Why We're Brilliant at 'How' But Struggle with 'Why': The Strategy Workshop Paradox

By Nathan Waterhouse · 2025-10-14

"What should we actually be focusing on in the next year?"

I posed this question to a senior leadership team last month. Within seconds, the room erupted with responses: "We need to improve our onboarding process," "Launch the new customer portal," "Implement better reporting dashboards," "Run more targeted campaigns."

All perfectly reasonable suggestions. All focused on execution. All missing the point entirely.

Here's what I've observed across dozens of strategy workshops with different organisations: we're exceptionally good at thinking about the 'how' but remarkably poor at articulating the 'why.' People instinctively default to actions and tactics when asked about strategy, finding it surprisingly difficult to describe the higher-level areas of focus that should guide those very actions. In this post we'll explore some scientific reasons why that might be, and I'll share some proven ways that I've found to help people overcome that bias.

The Tactical Reflex

This pattern plays out whether it's a non-profit or for profit, B2B or B2C, and seems to span cultures. Ask about priorities, and you'll get a shopping list of initiatives. Ask about goals, and you'll hear about deliverables. Ask about strategy, and you'll receive a project plan.

Just last week, I was facilitating a workshop where we were identifying strategic priorities for the coming year. One participant confidently proposed "university partnerships" as a key focus area. When I asked what outcome that would achieve, there was a pause—then the real answer emerged: "We need to build insight capability that helps our customers make better decisions." That shift from tactic to outcome changed everything. Suddenly, we could explore multiple routes to that goal, not just the first one that came to mind.

This is the pattern I see repeatedly: people gravitating towards solutions before articulating the problem they're trying to solve. Each time, I find myself gently pulling the group back up the ladder of abstraction, asking: "But why do we want to do that? What outcome are we really after?"

Why This Happens: The Neuroscience of Strategic Thinking

This isn't a failing of intelligence or capability, it's a predictable response rooted in both our evolutionary wiring and how modern organisations operate. Several forces conspire to create this tactical bias:

Our Brains Are Wired for Immediate Action. From an evolutionary perspective, our ancestors' survival depended on quick, concrete responses to immediate threats. As evolutionary psychologists Steven Pinker, John Tooby, and Leda Cosmides have argued, the human brain evolved to handle short-term, concrete survival problems, not abstract, long-range planning. The limbic system and amygdala prioritise immediate threat detection and reward-seeking (fight, flight, or food), whilst the prefrontal cortex (responsible for abstraction, planning, and delayed gratification) developed much later in our evolutionary history and demands significantly more metabolic energy to operate.

Neuroimaging studies reveal just how resource-intensive strategic thinking truly is. Research by Miller & Cohen (2001) and Raichle & Gusnard (2002) using fMRI and EEG shows that the brain consumes roughly 20% of the body's energy, with abstract reasoning and executive control tasks lighting up high-demand prefrontal regions. When we're tired or stressed, the brain economises energy by defaulting to habitual, tactical responses—explaining why that end-of-day strategy session so often devolves into a task list.

Daniel Kahneman's research on System 1 (fast, intuitive) versus System 2 (slow, deliberate) thinking helps explain this bias in everyday terms. When asked about strategy, our System 1 thinking immediately jumps to familiar patterns: "I know how to improve processes, build features, run campaigns." Strategic thinking demands the more effortful System 2 processing, which our brains naturally resist unless we consciously engage it.

Comfort in Concrete Thinking: tactics feel safer because they activate our brain's reward systems more readily. You can measure them, tick them off, and get that dopamine hit of completion. Strategy, by contrast, exists in the realm of the abstract. This requires sustained cognitive effort without immediate reward, making it inherently less appealing to our neurological makeup.

Organisational Reward Systems: most performance reviews focus on what you delivered, not whether those deliverables served a coherent strategic purpose. We get rewarded for checking boxes, not for challenging whether we're working on the right boxes.

The Immediacy Trap: daily pressures demand immediate responses, triggering our stress response systems that further bias us towards quick, tactical solutions. When every meeting is about "What are we going to do about X?", we condition ourselves to think in terms of actions rather than intentions.

The urgent literally hijacks the neural pathways needed for strategic reflection.

It’s unlikely that our hunter-gatherer ancestors spent much cognitive energy on ‘why’ reasoning in the abstract. Their brains were shaped to solve immediate survival problems. Many evolutionary models suggest that abstraction and meta-reasoning emerged gradually, once social coordination, tool complexity, and representational capacity allowed it. Some theorists argue that earlier cognition was more episodic and stimulus-driven, evolving over time into more symbolic, relational, ‘why’ thinking.

