A Master Class in Product Planning: Insights from John Cutler

As Lil Wayne once said, “The more time you spend contemplating what you should have done…you lose valuable time planning what you can and will do.” 

Depending on whom you ask, product planning can be extraordinarily strategic or an utter waste of time. To help product teams make extraordinarily strategic use of their valuable time we're sharing insights from our recent chat with the inimitable John Cutler to help teams during this season of annual planning.

John currently leads product enablement at Toast, and is regarded by many to be a true authority on all things product planning. He has honed a sharp perspective using years of experience as a product manager and UX researcher at companies like Amplitude, Pendo, AppFolio, and Zendesk.

In our conversation with John, we explored the nuances of product planning, focusing on key aspects such as adapting to macroeconomic headwinds, identifying signals of good and bad product planning, incorporating the Voice of Customer (VoC) into the process, and evaluating the effectiveness of product planning. Let's get to it!

Adapting to macro headwinds

It's been a challenging year for all companies who have had to adapt to the macroeconomic conditions. Product planning strategies can help companies build ways to meet these headwinds head-on. John emphasizes the need for a more continuous planning process rather than relying solely on annual planning. He suggests implementing shorter calibration cycles, such as quarterly or bi-annual planning, to keep pace with rapidly changing market dynamics. This approach ensures that companies remain agile and responsive to evolving circumstances.

Identifying signals of good and bad product planning

To distinguish between good and bad product planning, John highlights several key signals.

Good product planning leads to increasing clarity, shared language, and convergence of ideas within the team. Coherence, or a shared set of assumptions, becomes evident as discussions progress.

On the other hand, bad product planning results in confusion, fatigue, and political maneuvering within the team. Simplified strategies and local agendas take precedence, leading to a lack of clarity and unproductive tensions.

Incorporating the Voice of Customer (VoC)

To effectively product plan John recommends incorporating the Voice of Customer (VoC) throughout the year, rather than relying on recency bias or cherry-picking customer feedback to support existing strategies.

John recommends building a continuous feedback and VoC practice to prevent biases and ensure a holistic understanding of customer needs. Teams should also engage in both feature-oriented and initiative-based research to maintain a balanced view of customer feedback.

Measuring the quality of product planning

Assessing the quality of product planning involves two aspects:

• Evaluating the strategy itself
• Assessing the execution

John stresses the importance of documenting assumptions, beliefs, key decisions, and the diagnosis of the situation when formulating a strategy. This documentation serves as a reference point for later evaluation. Teams should conduct retrospectives four to six months into the year to review assumptions and beliefs and determine if the strategy was sound.

When evaluating execution, teams often focus on whether they achieved their goals. However, John emphasizes that a balance should be struck between assessing the strategy's quality and evaluating its execution. Shifting the focus to understanding if the right goals were set and whether the team exceeded those goals can provide a more comprehensive assessment.

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Strategies for increasing shared coherence

Increasing shared coherence (AKA the shared set of assumptions) across teams involves various strategies. John suggests:

1. Storytelling: Use storytelling to convey the vision and create a shared understanding.
2. Crystal clear statements: Avoid vague or fluffy statements; provide precise, non-fluffy descriptions of goals and strategies.
3. Pre-mortems: Project yourself into the future and evaluate how the strategy unfolds to uncover potential issues.
4. Identify confusing terms: Ask the team about words or terms that create confusion, and either agree on definitions or clarify their meanings.
5. Embrace diversity: Recognize that different team members may have diverse styles and approaches to solving problems and allow for this diversity to foster innovation.
6. Assess confidence levels: Include confidence intervals when presenting strategies to indicate the level of certainty associated with each component.
7. Operating assumptions vs. Assumptions to test: Distinguish between assumptions that the team will operate under and those that require further testing.

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Mastering product planning is an ongoing journey that requires adaptability, continuous feedback, and a commitment to assessing both strategy and execution. John Cutler's insights provide valuable guidance for product organizations looking to navigate the complexities of product planning successfully. By embracing these strategies and fostering shared coherence, companies can enhance their product planning processes and improve their chances of achieving their goals in a rapidly changing business environment.

Follow John Cutler @johncutlefish for more product insights!