Beyond the Old Playbook

What Nine Conversations Reveal About Leadership and Governance in an Uncertain World

From seeking certainty to developing the perspective, judgement and capabilities to shape what comes next.

What happens when the approaches that made us successful are no longer sufficient for the challenges ahead? How do we lead when the destination is uncertain, familiar assumptions are being challenged, and the decisions we make today will shape a future we cannot fully predict? These were the questions behind Beyond the Old Playbook, a nine-part series of conversations in the Digoshen Exploring Leaders Podcast.

Across the series, I invited experienced business leaders, board directors, coaches and governance thinkers to explore how we navigate a world being reshaped by artificial intelligence, sustainability, geopolitical fragmentation, changing competitive dynamics and evolving expectations of leadership.

We explored these questions through three interconnected perspectives: Leading Through Uncertainty, Navigating Change, and Governing for Renewal.

Each conversation began with a work of art. Not because art could provide answers to complex leadership challenges, but because it offered a different starting point: an opportunity to slow down, question familiar interpretations and consider possibilities that might otherwise remain unnoticed. Nine conversations brought different experiences, questions and perspectives. Yet, looking back, several common themes emerged.

Perhaps the greatest challenge is not simply that the world has become more uncertain. It is that we continue to approach emerging realities with assumptions, expectations and practices developed under different conditions. What, then, have we learned? And what might these insights mean for leadership and governance as we look towards 2030?

Leadership is not about eliminating uncertainty, but learning to navigate it 

We began the series by questioning something deeply embedded in our understanding of leadership: the expectation that leaders should know.

In our opening conversation, Lidija Drobež explored how the need for certainty can become part of the problem. When circumstances are unfamiliar, we often respond by seeking more information, more analysis and greater control. These responses can be valuable, but they can also become ways of postponing difficult choices.

In a later conversation, Rolf Pfeiffer brought another dimension to this challenge: what happens when there is no perfect choice? Many important leadership decisions involve competing values, incomplete information and consequences that cannot be fully anticipated. More analysis may improve understanding without resolving the underlying dilemma.

Returning to these questions in our conversation about the benefit of action, Lidija explored how movement itself can generate understanding. Sometimes we act because we know. At other times, we need to act in order to know.

Together, these conversations suggest an important distinction. Some uncertainty can be reduced through better information, analysis and expertise. Other uncertainty is inherent in the situation itself. It requires judgement, experimentation, dialogue and the willingness to learn from consequences.

The emerging insight is that effective leadership requires knowing when to analyse further, when to exercise judgement and when to begin moving without complete certainty.

This does not mean acting recklessly or abandoning careful preparation. It means recognising that waiting for certainty can itself become a consequential decision.

For boards, this raises a practical question: are our decision-making processes helping us navigate uncertainty, or encouraging us to postpone difficult strategic choices until more evidence becomes available?

What made us successful can also limit what we are able to see

Experience is one of leadership’s greatest assets. It gives us patterns to recognise, knowledge to draw upon and judgement developed through previous challenges. But experience also shapes our expectations.

In our conversation about perspective, Lidija Drobež explored how familiar ways of seeing can become limitations. We do not interpret the world neutrally. We notice what fits our existing understanding, recognise familiar patterns and sometimes overlook signals that challenge what we believe to be true.

Scott Newton extended this question from individuals to organisations. Companies develop strategies, business models, structures and routines that reflect what has worked in the past. These become sources of competitive advantage, but they can also create resistance to recognising when the environment has fundamentally changed.

The more successful an organisation has been, the more convincing its established assumptions may appear. This creates a difficult leadership challenge. We cannot simply discard experience, institutional knowledge or proven capabilities. But neither can we assume that yesterday’s success provides a reliable guide to tomorrow’s opportunities.

A useful distinction is between what is enduring, eroding and emerging.

What capabilities, relationships and principles remain valuable? Which assumptions or practices are losing relevance? And which new possibilities are beginning to emerge, even if they do not yet fit our existing understanding? This is where curiosity and constructive challenge become strategically important.

