May is always an interesting month in a large enterprise. Not because it’s exciting on its own—but because it sits at the fulcrum of Q2, the quarter that separates ideas from execution.
When you stop thinking about the year in 12 months and start thinking of it in four quarters of work, everything changes. Expectations shift. Timelines compress. The behaviors you see inside the business start to make more sense.
Here’s how it typically plays out:
When you stop thinking about the year in 12 months and start thinking of it in four quarters of work, everything changes. Expectations shift. Timelines compress. The behaviors you see inside the business start to make more sense.
Here’s how it typically plays out:
Q1 – Freeze and Frame
January is a wash. Either you’re finishing out the previous fiscal year, or your budget is frozen while Finance reconciles year-end numbers. You’re wrapping up ratings, closing out compensation cycles, or getting first hints at your budget. It’s a planning month in disguise.February is when strategy starts to peek through—what leadership wants to achieve, what incentives are in place, what themes will drive the year. By March, ambiguity starts to fade. Priorities begin to lock. People start putting markers in the ground: “This is what we’re solving for.”
January is a wash. Either you’re finishing out the previous fiscal year, or your budget is frozen while Finance reconciles year-end numbers. You’re wrapping up ratings, closing out compensation cycles, or getting first hints at your budget. It’s a planning month in disguise.February is when strategy starts to peek through—what leadership wants to achieve, what incentives are in place, what themes will drive the year. By March, ambiguity starts to fade. Priorities begin to lock. People start putting markers in the ground: “This is what we’re solving for.”
Q2 – Start and Surge
April kicks off execution. You’re traveling more. Offsites are happening. Teams are getting direction. Discovery efforts are heating up.
May is the make-or-break month.
This is when prioritization ends, and deep discovery begins. Key Results are getting locked. Budgets are aligned. The teams are primed to start building—because whatever gets started now is what we’ll be writing about in Q3 and Q4.
This is when leaders stop asking “what should we do?” and start asking “how fast can we do it?”
April kicks off execution. You’re traveling more. Offsites are happening. Teams are getting direction. Discovery efforts are heating up.
May is the make-or-break month.
This is when prioritization ends, and deep discovery begins. Key Results are getting locked. Budgets are aligned. The teams are primed to start building—because whatever gets started now is what we’ll be writing about in Q3 and Q4.
This is when leaders stop asking “what should we do?” and start asking “how fast can we do it?”
Q3 – Build and Validate
July through September is pure execution. We’ve moved from high-level ideas to real solutions.
July through September is pure execution. We’ve moved from high-level ideas to real solutions.
Clickable prototypes. Working code. Cross-functional feedback. Refinement in real-time. By the end of Q3, you’re not just building—you’re crafting a story. One that shows you solved the right problem, in the right way, and can scale the solution. Because Q4 is about telling that story.
Q4 – Reflect and Pitch
October is performance season. You’re prepping for reviews, comp, and promotion conversations. In some places they call it “promotion-driven development”—in others, just “playing the game.” By November, you’re showcasing MVPs or v1 solutions. You’re demonstrating impact and lining up investment for next year. December is a wind-down. Holiday celebrations, training budget spend-downs, and early finance reconciliation. The last two weeks are always quiet. Nothing moves.
And then?
Everything freezes until the end of January.
And then?
Everything freezes until the end of January.
The takeaway?
If you’re not moving in May, you’re already behind.
The window to shape the year is small—and right now, we’re in it.