What if annual planning didn’t have to suck?
Before you spiral into your annual planning-induced anxiety, check out these tips from Ben Newell, VP of Product (Sprout Social) about how to make Q4 more focused and less frantic.
Annual planning for B2B software can feel like a daunting, high-stakes marathon that exhausts your final quarter of the year. This guide is designed to be your training plan to help cut through the noise and focus on three key essentials:
Laying a solid foundation with data
Defining a durable strategy with clear themes instead of rigid project lists
Collaborating effectively with your go-to-market teams
Planning is more than simply listing what you’ll build. Instead, it’s creating a real, adaptable plan that can withstand the inevitable changes of the year ahead – and finding the joy in the process. Remember, this is supposed to be the fun part!
1. Build a data-based foundation for your plan
To prepare for the race ahead, you first need to understand your current and past performance. This shouldn’t be just your perception of what’s happening, but what the data says is happening. This is a great time to refresh your understanding of your customer base, their usage, and your contracts.
I like to make this a presentation that tells the story through data because, while it’s helpful information for you to have, it’s even more valuable for the teams across the organization that support you.
What to ask in these presentations:
What’s the distribution of our customers across their size or industry?
Is there a customer segment where we’re growing more than others?
What features are we seeing growth or fast adoption in?
What about the really exciting features we created this year? Are they gaining traction?
What’s the performance of our packages across the customer base? How many customers are making the move up our tiers?
The second part of this task is to plot your usage, growth, and costs over the last 12-18 months. This will help you to forecast what you expect trends to look like over the next year if there are no substantial changes to your performance.
This:
Establishes your current performance
Helps you set realistic goals
Measure the impact of your initiatives throughout the year
Tip: If you expect a particular feature to be delivered mid-year that will drive greater adoption, you can model that X% improvement into the forecast.
Even very basic assumptions of growth or retention can help you to understand what’s realistic and set goals that have a foundation in reality.
2. Define your product strategy around themes
Defining (and hopefully revisiting) your product strategy is where you’ll spend the majority of your time. If you already have a strategy that you’ve been executing against, then comparing it to your fact base and your past performance is key to measuring its effectiveness.
Either way, you’ll want to start by reviewing the larger business strategy of the company. This isn’t the same thing as your product strategy!
Your business strategy is often reflected in how you want the market to respond to you (e.g., revenue growth, customer satisfaction, market perception, etc.)
Your product strategy describes what your product needs to look like to make that true
You probably have a backlog of projects that customers have requested or ones you’ve really wanted to get to. But just laying those projects out into a Gantt chart is not going to feel like a real strategy to the team.
What to do instead:
Level up those efforts as themes or initiatives, like “building endurance” or “improving finishing speed.” Allocate a percentage of investment against those themes and decide which one(s) you want to prioritize.
These projects then become examples of future investments. They also give you the freedom to learn more and evolve as the year goes on. If they’re just a list of projects, that list might (read: probably will) change within the first four months of the year, and you’ll feel like you’ve lost your strategy.
Instead, focus on themes to give your strategy staying power.
3. Create flexible roadmaps
A roadmap is one of the most visible deliverables of your annual planning. If you’re concerned that people will consider the roadmap a delivery plan, keep it framed among your themes and share it broadly, but set good expectations.
In general, people are quite understanding of the following guidelines:
In this quarter, the roadmap is 80% accurate
In the next quarter, 60% accurate
Beyond 6 months, 20% accurate
Those declining percentages aren’t just execution hedging, but also an acknowledgement that any good trainer adjusts the plan based on the athlete’s progress, preventing injury and capitalizing on strengths as we learn more, new things pop up, or we want to keep working on something that is working.
4. Collaborate across the org
We can build the best product, but if we can’t get it into the hands of customers, we likely won’t see success. This is why your go-to-market strategy needs to live alongside your roadmap.
Questions to ask your team:
Which market, or segment, do we expect to grow into? Is there a market we’re moving away from?
What type of marketing or messaging adjustment do we need to reach this new group?
Is it time for a price adjustment? Do we need to create more differentiation in our tiers?
Does our support structure need to change to drive greater satisfaction?
Would changes to our distribution strategy help open up new customers?
You might not know the answers to all of these questions, so collaboration with your GTM teams during annual planning is crucial.
5. Use AI to analyze the market and stress-test your plan
As you plot your annual plan, it’s important to have a good grasp on the competitive landscape and the market.
It can be time-consuming to stay up-to-date, and while it’s important to understand the details of how you compare to competitors, the customer’s view is what matters most. Because many customers will start their research with publicly available information, LLMs can be a great way for you to get these insights. You’ll need to validate them, but AI tools are a great starting point.
Here’s a prompt to get you started. I am usually quite specific about the output structure I want, so I can spend less time reformatting:
Act as a senior product strategist preparing a competitive analysis for annual planning. I need a concise summary of our competitor, ‘Competitor X’, focusing specifically on their product strategy for ‘our market’.
Please structure your response in the following sections:
Core Value Proposition: What is the main promise they make to their target customers?
Target Audience: Describe their ideal customer profile (e.g., SMB, Enterprise, D2C brands, etc.).
Key Strengths: List their top 3 most-marketed or best-known product features.
Potential Weaknesses: Based on public information (like G2 reviews or forum discussions), what are 2-3 common complaints or perceived gaps in their product?
Strategic Threat Level: On a scale of Low-Medium-High, how would you rate them as a direct threat to a company like ours, and provide a one-sentence justification.”
After you’ve prepared the elements of your plan, you need to stress-test it.
My advice?
Use a well-worded prompt that looks at your plan with a pessimistic view. This can help you identify areas you might need to address or improve. It may also highlight some blind spots you missed in your first pass.
Here’s an example of a good prompt that goes beyond “What do you think of my strategy?”
Act as my strategic advisor with the following context:
You’re brutally honest and direct
You’ve built multiple billion-dollar companies
You have deep expertise in psychology, strategy, and execution
You focus on leverage points that create maximum impact
You think in systems and root causes, not surface-level fixes
Your mission is to:
Identify the critical gaps
Design specific action plans to close those gaps
Call out my blind spots and rationalizations
Force me to think bigger and bolder
Hold me accountable to high standards
Provide specific frameworks and mental models
For each response:
Start with the hard truth I need to hear
Follow with specific, actionable steps
End with a direct challenge or assignment
6. Communicate your plan
With your fact base, modeling, product strategy, roadmap, and GTM considerations complete, your next step is to generate excitement across the team.
This won’t be a one-size-fits-all communication package.
This is how I often think about it:
The elevator pitch (2 minutes): Short, clear, and repeatable
The presentation (20 minutes): This is the version you’ll present across the organization
The written detail (2 hours): This includes the data and assumptions behind your strategy
By grounding your training in data, aligning with your support crew, and leaving room to adapt as the process unfolds, you can turn annual planning from feeling like a chore to being a driver of your success.
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LogRocket’s Galileo AI watches user sessions for you and surfaces the technical and usability issues holding back your web and mobile apps. Understand where your users are struggling by trying it for free at LogRocket.com.
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