Why PMs should stop chasing the “right” planning window

At this point in the year, we’re past summer and everyone’s coming back to work from their vacations. However, for PMs, it’s an interesting time, as Q3 signals the start of H2. I recently had a chat with a few of my PM friends, and they’re all starting to plan and strategize for 2026. And if you’re reading this blog, chances are, you’re also about to kick off planning your team’s strategy and roadmap for 2026.

While I was thinking about this topic, I also read this thread on Reddit where PMs discussed the right time to start planning and strategy for the year. So in this blog, I want to share my perspective on how to approach yearly planning and strategy, how I did it in the past, the mistakes I made, and the lessons learned.

Since I’ve worked for big companies such as the ecommerce giant Zalando, as well as smaller startups, I also want to highlight the stark difference between the processes in both of these worlds and the pros and cons of each.

When is the right time to start roadmap and strategy planning?

The short answer is it depends.

But, the long answer is that it depends on the type of company you work at, the complexity and maturity of your product, and the speed at which your market and the competition move.

Fortunately, in my eight years of product management, I’ve experienced both extremes. In a large company like Zalando, we had structured early planning, and on the other side, we had late, flexible planning in startups and consulting. Both have their benefits and pitfalls.

Here’s my analysis across the three key factors:

Type of company

Different types of companies have unique needs that impact how and when planning happens.

Enterprises/large organizations

Think of these as companies with more than 10K employees. They have multiple products all connected to each other. The PMs at these companies often need to coordinate across dozens of teams, including sales, customer service, operations, marketing, legal, and higher management, in addition to the customers.

They need to understand the roadmap of all of these teams and get feedback to create/optimize their own feedback and determine dependencies and risks early on. That’s why planning for the next year in these companies starts early (often in Q3 of the current year)

The benefit is alignment. The risk is that the market shifts faster than the company can adapt, making the plan obsolete.

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Startups / scale-ups

On the other hand, these are the companies with fewer than 500 employees. The startup I worked for had nine employees. Here, planning usually happens much later.

Since the product is very founder-driven, the founders prefer to wait until they have more signals. Sometimes it’s about raising more funding, while sometimes it’s about increasing customer traction. This creates agility, but it can result in engineering and design teams feeling all over the place.

Maturity of your product

After considering the type of company you’re in, it’s time to determine the current state of your product.

• Mature products — If your product is already in the market, it’s used by many users and is well-established, then you have a strong understanding of your metrics, your customer base, and your recurring pain points. You also understand the tech side and the dependencies. That makes it easier to plan earlier because there are fewer surprises
• Early-stage products — If you’re working for a startup that’s still searching for product-market fit, then yearly planning will require a lot of estimation and guesswork. Priorities can change very quickly depending on market conditions and company goals. In these cases, it’s usually better to keep strategy high-level and avoid locking into detailed annual roadmaps

Speed of your market

The final factor you’ll want to consider is how quickly your market moves.

• Fast-moving markets — Companies in fintech are a good example of fast-moving markets. Regulatory changes happen very quickly, and this can flip the priorities of the companies overnight. In these environments, early planning helps with leadership alignment, but your roadmap must be agile
• Stable markets — Companies in SaaS are a good example of these. Here, customer needs evolve more slowly. It’s easier to stick to long-term plans because the ground doesn’t move as quickly

My experience in a large organization

While I was at Zalando, we started our planning in Q2. We began our planning early to ensure we determined our goals for the next year by the end of H1. Our process looked like this:

• Our teams talked to various stakeholders and customers and collected the learnings from the current year
• The PMs wrote strategy papers that included the problem we were solving for, why it needed to be solved, why now, who the customers were, how to solve the problem, and what the dependencies were. These were 10-15 pages long and very detailed
• These drafts went through multiple iterations and feedback cycles
• In most cases, the dependent teams took time to evaluate the strategy from their side

By the end of the planning, we had a clear 12-month roadmap outlining major priorities of the year, key dependencies, budget allocation, and resource requirements.

Why early planning worked well

Early planning provided us with three key advantages:

• Strong alignment — Every department and team knew what was coming and what their role was in it. Marketing could plan campaigns, sales could pitch confidently, and operations could prepare for demand. Also, every team knew what they had to do in order to achieve the yearly goal
• Predictability — Since a lot of assumptions, risks, and dependencies were already shared upfront, higher management had a sense of budgets, and the OKRs and hiring decisions were tied neatly to the plan
• Team confidence — Most of us used to be on vacation in December, but we all felt good to walk into January knowing what our big bets and themes were, as well as what was required out of each of us. It reduced ambiguity, which is often the hardest part of PM work

Where early planning fell short

But no plan is perfect, and this approach came with its own cons. In one such case, we were building a content management system and by the time Q2 hit, 70 percent of the assumptions were no longer valid.