Cognitive Load and Mental Fatigue: strategic thinking is cognitively demanding. Research shows that as our mental energy depletes throughout the day, we default to more automatic, tactical responses. This is why many strategy sessions scheduled at the end of busy days devolve into task lists rather than meaningful strategic dialogue.

The Hidden Cost

This tactical obsession isn't harmless. It leads to what I call "strategic drift"—organisations that are incredibly busy but mysteriously ineffective. Teams work harder but make less meaningful progress. Resources get scattered across worthy initiatives that don't add up to anything coherent.

I've watched companies launch brilliant products that solve problems nobody has, implement sophisticated processes that optimise for the wrong metrics, and execute flawless campaigns that reach entirely the wrong audiences. Not because they lacked capability, but because they never paused to ask whether they were aiming at the right target.

Making Strategy Stick: A Practical Toolkit

The solution isn't to abandon tactical thinking – execution matters enormously. Instead we need to scaffold strategic thinking before diving into execution. Here's what works:

The Core Shift: Outcomes Before Outputs

❌ Don't ask: "What should we build?" ✅ Ask instead: "What change do we want to create?"

The ladder technique: Anchor in concrete first, then climb to abstraction.

This grounds strategic thinking in actual experience before extracting patterns. You can also reframe "why" questions as "what if". This feels more exploratory and less interrogatory.

Five Workshop Interventions That Work

1. Make thinking visible: use physical tools to externalise abstract thought. At a workshop last week, I used Lego Duplo bricks to represent key market sectors. The participants found it really helpful because it gave them something tangible to manipulate whilst discussing abstract concepts. This literally offloads cognitive load from working memory to the physical environment. Whether it's Lego, post-its, or system diagrams, making the invisible visible helps our brains grasp abstract relationships without drowning in complexity.

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Workshop participants using Lego Duplo bricks to decide on which market sectors to prioritise

2. Dig beneath tactics with reverse questioning: when someone suggests an action, dig into the reasoning: "By implementing that, what outcome would it improve?" Keep asking "why would we want that?" until you uncover the strategic intent buried beneath the tactical suggestion. This archaeological approach reveals the thinking that's often there but unexpressed.

3. Design for cognitive energy: strategic thinking is metabolically expensive. Remember, your prefrontal cortex is burning glucose at a higher rate than tactical thinking. Work with this reality:

4. Embrace productive discomfort: strategy work should feel slightly uncomfortable. If everyone's nodding along immediately, you're probably not thinking at a high enough level. Remember: our brains naturally resist the cognitive effort of abstract thinking, so the discomfort is actually a sign you're engaging the right mental processes—System 2 rather than System 1.

5. Build in reflection moments. In a recent two-day workshop, we built in a reflection moment before starting day 2, for participants to pause, reflect with a partner, walk the room, and share back. This pair-and-share approach is powerful because abstract thinking improves when verbalised, and ensures all voices get heard. Small conversations let participants test half-formed ideas safely before group synthesis, strengthening both their thinking and their confidence.

Six Questions That Change Everything

Next time you find yourself or your team defaulting to tactical mode, try asking:

That last question uses an analogy to bridge the abstract and make it more relatable and concrete.

The Strategic Muscle

Like any skill, strategic thinking improves with practice. The more often we force ourselves to articulate the 'why' before rushing to the 'how', the more natural it becomes. We're literally strengthening neural pathways that support abstract thinking while weakening the automatic tactical responses.

The more we reward clarity of purpose alongside quality of execution, the more our teams will develop both muscles. Understanding that this tactical bias is neurologically (and probably evolutionarily) normal, rather than a personal failing, can help teams approach strategic development with patience and intentionality.

"He who has a why to live for can bear almost any how." — Friedrich Nietzsche

Because in an age of endless possible actions, the organisations that thrive won't be those that do the most things, they'll be those that do the right things, for reasons they can clearly articulate.

As Michael Porter reminds us:

"Strategy is about making choices, trade-offs; it's about deliberately choosing to be different."

Those choices become infinitely clearer when we understand our 'why' before rushing to the 'how'.

The next time you're in a planning meeting and someone asks, "What should we do?", try responding with a different question: "What are we really trying to achieve here?"

You might be surprised by how much strategic clarity emerges from that simple shift in perspective—and how much more engaged your prefrontal cortex becomes in the process.

What patterns have you noticed in your own strategic discussions? Are you seeing this same tactical bias, or have you found ways to keep teams focused on the bigger picture? I'd love to hear your experiences and what you've found helps in the comments.