Strategy & Leadership

Shape clear direction, alignment, and decision-making at every level.

Strategy & Leadership
Why this matters

Organisations don't fail because they lack talent or resources — they fail because they lack clarity. Without a clear strategy and strong leadership alignment, teams pull in different directions, decisions stall, and momentum is lost.

At Five, we believe strategy isn't a document — it's a conversation that never stops. We work alongside executive teams to shape direction, build alignment, and develop the leadership capability needed to execute with confidence. Whether you're navigating growth, restructuring, or entering new markets, having a shared strategic language and committed leadership team is non-negotiable.

This is where transformation starts: with leaders who know where they're going and can take their people with them.

Our team

Meet the Fivers who specialise in this area.

James Kitney

Chief Strategy and Transformation Catalyst

Nick Mackeson-Smith

Chief Curiosity Officer, Founder and Director

Sally Schmall

Head of Executive Leadership Development

Services we offer in this area

AI Compass

Performance
Every organisation knows AI will reshape how they operate, but the challenge is not awareness, it is knowing where you stand today and what to prioritise next. AI Compass gives leadership teams a clear, measurable view of readiness across strategy, performance, culture, people, and technology. We capture perspectives from every layer, surface the gaps that traditional approaches miss, and translate findings into a prioritised, board-ready roadmap your team can own, execute, and track over time.

AI Strategy & Enablement

Strategy & Leadership
AI is transforming the way businesses operate, but knowing where to start can be overwhelming. We help organisations explore how AI can support their teams, identify the most impactful opportunities, and develop a strategic roadmap for successful adoption. Our approach includes upskilling people, creating a deployment plan, and fostering engagement across the organisation.

Innovation Design Sprint

Strategy & Leadership
Kickstart Innovation with a Design Sprint

Futures

Strategy & Leadership
Take your organisation on a journey to explore a range of possible futures to shape and influence your course

Programme Leadership

Strategy & Leadership
Expert programme leadership for NZ organisations running complex, multi-workstream initiatives — ensuring your strategic programmes deliver on their promise.

Transformation

Strategy & Leadership
Connect your transformation to your strategy to enable organisational agility

Strategy Design

Strategy & Leadership
Strategy by Five is a highly collaborative approach to strategy development that enables you and your team to envision, design, test, and activate your strategy.

Executive Traction Labs

Strategy & Leadership
Transitioning into a new leadership role is the first step. We help you plan out the next 6 months to ensure your success.

Leadership Lab

Strategy & Leadership
Our leadership action labs help leaders to identify and develop the skills, mindsets, and behaviors necessary to create a high-performance culture. We combine experiential learning with coaching support to help leaders apply their learning to real-world challenges.

Executive Coaching

Strategy & Leadership
At Five, we believe coaching is a strategic investment — not a perk. Our approach is direct, outcomes-oriented, and grounded in our Values to Outcomes model, linking beliefs and behaviours to performance and measurable impact.

Board and ELT Advisory

Strategy & Leadership
Create world-class leaders who foster environments where the people in their care can thrive.

Organisational Design

Strategy & Leadership
We help you to design new strategies, processes, metrics, ways of working, methodologies, services and structures to deliver your strategic and cultural aspirations.

Strategic and Transformation Advisory

Strategy & Leadership
We help you to gain valuable insights and fresh perspectives at the executive table, with assessment and challenge of your existing strategies, capabilities, tactics and systems.

Related articles

James Kitney

Facing economic headwinds with a strategic advantage: using AI to play a different game

In 2026, leadership teams are facing a harder economic reality than expected, with stubborn cost pressures, uncertain demand, and growing limits to the traditional response of cutting costs harder. In that environment, the organisations that gain advantage will be those that use AI not as a standalone technology play, but as a strategic lever to redesign how work happens, offset external pressure, and deliver measurable commercial value.

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James Kitney

Let’s be honest: too many of our brilliant AI pilots in New Zealand are not scaling!

