How to make struggle more productive in learning and leadership

Executive overview

Real learning almost always involves discomfort. The instinct is to avoid or explain away struggle — but that discomfort is a signal you're in the right zone.

Productive struggle — the zone just beyond your current abilities — is where retention deepens, skills transfer, and growth compounds. Leaders who name it, scaffold it, and build team vocabulary around it turn a source of tension into a competitive advantage.

The zone of proximal development

• Psychologist Lev Vygotsky identified three zones: comfort, proximal development, and over-extension.
• The zone of proximal development (also called the learning zone or challenge zone) sits just outside what you already know.
• Too easy: no growth. Too far: no success. The middle zone is where meaningful learning happens.
• If you're uncertain where a project will land, that uncertainty is often a sign it's genuinely innovative.
• Feeling underwhelmed by your own work the night before a review is normal — it reflects care and stretch, not failure.

Foreshadowing struggle as a leader

• Name it in advance: tell teams there will be a period that feels uncomfortable.
• Use the design squiggle (Damian Newman) as a visual anchor — a tangled hairball that eventually resolves into direction.
• Borrow the term "productive struggle" from mathematics education, where students who struggle with problems retain and transfer skills better than those who solve easily.
• Build shared vocabulary on the team so members can recognise and support each other through difficult moments.

Getting unstuck: shift from talking to building

• When teams feel stuck or complain about time and resources, the underlying issue is usually discomfort or fear about outcomes.
• The fix: move into a short building sprint — three rough prototypes in 30 minutes, regardless of direction.
• Building forces conceptualisation; teams often realise their ideas are more compatible than the conversation suggested.
• Sharing rough prototypes with another team generates new data and breaks the closed loop of internal debate.
• A little data beats waiting for perfect data.

Getting honest feedback: the test of silence

• Test of silence: when sharing a prototype for feedback, resist the urge to explain, justify, or over-contextualise.
• Work has to live in the world without you narrating it — so observe what happens when you're not there to explain.
• De-emphasising your investment lowers the barrier for honest responses.
• Consider a two-layer approach: first, raw reactions with no framing; then share your goals and ask how well the work meets them.
• Power dynamics in organisations suppress candid feedback — structured critique practices counteract this.

The units of energy critique

• Anonymise work before group review to surface more honest and accurate feedback.
• Viewing a range of work together helps teams identify shared design principles.
• Reduces the effect of soft and formal power on feedback quality.

The learning journey map

• A retrospective tool: draw a horizontal time axis and a vertical positive/negative axis on one sheet.
• Plot two lines — one for learning over time, one for emotional highs and lows.
• Where the emotional line is low but the learning line is high: that's productive struggle.
• Comparing maps across a team reveals complementary working styles and builds mutual support vocabulary.
• Turns team tension and misalignment into a basis for better collaboration.

Predictable moments of productive struggle

• The sprint before a deadline — the forcing function surfaces decisions that have been deferred.
• Receiving feedback on unfinished work — opens up defensiveness and desire for validation over critique.
• Both are predictable; naming them in advance reduces their disruptive impact.