Complex transformations are among the most challenging endeavours an organisation can undertake. While strategy, budget, and execution plans are carefully scrutinised, the human impact of transformation—particularly the strain it places on the relationships between the CEO, executive team, and Chair—is often overlooked.
Through discussions with CEOs and Chairs across financial services, manufacturing, retail, and technology sectors, Osprey Clarke has identified consistent themes in the stress created by transformation programmes. These include leadership overload, executive misalignment, board scrutiny, and, in some cases, the removal of key figures when confidence is lost.
This paper examines these pressures in depth, incorporating real-world experiences from business leaders who have faced the breaking point in transformation. It also explores how independent expertise, in the form of interim Transformation Directors and specialist executives, can act as a stabilising force—both operationally and politically—within organisations undergoing major change.
The Consistent Themes of Transformation Stress
1. Leadership Overload: The CEO and Executive Team Are Pulled in Opposing Directions
One of the most shared challenges in transformation is leadership capacity. CEOs and their executive teams are expected to drive change while maintaining business-as-usual (BAU). The reality, however, is that many executives are unprepared for the sheer complexity of leading transformation while also managing their core responsibilities.
"We started off confident, thinking we could manage the transformation alongside everything else. But by month six, my COO was barely keeping BAU afloat, and my CFO was battling cost overruns. We were spread too thin, and it showed." – CEO, Financial Services
When key executives become overwhelmed, transformation slows, and business operations suffer. This creates a compounding effect, where programme delays and BAU failures feed board frustration and internal tension.
2. Executive Misalignment: Tensions Between the CEO and Their Team
Even high-performing leadership teams experience tension under transformation pressure. Departments with different priorities—Finance, Operations, Technology, and HR—begin to pull in different directions, leading to a fractured executive team.
"I had a CTO who was pushing for a new digital system, but my COO was resisting because of operational risk. They were constantly at odds, and I found myself mediating every week. Eventually, we had to step in and restructure the transformation leadership." – CEO, Manufacturing
These conflicts frequently manifest in three ways:
• Internal bottlenecks – Executives become locked in debates, delaying critical decisions.
• Inconsistent messaging – The workforce receives mixed signals, reducing engagement.
• Erosion of trust – Once an executive team is divided, alignment is difficult to rebuild.
3. Board Scrutiny and the Erosion of CEO-Chair Trust
For the CEO, board dynamics shift dramatically during transformation. What begins as a supportive oversight role can turn into intense scrutiny as deadlines slip, costs escalate, and early wins fail to materialise.
"The board went from being patient to frustrated in the space of two meetings. They wanted assurance, but I was spending more time managing their expectations than running the business. My Chair and I went from being aligned to having difficult conversations about my ability to deliver." – CEO, Retail
Chairs play a pivotal role in either supporting or undermining the CEO during transformation. The longer issues persist, the more Chairs face pressure from shareholders and non-executive directors (NEDs) to intervene.
In extreme cases, CEOs have been removed mid-transformation when confidence erodes beyond repair.
"We had invested millions into this transformation, and the CEO kept saying ‘trust the process’—but we had no tangible progress. The board lost faith, and ultimately, we had to make a leadership change." – Chair, Technology
Case Studies: Leadership Pressure in Action
1. The Overwhelmed Supply Chain Executive: Bringing in an Interim Director
A global manufacturing business undergoing a supply chain transformation faced severe internal bottlenecks when its Supply Chain Director became overwhelmed with execution.
"Our Supply Chain Director was brilliant, but he was drowning in detail—managing warehouses, suppliers, logistics, and now a complete technology overhaul. His stress levels were through the roof, and it was affecting morale across the leadership team." – CEO, Manufacturing
Recognising the risk, the business brought in an interim Supply Chain Director, allowing the existing executive to take a higher-level strategic role. This shift stabilised the programme and restored executive team alignment.
2. The COO Who Couldn't Manage BAU and Change Simultaneously
A financial services firm implementing a new core banking system faced internal strain when the COO—who was also leading the transformation—began struggling with BAU responsibilities.
"He was running at full speed, but cracks started showing—missed operational targets, unhappy clients, employee frustration. We thought we could push through, but the board was getting nervous." – Chair, Financial Services
To protect the business, an interim Transformation Director was brought in to take full control of programme execution, allowing the COO to focus on BAU. This move prevented a crisis and reassured the board.
3. The CEO Who Lost Board Confidence and Was Removed
Perhaps the most extreme case was a retail CEO leading a digital transformation who lost support from the Chair and NEDs.
