Many of us feel overwhelmed by technology, despite using countless tools designed to make us more efficient. Jeff Szczepanski, a successful software entrepreneur, recently spoke at the Business of Software Conference about this very challenge: Why isn’t technology making us more productive?
While technology has significantly boosted task-level productivity and helping individuals complete specific actions faster, it has often left us overwhelmed and misaligned at the organizational level.
Current digital tools are usually described as merely “paper in a screen,” lacking the ability to truly support collaborative thinking and the coordination of complex work.
Five Types of Thinking
Jeff Szczepanski argues that productivity failures often stem not from bad intentions, but from issues like time compression, poor planning, and strategy misalignment. To address this, he proposes a framework based on five types of thinking, suggesting that only one is instinctual, while the others require structure, vocabulary, and intent.
Let’s explore these five levels of thinking:
Type 1: Thinking Fast – Execution
This is our instinctual level, focused on action and reaction. While necessary, pitfalls here include:
- Time Compression: Rushing into action due to instinct or fear, neglecting necessary planning or broader context.
- Gyration: Getting stuck in cycles of debating different options (like option A vs option B) without a clear way to decide, often wasting time.
- Best Effort: Equating the completion of tasks on a checklist with achieving the desired outcome, even if the work doesn’t actually deliver the goal.
Type 2: Planning
This is the first level of “thinking slow” and involves building a plan.
A good plan is defined as a sequence of actions over time and resources that can achieve a specific outcome with high confidence.
Crucially, this level requires separating the goal (defined by quality attributes) from the actions or implementation needed to achieve it. This separation, formalized perhaps using tools like the GROW Model (Goal, Reality, Options, Will), allows for creativity and helps avoid endless debates about options.
Type 3: Strategy
Strategy is simply about prioritizing goals and the resources used to achieve them. It serves as the justification for your plans. A key diagnostic for a strategy problem is unclear priorities or confusion within an organization about what to focus on. This level also ties into the concept of Core vs Context.
Core activities are those that are new or different and require invention (thinking slow), while Context activities are standard practices that can be executed (often thinking fast). Strategy helps determine what needs to be core versus what can be context.
Type 4: Paradigm
This is the highest level of conscious thinking, representing your vision or beliefs about how the world should be, aiming to create a paradigm shift. Sustainable advantage comes from creating new paradigms, as doing context work can easily be copied by competitors. Articulating a new paradigm requires new vocabulary (sometimes using a “Froto” tool to describe the shift from one state to another) so that others can understand and align with the vision.
Type 5: Reality
The final type acknowledges that all our frameworks and paradigms are just models, approximations of underlying reality. It’s crucial to step outside our own models to understand their limitations and identify potential “meteors” – existential risks or disruptions – that could impact the business. These critical insights are often known within an organization but ignored.
The core issue is that current computers and software tools do not inherently support this layered way of thinking or working collaboratively. They excel at managing tasks within applications (task-level productivity) but don’t help us coordinate, align strategies, define paradigms, or navigate uncertainty.
Jeff’s new company, Reframe Technologies, aims to address this gap by building technology that can formalize these levels of thinking and help organize work environments. The goal is to move beyond “productivity theater” towards a new leap in human capacity for knowledge work. This involves creating systems that can understand the relationships between different activities, goals, and strategies, effectively helping the computer to manage the “messy desktop” and align work streams.
While personal habits like managing notifications or screen time can improve individual focus, the larger opportunity lies in designing technology that is genuinely assistive, helping us manage complexity and coordinate effectively across these five levels of thinking.
(This article draws on Jeffrey Szczepanski‘s talk “Why Isn’t Technology Making Us More Productive?” at Business of Software Conference.)