How to Rock Your Annual Planning to Come Out Ahead Instead of Exhausted
Annual planning is not always something we ask for, but it’s often something we have to do. Here’s everything you need to know to make the most of it
Everybody likes to hate on waterfall processes.
Annual planning often is the center of these jokes:
What can you actually decide one year in advance that won’t change?
—What most senior PMs will tell you
But here's the reality:
Annual planning isn’t going away. It’s a ritual most companies follow. And the next few months of your life? You’re spending 60+ hours in it.
Whether you’re at Meta, Thumbtack, thredUP, Apollo, or any other product-driven company, planning season is in the DNA of the team. It’s what shapes the next year of work, and ultimately, your career trajectory.
It’s Basically a Fall Tradition for PMs
For most PMs, fall means one thing: planning season. Sweater weather, pumpkin spice lattes, and hours of strategy sessions.
It’s the best of times and the worst of times. You’re looking back on 2024—what went well, what still needs finishing, and what’s possible to push across the line before the end of the year.
But, it’s also when you start the tough process of forecasting the future.
What should we actually do in 2025?
What’s realistic?
What’s pie-in-the-sky?
This is when your team starts dreaming big. There’s excitement in the air as everyone gets energized thinking about what’s possible. But it’s also when the tough conversations happen—priorities clash, resources are limited, and not everything will make the cut.
But if you do it right? Annual planning is your golden opportunity.
Annual Planning Matters For You and the Company
Planning is about so much more than just making a list of projects. It’s one of the few times in the year where everything is laid bare—what’s working, what’s not, and where things need to change.
Annual planning has two big roles in the organization:
Alignment across functions:
Your marketing, sales, support, and customer success teams need to know what’s coming down the product pipeline. Their strategies hinge on it. If you’re shipping new features or pivoting direction, these teams need to know now so they can build the right campaigns, support structures, and sales tactics.Executive decision-making on headcount and talent:
Execs use the planning process to decide where to allocate resources. Where do we need to hire? Where should our best talent go? Do we need to restructure? You can bet that the projects you prioritize during planning will influence these decisions.
And for you, the PM, it’s a credibility play. Done well, annual planning is your chance to grow your influence within the company.
Your voice, your vision, and your priorities get amplified across the org. If there’s ever a time to step up, this is it.
Introducing Yue Zhao
Yue Zhao knows a thing or two about company planning. She’s been CPTO at Fuzzy, led PM teams at Meta, and was the first PM hire at Thumbtack. She’s orchestrated countless planning cycles—at companies in hyper-growth, and at companies navigating steady scaling.
Now, she’s sharing her insights. She coaches PMs on planning and runs a Maven course on Executive Presence and strength-based growth.
Today’s Post
Words: 4,809 | Est. Reading Time: 22 mins
Today, Yue and I are combining our 30+ years of product leadership to bring you everything we’ve learned about annual planning:
What Makes a Great Company Planning Cycle
How to Rock Company Planning:
As a PM
As a Product Leader
As an Executive Setting it Up
Examples of Great Company Planning Processes
Mistakes to Avoid
1. What Makes a Great Company Planning Cycle
Planning is supposed to deliver clarity and alignment—input goals and strategy, output detailed projects and resources.
But a great planning process does much more than this. It prioritizes the work that moves the needle and avoids the dreaded mid-year re-plan because things went off the rails.
Here’s what separates a great planning process from a mediocre one:
Element 1 - Top-Down AND Bottom-Up
Great planning processes marry two things:
Top-Down Clarity — Leadership provides the high-level goals (revenue, growth, markets to pursue).
Bottom-Up Reality Check — Teams on the ground offer detailed tactics, reality checks, and challenges to the strategy.
This is especially true in product-driven companies.
For example, at Meta, Yue and team balanced leadership’s vision with data from teams working directly with users.
The top-down vision was critical, but the bottom-up input made the plan real and helped uncover flaws early.
Tactical tip:
When your team feeds in their ideas from the bottom up, have them call out risks and assumptions clearly. This forces leadership to acknowledge potential gaps in the strategy upfront.
(You’d be surprised how few leadership teams will get the feedback for these risks in reality. It’s very few.)
Element 2 - All-Function Involvement
Planning isn’t just an EPD (engineering, product, design) exercise. Growth, marketing, sales, partnerships, customer experience—each of these teams plays a crucial role in your product’s success.
For instance, in healthtech, your doctors and medical experts might have critical input on what’s realistic for clinical testing.
In AI companies, researchers could provide input on technical feasibility that could drastically change the timeline or priority of certain features.
Tactical tip:
Involve functional experts early by holding a cross-functional kickoff meeting. Don’t wait until you’re halfway through planning to loop in other teams.
Element 3 - A clear process (or system really) of who, when, what, and how
Planning usually spans 4-8 weeks, depending on the size and complexity of the company. But it’s not just about the length of time; it’s about the structure:
When are you holding brainstorming sessions?
When will the company goals be finalized?
When do teams need to lock in their resource requests?
When will feedback be given, and how long do teams have to incorporate it?
A clear timeline keeps everything moving smoothly. Without it, you’re facing constant re-prioritization and chaos as deadlines slip.
Tactical tip:
Start by mapping out a calendar for planning. For each key meeting, ask yourself, “Who needs to be in the room? What’s the exact output of this meeting? When does feedback need to be integrated?”
Element 4 - Adapt to Company Size, Stage, and Market Conditions
A planning process at a 10-person startup looks very different from one at a 500-person company:
Startups can pivot quickly and adjust plans on the fly.
Enterprises need to make longer-term commitments because they have more dependencies across teams.
But regardless of your company’s size, the framework matters. It gives you the structure you need while remaining flexible to market changes.
Tactical tip:
Consider tools like OKRs to keep the high-level vision steady, but allow teams to update their tactical goals quarterly. This balance ensures focus while maintaining flexibility.
2. How to Rock Company Planning
This section is broken down separately for PMs (2.1), product leaders (2.2), and architects (2.3) of planning processes.
We’ll cover all the strategy and tactics you need to go from exhausted to ahead…
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