4 Key Takeaways From Our Annual Planning Webinar

Most product professionals have mixed feelings about annual planning, and while they may vary widely, they’re held very strongly. 41% of product managers rated their happiness with their current product planning process a three out of five in Product Plan’s 2022 Annual Product Manager’s Survey.

Even worse, 29% of product managers said they were either unhappy or very unhappy with their product planning process. This paints a picture of some very frustrated and dissatisfied product folks involved in the planning process.

Benefits of Annual Planning

If there’s so much angst about annual planning, is it even worth doing? ProductPlan has found that planning does help the product organization. Planning can help you get to market faster and less expensive while improving your chances of success.

But there’s another important reason to do annual planning—it enhances your credibility and builds stakeholder relationships. The planning process should enable you to engage with your key stakeholders and understand what information they need from your planning process to do their best work.

At the same time, you can share your current thinking with them and solicit their feedback. After the exercise, regardless of exactly what shape your roadmap is in, everyone should have a better idea of what success looks like and how to get there together.

Before you clear your schedule for a month and schedule a zillion planning meetings, take a step back. Consider the importance in general of annual planning within your organization. Maybe it is the lynchpin to the entire year’s efforts, or perhaps you’re the maverick planner in your company. Calibrate your effort investment in product planning and give extra weight to the product organization’s own needs.

Finally, what do you want to get out of annual planning? This information helps you build a process that works for your company and team.

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4 key takeaways from our recent annual planning webinar

Whether the planning process fills you with dread or thrills you, our webinar Fireside Chat: How Companies Successfully Navigate the Annual Planning Process will give you plenty of confidence to tackle this important product strategy effort.

Connect to the company vision

Annual planning provides an opportunity to take a beat and ensure that each product and the company are still moving in the same direction. Begin with your organization’s latest vision, mission, and high-level objectives, ensuring you truly understand them and their impact on the product. Once aligned with your company’s direction and goals, you can start building yours.

The process of checking that alignment should spark new conversations and additional engagement, which adds extra value far beyond the planning process. But don’t let your desire to share this energy with others add additional layers of meetings or steps in the process.

A team leader wants everyone to be invested in the plan and participate in the process. Before you end up with a beautiful process that’s so inclusive it takes six months to complete, remember that’s not the only way to create buy-in and engagement. Standing team meetings or taking some time in a 1:1 meeting to share your goals with your reports and get their thoughts and feedback can be effective as long as your final approach reflects their feedback.

Connecting back to your company’s vision and objectives and then planning from there should give you fresh confidence you’re moving forward—powered by your team—toward your company’s goals.

Ditch the fixed mindset for a more flexible, curious approach

There’s plenty of talk regarding the pros and cons of a fixed vs. growth mindset, and it comes as no surprise that product management teams able to flex and evolve are more successful in the long run. Start by acknowledging that you’ll learn things throughout the year, and it would be irrational to wait until the next planning cycle to apply what you’ve learned.

With evolution as your backdrop, think about your roadmap as a tool to tell the story of what you’ve learned and how you’ve applied it to improve. Some customers leave dates off of their roadmaps to drive home that roadmaps are directional representations of product strategy, not a fixed itinerary to get there.

Changing dates often feels like and can be viewed as a failure. By avoiding dates altogether, however, teams are more likely to evolve their roadmap and have a better experience and a more useful artifact.

Your roadmap is your ambition, not your itinerary. You know you will get smarter, so embrace that evolution now and use planning as an opportunity to memorialize current thinking and then evolve it.

Create a rolling plan within your company’s context

So how do we reconcile having a flexible mindset with having a set plan? There is a middle path many ProductPlan customers opt for—the rolling plan. In a rolling plan, you acknowledge that you have the most information and detail about the near term and can reflect that in your plan. Later time frames, whether quarters or months into the future, will be less fully planned since there’s less concrete information available.

ProductPlan itself uses a roadmap with four columns: Recently completed, Now, Next and Future. Each column serves a specific purpose:

  • Recently completed is an opportunity to toot your own horn, acknowledge accomplishments, and thank partners.
  • Now is the segment with the most detail and likely what most will focus on, and for a good reason. Typically this is where decisions are made, and obstacles addressed.
  • Next, demonstrates that you’re looking ahead, providing a heads up to your stakeholders and partners for what is coming.
  • The future shows additional key activities that must happen, but it’s not yet time to do granular planning.

A rolling plan enables you to think about the year and what you know while recognizing that smaller, quarterly, or “next chunk of time” planning will need to occur as well.

Each organization’s rolling plan will look and function a little differently. An organization with a three-to-five-year roadmap approaches annual planning differently than an organization whose entire roadmap only spans the next six sprints.

The duration of Next and Future can be tailored to your needs, while still communicating the reality of plan evolution. ProductPlan frequently recommends rolling plans because they feel doable and help avoid the pitfall of having a rigid plan set up to fail.

Look back . . . and then look forward

Chances are you did something vaguely resembling annual planning last year. Start by looking at the output from that process. What worked? What didn’t? Did you get what you wanted to get out of the process?

A roadmap is, among other things, a communication tool that explains where you are and where you’re going. How helpful did your stakeholders and other users find your roadmap? Only the consumers of that communication can opine on its effectiveness.

After that look back, it’s time to look to the future. As mentioned earlier, this is where the plan’s intention is critical.

One team might realize, “last year we had a great roadmap that we used inside product, but none of our internal partners seemed to know what was coming next.” This leads to a goal of creating a planning process focusing on handoffs and engagement with other teams.

Meanwhile, a team smoothly engaging with internal partners—but struggling to tell the product story to senior management—intentions around setting checkpoints and demonstrating alignment with company goals will be the focus.

You’re doing this process, so make it work for you. Don’t agonize over a beautiful presentation.


Choosing what you are going to not do is almost as important as deciding what to do. Getting clear on what trends you won’t chase or tempting rabbit holes you’re avoiding falling—and why—helps you resist the temptation when it inevitably appears. Get in the habit of consulting with your “don’t do” list before taking on new features and product commitments.

Finally, consider whether you have the right mix of activities. You must get alignment around balancing net-new functionality vs. improving existing product functionality vs. basic housekeeping and addressing technical debt. As your plan begins to take shape, put on your effort allocation lenses and double check the amount of work in each category accurately reflects what you and the company want to invest in.

Take a deeper dive into annual planning

A gold-plated annual planning process does not guarantee success, but it has plenty of value. Planning allows you to think about your work. This allows you to understand timelines, constraints, and the challenges that need management.

Explore our resources about annual product planning and share your experiences with us in the 2023 Annual Planning Questionnaire.

Watch the full webinar on annual planning:  ➜