Think Outside the Box, Then Build a Better Box: Ambidextrous Leadership for the AI Age

As a leadership keynote speaker, I often get asked by C-level executives to help their leaders "think outside the box." Yet before I show leaders how to do this, I make sure we are all 100% clear: the box is actually extremely useful. It is essential to all effective organizational life.

The box contains our expertise, processes, playbooks, standards, controls, metrics, operating procedures, institutional memory, and tried-and-tested ways of getting stuff done. It is what allows organizations to deliver reliably, manage risk, improve quality, reduce waste, build efficiencies, and generate predictable returns.

The Box Is Not the Enemy.

For about 90% of organizational life, the box is exactly where we need it. It helps us focus, execute, optimize, control quality, manage risk, apply expertise, and deliver what we already know how to deliver.

I often call this Get Stuff Done Mode, and it remains essential for high performance.

Most people who make it into the senior leadership summits that I speak at a lot of the time have done so precisely because they have become very good at operating inside one or more boxes.

So telling them to get outside the box is both inaccurate and likely to make them react and reject what is required to move from what has worked before to what comes next.

In Brief: Thinking outside the box is essential when leaders need to rethink work for AI rather than simply automate business as usual. Ambidextrous leadership means knowing when to stay in Get Stuff Done Mode for efficient execution, and when to slow down, shift into Create & Connect Mode, and create enough space for customer insight, creativity, innovation, and transformative thinking. Leadership keynote speaker Nick Jankel explores why the box is not the enemy, why we cannot bypass biology, and why sometimes we must slow down before we can build a better, more efficient box.

You Cannot Redesign the Box From Inside It

The challenge comes when the world changes radically enough that the box itself needs to change.

Organizations everywhere are being asked to become faster, leaner, smarter, more innovative, and more AI-enabled, often all at the same time. Leaders are retooling processes, redesigning work, integrating intelligent technologies, reducing friction, improving customer experiences, finding new efficiencies, and searching for new sources of value.

Yet many are attempting to do all this while operating at 100 miles an hour. Their calendars are packed, their inboxes are overflowing, another transaction has landed, another client needs an answer, another crisis has flared up, another meeting starts in five minutes, and everything feels urgent.

Then we put everyone into a meeting room and say: now think differently.

As a keynote speaker working with senior teams across industries, I see the same pattern repeating. Smart, successful, experienced leaders have become exceptionally good at driving efficient, predictable outcomes, yet the challenges they increasingly face—including implementing AI-driven efficiencies—demand experimentation, adaptation, innovation, and entirely new ways of thinking.

These are the very behaviors the box is designed to block in order to lower risk.

This is one reason why so many AI leadership development interventions (see the kinds of programs we run at my AI-native leadership consultancy SOL), strategic off-sites, executive retreats, and AI transformation sessions struggle to produce genuine breakthroughs. We ask people to generate a fundamentally different quality of thinking while keeping them in the same state that helps them execute existing ways of working.

In my book Now Lead the Change, I explored how most 20th-century management tools were developed to solve known and knowable problems quickly and reliably. They are brilliantly adapted to stability, predictability, efficiency, and incremental improvement.

Yet a radically changing world also requires leaders to be adaptable, agile, ingenious, and nimble, able to sense when established approaches no longer fit emerging reality.

Get Stuff Done Mode remains vital. But it cannot be the only mode available to us.

A Mode Optimized for Outside-the-Box Thinking

Alongside Get Stuff Done Mode is another mode that I call Create & Connect Mode. This mode is optimized for customer empathy, employee insight, connection, reflection, curiosity, creative thinking, experimentation, and seeing new ways of doing things.

It is where we can loosen our grip on familiar answers, notice what others are really experiencing, connect disparate ideas, and explore possibilities that don't yet fit neatly inside the existing box.

Neither mode is inherently better. Get Stuff Done Mode helps us execute what we already know how to do with rigor and efficiency. Create & Connect Mode helps us sense, imagine, rethink, and redesign when the challenge itself is changing. Ambidextrous leadership is increasingly about knowing which mode the moment requires, and becoming able to shift between them deliberately.

A biological reality underpins that shift.