"The board wanted results, but the CEO kept promising that ‘the big picture’ would emerge. By year two, costs were rising, and we had no evidence of success. Investors started questioning our leadership, and ultimately, the CEO was replaced." – Former Chair, Retail Sector
4. The Chair Loses the Confidence of the CEO and Executive Team
Chairs walk a fine line between supporting and challenging the CEO. If a Chair becomes overly combative, disruptive, or misaligned with the executive team, they can undermine the transformation rather than enable it.
“The Chair started bypassing the CEO, going directly to senior executives and even outside consultants to question the programme. It completely eroded trust. The CEO eventually refused to work with them, and when the board saw how toxic the relationship had become, they decided to remove the Chair instead.” – CEO, Local Government
This typically happens when a Chair:
• Micromanages the transformation rather than providing high-level governance.
• Publicly undermines the CEO’s leadership in board meetings or shareholder discussions.
• Creates internal friction by aligning with factions within the executive team instead of maintaining neutrality.
If the board determines that the Chair is creating a dysfunctional working environment, they may opt to replace them rather than risk destabilising the entire transformation effort.
There was another example where the decision to remove the Chair was taken after a power struggle, this move was seen as just a delay tactic before the board ultimately decides to remove the CEO anyway.
“The board thought removing the Chair would fix the problem, but six months later, they fired the CEO anyway. The real issue was a lack of transformation expertise, not the Chair-CEO dynamic.” – NED, Private Equity
Key Takeaways for CEOs, Chairs, and Boards
One of the most common pitfalls in transformation is rushing into delivery without clear alignment on outcomes and benefits across the entire business. This is often compounded by executive overconfidence and a reluctance to rely on external specialist resources.
"There was an assumption that we had all the right internal capabilities. When we finally admitted we needed external expertise, we were already behind schedule and over budget. I had to challenge the leadership team to rethink their approach—not as a failure, but as a necessary adjustment to ensure success." – Chair, Private Equity
Organisations must recognise that transformation is as much about preparation as it is about execution. Independent expertise can provide critical insights and structure before issues escalate.
1. Recognise leadership limits early – Expecting executives to manage both BAU and transformation without additional support is a high-risk strategy.
2. Address executive misalignment proactively – Conflicts between transformation leaders must be managed early, before they become leadership fractures.
3. The board needs independent assurance – CEOs who bring in external transformation expertise early avoid micromanagement from the board.
4. The Chair-CEO relationship is critical – Chairs must balance holding the CEO accountable with providing support—or risk destabilising the business.
5. Interim leadership can be a stabilising force – Whether a Transformation Director, Supply Chain expert, or CFO, the right interim leader can decompress executive pressure and restore confidence.
How Independent Expertise Can Protect Relationships, Delivery, and Organisational Success During Major Transformation
In high-stakes transformations, the relationships between the CEO, executive team, and board can become strained, sometimes irreparably. When leadership tension escalates, it doesn’t just affect internal dynamics—it threatens delivery timelines, organisational stability, and ultimately, the success of the transformation.
In the examples we’ve explored, we’ve seen:
• Overstretched executives struggling to balance BAU and transformation
• Boards losing confidence in CEOs, leading to extreme scrutiny or leadership changes
• Chairs being removed when governance breakdowns emerge
Independent expertise—whether through interim Transformation Directors, Supply Chain specialists, or governance experts—has proven to be a stabilising force in such scenarios. By introducing objective leadership, risk management, and execution expertise, independent specialists can decompress internal tensions, ensure delivery stays on track, and restore confidence at all levels of the business.
1. Protecting Executive Relationships: Keeping the Leadership Team Aligned
One of the most common challenges during transformation is executive misalignment—when key leaders start pulling in different directions due to workload strain, competing priorities, or differing risk appetites.
How Independent Expertise Helps:
✅ Provides an unbiased third-party mediator to align executives with competing priorities.
✅ Supports overstretched executives, allowing them to maintain their leadership role without being buried in execution.
✅ Enhances internal communication, ensuring that strategic goals, transformation priorities, and BAU operations are clearly understood across the leadership team.
Example:
In the financial services transformation, the COO was overwhelmed with both BAU and change execution. By bringing in an interim Transformation Director, the executive team was rebalanced—allowing the COO to lead from a strategic level rather than drowning in operational detail.
