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

Aakash Gupta

for my archives. Subscribe to get access to these posts, and all past posts.

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(We all need a Spa Day after Annual Planning, Teddy the Corgi, California, USA)

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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:

1. Executive’s Guide to An Effective Planning Cycle (free)

2. How To Rock Company Planning (partly paid)

3. Four Common Mistakes That Kill Quality (paid)

4. A final word: Always Be Planning (paid)

5. Bonus: Planning and Vision templates for you to steal! (paid)

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Coaching Corner Updates:

• Allyson Letteri (VP Marketing, Startup Advisor, Author) and I did a free talk on How High Performing Executives Manage Their Time. Check out the recording here (and get 15% off my Maven course).

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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:

1. Escalate to your manager—Let them know the gap early on.

2. 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