When urgency, pressure, uncertainty, fatigue, and threat rise, our nervous systems adapt. Attention can narrow. Familiar habits and established solutions become more attractive. We become primed to solve, control, protect, decide, and move.

These capacities are immensely useful when we already know roughly what needs to be done. They are much less helpful when the challenge requires us to question assumptions, see a situation from a radically different perspective, connect disparate ideas, listen deeply to customers or colleagues, sit with ambiguity, or imagine something that does not yet exist.

We Cannot Bypass Biology.

The research supports this broader pattern. A meta-analysis of 51 studies involving 2,486 participants found that acute stress impaired working memory and cognitive flexibility, two capacities that matter when we need to hold different possibilities in mind and shift between perspectives. The researchers concluded that stress can produce a more reactive, automatic style of cognitive processing, which may help with rapid responses but be less useful when a novel challenge demands flexible thinking.

More recently, a 2025 systematic meta-analysis published in Neuroscience & Biobehavioral Reviews examined experimentally induced stress and creative performance. Across the studies, stress had a modest overall negative effect on creativity, but the most interesting finding for leaders was how much the type of pressure mattered. Non-social stressors, including time pressure and physical stress, significantly hindered creative performance, and among adults, time pressure produced the strongest negative effect.

None of this means that pressure is always bad, that creativity requires endless calm, or that leaders should spend their working lives in some permanently relaxed state. The 2025 analysis itself found a much more complex relationship for competition, evaluation, and milder forms of social pressure. But it does reinforce something I have observed repeatedly over almost 30 years of breakthrough innovation and transformation work: relentless urgency is a poor default condition for asking experienced people to loosen their grip on what they already know, question the box that has made them successful, and generate genuinely different ways forward.

Ambidextrous Leadership for AI Efficiency and Transformation

This is where ambidextrous leadership matters most.

The idea of organizational ambidexterity has long distinguished between exploitation, where organizations refine, optimize, and execute what they already know, and exploration, where they experiment, search, learn, and create something new.

The challenge is not choosing one forever. It is developing enough agility to do both. The deeper capability lies in sensing what kind of problem is actually in front of us and becoming flexible enough to meet it with the right state of mind and body.

My framing of ambidextrous leadership is deliberately practical. Ideally, leaders become increasingly able to shift states from driving efficient, predictable outcomes to unfolding more explorative and adaptive outcomes as the market, technology, customer, and organization evolve.

Sometimes a challenge needs tighter execution, greater discipline, faster decisions, clearer accountability, or a more efficient process. Other times, the same instincts can keep us trapped in a system whose underlying assumptions are becoming obsolete.

The art is discerning which situation we are actually in.

A leader might ask, "How can we make this process 10% faster?" That may be precisely the right question.

But sometimes the more powerful question is: "If we were starting today, knowing what we now know and having access to the technologies we now have, would we design this process like this at all?"

The first question optimizes the box. The second steps outside it.

AI Makes Thinking Differently Urgent

This distinction has become particularly important with generative AI, intelligent automation, and increasingly agentic technologies.

It is remarkably easy to take an existing workflow, identify each stage, and attach an AI tool to it. This can save time and money, and incremental automation fits in many places.

But if we use AI only to accelerate inherited processes, we risk becoming extraordinarily efficient at doing things that no longer need to be done that way.

The evidence already shows this. McKinsey's 2025 State of AI research found that organizations it classified as AI high performers were nearly three times as likely as others to have fundamentally redesigned workflows, and identified workflow redesign as one of the organizational practices most strongly associated with meaningful AI impact.

That finding fits what I have seen over decades working at the intersection of technology, innovation, transformation, and leadership. Real technological transformation rarely comes from simply bolting the new onto business as usual.

It requires us to rethink what the work is for, how value is created, what customers actually need, which assumptions belong to an earlier technological era, and where human judgment, imagination, ingenuity, connection, and care will create more value as machines become increasingly capable.

This is the territory I increasingly explore as an AI keynote speaker and innovation keynote speaker: not simply how to use AI, but how leaders can become adaptive enough to rethink work, organizations, products, processes, and business models around what is now possible.

The Power of the Pause: Slowing Down to Speed Up

This creates one of leadership's great paradoxes in a world obsessed with acceleration.

