What happens when the people charged with fixing an organisation are, in important respects, the architects of its current condition?
In this episode of On the Subject of Leadership, I speak with Nick Hassett—an independent strategy execution advisor who has spent more than three decades working at the intersection of boards, executive teams, and the operational realities they are often shielded from—about why transformation programmes fail, and what it takes to intervene when the gap between what an organisation says it is doing and what it is actually doing has grown wider than anyone has yet said aloud.
This is not a conversation about methodology. It is a conversation about the structural and relational conditions under which change becomes possible, and about the discipline required to think clearly when an organisation's existing habits of mind are precisely what produced the problem.
Nick's career spans banking, technology, essential infrastructure, and sport across Australia and Asia. He works across what he calls the full arc of an organisation under pressure: mobilisation, intervention, and recovery. His central proposition borrows from Einstein: the problem cannot be solved by the same thinking with which it was created. The practical corollary—and this is where Nick's work begins—is that someone must bring a different structure to bear. Not a rigid framework imposed on a fluid situation, but a disciplined way of reading what is actually in front of you.
The Tyranny of Existing Thinking
Most organisations that embark on transformation do not fail for want of ambition. They fail because the assumptions that produced the current strategy are still running quietly in the background, shaping which options are considered and which are dismissed before they reach the table.
Nick encounters this pattern with considerable regularity. A board or executive team identifies persistent problems—regulatory performance, financial trajectory, customer engagement, operating model fitness—and concludes that something must change. Often, they have already diagnosed the issues. The problem statements are articulated with precision. The analysis is thorough. The action plans are in place.
And yet, the organisation is still failing.
The reason, as Nick sees it, is rarely technical. It is conceptual. The same leadership cohort that built the current operating model is now tasked with dismantling it. Their assumptions about what constitutes a good strategy, an acceptable risk, or a reasonable pace of change remain embedded in every decision. They are, in effect, trying to solve the problem using the thinking that created it.
This is not a failing of intelligence or goodwill. It is a structural limitation. Thomas Kuhn's observation about paradigmatic thinking in science applies with equal force to organisational life: incumbents do not easily abandon the frameworks within which their expertise was developed, even when those frameworks have ceased to explain the data.
The Valley of Despair and the Work of Realisation
Nick's approach to this impasse is neither prescriptive nor theoretical. He does not compete with the subject matter expertise already present in the organisation. Instead, he brings a different structure of thinking: a discipline for assessing the gap between current-state performance and target-state performance, and for sequencing the work required to close it.
But the technical work, he is clear, is necessary and insufficient. The deeper challenge is relational.
In nearly every engagement, there comes a moment when the board or executive team must confront an uncomfortable possibility: that they are, at least in part, the problem. Nick describes this with characteristic directness. The individuals who hold custodianship of the organisation's strategy and its execution must eventually reckon with the fact that their existing approach has not delivered. This is what he calls the valley of despair—borrowing from the familiar change curve that traces the arc from denial through resistance to eventual acceptance.
His role, as he frames it, is to coach leaders through that valley. The word "coach" is chosen deliberately, though he notes that boards and executive teams are rarely enthusiastic about being thought of as recipients of coaching. The work is confronting, always respectful, and oriented towards a specific outcome: getting leaders past resistance and into a position from which they can envision a future that may look quite different from what they had planned—and, in some cases, a future that does not include them.
Chris Argyris' concept of double-loop learning is relevant here. Single-loop learning asks whether we are doing things right. Double-loop learning asks whether we are doing the right things—and whether the governing variables themselves need to change. Nick's interventions operate at the second level, challenging not just the plans but the assumptions that produced them.
Alignment That Is Only Room Deep
One of the most striking observations in our conversation concerns the fragility of organisational alignment.
Nick describes a pattern that will be instantly recognisable to anyone who has sat in a senior leadership forum. A board meeting or executive session concludes with apparent consensus. Priorities are agreed. Direction is set. Everyone leaves the room ostensibly aligned.
Then they return to their functions and proceed to do something quite different.
The reasons are various. Some executives disagreed but lacked the confidence or the language to articulate their objection in the moment. Others agreed in principle but had already set expectations with their own teams that conflicted with the newly agreed direction. Still others simply defaulted to the operational priorities that were already consuming their attention.
