The Strategic Value of Rethinking your Calendar: Why, and How, New COOs Should Take Control of Their Time
Introduction: Your First Year as a COO
This article marks the kickoff of a series of playbooks and practical guides intended for those new to the COO role, describing what COOs actually do all day. Advice for new executives is often vague, aspirational, or overly conceptual, and those transitioning into a C-Suite position for the first time—or stepping up from a position like Chief of Staff—have a great deal to gain from guidance that can help them find their feet. That’s what I aim to do here.
Other articles in the series will cover variation in the job’s key responsibilities, methods for task assessment and prioritization, relationship building and boundary setting with the rest of the executive team, carrying over workflows and workplace practices from previous positions, and other aspects of the daily life of a Chief Operating Officer.
This first piece, though, has a narrow and specific focus: taking control of your calendar as it fills up—and quickly overflows—with your new responsibilities. You’ll very quickly find that a day in the life of a COO is a delicate balance. Take on too much, and nothing gets done.
Systems and Structure
“Your calendar is a better measure of success than your bank account.” – James Clear
In this new role, you will succeed or fail by your calendar. It requires constant, proactive management as well as tight coordination with your administrative assistant. It also requires a shift in both mindset and priorities.
I realize that updating your approach to calendar management seems like a tactical change, but it’s actually strategic—and fundamental. Protecting your time is essential to meeting the demands of your position. Like Chief Executives, COOs will always have more requests for their time than they are able to fulfill.
So, to succeed, you must have a rationalized system to triage time requests, the system has to be placed in the hands of a genuinely great Executive Assistant (EA), and you’ll need to regularly revisit and evolve the system’s rules to ensure it’s serving your needs.
Then there’s mindset. As a newly appointed COO, one of your biggest adjustments will be learning to say “no” much more often. The skills that got you here are about staying involved—you probably have a track record of getting things done, and your presence has likely been critical to keeping teams together and projects moving forward. That high level of engagement is a great quality right up until everyone, all at once, is asking for some of your time. One key benefit of systematizing your calendar is that it streamlines your decisions about which meetings to take and which to delay.
Developing Your New Calendar
I’ll start by sharing my own current guidelines as an illustrative example. Here’s how my Executive Assistant triages incoming requests. If you don’t work with an EA, I use and love reclaim.ai which automates prioritization, syncing work/personal calendars to prevent being double-booked, and allows you to schedule/manage heads-down work blocks.
1. One-on-one meetings are sacred. Move them only with my explicit permission and, when we do move one, remind me to reach out to the invitee before the calendar event is updated.
E.g., Head of Sales requested a 1:1 to discuss new hires. On the day, you have to put out fires in finance, but I make a moment to message the HoS before my EA reschedules.
2. Proactively schedule one-on-one’s following team or group meetings, with an eye toward preventing redundant discussion across multiple 1:1s.
E.g. Following a recurring Monday Executive team meeting, schedule recurring 1:1s on Tuesday to serve as a feedback loop for what did or didn’t land in the team meeting.
3. Preference certain times of day (chosen based on my energy level).
E.g., I tend to be most tired after 2pm, so lower-stakes check-ins are scheduled then.
4. Preference putting as many meetings as possible back to back, to allow space for deep work and other priorities.
E.g., Start-of-week meetings scheduled in a block Monday midday, and project status meetings clustered on Thursday mornings, which allows two days to recover if we’re off-track.
These specific rules should fit within a broader system priorities, roughly mapping out ranks of stakeholders by time-sensitivity or other factors affecting which meetings should be booked first. That system will shift often—sometimes daily, always at least weekly—and you’ll want to set up a consistent way to communicate those changes.
Both the stakeholder ranking and the triage guidelines you’ve established for incoming requests will also need to fit within the constraints imposed by your other work obligations. Deep work, time spent on collaborative projects, travel and breaks, and so forth.
That problem, too, is a question of priorities. One of actionable books on this topic is Demir and Carey Bentley’s excellent Winning the Week, and they get right to the point:
“Go ahead and estimate the amount of time it will take to get your number one priority done this week. Then add some buffer to that estimate. Now schedule that time directly into your calendar, ideally on Monday or Tuesday (when your energy and attention are at their peak).”
Once you have a conceptual grasp of how your time is going to be allocated, you’re ready to translate it into a concrete schedule (and ongoing scheduling system). I suggest doing this in two phases.
First, re-frame your calendar as an equation:
What are you solving for? (What are your key outcomes?)
What are your most common and/or important inputs? (These are the constraints: time alone, time with people, etc.)
Add in your stack-ranking of stakeholders: whom must you meet with, in what order, and at what cadence?
Adjust the results to account for realistic constraints: schedule as many meetings back-to-back as possible, determine when to delegate, etc.
As you work through these steps, don’t start with your current calendar—that way lies madness. Instead, draft the basics on a blank piece of paper or a fresh spreadsheet.
The second step I recommend is working through Ali Abdaal’s “Ideal Week” exercise, limiting it to the context of work and separating out the various elements of your workday. It will help you translate your new system into calendar alerts and notifications.
With those basics in place and the system is clear as a plan of action, it needs to be clear on the screen. Importantly, it needs to stay clear as you and your EA (and your other colleagues) coordinate the schedule and update your plans over the course of the day.
I prefer a color coding system for communicating degrees of availability at a glance. I suggest a scheme along these lines for conveying to your EA which time blocks are flexible and which are fixed.
Green. I most likely will not join this meeting, and will instead send a delegate or debrief afterward with one of the other attendees. Go ahead and take this slot if you need to squeeze in a last-minute check-in.
Yellow. I need this block available same-day to complete a priority task or meeting.. Move as needed within the day so long as the block doesn’t get broken up.
Red. This is not a flexible time block, don’t book over it. The inviolable barrier of the red calendar block is my saving grace during crunch periods. Red means that I know exactly what I need to get done and the deadline is measured in hours rather than days.
You can include other options as needed. Standing meetings are powerful tools, for instance, allowing for flexible “layering.” I have 10-11 AM every day blocked off to meet with my CEO, meaning we always have the time if we need it and our EAs can easily pull others into a meeting with both of us present.
I also suggest blocking off a full hour for lunch. With any luck, that extra cushion means you’ll end up with 20 or 30 minutes of actual downtime.
Two final notes to close this out. One is that your new scheduling system is going to need updates. Be prepared to reflect at regular intervals and work to recognize what’s working and what isn’t—both among the guidelines your EA follows and among your own priorities.
The other is about your EA themselves. If you aren’t used to working closely with an assistant, the transition to COO is the time to start. The best option is typically to hire a full-time professional EA with substantial experience; as an alternative, you can work with a service able to place a pre-trained admin. I meet with my EA at least weekly, and often every morning, to brief her on current priorities and stakeholder rankings.
Okay. That’s my guide to establishing a schedule that opens a path to success in your new job. Keep reading the rest of my First Year as a COO Series.
Further reading on managing your calendar
Winning the Week, by Demir Bentley & Carey Bentley
High Output Management by Andy Grove
This excellent piece by Jassim Latif, formerly of Slack
The 5 mistakes you’re likely making in your one-on-one meetings with direct reports by Claire Lew