Getting your head in the (planning) game
Week 1 of The Annual Planning Series — mindset before mechanics. Working title: "How to survive planning season without crying or quitting."
Welcome to Week 1 of my “learn from my mistakes” series on annual planning!
Jumping right in: planning is as much a mindset game as it is a strategy one. It’s about balancing optimism and ambition with honesty. As an operator, you get the distinct honor of bringing everyone back to earth.
I used to think the right framework solved everything. Turns out, mindset does most of the heavy lifting.
So before we talk frameworks or goal-setting processes, this week is about headspace: getting centered, getting honest, and collecting the facts that’ll make next week’s work mean something.
*Cue pump-up music*
Some ✨Annual Planning Affirmations ✨
If you’re anything like me, planning season brings out every overachiever instinct you’ve got. You want clarity, buy-in, and progress… ASAP. When alignment feels hard, it’s easy to take it all onto yourself.
This work is hard, and that’s what makes it worth doing.
Here are a few mantras to keep you grounded if things start spiraling. Repeat after me:
I can’t make everyone happy, and that’s okay. Disagreement means people care enough to engage. If everyone’s agreeing, that’s usually a bigger problem.
I can lean into discomfort. There will be debate, tension, and a little chaos. Planning is supposed to feel messy! The best ideas show up in that pesky gray area.
I plan knowing that things will change. Planning is guessing. Change is inevitable, but that’s what keeps the work interesting.
The year isn’t ruined if I don’t finalize plans by January 1st. There are plenty of valid reasons to set plans off-cycle. Keep things moving in the meantime.
If I assume it’ll be a shit show, it probably will be. My mindset sets the tone. Calm confidence with a side of realism always wins.
Come back to these when planning starts to feel heavy. ♥️
Why bother with annual planning anyway?
It’s easy to go through the motions and forget what we’re actually doing this for. Planning isn’t about creating the perfect roadmap or pretending you have all the answers. It’s about making sure everyone is pointed the same direction and understands the bigger “why”.
The best plans meet the company where it really is. They don’t try to predict the future. They help you navigate it with confidence.
So let’s start by grounding in reality, then we’ll layer on structure next week.
Your homework
The fun part! Spend a few hours this week pulling signals and taking stock. Think of it like a personal fact-finding mission that sets the foundation for next week.
➡️ For Execs & Cross-functional Leaders:
Your job is to zoom out and make sense of how the whole system is currently performing. Look for patterns, risks, and truths people might be avoiding.
Financials: sales trends, burn, runway, and investor or board expectations. Make sure you understand what “good” looks like this year from a financial perspective.
People: morale, leadership stability, capabilities, and gaps. Pay attention to whether the org still has the muscle to deliver what’s being asked of it.
Market context: customer signals, competitor moves, and macro trends shaping demand. Note where reality has shifted since your last plan was written.
Non-negotiables: launches, restructures, or contracts already committed for next year, and how much capacity they’ll consume. Make sure you know where the immovable pieces are so you can flex around them.
➡️ For Department Leaders:
Think of this as an independent retro**, not a report. You’re trying to understand what this year taught you about your team, your customers, and your focus.
Performance: what worked, what didn’t, and what patterns you can learn from. Celebrate the bright spots and be honest about where you fell short.
Team: morale, energy, skill gaps, and who’s ready for more responsibility. Pay attention to where burnout or bottlenecks showed up.
Customer Insights: what resonated most, what missed the mark, and what feedback or data keeps resurfacing.
Don’t skip this part or shortcut this process with AI-generated summaries. This is often where next year’s best ideas hide.
Focus/Tradeoffs: where your team spread too thin, what priorities got squeezed, and what you’d do differently if you had to choose again.
**You should absolutely validate your perspective by running a team retro. High-performing teams will help you uncover blind spots and sharpen your view.
TL;DR
Good planning starts with clear thinking. Before you jump into frameworks and goals, take time to get honest about what’s true today. Everything gets easier from there.
Next week, we’ll talk frameworks and how to pick the one your company actually needs, not the one you saw on LinkedIn. Spoiler: OKRs don’t work for every company.
And in case you forgot: you’ve got this!
Rooting for you,
- Keely