“It took the pressure off the whole team. Instead of fighting internal battles over workload, we had someone fully focused on making the transformation happen.” – CEO, Financial Services
2. Protecting CEO-Board Relationships: Providing Independent Assurance to Avoid Leadership Fallout
The relationship between the CEO and the board is critical during transformation. If a board loses confidence, scrutiny increases, tensions rise, and in some cases leadership changes follow.
How Independent Expertise Helps:
✅ Provides clear, objective reporting to the board, reducing the risk of misalignment with the CEO.
✅ Identifies risks early, ensuring that transformation challenges are addressed before they escalate.
✅ Gives the CEO breathing space, preventing excessive board interference in day-to-day execution.
Example:
In the retail sector case, the board lost confidence in the CEO due to a lack of visible transformation progress. Had an independent transformation expert been introduced earlier, they could have provided clear risk reporting and a structured roadmap—potentially preventing the CEO’s removal.
“If we had someone independently verifying progress, we might have avoided the whole leadership crisis.” – Former Chair, Retail
3. Protecting Transformation Delivery: Keeping Execution on Track Amid Leadership Disruptions
When leadership disputes, executive overload, or boardroom politics disrupt transformation, the programme itself suffers. Execution stalls, costs escalate, and the workforce loses confidence.
How Independent Expertise Helps:
✅ Ensures continuity—if leadership changes occur, transformation execution continues without disruption.
✅ Brings in specialised knowledge, reducing delays caused by internal capability gaps.
✅ Establishes governance frameworks that prevent internal friction from derailing the programme.
Example:
In the manufacturing supply chain transformation, an overwhelmed Supply Chain Director was delaying the programme due to resource constraints. By bringing in an interim Supply Chain Director, the business was able to regain control over execution and prevent transformation delays.
“Our interim leader hit the ground running. Without that expertise, we would have wasted another six months debating next steps.” – CEO, Manufacturing
4. Protecting Organisational Success: Stabilising Leadership During High-Stakes Change
In extreme cases, transformations result in leadership removals—either the CEO, Chair, or both. When this happens, the organisation is at risk of instability, talent drain, and lost investor confidence.
How Independent Expertise Helps:
✅ Acts as a stabilising force during leadership transitions, ensuring continuity in the business.
✅ Reassures investors and employees, preventing uncertainty from spreading through the organisation.
✅ Supports succession planning, allowing for a smoother transition if leadership changes are unavoidable.
Example:
When a board removed the Chair instead of the CEO, tensions remained high. Had an independent governance advisor or an interim board advisor with transformation expertise been engaged earlier, the leadership change could have been managed more effectively preventing unnecessary boardroom divisions.
“We lost six months trying to rebuild governance structure after the Chair left. Bringing in external transformation governance earlier would have saved us that disruption.” – NED, Private Equity
Key Takeaways: How Organisations Can Proactively Use Independent Expertise to Protect Leadership and Execution
✅ Don’t wait for executive burnout – Introduce interim transformation leaders early to reduce strain before it escalates into leadership disputes.
✅ Boards need independent assurance – Bringing in external transformation oversight helps prevent CEO-board tensions from spiralling out of control.
✅ Specialist expertise saves time and cost – Transformation delays are often caused by internal capability gaps—independent experts bring immediate solutions.
✅ Leadership changes don’t have to derail transformation – If governance or executive shifts happen, interim leaders can ensure continuity, stabilise relationships, and keep transformation on track.
“Without independent transformation expertise, leadership teams risk making the same mistakes over and over again.” – Chair, Financial Services
Final Thoughts: Why Independent Leadership is Essential for High-Stakes Transformations
Transformation success isn’t just about strategy and execution—it’s about maintaining leadership stability, board confidence, and executive alignment throughout the journey.
By embedding experienced interim executives, businesses can:
✅ Protect executive relationships from breaking down under transformation pressure.
✅ Prevent boardroom conflicts that threaten CEO and Chair positions.
✅ Ensure delivery stays on track, even in times of leadership transition.
We would like to extend our sincere gratitude to all the CEOs, Chairs, Non-Executive Directors, and executive leaders who generously shared their experiences and insights for this research. Though this article has been written anonymously to protect confidentiality, you know who you are—and we deeply appreciate your honesty and willingness to discuss the real pressures, challenges, and decisions that come with leading complex transformations.
The pressures of executive leadership are immense, but with the right support, resilience, and expertise, businesses can emerge stronger, more aligned, and more successful than ever.
If you recognise any of these challenges within your own organisation, Osprey Clarke is here to help. Let’s continue the conversation