Eight Product Pros on How to Ace Annual Planning

For those who embrace the annual planning ritual, Q4 can be a refreshing time to look back at what we’ve accomplished and set a plan in motion to capture new opportunities.

For everyone else, the holiday season can feel like the worst time to wedge in annual planning. User behavior is erratic. Campaigns planned months ago are finally put into play. And with only 16 working days between Black Friday and Christmas Eve, there’s hardly enough time to finish this year, let alone plan for next.

Despite the time challenges and the tasks at hand, annual planning is an essential part of every mature product team’s success. We asked eight digital leaders for their take on how to make OKRs and roadmaps sing.

Keep reading for insights and advice from:

• DiAmanté Astillero, Sr. Manager of Product Strategy & Operations at Skims
• Christine Basile, Director of Product Management, Spins
• Rosie Hoggmascall, Fractional Head of Growth and Founder at Growth Dives
• Sumita Paulson, Senior Strategist at The Good
• Ariana Cofone, Fractional COO and Founder at Secret Ops
• Yao Wang, Group Director at Mercury Insurance
• Maggie Paveza, Senior Strategist at The Good
• Trina Moitra, Head of Growth at Convert

Start with goals, then tap your team for intuition

So, what is the best first step for annual planning?

According to successful product teams, the recipe is a clear North Star, the right people in the room, and a data-driven mindset.

Layering these three elements gives you a great foundation to start your planning.

Start with a clear North Star

Our experts were clear on one thing, which is that rallying the organization starts with a clear vision at the top. Without direction from leadership, it’s hard to involve the team.

“Annual planning really does start at the top,” says DiAmanté Astillero, Sr. Manager of Product Strategy & Operations at Skims.

“It’s super important for us to understand what the North Star is. If [leadership] is able to set that vision, set those goals for the company, then your team or your organization can start to bubble up and speak to what initiatives can drive and march to that North Star.”

Tap the team for insights

Once the North Star is clearly defined, Astillero suggests tapping into the embedded wisdom within each department, including engineering, marketing, product, and customer service, among other disciplines.

“Every team - whether it’s sales, marketing, customer success, legal, or product - contributes unique insights, from revenue trends to customer feedback to market shifts. It really requires teamwork to shape the bigger picture,” says Christine Basile, Director of Product Management at Spins.

Ariana Cofone, Fraction COO and Founder at Secret Ops, puts it this way, 

"Annual planning is like hosting a potluck—you need everyone to bring their best dish to the table. Founders, leadership teams, department heads, and customer-facing voices (like sales or support) are non-negotiable. You want high-level strategic thinkers and those who are in the trenches daily, so you get a well-rounded view of what’s working, what’s broken, and what’s got potential.”

Using this embedded knowledge helps leaders understand what challenges and opportunities are at the top of each department's mind and what themes are common across the company.

Give users a seat at the table

In addition to tapping departments for their perspective, experts stressed the importance of giving the end user a seat at the table in your annual planning. “I consider customer data non-negotiable in planning,” says Basile.

For Rosie Hoggmascall, Fractional Head of Growth and Founder at Growth Dives, the key is using data to understand where users get hung up in the conversion funnel.

“Look at the bottlenecks. Really look at the data and work out where the biggest area of improvement needs to be. That’s a full-funnel analysis of each step of the customer journey.”

Astillero suggests that customer experience teams should play a big part in forming your OKRs. Common complaints that come from users directly are an incredible way to include the user perspective in your work. “That first-party, real, qualitative data is super super important.”

So, for Hoggmascall, analyzing user bottlenecks through data is essential, while Astillero emphasizes leveraging customer feedback to inform planning directly. Together, these approaches ensure the user’s voice is present at every stage of the process.

Evaluate the previous year’s experiments

While we’re planning for next year, it’s important to evaluate the current year. “Lessons from 2024 should guide where you double down, experiment, or pivot,” says Cofone. 

If you have an active experimentation program, our experts suggest you review the tests you’ve run in the past year.

“Previous experiments offer a trove of insights,” says Sumita Paulson, Senior Strategist at The Good.

“Reviewing ‘learners’ especially, which is what we call tests that don’t win, is a great way to understand what you haven’t been able to adequately solve for. There’s usually a ton of opportunity there.”

To Paulson, reviewing learners is a critical step because it helps shorten the time-to-action.

“You have the background from original research, and you’re armed with insights from the variant that didn’t perform as you hypothesized. You’ll be able to apply that to a roadmap.”