For boards, the question is not only whether management has developed a credible strategy. It is also whether the board and management are willing to examine the assumptions on which that strategy depends.

The emerging insight is that renewal begins with recognising the limits of our own perspectives—not with immediately searching for a new plan.

Sometimes the most valuable contribution a leader or board member can make is to ask a question that changes how everyone understands the problem.

Governing risk is essential, but governing opportunity is equally important

Three conversations brought the discussion directly into the relationship between governance, competitiveness and business renewal.

With Fernanda Torre and Sylvia Robben, we explored whether European boards can contribute more actively to competitiveness, growth and resilience. The discussion raised questions about how boards can move beyond protecting existing businesses to helping organisations navigate structural change and create future value.

With Lars Husberg, we examined what it means to move from governing AI to shaping what comes next. AI creates important responsibilities relating to risk, ethics, accountability and oversight. But it also opens possibilities for rethinking products, services, business models and competitive positioning.

The challenge is that organisations may become increasingly sophisticated at managing AI risks and incremental efficiency improvements while failing to explore the larger strategic opportunities.

With Jaap Winter, we approached a similar question through sustainability. Companies have invested significantly in reporting, compliance, targets and risk management. Yet sustainability can also become a starting point for innovation, new customer propositions, different business models and organisational renewal.

These conversations reveal a common tension. Risk management tends to begin with what could go wrong. Strategic renewal also asks what could become possible. Both are essential.

A company that pursues opportunities without understanding its risks may undermine its resilience and responsibilities. But a company that focuses predominantly on protecting its existing position may gradually lose its relevance.

The emerging insight is that governance needs to give opportunity the same seriousness, discipline and attention that it gives risk.

This has implications for board agendas, information flows, capital allocation and relationships with management.

How much board time is devoted to protecting today’s business compared with exploring tomorrow’s? How systematically are emerging opportunities assessed? And are boards creating space for experiments whose value cannot yet be demonstrated through conventional financial projections?

Governing for renewal is not about encouraging uncontrolled risk-taking. It is about ensuring that strategic uncertainty becomes something organisations can explore intelligently rather than merely something they seek to contain.

The future requires collective intelligence, not just stronger individual leaders

Across the conversations, another theme emerged: the challenges facing organisations increasingly exceed what any individual can fully understand.

AI, sustainability, geopolitics, workforce transformation and competitive disruption do not operate independently. They interact, often producing consequences that are difficult to anticipate from any single functional or disciplinary perspective. This became particularly visible in the conversations about European competitiveness, AI leadership and governance towards 2030.

Boards traditionally bring together people with different experiences and expertise. Yet diversity of knowledge does not automatically create collective intelligence. That requires the ability to listen, question, challenge assumptions, integrate perspectives and develop shared judgement. It also requires a relationship between boards and management in which constructive challenge and trust reinforce rather than undermine one another.

Our research on Dynamic Board Capabilities—Sensing, Pivoting and Aligning provides one way of understanding this challenge.

Sensing involves recognising emerging changes and interpreting their significance. Pivoting requires questioning established approaches and supporting strategic adaptation. Aligning involves creating the shared understanding and commitment needed to act. These capabilities are interconnected. Organisations may identify important changes but struggle to respond. They may develop new strategic options but fail to build the alignment necessary for implementation.

And the challenge is not confined to boards. Executive teams, professional networks and individuals navigating career transitions face similar questions about how they combine knowledge, relationships and perspectives.

The emerging insight is that leadership effectiveness increasingly depends on what people can understand, question and accomplish together—not simply on the expertise they bring individually.

For boards, this raises a fundamental question: are we organised primarily to review and approve decisions, or also to contribute to the collective capabilities that help the organisation recognise and shape emerging possibilities?

Strategy must provide direction while allowing learning through action

A recurring tension throughout the series concerned the relationship between having a clear direction and accepting that the route cannot be fully known.

Scott Newton explored what happens when established strategies and business models no longer fit changing conditions.