Too many AI pilots in New Zealand are stuck in pilot more, and it’s time we addressed the uncomfortable truth, experimenting with tools is not a strategy. While the initial "buzz" of AI is exciting, the leap from a successful PoC to a truly transformative, scalable solution is where many of our organisations are stalling. This isn't just a technical hurdle, its a leadership and mindset gap that keeps us stuck in a cycle of experiments. In my latest article, I break down the five fundamental ideas required to move past the "shiny object" and build a culture of scalable AI… from planning for 100x adoption on day one to rethinking ROI beyond the pilot.

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James Kitney

The Rebirth of Co-operative Business Models for the AI Era

In this article, James Kitney explores how AI is eroding entry-level roles and reshaping traditional career pathways. He considers the rise of AI-enabled solo founders and new co-operative models as alternative responses. Ultimately, he challenges leaders to redesign strategy and organisational models for a radically different competitive future.

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Sally Schmall

From delivery to direction-setting – the executive leadership mindset shift(s)

This blog explores the often-overlooked truth in executive leadership: success is driven more by mindset than job title or technical mastery. Drawing on insights from Five’s work with senior leaders across New Zealand and Australia, the piece outlines five critical mental shifts that new executive leaders must embrace — from developing comfort with ambiguity to cultivating self-awareness under pressure. Rather than focusing solely on skill development, it highlights how mindset directly shapes leadership behaviour, decision-making, and impact at the executive level. A must-read for high potentials, new executives, and organisations building leadership capability at scale.

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Sally Schmall

Leading through the grey

Research and client insights reinforce that leading others during uncertainty and change requires an abundance of personal resilience. Not a little - but a lot of resilience by building awareness and skills to create balance and harmony across our emotional, physical, spiritual and mental wellbeing.

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Sally Schmall

Beyond the To-Do List: The Critical Distinction Between Leadership Accountability and Responsibility

There is an often-blurred line between responsibility and accountability in leadership. Drawing on real-world experience, Sally Schmall unpacks why understanding this distinction is critical for cultivating ownership, strategic alignment, trust and high performance within teams. Here, Sally highlights the role of accountability in driving outcomes—emphasising that while responsibility can be delegated, accountability cannot. Leaders will find practical strategies to embed accountability in their organisations and lead with integrity, clarity and impact.

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Sally Schmall

Leading Through Uncertainty: The Essence of Resilient Leadership

Resilient leadership is about navigating uncertainty with confidence, adaptability, and a clear sense of purpose. True resilience isn’t about avoiding challenges but responding to them with agility, emotional intelligence, and strong communication. Leaders who embrace change, foster a supportive culture, and maintain a growth mindset can guide their teams through adversity and emerge stronger.

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James Kitney

How Experience Can Reinvent Boring Products

In today's competitive landscape, strategic innovation doesn't always require a ground-breaking invention or an amazing new product. Often, the key to success lies in reimagining the way your customers interact with your existing products. By focusing on experience, businesses can completely transform the value proposition they offer, leaving competitors who are solely focused on functionality behind.

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James Kitney

Cut with a scalpel, not a Chainsaw: Strategic cost management and investment beyond the economic cycle

We've all seen the headlines in recent weeks with a number of public and private businesses across New Zealand announcing staff reductions. It's a familiar pattern – economic contraction leads to reduced consumer spending, which then necessitates cuts to operating expenditures. Then, when consumer confidence rebounds, it becomes an all-out scramble to capitalise on the upswing. This cycle seems logical on the surface. But is it truly optimal? Do we really need an economic downturn for us to focus on cost efficiency? Conversely, do we need economic growth to even consider strategies for expanding market share?

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Nick Mackeson-Smith

(Why) should we return to the office?

It’s a consistent theme we’re hearing right now - “it’s time to get people back into the office”. But is it? Are we prepared to erode all of the gains we’ve made in new ways of working over the pandemic and post-pandemic years? Employees have been empowered to work with new levels of trust and freedom, and have incorporated work into their life routines. What should we do next? Nick Mackeson-Smith shares his thoughts and observations.

