The CEO First Semester Toolkit (Free Download)
A Semester Calendar and 90-Day Readout for School Leaders
Every new leader hears the same advice: spend your first months listening. Almost nobody tells you how to schedule that, or what to do with everything you hear once you have heard it.
Dr. Remy Washington has an answer for both. Eight months into her role as CEO of Uplift Education, a network serving more than 23,000 students, she calls her approach strategic sense making. Listening sessions, campus visits, focus groups, data, and highly intentional planning, all pointed at understanding what is really happening before deciding what comes next. On episode 59 of the CheckBox Pro Series, she walked through how she structures her week to make that possible.
Remy shared two of the tools behind that work with CheckBox Pro so other leaders could use them: the calendar template that protects her time for listening and thinking, and the readout template that turns ninety days of listening into a short list of priorities. You can download both below.
Why listening needs a calendar
Most leaders do not stop listening because they stop caring. They stop because the calendar fills up. A check-in lands on the morning you meant to be on a campus. A board prep call eats the afternoon you had set aside to think. By October, the listening tour has quietly become a list of meetings.
Remy’s calendar is built to prevent exactly that. Campus visits are treated as major CEO work, not something you fit in around the real work. Mornings are protected for proximity to schools. Late afternoons are protected for synthesis and follow-through. Friday is protected for planning, writing, and getting ready for the week ahead.
None of that happens by accident. It happens because the calendar was designed before the invitations started coming in.
Inside the CEO Semester Calendar
The first file is a Google Sheets workbook with eleven tabs that take you from a blank semester to a fully mapped one. Start with the Template Instructions tab. It walks through the order to fill everything in and lays out the four design principles behind the whole thing: protect CEO altitude, protect proximity, protect synthesis, and use exceptions intentionally.
The Semester Overview tab is where you set the rules. Your semester dates, how many campuses you will visit, how many teacher and scholar focus groups you will hold, the time routine meetings end each day, your protected Friday block, and your out-of-office dates. It also holds a short list of operating protections. One of our favorites: when a campus visit happens, the afternoon is capped at three short meetings.
The Weekly Architecture tab sets your default Monday through Friday rhythm before a single one-off event goes on the calendar. The Week A and Week B tabs then spread direct report check-ins across alternating weeks, so every leader gets real time with you without every week turning into back-to-back one-on-ones.
Campus visits and focus groups, planned in advance
The Campus Visits tab schedules every visit for the semester in one place, with the campus, the date, and the focus of each visit. Remy’s standard visit follows the same shape every time: about an hour in classrooms, a collective conversation with the campus leadership team, then a teacher or scholar focus group with a short closeout.
The Focus Group Guides tab is where that listening gets sharper. Each session has a defined audience, a purpose, and five questions written ahead of time. A group of new teachers might be asked what has been hardest to learn and which support actually changed what they do. A group of seniors might be asked where they still feel least prepared for life after graduation.
It also includes a simple thirty-minute facilitation protocol. The step we would steal first is the last question: “What did I not ask that I need to understand?”
The meeting map that keeps it all honest
The last four tabs turn the design into a working calendar. The Semester Meeting Map lists every standing block with its day, time, category, cadence, and status. The Cadence and Decisions tab lets you and your team approve or revise each recurring meeting before anyone sends a single invitation. The Week-by-Week View shows the whole semester at a glance, and the Board Schedule tab holds your board dates so they get built in from the start instead of squeezed in later.
If you work with an executive assistant, this is the tab to hand them. It gives them a clear set of rules to protect your time without asking you about every request.
The 90-Day Readout: from listening to priorities
Listening only matters if it turns into decisions. The second file is a Google Doc that helps you write what you learned in your first ninety days in a role, then translate it into a short, focused plan.
It moves through eight sections:
Scope of listening and learning, with real numbers for who you talked to and where you went
What is working, with the strengths and practices worth protecting
Where you are falling short, with the gaps that matter most and the evidence behind them
What this means, including a core diagnosis that finishes the sentence “We are not primarily facing a ___ problem; we are facing a ___ problem.”
What comes next, with a small set of priorities, what will change, early evidence of progress, and owners
What will wait, naming important work you are choosing not to prioritize yet
Decisions and support needed from your CEO, board, or team
A closing reflection on what you know now that you did not know ninety days ago
The What Will Wait section is the one most leaders skip, and it may be the most useful page in the document. Naming what you are not doing is how you keep a short priority list short.
The readout works for any role, not only the CEO. A new principal, a new chief academic officer, or a leader stepping into a bigger job can use it the same way.
How to use the toolkit this semester
You do not need to be new in your role to get value from this. Here is a simple way to start.
Make a copy of both files. The calendar is built to be customized, so rename the tabs and meetings to match your organization.
Set your rules first. Fill in the Semester Overview before you touch the weekly views. Decide when routine meetings end, which block is protected, and how many campus visits you are committing to.
Put the campus visits on the calendar now. Every visit you schedule in September is one you actually take. Every visit you plan to schedule later is one that probably does not happen.
Write your focus group questions before the visits. Five good questions, tied to what you most need to understand this semester.
Block time for the readout. Pick a date roughly ninety days out and protect two hours to write it. Then share it with your team or board so the priorities are visible.
Download the free CEO First Semester Toolkit
Both templates come together: the CEO Semester Calendar and the 90-Day Readout. Make a copy, set your rules, and get your first campus visit on the calendar this week.
Listen first. Then decide.
