Annual Planning is the Time to Show Up and Get Noticed
Annual planning is your chance to grow your influence within the company. Here's how to do it well.
👋 Hi! I'm Yue. Chief Product Officer turned Leadership Coach. Welcome to a special edition Sunday issue of The Uncommon Executive. I am sharing a guest post I wrote two weeks ago with
for my archives. Subscribe to get access to these posts, and all past posts.
(We all need a Spa Day after Annual Planning, Teddy the Corgi, California, USA)
Planning is about so much more than just making a list of projects. When done well, annual planning is your chance to grow your influence within the company. This week’s post covers annual planning from the perspective of an executive running it and a PM participating in it.
Here’s what we’ll cover in the post:
Executive’s Guide to An Effective Planning Cycle (free)
How To Rock Company Planning (partly paid)
Four Common Mistakes That Kill Quality (paid)
A final word: Always Be Planning (paid)
Bonus: Planning and Vision templates for you to steal! (paid)
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Executive’s Guide to An Effective Planning Cycle
The executive team of the company and the heads of each function are responsible for steering the ship of the company. Planning season is when they sit down with all the maps and financial records and see where the ship may be headed for the next year. Quite a few larger decisions get made that affect a large portion of the company — from resourcing budget (e.g. layoffs, starting/stopping large investments, revisiting people policies).
Well-run companies have well-run planning cycles. As executives, it’s a great time to set new direction and to ensure that the strategy and vision is well understood by everyone at the company. Here’s what to keep in mind to do it well.
Top-down and Bottom Up
Great planning processes marry two things:
Top-Down Clarity — Leadership provides 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 the 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.
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.
Plan the Plan
Write up a Plan for Company Planning. Yes, you need a plan for the plan. It should outline the critical dates, who’s doing what when, and link to output templates. Then, assign someone to drive the overall process and keep everyone accountable and updated. This can be a PM, a Chief of Staff, the CEO…
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.
Review Twice
Don’t shortcut this. Plan on reviewing deliverables twice—once for feedback and once for final alignment.
Otherwise, unresolved debates linger, and decisions get made informally.
At Instagram where Yue led the consumer feed and profile teams, there were officially different types of reviews for context sharing, decision-making, and final review.
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.
How To Rock Company Planning
Some PMs put it all on themselves to “figure it out” and go to leaders with the perfect plan. Guess what? That’s just a waste of time. Instead, bring your leaders along, ask them for help, and communicate often. Your ability to drive a process and overcome real-time challenges will show your stripes as a leader.
Escalate Conflicts Quickly
Planning season inevitably brings up conflicting priorities—whether between teams, features, or resources. The key is to surface and address these conflicts early. Whether it's a disagreement about resource allocation, prioritization, or technical feasibility, don't let these issues simmer.
One common mistake is waiting until leadership reviews to raise the conflict, but by then, it’s too late. Raise the flag early so it can be addressed by managers and executives before your plan is due.
Surface resourcing constraints
A classic planning team will have support from analytics, research, design, and engineering.
But sometimes, you might be running short on one or a few of these resources. When this happens, take a 2-step approach:
Escalate to your manager—Let them know the gap early on.
Cover what you can—If your team can compensate for missing resources, figure out how. But don’t stretch too thin. If the gap is too large, escalate again.
If you don’t have an analytics person to support you during planning, you probably also don’t have that person day-to-day.
Planning is sometimes a condensed view of the effectiveness of the team overall — so where you have big gaps, it’s important for leadership to fill them.
At Meta, when planning for multiple teams, Yue always made sure that there was a Resources section to the planning document with the current team and gaps. This helped leaders quickly see what the team needed to succeed.
Do a Planning Pre-mortem
Ask your teams upfront, “What challenges do you foresee during planning?” and “What do you need from me to make this successful?” This surfaces potential roadblocks early and allows you to take action before they become bigger problems. Hold weekly check-ins during the planning process where you ask these questions. The more regularly you check in, the less likely small issues will grow into bigger problems.
Separate Workstreams for Goals, Projects, and Resourcing
Don’t try to handle everything in one big meeting or session. Split the planning into distinct workstreams—Goals (driven by data science), Projects (driven by PMs), and Resourcing (driven by managers). This ensures that each topic gets the time and focus it needs without feeling rushed or overlooked.
For each workstream, appoint a single owner who’s responsible for driving it forward and keeping the team on track. This prevents any one person from getting overwhelmed and ensures accountability.
Know the Informal Decision Paths
With every company, there’s the formal process, and then there’s the informal process. Have you run a planning process where there are few questions and little input during the process, and then in 1 or 2 meetings, everything changes and then is decided? Depending on the culture of the company, this may be more or less pronounced. If you’re in a company that has a highly informal culture, then it’s important to understand what “actually” decides the outcome of planning.
