when every task feels urgent

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😵‍💫 How Can Chiefs of Staff Manage Context Switching & Stay Focused?

This week’s issue was inspired by a question I received from a community member that likely resonates with many of you:

“Tips and tricks when your job requires a lot of context switching over the course of the day/week? I work fully remote and often meet with execs, so I don’t always have the most control over my calendar and often find myself leading or attending back-to-back meetings where the topic switches. Any strategies for how to either switch between topics without feeling brain fog, or calendaring approaches to better sequence/manage the topics?”

It’s a challenge that sits at the heart of the Chief of Staff role, so I turned to our community for their tried-and-true strategies. A huge thank you to Claire Podulka, Elizabeth Barr-Jobson, Katherine Huang, Harry Siggins, and others who shared their insights and practical approaches.

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🖼️ Picture this: You’ve just wrapped up a detailed financial review with your CFO, and in exactly two minutes, you need to pivot to a product roadmap discussion with the engineering team. 2️⃣ 0️⃣  after that, you’re facilitating a culture committee meeting, and somewhere in between, you need to process 4️⃣ 7️⃣ Slack notifications that accumulated during your back-to-backs. Sound familiar?

For Chiefs of Staff, especially those working remotely, context switching isn’t just an occasional challenge—it’s a fundamental part of the role. While the ability to move fluidly between different topics and stakeholders is part of what makes Chiefs of Staff invaluable, it also presents a unique cognitive challenge that requires very intentional self-management.

The Context Switching Challenge

The modern Chief of Staff role demands a delicate balance between being responsive to immediate needs and maintaining the mental clarity required for strategic thinking. As one community member, Elizabeth Barr-Jobson, puts it:

“I found that if I booked literally back to back, then someone always suffered. Either me or one of the people I was meeting with because I needed those breathers to be effective.”

The cost of constant context switching goes beyond mere fatigue. For Chiefs of Staff, who might switch contexts dozens of times per day, it presents a significant challenge to both productivity and effectiveness.

While we can’t eliminate context switching from the Chief of Staff role, we can be strategic about how we manage it. 

The key lies in building systems and habits that support smooth transitions while protecting our mental and physical resources.

In this week’s issue, we’ll explore:

• Calendar strategies for more effective context switching

• Techniques to stay sharp during transitions

• Systems for managing the unexpected

• Habits to maintain physical and mental wellbeing

📅 Calendar Strategies For Better Context Switching

When it comes to managing context switching, your calendar is your first line of defense and most powerful tool. Even today, I’m ruthless about my calendar management. My EA knows not to schedule over lunch and to avoid booking meetings on Fridays since I need the no meeting days to catch up.

Strategic Meeting Blocks ⏰

Start by organizing your calendar to support your natural rhythms and energy levels. 

• Group similar types of meetings together to minimize mental transitions

• Schedule complex or strategic work during your peak performance hours

• Use color coding to quickly identify meeting types and required preparation

• Build in buffer time between meetings to reset and prepare

“I live and die by calendar blocks and recommend these to my clients as well. It’s so crucial to take time to evaluate your meeting schedule vs. free time and block off dedicated time for larger projects, research, or whichever other task could otherwise fall by the wayside. I suggest labeling calendar blocks specifically and including any relevant links so you reduce the friction of getting started on that specific task.” -Katherine Huang, 2x Chief of Staff, Executive Coach

Smart Meeting Design 🎯

Small adjustments to how you structure individual meetings can have a big impact on your overall effectiveness.

• Schedule 25 or 50-minute meetings instead of 30 or 60 to create natural transition time*

• Use tools like Ambient to securely generate pre-reads, agendas, follow up emails and more.

• Set clear agendas and expected outcomes in meeting descriptions

• Connect your calendar to Slack to automatically update your status

• Use recurring meetings strategically to create predictable rhythms in your week (also regularly audit recurring meetings to make sure they’re still relevant)

“I’ve gotten super diligent about having links in my calendar events for the tasks I’m going to work on then. Links to emails, slack threads, websites, docs/sheets - whatever I need to get me up to speed fast when the time comes.” -Elizabeth Barr-Jobson, Chief of Staff at Simplero

* Pro Tip: Have meetings start at 5 or 10 after the hour versus planning them to end 5 or 10 before the hour. It’s natural that once you’re into an interesting conversation, you could run over time. But starting “later” gives you the break before the meeting starts rather than forcing you to cut off a conversation mid-flow.

Setting Boundaries 🛡️

While Chiefs of Staff need to remain flexible, it’s also essential to establish–and maintain–clear boundaries.

During my time as a Chief of Staff, I did not have the Slack app on my phone - something that shocks the majority of Chiefs of Staff I’ve talked to. I also have badge notifications turned off. I remind people constantly that while your job is important, we’re not doing brain surgery. Giving yourself the time to be “off” on personal devices is so important and if something was truly urgent, my Principal had my phone number.

• Block and protect focused work time for strategic projects

• Remember: if you don’t stand up for your time, nobody will

• Learn to say “no” firmly but professionally. For example, “I have held that time for productivity reasons, and it cannot be rescheduled."