The result is what Nick calls alignment that is only room deep. The lead and lag indicators that the organisation is monitoring begin to produce unexpected results—not because the strategy was wrong, but because it was never actually implemented. The board, seeing anomalous data, questions the strategy. In reality, the strategy was never tested. What was tested was the organisation's willingness to execute it, and it was found wanting.
This dynamic is well documented in the organisational behaviour literature. Jeffrey Pfeffer and Robert Sutton's concept of the "knowing-doing gap" captures the phenomenon precisely: organisations that are adept at generating strategic insight but structurally incapable of translating it into operational reality. The gap is not one of knowledge but of execution discipline—and, as Nick would add, of the cultural conditions that either support or undermine that discipline.
The Chair-CEO Relationship as First Point of Failure
Nick is unequivocal about where alignment must begin: the relationship between the board chair and the chief executive.
This is the single most critical relationship in any organisation, and when it is functioning poorly—when there is a disconnect in strategic priorities, risk appetite, or expectations of performance—the consequences cascade. The board's priorities must translate into the executive team's focus, which must in turn wash through the organisation's policies, management systems, and operational rhythms. If the translation is imprecise, or if the executive team has already established goals that conflict with the board's newly articulated direction, confusion follows.
Nick's metaphor is apt: do not simply add four new priorities and expect the organisation to absorb them alongside the sixty it is already juggling. Reconfirm the seven that matter for the next twelve months. Without that clarity, operational staff—the people who face into customers daily—are left to navigate competing signals. The organisation's control environment begins to produce results that no one planned for, and the board finds itself asking how something happened that was never part of the strategy.
This is not merely a communication problem. It is a governance design problem. The mechanisms by which board-level priorities are translated into operational settings—policy frameworks, performance metrics, resource allocation, decision rights—must be deliberately engineered. When they are not, the gap between strategic intent and operational reality becomes the organisation's defining vulnerability.
Silos, Accountability, and the Casualty of Collaboration
Nick offers a case study—anonymised but vivid—of an organisation that had invested heavily in what he calls a technical approach to solving persistent problems. The analysis was rigorous. The action plans were in place. Accountabilities were clearly allocated. Risk assessments had been completed. Every procedural box had been ticked.
The organisation was still failing.
The root cause, as Nick diagnosed it, was cultural rather than technical. The organisation operated with a strong bias towards action and an explicit accountability culture. On their face, these are virtues. In practice, however, they had produced an unintended consequence: each executive, driven by the imperative to satisfy their superior, had isolated their problem into the domain they could individually control. The result was siloed thinking across every function.
The first casualty of silos, Nick observes, is cross-functional collaboration. And without cross-functional collaboration, the organisation's capacity to address problems that span multiple domains—which is to say, most problems of any significance—is fundamentally compromised. The accountability culture had, paradoxically, produced a blame culture. When things went wrong, the refrain was predictable: legal failed, or IT failed, or finance failed to engage early enough. The pattern is one that Diane Vaughan might recognise as a form of normalised deviance—a gradual drift in which individually rational behaviours accumulate into systemic dysfunction.
The corrective, in Nick's framing, is not to abandon accountability but to redirect it. The focus had become fixated on input measures—what people were doing—rather than outcome measures—what the organisation was achieving. A shift from micromanagement of activities to collective ownership of results required not a new process but a different set of cultural permissions: permission to collaborate across boundaries, to share problems rather than hoard them, and to define success in terms that no single function could deliver alone.
AI, Shadow Adoption, and the Board's Blind Spot
Our conversation turns, inevitably, to artificial intelligence—but not in the way most discussions of AI and leadership proceed.
Nick's concern is not with what AI can do. It is with what boards are failing to see. He describes a pattern that mirrors the organisational response to digital technology a decade earlier: some boards are workshopping how the organisation should use AI, while remaining oblivious to how individuals within the organisation are already using it.
The phenomenon of shadow AI—employees adopting AI tools without organisational sanction, often because they are under pressure and the organisation has not provided adequate tools or clear policy—introduces risks that most governance frameworks are not yet calibrated to detect. Staff under pressure from headcount reductions and unsustainable workloads are loading sensitive company data into publicly accessible models, exposing the organisation to privacy and confidentiality risks that the board has neither anticipated nor governed.