Sometimes the fastest way to move forward is to slow down first.

An afternoon spent questioning a workflow that thousands of employees execute every week could eliminate hundreds of thousands of hours of future work. A day spent deeply understanding changing customer needs could prevent months of developing the wrong product. A leadership team that makes enough space to reconsider one outdated assumption may create more value than another year of optimizing around it.

Sometimes we have to slow down before we can intelligently speed up.

This is not an argument for becoming slow, passive, indecisive, endlessly contemplative, or bureaucratic. I have spent my adult life building businesses, leading teams, facilitating transformation, driving breakthrough innovation, and helping organizations turn ideas into reality. I remain deeply committed to what I once called the creative harmony of glorious imagination and genius execution.

A leadership keynote, leadership summit, or leadership workshop can create a rare and valuable pause in the relentless flow of Business As Usual: a moment to take a breath, reconnect with our peers, listen more deeply to customers, remind ourselves what a process, tool, or product is really there to achieve, and allow our nervous systems to settle enough to shift state, shift mode, and return to the challenge with the openness needed for genuinely transformative thinking.

We slow down sufficiently to sense more clearly, connect more deeply, challenge what has become automatic, metabolize uncertainty, generate new possibilities, and discern what matters. Then we move.

Feeling Safe Enough to Leave the Box

Another reason thinking outside the box is much easier to say than to do. Outside the box is uncertainty. Inside the box, we know the rules. We understand how our expertise creates value. We know which metrics matter, which processes are approved, how decisions are made, and what good performance looks like. Senior leaders may have spent decades becoming extraordinarily accomplished inside these systems.

Stepping outside them means temporarily admitting that we may not know.

We may need to question something we helped build, change our minds in front of others, listen to someone whose expertise threatens our own, challenge an industry assumption, explore an idea that could fail, or let a complex question remain open before reaching for a neat answer.

This requires more than intelligence. It requires enough emotional stability, relational trust, curiosity, and psychological safety to loosen our grip on certainty.

Psychological safety matters here because experimentation, learning, speaking up, challenging assumptions, admitting uncertainty, and offering half-formed ideas all involve interpersonal risk. It does not mean making everything comfortable or protecting people from challenge. It means making it sufficiently safe to be brave.

This connects deeply with my recent work on relationally intelligent leadership. Leaders cannot generate fresh thinking simply by demanding it. The quality of relationship in the room shapes how much uncertainty people are prepared to tolerate, how candidly they can challenge one another, and whether novel possibilities can surface before hierarchy, expertise, or anxiety close them down.

Connection is not separate from innovation. It is often a precondition.

A great leadership keynote can do more than dazzle, provoke, and inspire. When the speaker also has deep mastery of facilitation, group dynamics, and human transformation, they can shape the space and energy in the room so people feel sufficiently safe, settled, and connected to loosen their grip on certainty, shift out of relentless Get Stuff Done Mode, and access the curiosity, creativity, and relational intelligence needed to think differently.

This is one reason I now so often combine a leadership keynote with an interactive workshop. The keynote creates the shared shift, shared language, and emotional momentum; the workshop then gives leaders the protected space to apply that new mode of thinking to real strategic challenges, cultural tensions, AI opportunities, customer problems, or process redesign, turning inspiration into insight, and insight into action.

Think Outside the Box, Then Build a Better Box

The point is not to abandon the box. The box gives us rigor, efficiency, repeatability, expertise, control, and the ability to get stuff done. But when the world changes, when AI reshapes what is possible, when customers shift, or when an old process starts creating more friction than value, leaders need the ambidextrous capacity to step outside it for long enough to see differently.

That means creating a pause, settling the nervous system, reconnecting with people and purpose, and shifting from relentless execution into the curiosity, connection, insight, and creativity needed for genuinely transformative thinking.

A powerful leadership keynote, summit, or workshop can create exactly this kind of temporary interruption to Business As Usual. Done well, it gives leaders enough safety, stability, shared language, and collective energy to question assumptions without losing confidence, challenge established ways of working without dismissing what made them successful, and explore what a better system, process, product, or way of leading could look like.

Increasingly, this is why I combine a transformational leadership keynote with my role as a leadership facilitator: the keynote creates a memorable shift in perspective, and the workshop turns that shift into practical action on real organizational challenges.

