Planning with Precision: The Secrets to Successful Quarterly Planning

Batya Mayer
Engeineering Operations
6 min readNov 23, 2023

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Explore the world of quarterly planning along with Michal Dery, Michal is Head of Product & Engineering Operations and an experienced Engineering Program Management Group Leader with over two decades of experience. This article looks closer at the significant foundation for quarterly planning, the ideal timeline, the challenges faced during the process, and Michal’s professional tips for successful planning.

Setting the Pace: From Yearly Goals and OKRs to Quarterly Actions

To fully understand the significance of quarterly planning it is important to first understand the foundational role of the Objectives and Key Results (OKRs) that are set annually and act as the compass for the yearly planning. Michal distinguishes between OKRs and the roadmap, explaining that while OKRs provide direction, the roadmap is a tool to achieve those objectives. “Around 70–80% of the roadmap should be traceable back to the OKRs, ensuring every effort contributes to our main objectives,” she advocates. OKR planning predominantly takes place in Q4, laying the foundation for the annual roadmap, which in turn influences the quarterly plan. The majority of epics added to a quarterly plan should directly correlate with one or more OKRs, maintaining strategic alignment.

Furthermore, Michal emphasizes the importance of a top-down approach, starting with the yearly plan, “Every quarter is a piece of a larger picture”. She mentions that before diving into quarterly planning, it is crucial to understand the company’s cadence, yearly plan, and its expected outputs, such as QBRs. “The main thing I keep in mind is the yearly skeleton,” she says.

Michal points out that each quarter has unique characteristics and ceremonies influenced by the yearly plan. For instance, Q1 is about concluding the previous year and retrospectives, while Q4 is dedicated to yearly planning and annual comparisons. “It’s not just about planning a standalone quarter; it’s about observing from a yearly perspective.”

Timing is Everything: When should quarterly planning start and what are the timelines?

“A quarter contains 13 weeks. Around week 4 I would usually send a friendly reminder followed by a quarterly planning kickoff email that shows the planning timeline. Week 5, is a good time to take a ‘snapshot’ and assess the standpoint (without disregarding the agile environment and rapid dynamic shifts),” Michal explains. This is when she advocates for business processes to take place so conclusions can be drawn from their findings (such as Voice of the Customer, business goals, industry feedback, competitive analysis, and more). With the conclusions gathered, the company’s OKRs, and the roadmap, a list of quarterly initiatives can start to be formed. By week 6 or 7, based on the business analysis, the product goals are set by the product manager in collaboration with the development. Michal highlights the importance of a checkpoint review meeting with senior management by week 9 or 10 where a complete, organized, and prioritized list would be presented. She explains how having this meeting scheduled ahead of time keeps everyone motivated, and ensures the planning process comes together.

As the quarter progresses, the approach shifts. “The transition is from a top-down approach to a bottom-up planning strategy,” Michal notes. This involves consolidating the initiative list into quarterly goals and breaking them down into significant tasks, known as Epics. These Epics are defined by their alignment with the quarter’s objectives and the criteria for success. By the time week 13 rolls around, all teams are deeply engaged. The final week is dedicated to collaboration and resolving dependencies. Each team partners closely with the Product department to refine and ‘groom’ the Epics, adding estimations and delving into the required technologies. They assess risks, consider headcount, and ensure a comprehensive understanding of the tasks ahead.

Michal further details the concluding stages of the planning process. Lastly, the list is refined, categorizing the initiatives into achievable, stretch objectives, and those that are unlikely to be completed within the quarter. This distinction shapes the quarterly plan. The planning phase is wrapped up with a meeting involving all departments — from product and design to R&D. Each domain/solution is allocated a single slide, with a strict time limit, to present their quarterly objectives. This ensures everyone is aligned and has a clear understanding of the broader company goals and each team’s focus, for the upcoming quarter.

Quarterly Planning Process — Week by Week

Challenges: What are the challenges?

Michal addresses the intricacies and challenges she encounters during the planning process. “One of my primary challenges is seamlessly integrating the OKRs, roadmap, and planning, while also aligning the quarterly planning with the company’s cadency in a way that the planning process doesn’t become an additional burden to the teams.” Michal’s aim is to create a common ‘language’ if you will, that simplifies the planning stages. “It’s about reducing redundancy. I’ve observed team members preparing multiple presentations tailored to different audiences. My goal is to minimize this, ensuring that every step we take during the planning contributes cohesively to the bigger picture.”

Furthermore, Michal acknowledges that in certain organizations, intricate interdependencies between teams can pose significant challenges. “In such contexts, it might be prudent to initiate the planning earlier, allowing ample time to incorporate initiatives across teams”.

To navigate these intricate dependencies, Michal refers to the iterative approach, “Managing these iterations can sometimes feel like a loop, where one team’s requirement hinges on another’s, creating a chain of dependencies,” she describes. In these multifaceted situations, Michal advocates for mapping of dependencies and establishing explicit parameters. “For instance, determining the timeframe for a response, the specificity of the response (like whether a task will be completed within a particular quarter or sprint), and the level of commitment. Broad, straightforward commitments are always preferable. All these measures are geared towards finalizing the plan effectively”.

Pro Tips for Successful Planning: Can you share some?

Michal offers some pro tips based on her experience. “One invaluable tip I’ve found is scheduling a review meeting with senior management in the company (CTO, CEO, or another significant figure). Scheduling this meeting right when the planning kick-off email is sent, has a profound influence on the success of the planning; it sets a concrete deadline and motivates teams to proactively participate in the planning.”

The agenda of this meeting also has an influence on the entire planning, “For example, if the review meeting revolves around alignment with OKRs, it’s crucial to be equipped with insights on how each initiative ties back to a specific business objective.” This meeting gives direction, and structure to the planning process.

Another tip Michal shares is to distinguish between two domains: the planning domain and the execution domain. “The planning domain should be a space reserved for what I like to call a ‘fluffy’ backlog. This is a dynamic space unseen by the teams, allowing for flexibility and change.” Once an initiative meets the set criteria, only then does it progress to the execution domain. Having a clear separation is key, this ensures a more focused approach to both planning and implementation.

Closing Thoughts

Both product and engineering operations play a role in the quarterly planning process. “Our responsibility is to facilitate the process, ensuring everything happens timely and that the set objectives are achieved.

Michal fondly recalls the quarterly planning wrap-up meeting. “When teams proudly present their mock-ups, showcasing what they aim to achieve within the quarter, with a clear understanding of their initiatives it makes all the effort worthwhile and I feel rewarded.” However, The satisfaction is short-lived as she soon gears up for the next planning cycle.

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