• Request to be included in recap emails instead of attending non-essential meetings

“I find that I get interrupted CONSTANTLY with Slack pings, emails, text and Telegram notifications, etc. It’s not always possible for me to turn them off. I’ve learned to be ruthless about what I actually read and switch to. If it’s not on fire urgent or critically important, I’ll read it just enough to decide ‘yes or no’ on it. It’s almost always no. But I have to be firm with myself.” -Elizabeth Barr-Jobson, Chief of Staff at Simplero

🧠 Techniques For Sharp Transitions

Even with the best calendar management, context switching demands significant mental energy. Developing strong transition practices helps you maintain clarity and effectiveness throughout your day.

Physical Reset Routines 🚶‍♀️

Small physical changes between tasks can help your brain register the context switch.

• Stand up and stretch between meetings or take a short walk 

• Change your physical position or workspace when possible

• Look away from screens periodically to rest your eyes

• Use transition time to handle quick household tasks

“In a perfect world, I do some kind of physical transition between tasks. I stand up to get a drink of water, do some stretches, maybe even take care of something menial at home like throw in a load of laundry, to allow my brain processing/switching time while still ‘getting stuff done’ because life is busy like that.” -Claire Podulka, Chief of Staff at TXI

Workspace Management 💻

Your physical and digital environment also plays an important role in smooth context switching. If you work remotely, make sure you have a dedicated work area for deep working and thinking. While it may be tempting to work from bed (and that’s ok for low effort tasks like answering emails!), having a specific place for when your best work is done gives your brain a chance to “switch on” into “hard work mode.”

• Keep only relevant tabs open for the current task

• Organize documents and links by project or meeting

• Create clear verbal or written markers between tasks

• Take quick notes about next steps before switching

• Keep a running priority list to stay oriented

“To get started on a new task and switch contexts, I like the Pomodoro technique, which I apply a simple version of by starting the stopwatch and seeing if I can work for 5 or 10 minutes initially on a task that has been on my plate for a while. That’s often enough to get myself into the flow and knock the task off my to-do list.” -Katherine Huang, 2x Chief of Staff, Executive Coach

🌊 Managing The Unexpected Without Losing Your Flow

Every Chief of Staff knows that unexpected switches are inevitable and can be jarring. The key is to build flexibility into your systems. Give yourself the time to react to unknowns and if nothing happens during that time, you get it back!

Planning for Change 🎲

Set yourself up for success by making adaptability part of your daily plan.

• Leave strategic gaps in your calendar for urgent matters

• Keep a running list of tasks that can be done in short bursts

• Document ongoing projects clearly so you can quickly pick them up again

• Have templates ready for common urgent requests

“I typically outline tasks and prioritization the night before, considering calendar and personal objectives. Usually, assume that there’s an 80% chance it goes to plan, with a 20% expectation that at least something changes. If you can expect a slight change, it’s easier to manage when it happens.” -Harry Siggins, former Chief of Staff

Quick Recovery Strategies ⚡

When unexpected switches occur, use these techniques to maintain momentum.

• Take 30 seconds to document where you’re leaving off

• Set a clear stopping point in interrupted work

• Keep important reference materials easily accessible

Communication Tactics 💬

Clear communication helps manage expectations with your team during unexpected transitions.

• Let stakeholders know when you need to context switch

• Set realistic timelines for returning to interrupted work

• Update project trackers to reflect new priorities

• Establish clear criteria for what constitutes an urgent interrupt

“Be transparent with others. I say something like, ‘My head has been in this thing and I’m not as up to speed on the thing we have this meeting about as I’d like. Can you give me two minutes to refresh my memory and then walk me through what’s top of mind for you about it?’” -Elizabeth Barr-Jobson, Chief of Staff at Simplero

🧘‍♀️ Healthy Habits To Reduce Stress

Regardless of what systems and processes you implement during your work day, it’s essential to prioritize your mental and physical wellbeing to avoid burnout.

• Protect a consistent sleep schedule 

• Take breaks to close your eyes and practice deep belly breathing to reset your parasympathetic nervous system

• Stay hydrated throughout the day to maintain mental clarity

• Build in quick stress-release activities like stretching or yoga 

⭐ Bringing It All Together

As Chiefs of Staff, our ability to move fluidly between different contexts is both our superpower and our greatest challenge. 

That financial review, product roadmap discussion, and culture committee meeting? They’re all important, and with intentional practices, you can bring your best to each by:

• Structuring your calendar to support your natural rhythms

• Creating consistent transition routines that work for you

• Building in flexibility for the unexpected

• Communicating openly about your needs

• Taking care of yourself 

The goal isn’t to switch contexts faster—it’s to maintain effectiveness while preserving your energy for what matters most. Start by implementing one strategy from this article today, and build from there!

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💼 Open Roles:

Looking for a new Chief of Staff role? Check out the 🔟➕ Chief of Staff roles we’re hiring for. Just a small sample of some of the jobs we’re helping hire for below:

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If you’re interested, submit your application with the button below. If there isn’t a role that catches your eye right now, submit a “General Interest” application and we’ll reach out if we have something that’s a fit in the future!

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