How Can Leaders Support and Promote the Idea that Learning Occurs at the Point of Challenge
I’ve written and spoken a lot about the importance of challenge to students’ learning. Without challenging content, students’ have little to think about. Developing powerful learners requires regular opportunities to grapple with new ideas, content, and problems. Thus, we really can’t create a culture of thinking without challenge. I recognize that this requires a transformation in schools where performance is often equated with learning and coverage with teaching. Recently a set of school leaders asked me some questions (over 40 of them!) about how they can step into and support this transformation. I boiled this down to 10 big, overarching questions and put together the following, which I hope will be useful to many more educators navigating this space.
Big Picture Framing.Challenge is not simply making work harder. When we normalize learning from mistakes and create purposeful, engaging, challenging, and self-differentiating tasks—while supporting students without removing the thinking—we promote deeper, longer-lasting learning and greater self-direction.
1. What does productive challenge look like in secondary classrooms, and how can teachers distinguish challenge that advances learning from challenge that overwhelms students?
Productive challenge is not synonymous with making work harder. It is the “stretch” where students must make sense, reason, connect ideas, develop an original response, or grapple with ambiguity and complexity. It often involves perplexity or cognitive conflict: something that makes learners want to know more. The experience resembles flow—too little challenge produces boredom; too much produces frustration; the productive zone combines effort, focus, support, and a sense that success is possible. Teachers distinguish productive from destructive struggle by attending to what students are experiencing. Productive struggle generates strategies, questions, collaboration, and movement in thinking. Overwhelming difficulty produces sustained helplessness, withdrawal, or dependence without new learning.
Research connection: Robert Bjork’s “desirable difficulties” distinguish short-term performance from long-term learning. A difficulty is desirable only when it prompts useful processing and the learner has sufficient knowledge and support to respond to it.
2. How can teachers calibrate challenge for students with widely differing starting points, learning needs, and levels of readiness within the same classroom?
We cannot identify one fixed point of challenge for an entire class. A better approach is to design low-threshold, high-ceiling opportunities: tasks with accessible entry points, multiple methods or representations, and room for increasing complexity, abstraction, efficiency, or generalization. Such tasks allow students to self-differentiate and find their own stretch while working toward a shared intellectual purpose. Teachers then listen closely, notice where students are getting hung up, and adjust time, grouping, tools, prompts, or extensions. The key is to increase access without placing a ceiling on learning or reducing the task to a procedure.
Research connection: Jeffrey Choppin found that teachers who seek to understand students’ thinking can adapt challenging tasks in ways that enhance complexity and conceptual engagement. Teachers focused mainly on right answers are more likely to simplify the task merely so students can complete it.
3. How can teachers design learning experiences that combine high challenge with the support students need to persist and succeed?
Challenge needs to be planned for, anticipated, and supported. Begin with a task that asks students to make sense, reason, connect, explore alternatives, or produce an original response—not simply reproduce a demonstrated method. Do the task yourself, anticipate likely strategies and misconceptions, and prepare prompts, tools, representations, and extensions. In the moment, scaffold only as needed. Avoid “funnelling.” The most useful hints increase students’ capacity by reminding them of a strategy, naming a potentially useful kind of thinking, or offering a tool or representation. Less useful hints decrease the challenge by supplying partial answers or turning the task into steps. The aim is to support students through the terrain, not carry them across it.
Research connection: Eric Mazur’s Peer Instruction exemplifies high challenge with high support: students first commit to an answer, explain and test their reasoning with peers, and then respond again. Peer explanation preserves the conceptual work while making other students intellectual resources.
4. What helps students move through anxiety, disengagement, or fear of failure so that productive struggle feels safe and worthwhile?
Challenge must first be normalized. Students need an explicit understanding that mistakes, uncertainty, productive failure, and being “stuck” are expected features of learning—not evidence that they lack ability. Shared metaphors such as “get off the escalator” (video link in chapter) or the Learning Pit, What Zone are your in? are helpful as are collective definitions, examples and non-examples, and anchor charts of ways to get unstuck give students both a language and a repertoire of action. Teachers can notice and name strategies, initiative, revision, and learning from mistakes; model their own struggles; and regularly reflect on and celebrate emerging learning using routines like the 4 S’s or ESP+I. Psychological safety does not remove challenge. It enables students to remain intellectually present within it.
Research connection: Adam Grant’s “confident humility” captures the desired stance: confidence in our capacity to learn alongside humility about whether our current answer is right. Students can commit to an idea without treating it as a verdict on their intelligence.
5. How can schools shift students from compliance and grade-seeking toward cognitive engagement, curiosity, and a willingness to take intellectual risks?
Compliance is a predictable response when school is organized around following directions, reproducing procedures, finishing assignments, and obtaining quick right answers. The shift begins with the opportunities students regularly encounter. Tasks should provoke perplexity, invite different approaches, expose ideas and misconceptions, and require students to explain, connect, debate, and refine their thinking. Interactions should communicate, “Your job is to make sense of this,” rather than, “Your job is to reproduce what I showed you.” Over time, the cultural forces—expectations, language, time, modeling, opportunities, routines, interactions, and environment—must consistently convey that thinking and learning matter more than mere completion.
Research connection: Erik Mazur’s work highlights the limits of information transmission for conceptual learning. Adam Grant’s rethinking cycle similarly moves learners from proving and def ending what they know toward questioning, testing, and revising ideas. Soderstrom and Bjork identify this as the difference between performance and learning.