Nick draws a parallel with the digital adoption cycle that Australian organisations navigated—often slowly and painfully—over the preceding decade. The technology changes, but the organisational response remains remarkably consistent: impetuous adoption without thinking through the implications, or outright prohibition without understanding that a ban does not eliminate the risk. He recalls an MD who, having read about Six Sigma in a flight magazine, hired sixteen black belts into an organisation that needed four. The anecdote is dryly amusing, but the underlying pattern is serious: executive enthusiasm untempered by disciplined thinking about implications, capacity, and sequencing.
The question, as Nick frames it, is not what can we do with AI, but what should we do—and, equally, what are the consequences of doing nothing while competitors move ahead?
The Importance of the Exit Strategy
Perhaps the most revealing moment in our conversation comes when Nick is asked whether there is a question about strategy execution that nobody ever asks but should.
His answer is disarming: the first question he asks a new client is, what is my exit strategy?
The response, he says, is invariably bewilderment. You have not even started, and you are already planning how to leave? But the question is not about departure. It is about defining success. If we fast-forward eighteen months and agree to close down this programme because we have achieved all of our objectives, what have we done and how did we measure it?
The exercise forces a confrontation with a deficit that Nick encounters in nearly every engagement: the absence of clear, measurable objectives. Organisations are fluent in activity—we replaced a system, we restructured a team, we implemented a framework—but far less disciplined about outcomes. When circumstances change, as they inevitably do, the absence of a clear flight path means there is no basis on which to make corrective decisions. The programme drifts, the scope mutates, and the eventual result bears little resemblance to the original intent.
Nick invokes the Apollo programme: the spacecraft was on the planned flight path for only three per cent of the journey, but because a flight path existed, continuous correction was possible. Without it, there is only improvisation—and improvisation without objectives is merely activity.
The Discipline of Thinking Through Implications
If there is a unifying thread in Nick Hassett's work, it is the insistence on thinking through implications. Not just the first-order consequences of a chosen course of action, but the second, third, and fourth-order effects as they cascade through stakeholders, regulatory obligations, customer relationships, and the organisation's own capacity to absorb change.
He credits this discipline, in part, to his time at Cisco Systems under John Chambers in the late 1990s and early 2000s—a period of immense organisational growth led by a CEO who, in Nick's account, combined intellectual rigour with genuine humility and an almost obsessive commitment to stakeholder engagement. Chambers' lesson, as Nick distils it, is deceptively simple: never stop engaging your stakeholders, and never underestimate the importance of understanding the implications of a chosen course of action—or of inaction.
The inaction piece is worth underscoring. There is a tendency, particularly at senior levels, to conflate a pause with stability—to believe that holding steady projects confidence and competence. Sometimes it does. But when that pause extends into weeks and months, the organisation is not standing still. It is falling behind. And the cost is not merely financial. It is temporal. Time, unlike capital, cannot be replaced.
Nick recounts a conversation with the managing director of a regulated monopoly who, when presented with two courses of action, responded: if we still have options, we have not waited long enough. The anecdote is delivered without commentary, but none is needed. It captures, in a single sentence, the pathology of institutional inertia dressed up as strategic patience.
A Practical Epistemology of Change
Nick Hassett is not a theorist. He does not publish frameworks or build certification programmes. He is, by his own description, someone who is called in when the situation is already dynamic, the politics are already difficult, and the gap between declared intent and observable reality has become untenable.
What he offers is not a method but a discipline: a structured way of interrogating what is actually happening in an organisation, as distinct from what its leadership believes is happening. The strategy, the operating model, the capability gaps, the culture, and the distance between where the organisation says it is going and where its behaviour suggests it will actually land.
The work is pragmatic, politically literate, and unapologetically focused on outcomes rather than activity. It is also, by necessity, confronting—because the first obstacle to change is usually the set of assumptions held by the people who commissioned the change.
If you lead an organisation under pressure, sit on a board navigating transformation, or are responsible for the execution of strategy in complex, regulated environments, this is a conversation worth hearing in full.
Good night, and good luck.