Market conditions ultimately forced us to change our plans. Early planning also cost us in the following situations:

• A competitor launched a feature we hadn’t anticipated, changing customer expectations and requirements
• A new compliance rule in one of Zalando’s markets forced the team to divert resources
• A marketing experiment showed different customer behavior than we had predicted when writing the strategy

This kind of planning process might be a little too rigid for an agile environment, as well as for companies in heavily regulated markets like finance and AI.

My experience in startups

In smaller companies, I’ve experienced the opposite. While I was at Placker, we didn’t start planning until the end of the year for next year. Our process looked like this:

• Founders would wait for signals. These would include investor pitches for funding rounds, big customer wins (if it were B2B), or competition coming up with a new strategy
• Instead of 20-page strategy docs, I’d put together a Notion page, or even just a shared doc with three to four bullet points: “Double down on customer acquisition, reduce churn, launch MVP of feature X.” The goals were very clear and measurable
• Since the teams were small, there was no need to chase the stakeholders and ask for buy-in. In most cases, the founder was the stakeholder and the decision maker
• Roadmaps were kept deliberately loose. At best, you’d have a clear picture for the next quarter. Beyond that, the plan was more like broad themes. In one instance, the founder wasn’t ready to have a plan beyond Q2 for that year because he knew things would change

Why late planning worked well

In the startup environment, late planning helped because it was:

• Closer to reality — Since decisions were made close to execution, in most cases, they were close to reality. We didn’t over plan, since we knew there would be considerable changes in the market in a few months. This helped us not to waste resources incorrectly
• Flexibility and adaptability — We were able to adapt to market changes, funding updates, or competitor launches very quickly. In one such case, we got a requirement from one of our top clients. Since the revenue from this client was as high as 20 percent, we had to prioritize their requirements. We were also able to implement these changes for the rest of the clients, which was not a part of the original roadmap we created three months back
• Less overhead — A Smaller company means fewer stakeholders. And this also means fewer documents and fewer alignment meetings. It was also very easy to get feedback from everyone and incorporate the feedback into the roadmap. The process was lightweight and didn’t slow down execution

Where late planning fell short

However, late planning also came with a few downsides:

• Reactive mindset — Without a long-term, clear direction, it was challenging for me to establish specific goals. We experienced chaotic times that often resulted in doing things that were important from the team’s perspective. Data took a backseat, and the loudest customer or the sales team drove the prioritization
• Leadership doubts — Because there was no clear long-term plan, leadership from some big customers doubted what the plans of the company were. This resulted in multiple meetings with them where we had to reassure them that the company was focused on solving their problems
• Team uncertainty — In one startup I worked with, engineers often asked, “What’s our North Star?” Since strategy discussions happened so late, the team felt like they were executing in the dark. Unlike Zalando, where December meant walking into January with clarity, smaller companies sometimes walked into January still figuring out what the year’s big bets were

The hybrid approach that’s worked best for me

From my experience working at large enterprises and small startups, I can confidently tell you that no one approach is perfect. However, over time, I’ve landed on a middle ground that balances alignment with flexibility. Here’s my approach:

1. Draft in Q2/Q3:
   • Use learnings from the current year to identify big bets and opportunities
   • The goal isn’t to be perfect but to set a direction
   • Skip the details and focus on the bigger picture
2. Align and finalize in Q4:
   • Collaborate with leadership, engineering, design, and other stakeholders to draft the initial version
   • Secure buy-in for resources
   • Align with the priorities
   • Negotiate if needed
3. Keep a rolling roadmap:
   • Update every quarter based on new insights
   • Treat it as a living document, not a final document
   • Use quarterly reviews to re-prioritize and adjust focus

The idea behind this approach is to start early but keep the plan loose in order to consider the best of both worlds. This hybrid approach gives you the long-term clarity that every team craves without sacrificing the short-term flexibility customers need.

Actionable tips for PMs if you’re worried it’s too late

Chances are if you’re reading this and if you haven’t landed on a strategy for 2026, you might think you’re late to course correct. But that’s not the reality. You’re not necessarily behind since it’s not about having a strategy by a certain date/month. It’s about creating a process to adapt things as they come.

Here are a few actionable tips that’ll help you do a quick sanity check:

1. Do you know the top five opportunities your team should focus on in 2026?
2. If not, collect customer insights, company goals, competition insights, and other relevant data. Use the OST (opportunity solution tree) framework and come up with the top three to five opportunities
3. Have an initial alignment with the relevant teams. Also include the teams that might have a dependency on your team, or you might be dependent on them
4. Have a quarterly review to revisit the strategy

The idea is to create a loose plan, gain buy-in from the stakeholders, and continue to solidify it as you get closer to 2026.

Final thoughts

As mentioned earlier, there’s no right or wrong, or late or early when it comes to strategy. The key is to create a process around strategy and roadmap creation that supports flexible, adaptive, and loose roadmap. Also, it’s important to understand at what stage the company is and what the stakeholders are looking for.

Smaller companies will always focus on flexibility while enterprises will focus on early alignment and preciseness. As a PM, you’ll have to understand the dynamics and use the tools and frameworks in this article to build a strategy that considers the business, customers, market, and the competition equally.

Featured image source: IconScout

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