6. How can assessment recognize thinking, growth, and productive struggle without making students feel that accepting challenge will jeopardize their grades?
We need to treat lessons as episodes of learning rather than constant final performances. Use low-stakes formative challenges, drafts, discussion, self-assessment, and revision so students can expose incomplete thinking without being punished for it. Assessment should make visible students’ reasoning, representations, conceptual connections, responsiveness to feedback, and growth in understanding (this will only increase in importance with AI)—not reward struggle for its own sake. Grades should reflect what students ultimately understand and can do. When every attempt is scored, students sensibly avoid uncertainty; when assessment helps locate the stretch and guide the next move, challenge becomes useful information.
Research connection: Bjork warns that immediate fluency can create an illusion of mastery; performance during instruction is not the same as durable learning. Mazur’s individual–peer–individual sequence uses assessment first to reveal and advance thinking, not merely to judge it.
7. How can leaders help teachers take risks, reconsider established practices, and experience their own point of challenge—particularly during curriculum or organizational change?
Schools must be cultures of thinking for adults as well as students. Leaders can normalize professional uncertainty, model their own learning, and frame change around shared problems of practice rather than implementation compliance. Teachers need time to investigate, observe one another, examine student thinking and perceptions, experiment, and revise. Non-evaluative walkthroughs (see street data task) can ask, “How would students here get the message that people learn through challenge?” rather than checking whether teachers are implementing prescribed behaviors. The resulting evidence can help staff decide what to amplify, modify, remove, or create. This makes change a disciplined process of collective inquiry.
Research connection: Grant’s rethinking cycle—humility, doubt, curiosity, and discovery—offers a useful leadership stance. Choppin’s research also shows that sustaining ambitious instruction requires organizational resources and collaborative structures, not just better tasks or individual teacher will.
8. Across Years 7–12 and different learning areas, what should be consistent in a school’s approach to challenge and thinking, and where should teachers retain flexibility?
Consistency should lie in the shared mindset and principles, not in identical lessons. Across Years 7–12, students should receive the message that challenge is expected, mistakes can generate learning, thinking should be explained, and help-seeking is normal rather than a sign of weakness. The school can share four broad commitments: define and explore challenge; plan for stretch; support struggle in the moment; and reflect on and celebrate learning from it. Subject areas and teachers should retain flexibility in the tasks, disciplinary practices, routines, representations, grouping, pacing, and language through which those principles come alive. Culture provides coherence; professional judgment provides responsiveness.
Research connection: Jeffrey Choppin’s work reminds us that cognitive demand is shaped during enactment. Adopting the same task, routine, or curriculum everywhere does not guarantee the same level of thinking.
9. What progression should we expect as students move from using teacher-introduced thinking routines to independently selecting, adapting, and applying thinking strategies?
The progression is from supported participation to metacognitive independence. Initially, teachers introduce routines and explicitly connect them to a thinking purpose. They model language for getting unstuck and build collective resources: reread, represent, look for a pattern, ask a question, test an example, seek another perspective, or explain the difficulty aloud. Teachers must gradually release responsibility as with Cognitive Task Analysis. This is an ongoing process not a single step. Students then begin to recognize which strategies are useful, select among them, adapt them, and reflect on what helped. The strongest evidence of development is spontaneous action: students initiate a strategy, seek a peer’s thinking, identify the nature of the challenge, revise an approach, or propose another way forward without waiting to be rescued.
Research connection: Robert Bjork’s work on varied and interleaved practice suggests that transfer grows when learners must choose a strategy rather than repeatedly apply one already named for them. Adam Grant adds the metacognitive habit of recognizing when an assumption or conclusion needs to be reconsidered.
10. What evidence—in classroom interactions, student work, assessment, and student agency—shows that a culture of productive challenge is becoming embedded?
Look for recurring patterns and messages rather than isolated activities. Students should be able to identify where they were stretched, explain why challenge matters, describe how they get unstuck, and connect struggle with accomplishment and growing efficacy. Classroom interactions should show students externalizing, debating, analyzing, and refining thinking; using peers as intellectual resources; and seeking help without surrendering agency. Work should reveal multiple approaches, revision, conceptual connections, and changing ideas. “Where’s the Stretch?” reflections, student interviews, work samples, and non-evaluative walkthroughs provide useful street data. The strongest evidence is unprompted: students pursue complexity, persist strategically, request useful feedback, and initiate further inquiry. However, this can only occur where students are given the opportunity to do so.
Research connection: Mazur offers visible evidence of conceptual movement before and after peer discussion; Bjork cautions against treating smooth performance as proof of learning; and Grant draws attention to whether people genuinely revise beliefs in response to stronger evidence.
Selected References
Ron Ritchhart: Cultures of Thinking in Action; Creating Cultures of Thinking; The Power of Making Thinking Visible.
Erik Mazur: Peer Instruction and research on conceptual questions, peer explanation, and active learning.
Jeffery Choppin: Research on cognitively demanding and nonroutine mathematics tasks, ambitious instruction, and sustainable schoolwide implementation.
Bjork and Bjork: research on desirable difficulties, retrieval, spacing, interleaving, and the distinction between performance and learning.
Adam Grant: Think Again and the ideas of confident humility, rethinking cycles, and learning cultures.