Lidija Drobež examined why action can become a source of learning rather than merely the execution of an already determined plan.

And in our final conversation, Steen Buchreitz Jensen brought these themes together through the question of what leadership and governance will require by 2030.

When technological, environmental and geopolitical transitions interact, organisations cannot expect to predict every consequence or prepare a complete roadmap. Yet they still need to make choices, allocate resources, provide direction and maintain accountability. This suggests a more dynamic understanding of strategy.

Purpose, principles and strategic ambition provide orientation. Experiments, partnerships, dialogue and continuous learning help organisations discover which routes are promising and which assumptions need revision. The ability to adapt is not a substitute for strategic discipline. It is part of that discipline.

Leaders need to distinguish between commitments that should remain stable and approaches that must remain open to reconsideration.

Boards need to understand not only whether management is delivering against agreed plans, but also what the organisation is learning, which assumptions have changed and whether resources are being redirected accordingly.

The emerging insight is that effective strategy combines clarity of direction with the capacity to learn and adapt while moving.

Perhaps the most useful question is not simply whether we are following the plan, but whether the plan is still helping us move towards what matters.

The more technology advances, the more important our human capabilities become

One of the most interesting conclusions from the series concerns the changing meaning of human leadership.

AI is expanding the capacity to analyse information, generate alternatives, identify patterns and support decisions. These developments can significantly strengthen organisational capabilities. But they also raise questions about which responsibilities should remain with people, how human judgement is exercised and what leadership contributes when technological systems become increasingly capable.

Across the conversations, qualities such as curiosity, humility, courage, imagination, self-awareness, empathy and practical wisdom repeatedly appeared—not as abstract virtues, but as capabilities needed to navigate real challenges.

Leaders must recognise their own assumptions, acknowledge uncertainty, consider competing values, make difficult choices and remain accountable for their consequences. They must also create conditions in which others can contribute, challenge and learn.

This is one reason we used art throughout the series. We began with works by artists including Caspar David Friedrich, René Magritte, Gustav Klimt, Edvard Munch, Hilma af Klint and André Derain. The artworks were not illustrations of management theories. They invited us to approach familiar questions from unfamiliar directions.

An image can make us aware of how quickly we interpret what we see. It can reveal different perspectives without requiring us to choose one immediately. It can create a moment of reflection before we return to analysis and decision-making. In that sense, art became part of the exploration of leadership itself.

The emerging insight is that technological intelligence and human wisdom should not be understood as competing alternatives. The opportunity lies in developing them together.

The more capable our technologies become, the more important it may be to develop our capacity to ask meaningful questions, exercise judgement, connect with others and imagine possibilities worth pursuing.

From Insights to Action — Six Shifts and Five Questions

Looking across the nine conversations, I see six interconnected shifts in how we approach leadership and governance. They do not make established practices irrelevant, but point to capabilities we need to strengthen as familiar approaches become less sufficient.

 

 

 

 

 

 

Moving beyond	Developing instead
Seeking certainty before acting	Navigating uncertainty through judgement
Relying on established assumptions	Questioning perspectives and recognising change
Focusing predominantly on risk and control	Governing opportunity, renewal and resilience
Depending on individual expertise	Developing collective intelligence and capabilities
Predicting, planning and executing	Orienting, experimenting, learning and adapting
Leadership as having the answers	Leadership as continuous human and collective development

These shifts reinforce one another. Seeing differently helps us recognise emerging possibilities. Judgement enables us to act despite uncertainty. Experimentation creates opportunities to learn, while collective capabilities help organisations navigate complexity and renewal.

Together, they suggest four continuing practices: See differently. Judge wisely. Act responsibly. Learn continuously.

Rather than offering another fixed playbook, these practices invite us to keep questioning, adapting and developing our capacity to shape what comes next.

