It's Planning Season!

Let’s be honest.

This time of year feels like you’re “planning for the next year,” but what you’re actually doing is getting a very loud, very passive-aggressive performance review from your own calendar.

And it is soooo not subtle.

That Q4 doc you’re making? It’s asking: So… what exactly did you do with Q1 through Q3?

That OKR reset session on your calendar? Yeah, it’s quietly whispering: Was that even the right goal?

And that deck you’re building for leadership? It’s smiling at you with dead eyes and mouthing: You have no idea if any of this worked, do you?

Welcome to planning season… welcome to the main event! Where we pretend we’re “mapping the future” but what we’re really doing is decoding the year we just lived through.

Planning as Translation

Planning season isn’t just ‘strategy,’ it’s translation. You take 12 months of action, chaos, effort, budget, pivots, Slack and Teams threads, breakdowns, breakthroughs, and vague leadership affirmations… and it’s your job to convert that into a coherent operating system.

Really, that’s less of a document-on-a-page (or several), that’s a miracle. And in the movies when miracles happen, it’s usually on the heels of a protagonist or two getting real honest with what they are. Or for planning season, what it is.

A mirror. A microscope! One that asks if your engine was built for all the places you said you wanted to drive it to.

Planning as Stress Test

Here’s the truth I’ve learned (the annoying way): You can’t plan well if you’re avoiding performance conversations. And I don’t mean your team’s performance, so don’t worry about your boss’s commentary about your intangible way of driving culture and showing the team you’re committed to success (then terminating the committed).

I mean your systems and your priorities, your time allocation and your org design. Your “I’ll-fix-that-later” spreadsheet of death.

It’s a season that reveals the prior year’s gaps that you told yourself were a-okay. The gaps you said you’d revisit after the re-org. Gaps that show up like bad exes during budgeting, going “why you no invest in me?!?”

The KPI you didn’t fight hard enough to change? It’s winning.

That one system that you duct-taped together in March? Yeah. It’s leaking again.

Planning Is Power

Here’s the flip side: There IS hope!

Planning season is also where the power lives… because whomever write the plan? Shapes the resources. Builds the narrative. Sets the direction.

Planning isn’t just  a performance review, it’s a job application for future influence.

So while most folks are dreading the doc, or burning calories making it look smart, put-together leaders have a better move. They use the season to say the thing nobody else wants to say out loud: “We’ve outgrown that old plan… and now we build what’s next.”

So grab a notebook. Or a slide. Or your overpriced Notion template.

Ask yourself these 3 questions:

1. What’s the thing we pretended worked this year but actually didn’t?

2. What did we build that deserves more fuel next year?

3. Where does the team deserve better from us as leaders?

If you can answer those clearly, sweet. You’ve already started planning like an operator. And this time next year? You can review performance you’re actually proud of.