First, if you are new to a company and this is your first time doing planning, consider grabbing lunch with those who have been around for 2-3 cycles. Get their take on “how the process actually works” and what is important to watch out for.
Then, when you are going through the process with your teams, keep an eye out for what other leaders are doing.
How much does the presentation matter? In some companies, whether a plan lands or not depends on how well it is presented. In other companies, this doesn’t matter at all.
Where are the skeletons in the closet? the hot-button topics for the C-suite? Biases of the group? Know these and be intentional about which battles you fight in the planning process.
How much of the decision-making is top-down? Is it about convincing a C-suite executive?
When Aakash was at Apollo.io, his VP of marketing showed up at the CEO’s house to talk about planning. That’s the level of effort it took there, and it’s worth knowing that as a leader.
Common Mistakes That Kill Quality
After 15+ years of planning cycles, some of which I was a part of, and some of which I’ve run, I’ve made my share of mistakes. Here are the top 4 that affect the quality of the output the most:
Seniority ≠ Driver
There’s a natural tendency to let the most senior person dictate the planning process. After all, they have the experience, right? But that experience can backfire when it shuts down the creative energy or detailed input from the rest of the team.
When the senior person dictates everything, the team becomes hesitant to push back, even when they see potential landmines ahead. What results is a plan that looks great in theory but collapses in execution because it lacks the insights of the people doing the day-to-day work.
At a not-to-be-named company, Aakash had a senior leader who laid out a grand vision that ignored resource constraints in engineering. No one on the engineering team felt comfortable challenging him in meetings, and the result was an over-scoped plan that led to burnout. Eventually, we had to revisit the entire roadmap six months later. A wasted half-year due to a lack of upfront realism and team input.
Stopping at Middle Management
Often, executives want to involve all levels of the organization but don’t leave enough time in the process for it to actually happen.
If you are in an org with more than 2-3 layers, you’ll need to build in extra cycle time for individual contributors on teams to weigh in on planning.
Otherwise, managers and directors will rush to put something together with “input from the teams”, but don’t actually run a proper cycle.
Remember, a full brainstorming —> prioritization —> x-team alignment —> resourcing planning cycle takes at least two weeks.
If you have 3 layers in your organization, then give it at least 6 weeks before you are doing a first review.
Skimping on Follow-Up Time
Many a time, companies will run through the planning loop once and run out of time. There’s a long list of follow-ups, debates still happening, and analyses that need to get done. And yet, somehow, the latest version of the document is now the final plan.
This breaks the trust the teams and people have in the process. They’ll realize that whatever is written is final, even if you say that there’ll be a “follow-up”.
The quality of the plan also suffered, because debates were not brought to their best conclusions and additional analyses were not valued.
Not Starting Early
Either get done planning or get planned for you.
Leaders and Executives love to fill gaps with their imagination. If you don’t have a clear strategy or plan early in the planning process, they may start trying to problem-solve for you (with the best intentions). This hardly ever leads to the highest quality plans.
Then, they fall in love with their (often not as well-informed) ideas. And now you have to defend and sell your plans and ideas. The best teams and leaders get done with planning early and stay ahead of the game throughout the year.
Get your top priorities out there early for feedback and reassurance to the leaders that you’ve got it handled.
A final word: Always Be Planning
And that leads me to a word for next year’s planning (which yes, will inevitably come around): Make it a year-round activity
If you’re waiting until October to start thinking about next year, you’re behind. The best PMs treat planning like a continuous process. There’s always a strategy they’re working against that has the buy-in of their leaders and their teams.
Here’s how to get ahead:
Keep a Living Backlog
As you execute throughout the year, maintain an updated backlog of ideas and feature requests. Don’t let this become a “black hole”—review it regularly, and reference it during each sprint retrospective or team meeting. It’s your central hub for innovation and iteration.
Include Forward-Looking Insights in Feature Results
When you finish a feature, always include future ideas in your write-ups. Even if you know you won’t build them now, they’ll help you frame next year’s planning more strategically. These future features are often derivative of what you learned in the current feature launch.
Use Leftover Time in Customer Discovery Calls
When you’re running customer interviews or discovery calls, don’t just stop when you get the insights for the current project. Use the last 10-15 minutes to explore broader pain points that might not be directly related to your current work. This way, you’re gathering early data for next year’s roadmap.
Templates!
If you’ve made it this far, you’re super into planning and process!! Here are some templates that you can steal for your next planning cycle. They’re from a product-led company with ~500 people. Please adapt it based on your needs!
That’s all folks! Thanks for being here this week. Like, Share, and Subscribe. =)
Yue
This post is summarized and edited from a guest post I made two weeks ago with Aakash Gupta of the newsletter: How to Rock Your Annual Planning to Come Out Ahead Instead of Exhausted. I am creating this post to make it accessible to my paid subscribers in the Archives. Parts have been edited for focus. You can read the full original post here.
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