It’s not too early to prepare for the end of the year
Yes, I know it’s only September, but I promise you, now is a strategic moment to start thinking about the end of the year because time moves fast in these next few months. Don’t leave decisions for the last minute.
While we may not have all the answers about the rest of the year, we can prepare for multiple possible outcomes. Think, budget decisions that shouldn’t wait until December 31st. Or staff burnout around the holidays and ensuring staff have flexibility and time off as needed. Not everyone's holidays are the same - the major Jewish Holidays just passed by! Now is a great time to set yourself up to be able to be intentional about the end of the year rather than racing up against the clock and running into the way we all feel by the time the final month of the Gregorian year is here.
Take advantage of October.. By the time we get to November, we are lost in turkey day, black friday, holiday season momentum, and it’s hard to get into deep thinking. Here are some questions to begin with this month.
What has your progress been over the last 12 weeks? How about the year? Take a look at the strategic goals you or the team have been working towards. Don’t judge it yet. Just get the facts down!
Identify what is working and what’s not, so you can see what to work on this last quarter of the year
Name the non-negotiables for the rest of the year and notice what’s possible to shift and change. Consider if it would make sense to have each person come to a meeting prepared with this information so you can discuss (knowing there will be differences in opinion).
What budget decisions need to be made soon? (End of year, tax implications, carryover, etc.)
What projects need more time and which are sprints that will need to be done in the next 12 weeks? What can take a back seat? Knowing energy will need to flow into the identified key place, it could be easier to prioritize for the end of the year.
Check out a few blogs where you can learn more When Life Happens to Your Strategic Plan" and "Creating Space to Think"because this isn't about rigid planning, it's about intentional adaptation.
Culture & Team Sustainability (November Focus)
The "Why": November is when burnout accelerates, it’s time to plan for rest and recalibration (Rather than waiting for things to get that bad.)
What to consider:
How are people actually doing? (Beyond surface-level "fine.") This is relational, so if you haven’t been doing this all along, people may not trust that they will be heard. This could mean checking in with people outside of a meeting times or creating space for people to ask for what they need in the remaining months of the year.
What will holidays look like for your team members? (Not everyone celebrates the same way, or at all.) Have you looked at what the team is asking for? What if everyone on the team needs the day before or after the holiday they share off? Is there flexibility to allow for slower business or close the office on those days and if not, what options are there for a rotating schedule of who works on less desirable holidays? Consider if there are options for temp workers or the bare minimum to be done on holidays. It’s okay to be closed.
When and how will people actually rest? A lot of paid time off is use it or lose it, so it’s a good time to check in and make sure people are using this benefit and spacing it out over 12 weeks is better than the last week of the year.
What's one cultural practice you want to be known for during crunch season? I know that not every organization is working on the Gregorian calendar, but if you know there is a crunch towards the end of the year. What's something the team needs or wants that could be a part of it? Consider not having a “hell week.” (I remember these from high school production weeks before the plays went live!) Or if it’s unavoidable, how are you making sure employees are cared for through the stressful times?
How will you celebrate incremental wins in Q4?
Practical practices:
Start November with a team conversation about how people want to show up and what they need.
Use one of your daily practices (like the "How are you arriving?" check-in) to notice shifts in energy.
Plan 1-2 celebration moments, not just a big "holiday party."
Create a conversation about what rest means for different people.
Read more on these in the blogs posts
and the focus on joy/rest from Adaptive Strategic Planning
Rest & Time Off (December Planning—Yes, Really)
The "Why": December planning isn't an oxymoron. It's when you're protecting space.
What to plan:
Who's taking time off and when? (Avoid the mid-December crisis)
How will coverage work without burning people out?
What actually needs to happen in December vs. what's just "tradition"?
How will you hold the year (reflection) without making it feel like another meeting?
What's one thing your team could stop doing in December to make space for rest?
Practical practice:
Lightweight year-end reflection (not a huge intensive—just 30 minutes)
Create a simple "wins and learning" capture process (ties to your reflection)
Name what's off the table for December (meetings, projects, decisions that can wait)
Build in actual closure rituals (not forced fun, but intentional reflection)
Check out this blog posts for ideas
The Integration
Preparation doesn't mean perfection, it means more transparency in the process and intentionality. By thinking about October, November, and December separately, you have this ability to avoid reactive scrambling and you actually make space for humans in the process. Invitation to pick one thing from each section to begin your process of preparing for the end of the year.
This blog post draws from past blog posts of Erin-Kate Escobar Consulting and examples form their work with clients and used Duck AI’s Claude Haiku 4.5 to help organize ideas.
