Executing business-critical programs is hard. That’s why we work directly with CEOs to help them navigate the scale, complexity, and pressure that comes with delivering transformation programs that matter.

The stark reality is that only one in ten transformation programs achieve their objectives. The rest arrive late, over budget, or worse, don’t deliver their intended benefits.*

Why? Business structures that excel at day-to-day operations often struggle when tasked with managing the unique demands of major transformation initiatives.

Many programs attempt to drive significant change through structures designed for day-to-day operations. Traditional hierarchies set up with functions often become silos, unable to handle cross-functional initiatives that require rapid decision-making and resource flexibility.

CEOs can significantly increase their chances of success by making important organisational changes early in the lifecycle of a major program.

As practitioners who have guided many telecoms and IT organisations through successful transformations, we’ve identified six essential questions every CEO should ask.

Answering these honestly will give you invaluable insight into how well your organisation is set up to deliver your vision and objectives.

1. Is There Genuine Alignment Among Your Leadership Team?

Surface-level agreement in the boardroom often masks more profound disagreements about priorities, approaches, and even the fundamental need for the program itself. When challenges arise – and they inevitably will – these hidden misalignments emerge as passive resistance or competing agendas.

Ask yourself: If I interviewed each executive individually about our goals, would I receive consistent answers regarding priorities, timeframes, and acceptable trade-offs? Has each leader publicly committed to the transformation goals, even when they conflict with departmental interests?

Misalignment at the leadership level is the strongest predictor of transformation failure. Ensure your leadership team has had the difficult conversations necessary to achieve genuine consensus.

2. Do You Have the Right Leadership In Place to Execute?

Every business-critical program needs a Program Director supported by a multidisciplined “Core Team” that’s independent of the business-as-usual organisation and fully dedicated to the program.

Ask yourself: Does your current structure facilitate cross-functional collaboration? Do you have a dedicated Program Director? Are decision rights and accountabilities clear? Can resources be easily reallocated as priorities evolve? Are the team compromised by having to juggle their “day jobs”?

Successful transformations often require temporary structures that exist alongside, rather than within, the regular hierarchy, with clear decision-making rights and direct reporting lines to senior leadership.

The pressure from functional line managers responsible for pay and rations can be subtle in creating a conflict of priorities for those assigned to a strategic program.

3. How Will You Know If You’re Making Progress?

Transformations fail when organisations can’t accurately measure incremental progress…or lack of it! Without clear milestones and metrics, teams may appear busy but deliver little actual business value.

Ask yourself: Have you defined specific, leading indicators that link directly to business outcomes? Do you have mechanisms to track these measures in real-time? Are these metrics visible to everyone involved?

The most successful program implementations establish clear metrics that combine leading indicators (measuring activities) with lagging indicators (measuring outcomes), creating an early warning system for off-track initiatives.

4. Do You Have the Right Skills and Capabilities in Place?

Most organisations totally underestimate the specialised capabilities required for successful business-critical execution. Technical expertise, change management skills, and big program experience are often in short supply internally.

Ask yourself: Have you honestly assessed the gaps between your current capabilities and those required? Do you have a plan to close these gaps? Are your most talented people assigned to the business-critical program?

The skills gap is often most acute in middle management – the layer responsible for translating strategic vision into operational reality. Investing in increased capability at this level yields disproportionate returns.

5. Do You Have the Right Program Governance in Place?

Having worked on over 100 program “rescues,” we’ve seen that program governance processes typically range from weak to useless. Few control systems flag substantive issues early enough for timely remediation.

Ask yourself: Is decision-making quick and straightforward? Are people held accountable? Are stakeholders’ expectations being managed? Are external suppliers being managed? How effectively are program teams and business-as-usual teams collaborating? Is the program team open to honest, fact-based assessments?

6. How Will You Manage the Human Side of Change?

Even perfectly designed programs fail without effective change management. Employee resistance, confusion, or disengagement can undermine even the most strategic initiatives.

Ask yourself: Have you invested sufficiently in communication, training, and incentive alignment? Do employees understand both the “why” and “how” behind the program? Have you identified influential individuals at all levels who can champion the change? Have they “bought into” the objectives and timescales? Can anyone, irrespective of rank, involved in program delivery confidently voice their opinion?

The most successful transformations dedicate as much attention to the human elements as they do to strategic and technical elements.

Honest Assessment Leads to Successful Execution

These six questions offer a framework for honestly assessing your organisation’s readiness. Addressing weaknesses early significantly increases your chances of success.

Organisations that conduct this “pre-mortem” assessment and address identified gaps tend to see a dramatic improvement in their outcomes. Those who rush ahead typically find themselves among the 90% of programs that are late and over budget – wasting resources, damaging credibility, and missing critical market opportunities.

Before committing to your next major transformation initiative, make sure you’ve asked – and honestly answered – these six critical questions.

If you think a fresh, independent view might help you assess whether your organisation is ready to deliver a business-critical program, I’d be happy to have a conversation.

…………………………………………………………………………………………………………………………………………………………………………

*Evidenced by our research and experience from running more than 130 programs, supported by Bent Flyvbjerg’s extensive research in his book “How Big Things Get Done” published 2023.

 

About the author

David Hilliard is founder of Mentor, specialists in strategic program execution.

You can call him on 0118 359 2444 or email david.hilliard@mentoreurope.com.