A Master Class in Product Planning: Insights from John Cutler

Tiffany Go
Head of Product Marketing
October 9, 2023

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.

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.

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!

Get a demo with your data
We are laser-focused on giving customers more than they expect through a hospitality-first, individualized approach to drive retention and loyalty. Enterpret has allowed us to stitch together a full picture of the customer, including feedback and reviews from multiple data points. We now can super-serve our loyal customers in a way that we have never been able to before.
Anna Esrov
Vice President of Customer Experience & Loyalty
Enterpret allowed us to listen to specific issues and come closer to our Members - prioritizing feedback which needed immediate attention, when it came to monitoring reception of new releases: Enterpret picked up insights for new updates and became the eyes of whether new systems and functionality were working well or not.
Louise Sellars
Analyst, Customer Insights
Enterpret is one of the most powerful tools in our toolkit. It's very Member-friendly. We've been able to share how other teams can modify and self-serve in Enterpret. It's bridged a gap to getting access to Member feedback, and I see all our teams finding ways to use Enterpret to answer Member-related questions.
Dina Mohammad-Laity
VP of Data
The big win-win is our VoC program enabled us to leverage our engineering resources to ship significantly awesome and valuable features while minimizing bug fixes and" keep the lights on" work. Magnifying and focusing on the 20% that causes the impact is like finding the needle in a haystack, especially when you have issues coming from all over the place
Abishek Viswanathan
CPO, Apollo.io
Since launching our Voice of Customer program six months ago, our team has dropped our human inquiry rate by over 40%, improved customer satisfaction, and enabled our team to allocate resources to building features that increase LTV and revenue.
Abishek Viswanathan
CPO, Apollo.io
Enterpret's Gong Integration is a game changer on so many levels. The automated labeling of feedback saves dozens of hours per week. This is essential in creating a customer feedback database for analytics.
Michael Bartimer
Revenue Operations Lead
Enterpret has made it so much easier to understand our customer feedback. Every month I put together a Voice of Customer report on feedback trends. Before Enterpret it would take me two weeks - with Enterpret I can get it done in 3 days.
Maya Bakir
Product Operations, Notion
The Enterpret platform is like the hero team of data analysts you always wanted - the ability to consolidate customer feedback from diverse touch points and identify both ongoing and emerging trends to ensure we focus on and build the right things has been amazing. We love the tools and support to help us train the results to our unique business and users and the Enterpret team is outstanding in every way.
Larisa Sheckler
COO, Samsung Food
Enterpret makes it easy to understand and prioritize the most important feedback themes. Having data organized in one place, make it easy to dig into the associated feedback to deeply understand the voice of customer so we can delight users, solve issues, and deliver on the most important requests.
Lauren Cunningham
Head of Support and Ops
With Enterpret powering Voice of Customer we're democratizing feedback and making it accessible for everyone across product, customer success, marketing, and leadership to provide evidence and add credibility to their strategies and roadmaps.
Michael Nguyen
Head of Research Ops and Insights, Figma
Boll & Branch takes pride in being a data driven company and Enterpret is helping us unlock an entirely new source of data. Enterpret quantifies our qualitative data while still keeping customer voice just a click away, adding valuable context and helping us get a more complete view of our customers.
Matheson Kuo
Senior Product Analyst, Boll & Branch
Enterpret has transformed our ability to use feedback to prioritize customers and drive product innovation. By using Enterpret to centralize our data, it saves us time, eliminates manual tagging, and boosts accuracy. We now gain near real-time insights, measure product success, and easily merge feedback categories. Enterpret's generative AI technology has streamlined our processes, improved decision-making, and elevated customer satisfaction
Nathan Yoon
Business Operations, Apollo.io
Enterpret helps us have a holistic view from our social media coverage, to our support tickets, to every single interaction that we're plugging into it. Beyond just keywords, we can actually understand: what are the broader sentiments? What are our users saying?
Emma Auscher
Global VP of Customer Experience, Notion
The advantage of Enterpret is that we’re not relying entirely on human categorization. Enterpret is like a second brain that is looking out for themes and trends that I might not be thinking about.
Misty Smith
Head of Product Operations, Notion
As a PM, I want to prioritize work that benefits as many of our customers as possible. It can be too easy to prioritize based on the loudest customer or the flavor of the moment. Because Enterpret is able to compress information across all of our qualitative feedback sources, I can make decisions that are more likely to result in positive outcomes for the customer and our business.
Duncan Stewart
Product Manager
We use Enterpret for our VoC & Root Cause Elimination Program - Solving the issues of aggregating disparate sources of feedback (often tens of thousands per month) and distilling it into specific reasons, with trends, so we can see if our product fixes are reducing reasons.
Nathan Yoon
Business Operations, Apollo.io