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Sally Schmall

Gaining traction at the executive table

Stepping into a new executive or senior leadership role is both exhilarating and daunting. Whether you’re moving to a different organisation or taking on your first senior-level position, the initial six months are critical. Challenges include managing energy, aligning stakeholder expectations, overcoming imposter syndrome, and crafting an effective transition plan. Sally Schmall discusses how by addressing these challenges, new executives can set themselves up for success and positively impact their teams and organisations.

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Nick Mackeson-Smith

Navigating the Emotional and Mental Challenges of Right-Sizing

Right-sizing is an emotionally and mentally taxing process, yet with the right approach, it is possible to navigate these challenges with integrity and care. By prioritising dignity, transparency, safety, and care, and leveraging the support of experts like Five NZ, organisations can not only manage the immediate impacts of right-sizing but also build a stronger, more resilient foundation for the future. In the face of change, the true measure of leadership is the ability to lead with humanity, ensuring that every decision, no matter how difficult, is made with a profound respect for the individuals who contribute to our collective success.

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James Kitney

Ditch the Decks, Unleash the Dragons: Why Strategy Isn't a Game trapped in spreadsheets and PowerPoint

Step into a world where strategy is not confined to boardrooms but thrives in the chaos and creativity of real-world challenges. This post explores how today's leaders are ditching traditional, rigid planning for a dynamic, design-led approach. Discover how embracing uncertainty, fostering a culture of experimentation, and engaging directly with the market through rapid prototyping and iterative testing can lead to spectacular successes.

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Nick Mackeson-Smith

Creating an inclusive environment for LGBTQI+ and MVPFAFF+ communities

Explore the importance of LGBTQI+ and MVPFAFF+ inclusion in the workplace. Pride month is the perfect time for organisations to reconsider the need for comprehensive policies, allyship, and education to combat discrimination. Learn how you can take steps to create a supportive environment in your organisation, ensuring equal opportunities and respect for all, regardless of gender identity or sexual orientation.

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James Kitney

A more Human Centred Approach to Strategy

Traditional strategy making has long been the domain of Corporate Strategy Teams, Executives and Consultants. For most employees in an organisation the first time they see or hear about any changes to strategy is when a new poster goes on the wall or their manager ‘informs’ them what the new strategy is.

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Nick Mackeson-Smith

Case study: The Warehouse Group’s digital agile bootcamp - Success through sustained grit, teamwork, and innovation

Something special happened this week. In New Zealand, a large retailer ran a fully virtual 2-day agile transformation event. That in itself would be a massive achievement, given the complexities of designing, planning, and executing such an event - let alone maintaining the attention of 1000 people, keeping it fun, educating them, and building a great sense of momentum in launching a new way of working. What made it all the more challenging was that this entire event had to be rebuilt from the ground up, with only 2 weeks notice, and whilst dealing with Covid-19 lockdown restrictions. Original plans were for an arena-event, with a whole range of tactile interactive exercises, and lots and lots of close contact and relationship building. All of that had to go out the window. Grit was needed...

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Nick Mackeson-Smith

How To Lead Your Team Well When Working Remotely

I’ve been working with leaders for almost two decades now, and throughout this time I’ve found that the very best leaders share a common set of behaviours and mindsets. These leaders create engagement, excitement, clarity, purpose, and drive exceptional performance. Many leaders I have spoken to throughout this crisis have felt paralysed by the magnitude of the change we’re all collectively facing, yet others have demonstrated how they can set themselves up to thrive and in turn help others to succeed. Why did these leaders have such different responses? What’s the secret sauce?

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Nick Mackeson-Smith

Leading brilliantly through change

Change can be tough. It can be hugely unsettling for people who are going through it, and overwhelmingly stressful for those leading it too. It also can be exciting, exhilarating, and an amazing ride. Regardless - being a great leader through change means putting people first.

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Nick Mackeson-Smith

The critical connection between organisational culture and strategic success.

The success of an organisation is heavily reliant on the alignment between its culture and strategy. While strategy defines an organisation's long-term direction, culture determines how things get done within the organisation. A misalignment between culture and strategy can have severe consequences, both financially and reputationally. Despite this link, many organisations fail to develop a deep understanding of what their culture is, could be, or needs to be in order to drive their strategic ambitions. It’s time to dig deeper.

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