The invitation, then, is not simply to think outside the box. It is to become better at knowing when the box is serving us and when reality is asking us to step beyond it. Slow down just enough to see what you could not see at full speed, reconnect with what really matters, rethink what no longer fits, and then bring all the discipline, expertise, and executional power of Get Stuff Done Mode back to bear. Think outside the box, then build a better box.

A better box might be dramatically simpler than the old one. It might use AI to remove whole categories of manual work. It might place the customer at the center rather than inherited functional boundaries. It might allow decisions to happen closer to the problem. It might reduce bureaucracy while improving controls, or create more space for human judgment precisely because machines now handle more routine cognition.

Once the new model becomes clear, we need rigor, process, discipline, measurement, accountability, operational excellence, and genius execution to bring it into being.

Ambidextrous leadership therefore does not denigrate efficiency in favor of creativity. Nor does it worship innovation while dismissing the extraordinary value embedded in experience, expertise, process, and precision. It honors both.

FAQs: THINKING OUTSIDE THE BOX AS A LEADER

What is ambidextrous leadership?

Ambidextrous leadership is the ability to move between two different but equally important ways of leading. At times, leaders need focus, discipline, efficiency, and what I call Get Stuff Done Mode. At other times, complex or novel challenges require Create & Connect Mode, where curiosity, reflection, customer and employee insight, creativity, experimentation, and connection become more valuable. The real capability is knowing which mode the moment requires and shifting between them.

Why is thinking outside the box important for leaders?

Thinking outside the box becomes important when the assumptions, processes, or operating models that created past success no longer fit emerging reality. The box itself is not the enemy. It gives organizations discipline, consistency, efficiency, and scale. But when AI, customer needs, technology, or markets fundamentally change what is possible, leaders need enough distance from Business As Usual to question whether they should optimize the existing box or redesign it.

Why do leaders sometimes need to slow down to speed up?

Relentless urgency can make it harder to step away from familiar assumptions and see a challenge differently. A purposeful pause, whether during a leadership keynote, summit, offsite, or workshop, creates space to breathe, reconnect with colleagues, listen more deeply to customers, and reconsider what a process, product, or tool is really there to achieve. The purpose isn't to slow down. It is to find a smarter way forward and then accelerate with greater clarity and efficiency.

How does ambidextrous leadership help with AI transformation?

AI can make existing processes faster, but the greater opportunity is often to rethink the process itself. Ambidextrous leaders can distinguish between situations where AI should optimize what already works and those where intelligent technologies enable an entirely different workflow, customer experience, operating model, or way of creating value. This helps organizations move beyond additive change towards genuine transformation.

What is the difference between Get Stuff Done Mode and Create & Connect Mode?

Get Stuff Done Mode helps us execute, focus, analyze, manage risk, optimize, and deliver predictable outcomes. Create & Connect Mode gives us greater access to customer and employee insight, curiosity, connection, reflection, experimentation, creativity, and new ways of seeing a familiar problem. High-performing leadership increasingly requires access to both rather than treating either as the single right way to operate.

Why does psychological safety matter for thinking differently? Thinking differently often requires leaders to take interpersonal risks. They may need to question something they helped create, admit they do not yet know the answer, change their minds, challenge a senior colleague, or explore an unfinished idea. Psychological safety does not remove challenge or discomfort. It creates enough relational stability for people to be candid, curious, experimental, and courageous together.

Can a leadership keynote really help leaders think outside the box?

A powerful leadership keynote can create a rare interruption to business as usual. Rather than simply telling leaders to be more innovative, an experienced leadership keynote speaker can use insight, story, neuroscience, interaction, and facilitation to create a shared shift in perspective and energy. This can help a leadership group become more open to questioning assumptions, connecting differently, and seeing possibilities that relentless execution can obscure.

Why combine a leadership keynote with an interactive workshop?

The keynote can create the memorable insight, shared language, emotional momentum, and shift in state. The workshop can then turn that shift into practical application, using real AI opportunities, customer challenges, processes, cultural tensions, or strategic hotspots as raw material. The two can form one coherent arc from inspiration to insight, and from insight to action.