John Cutler Questions Traditional Strategy Layers on LinkedIn

J

John Cutler

LinkedIn Author

Head of Product @Dotwork ex-{Company Name}

In a recent LinkedIn post, John Cutler questions the conventional, multi-layered approach to strategy and goal setting within organizations. Cutler’s series of probing questions challenges the assumed linearity and stability of strategic frameworks, suggesting a need for more agile and responsive systems.

Cutler opens his post by highlighting the disconnects often found in current strategic planning, asking:

What about short-term goals? Or goals that feed other goals?

What if we need a near-term strategic shift?

Why aren’t teams involved in initiatives?

What if a story impacts a goal? Why all the layers?

These initial questions set the stage for a broader critique of how strategy is defined, communicated, and executed.

Challenging the Hierarchy of Goals

A core theme in Cutler’s post is the rigidity imposed by traditional strategy structures. He points out the common practice of creating distinct layers – from high-level vision and pillars down to epics and stories – and questions the assumption that these layers are always clean and logically connected. Cutler asks, “Why aren’t teams stuck at epics, stories, features?” This suggests that teams may be too far removed from the strategic intent, leading to a lack of understanding or buy-in.

Furthermore, Cutler probes the flow of information and decision-making. He questions the assumption that “time flows top-down” and wonders where “upward insights into strategy” are meant to surface. This highlights a potential bottleneck, where valuable ground-level information or emergent opportunities might not reach senior leadership effectively.

The Pace of Change and Business-as-Usual

Cutler also addresses the tension between strategic agility and the demands of ongoing operations. He directly asks, “What about business-as-usual work?” and “Why must everything take a long time?” This points to a common organizational challenge: balancing the need for rapid adaptation and innovation with the necessity of maintaining stable, day-to-day operations. The inclusion of questions like “What about quick features or quick goals?” and “How fast can new insights change direction?” underscores the desire for faster feedback loops and more dynamic strategic adjustments.

The post further delves into the inherent uncertainties in business strategy. Cutler challenges the notion of stable layers by asking, “Why assume all layers are equally stable?” He also brings up critical aspects often overlooked, such as risk and uncertainty, with questions like “Where is risk acknowledged?” and “Where is uncertainty represented?”

Rethinking Strategy Formation and Measurement

According to Cutler, the very definition and formation of strategy are areas ripe for re-evaluation. He asks, “What about defining strategy itself?” and “What about early-stage opportunities?” This suggests that strategy shouldn’t be a static, pre-defined plan but rather an evolving process that incorporates ongoing learning and exploration.

A significant part of Cutler’s critique revolves around impact and feedback. He pointedly asks, “Where are feedback loops?” and “Where is real impact measured?” This implies that current systems may not adequately capture or respond to the actual value being delivered to customers or the market. Cutler also questions the traditional top-down assumption of knowledge: “Why assume senior leaders know reality best?” and “Where is customer value actually sensed?”

In essence, John Cutler’s LinkedIn post serves as a call to reconsider the fundamental assumptions underlying strategic planning and execution. By posing a series of critical questions, he invites organizations to move beyond rigid, hierarchical models and embrace more adaptive, team-involved, and impact-focused approaches to achieving their goals.

📝 About This Content

This article is based on insights shared by John Cutler on LinkedIn.

📅 Originally posted on December 6, 2025 | View original post on LinkedIn →