This retrospective approach not only identifies gaps but also accelerates progress by building on past learnings.

Opportunity size with the right data

Once you’ve touched base with the experts around you, reflected on the last year, and know what might move the needle, it’s time to do some opportunity sizing. That’s where good data is essential.

“You may have a hunch as to what you need to work on, but bringing data to the conversation adds a level of clarity and direction that is non-negotiable,” says Maggie Paveza, Senior Strategist at The Good.

For prioritizing on-site or in-app changes, Paveza recommends running a report in Google Analytics for a 12-month period, paying special attention to the effectiveness of various segments and understanding how metrics vary across page, device type, user groups, and channel groups. To Maggie, it’s all about understanding where effort and impact are at an optimum. “I like to ask myself, ‘If I could get a 5% uplift in any of these areas, what would that look like?’” says Maggie.

For Astillero, being able to define the potential ROI of the opportunities doesn’t just support prioritization but helps you advocate for resources.

“If you're able to assign some dollar amount impact or KPI-driven impact to whatever initiatives that you're working on, you have a better chance of negotiating and compromising with your stakeholders and the resources that you need to get those things over the line.”

Practice two-way communication

The level of fidelity decided on during annual planning varies widely from company to company. While some leaders build roadmaps with Gantt charts and loose timelines, others simply set OKRs and expect apt teams to figure out how to do it.

Each approach has earned valid criticism:

• Roadmaps with rigid sprints can instill a false sense of confidence, and their inflexibility can put unnecessary pressure on the team
• OKRs that come top-down without loose initiatives often feel like “extra work” to the individual contributors on the ground

Whatever approach you decide on, experts agree that the key to making a plan that’s both meaningful and actionable is transparency. “When in doubt, involve the team; they’ll often have great insight on what matters most,” says Cofone.

Yao Wang, Group Director at Mercury Insurance, says transparency and authority are key to making OKRs meaningful at every level of the company. “We are trying to find a balance of OKRs that guide the specialist on the ground to make a decision.”

To Wang, transparency is a two-way street. Leaders need to provide clarity about how the vision was formed, and individual contributors need a mechanism to share how their work contributes to the larger objectives.

Don’t forget about research

While it’s tempting to look at the opportunities at hand and want to jump into action, experts caution not to forget about research. Hoggmascall puts it bluntly: “Put research on the roadmap.”

“It’s a valid use of time and can mean that you are not wasting resources on areas where you don’t understand the customer.”

Paulson says carving out time for research initiatives is especially important for those who don’t have an “always on” research mechanism like on-site surveys or CSAT scores.

“We’re always working to improve the customer experience, and an important part of that is just keeping an eye out for hidden friction. It’s a great way to catch bugs and make immediate improvements, but it also means that we’re always adding things to the backlog and building a deepened understanding of your audience.”

Paulson stresses that for her clients, “once per year research is nowhere near enough to get an edge.”

Trina Moitra, Head of Growth at Convert, agrees that research can make or break your annual planning efforts.

"Original research is non-negotiable. Put together a team if you can … and go after qual/quant data. You are sitting on both. You just don’t know it."

Prioritize ruthlessly

Once you’ve crafted an aspirational yet actionable annual plan, don’t be afraid to express priorities with cutthroat clarity.

As Wang expressed, giving employees clarity as to which objectives and KPIs are top priority emboldens them to make decisions that truly support the company.

“It's hard for the top to guide everything. But if each person can ask in their own right ‘Is that the most important thing?’ that’s valuable to everyone.”

Moitra added that the team at Convert uses a helpful three-step framework to prioritize initiatives. The team asks:

• What are the current business priorities (strategy review) and how would the undertaking impact them? 
• What can I project about the outcome? 
• What can I delete to free up additional resources to tackle both?

"By the time we’ve answered all three questions, we know what to do," she says.

Set a good foundation for 2025

Instead of approaching annual planning like a task to check off, embrace the opportunity to align your organization around common goals.

“Planning is about bringing people together to create a shared understanding of what success looks like and crafting a roadmap that everyone can rally behind,” says Basile.

Hopefully, you can find inspiration in the delicate balance of strategic vision and practical execution that the experts summarized in their tips. Their success is proof of concept.

If you’d like to learn how to incorporate experimentation and compounding growth into your planning, get in touch here. The Good works with product teams to optimize the digital experience with research, validation, and implementation.