Step 2: A Better Calendar
Feb 25, 2025
"Better Work" Series: (3 of 5)
Let’s keep this one short and sweet because the idea is pretty darn simple: If our plans stop at the list we build, so does our productivity.
I don’t care if you’re old school and use a journal or notepad or if you’re with it and use Monday.com or Asana. If the list we build doesn’t graduate to our calendar, we’re just writing—not building.
Not only that—what good is the documented clarity you just spent hours of big-brain time on if you don’t use it?
How your calendar uses your documented clarity
You take its amazing contents (Primarily "The Playbook" elements) and bake them into the agendas of four specific conversations throughout the year.
We’ll call it the “Core 4” because it's catchy, it rhymes, and I’m trying to make my marketing coach proud of me.
The Core 4 is a structured planning system that ensures we’re consistently working on the right things at the right time in the right direction. I know, right?
It includes four conversations that drive focus, alignment, and momentum:
- Annual Retreat – Big-picture, long-term strategic direction and planning.
- 90-Day Score – Translating the long-term into actionable segments and priorities.
- Monthly Scorekeeping – Measuring results, tracking progress, and adjusting effectively.
- Weekly Wrap-Up – Keeping day-to-day execution tight and focused.
Let’s break down how each of these plays a role in building a calendar that works for us instead of against us.
1. The Annual Retreat: Big-Picture, Long-Term Strategic Direction and Planning
Once a year, we need to step back from the grind and focus on the big picture. The Annual Retreat is where we answer essential questions like:
- What are we learning?
- Are we heading in the direction of our vision and long-term objectives?
- What’s working, and what needs to change?
- What are our biggest opportunities and challenges?
- How’s the team doing, and how can we equip them better?
- What priorities will drive meaningful progress this year?
- What do we need to do to be proud a year from now?
Without this, we risk letting the inevitable twists and turns of the week-to-week and month-to-month take us way off track. We need this level of thinking and direction to equip our resolve as we set out to sea.
Action Step: Schedule your next Annual Retreat ASAP and make sure you’re not walking around in the wrong jungle.
2. The 90-Day Score: Turning Vision into Action
I’ll be the first to tell you that having long-term objectives is vital for success—that’s what the Annual Retreat is for. But big-picture goals don’t drive performance—a score does.
Once we have the business objectives for the year, we need to chunk them down into 90-Day roadmaps to secure aligned action. A 90-Day Score allows you to pivot fast and ensures you kill threats and grab opportunities before it’s too late.
Every 90 days, take 90 minutes to clearly:
- Define the 1-3 most important milestones for the next 90 days.
- Determine the exact score (or result) you need to produce to get there.
- Design an action-packed game plan to achieve those results.
Without a 90-day roadmap, we become subject to the tyranny of the urgent or paralyzed by the aspirations of the future.
One of the most compelling illustrations on this idea comes from Stephen Covey, author of The 7 Habits of Highly Effective People:
Imagine a team hacking their way through a dense jungle. They are busy cutting through the thick brush with machetes.
Then one of them gets the bright idea to climb a tree and check their progress. With a shocking discovery they shout:
“We're going the wrong way, we're in the wrong jungle!”
And what happens? Everyone else responds:
“Shhh, we’re making great progress!”
Action Step: I built a 90 Day Score Builder, just for you. It takes you step by step through the process of getting a focused plan for your next 90 days. You can check it out HERE, and get confident you're not walking around in the wrong jungle.
3. Monthly Scorekeeping: Measuring Progress & Adjusting the Plan
So now you have a score—you must actually use it and “keep” it.
Monthly Scorekeeping is where we step back and assess how we’re doing (climbing the tree, remember)
Every 30 days, we should intentionally:
- Review the score (results and data) for each milestone.
- Assess what’s working and what’s off track.
- Make necessary adjustments before the 90 days is over so we actually hit our milestone.
Fun fact: During the filming of The Dark Knight, director Christopher Nolan held monthly progress reviews with his production team to assess how well the film was aligning with his vision. These regular check-ins ensured the project stayed on track without needing major last-minute course corrections.
Action Step: I built a 90 Day Score Builder, just for you. 😉
4. Weekly Wrap-Up (Or Wind-Up)
This short, tactical meeting (15-30 minutes max) ensures we’re organized with the right priorities before the week comes at us.
A great Weekly Wrap-Up includes:
- A quick review of progress from the past week.
- Identify priorities for the coming week.
- SCHEDULE EVERYTHING THAT NEEDS TO HAPPEN NEXT WEEK ON THE CALENDAR.
I used to be a fan of the Monday morning “pop-up”, but I’ve come to prefer the end-of-week wrap-up. Why? The week is fresh on my mind, which allows for better processing. Then, the next week gets locked and loaded before I roll into the weekend. That last part allows me to actually rest and be present with the people I work so hard for.
When you do your weekly review isn’t the point—doing it before the week starts is.
Some people prefer to do this at the end of the week (Friday or Saturday) to protect their weekends and start fresh on Monday. Others do it on Sunday evening or Monday morning. The timing is a preference, not a best practice.
The real best practice? Ensuring that once a week—before your days begin—you’ve identified and scheduled your priorities. This isn’t just planning; it’s applying Habit #1 from Covey’s 7 Habits: Proactivity.
Action Step: Pick a time each week for a Weekly Pop-Up. Keep it short, focused, and action-driven.
Let’s Keep It Simple
When we don’t make time for intentional planning, we waste even more time fixing mistakes, chasing distractions, and scrambling to catch up.
The Core 4 is a rhythm, not a rigid system. Start with one. The real game changer is the 90-Day Score, and that's why I took time to capture it's process in a virtual coaching experience. But maybe you need to start smaller with a Weekly Wrap-Up. Honestly, that 30 minutes will change your life if you’re not doing something like it right now.
So—what’s one planning rhythm you can implement this week?
In the next post we're going to take a side step so I can give you a behind the scene look at the 90 Day Score.