Five Questions for Your Next Leadership or Board Conversation

The real value of these reflections lies in what we do differently. Five questions can help translate them into meaningful conversations and choices:

1. What are we still assuming to be true? Which established beliefs about our business or environment deserve to be reconsidered?
2. What might we not be seeing? Whose perspectives are missing, and which emerging signals are we overlooking?
3. Are we governing opportunity as rigorously as risk? Are we giving sufficient attention to innovation, renewal and future value creation?
4. What can we only learn by acting? Where might experimentation create more insight than further analysis?
5. What capabilities must we develop together? How are we strengthening collective judgement, relationships and the capacity to learn?

These questions will not eliminate uncertainty. But they can help us create better conversations, make more conscious choices and strengthen our ability to respond to change.

The challenge is not to find another playbook, but to develop the curiosity, courage and judgement to recognise when established approaches are insufficient — and help shape what comes next.

 

Explore the nine conversations — Beyond the Old Playbook

The nine-part series is part of the Exploring Leaders Podcast by Digoshen. Each conversation is accompanied by a blog article that explores the topic, connects it to research and uses art as an invitation to reflection.

Episode and blog article	Interviewee(s)	Central question
1. What If the Problem Is Our Need for Certainty?	Lidija Drobež — Executive coach and experienced international business leader	How can we navigate uncertainty without becoming trapped by our need for answers?
2. Can European Boards Help Europe Compete Again?	Fernanda Torre and Sylvia Robben — Board governance and strategic leadership practitioners	How can European boards contribute to competitiveness, resilience and renewal?
3. From Governing AI to Shaping What Comes Next	Lars Husberg — Board chair and technology transformation advisor	How can boards move beyond AI oversight to shape strategic opportunities?
4. When There Is No Perfect Choice	Rolf Pfeiffer — Business leader, board chair and executive coach	How do leaders exercise judgement when every available choice involves trade-offs?
5. What If the Limitation Is How We See?	Lidija Drobež — Executive coach and experienced international business leader	How can changing perspective reveal possibilities we might otherwise overlook?
6. What If Sustainability Is Where the Next Business Begins?	Jaap Winter — Board chair and professor of corporate governance	How can sustainability become a source of business renewal rather than primarily an obligation?
7. What If What Made Us Successful Is Now Holding Us Back?	Scott Newton — Strategy and transformation advisor	How do we recognise when established approaches are no longer serving us?
8. Moving Without Knowing — The Benefit of Action	Lidija Drobež — Executive coach and experienced international business leader	What can we discover through action that we cannot learn by waiting?
9. Leading Into the Fog: What Will Leadership and Governance Require by 2030?	Steen Buchreitz Jensen — Founder, Scandinavian Executive Institute	What capabilities will leaders and boards need to navigate interconnected transitions towards 2030?

Each linked article includes the corresponding podcast conversation, available through YouTube and Spotify.

Thank you to all our guests for sharing their experiences, questions and perspectives, and to everyone who has followed the series. The conversations may have reached their conclusion, but the questions they raise remain open.

Beyond the Old Playbook is an invitation to keep exploring—not only how we respond to a changing world, but how we contribute to shaping what comes next.

 

About Digoshen

This blog post was originally published on the Digoshen blog and the personal blog of Digoshen founder Liselotte Engstam.

At Digoshen, we help leaders and boards navigate an increasingly complex world shaped by AI, digital transformation, sustainability, geopolitical change, and evolving workforce dynamics.

Through research, executive education, thought leadership, coaching, and international networks, we translate emerging trends into practical insights that strengthen leadership, governance, innovation, and long-term value creation. We believe that the future belongs to organizations that successfully combine technological intelligence with human wisdom.

If you are a board member, executive, or leader interested in shaping the future of your organization, we invite you to explore our articles, research, podcasts, learning programs, and international communities.

You are also welcome to discover the Boards Impact Forum, chaired by Digoshen founder Liselotte Engstam, and Novisali, her artistic practice exploring leadership, reflection, and human experience through art.

Find more insights on the Digoshen website, explore Liselotte Engstam’s research on Google Scholar, and follow Digoshen on LinkedIn.