The Hard Truth About Organisational Transformation: A Practitioner's Perspective

Having led numerous organizational transformations from an operational and consultancy point of view, I've learned one crucial lesson: the path to successful change begins with brutal honesty, not comforting illusions. As a transformation specialist working directly with companies navigating complex changes, I've seen firsthand how organizations often rush to implement trending methodologies without first understanding their readiness for change.

Why Diagnosis Comes First

When I step into an organization, my first task isn't to prescribe solutions – it's to diagnose and work with that understanding to build a path to strategic objectives. Too often, I encounter leaders eager to hear that their organization is ready for advanced operating models or cutting-edge methodologies. But my role isn't to tell them what they want to hear; it's to reveal what they need to know.

My diagnostic approach is comprehensive and data-driven, built on multiple assessment methods that provide a 360-degree view of the organization. This includes:

• Extensive questionnaires across all organizational levels to gather quantitative data on current practices, pain points, and readiness for change

• In-depth governance reviews to understand decision-making frameworks, accountability structures, and existing processes

• One-on-one interviews with key stakeholders to uncover nuanced perspectives and potential resistance points

• Detailed customer journey analysis to identify service gaps and improvement opportunities

• Product portfolio assessments to evaluate alignment with market needs and organizational capabilities

• Development workflow analysis to understand technical practices, bottlenecks, and improvement areas

• Cultural readiness evaluations through team dynamics observation and feedback collection

• Technical infrastructure and debt assessment

  • Resource allocation and capacity reviews

This diagnostic phase often uncovers uncomfortable truths. I've seen organizations claim they're ready for DevOps, Agile, Product, and Customer-Centric transformations while struggling with basic collaboration practices, conflicting goals or strategic alignment. Others insist they're prepared for agile and product management methodologies while maintaining rigid hierarchical structures, cultures with limited emergence capabilities and misaligned functional operations and governance that prevent true agility.

Connecting Diagnosis to Strategic Objectives

The real value of diagnosis emerges when we map findings against strategic objectives. In my practice, I often ask leadership teams:

• What specific business outcomes are you targeting?

• How do your current capabilities align with these goals?

• What gaps exist between your aspirations and reality?

• What have you tried that worked or didn’t, and why?

• Are you looking for holistic or incremental change?

• Are you prepared to make the necessary changes, and what is the time horizon and scope for change?

• If they have a statement such as “we want to be customer-centric” or “Product-driven”, I am sure to align with what they mean with that and share alignment on suchdefinitionsns to set expectations.

This alignment process frequently reveals stark disconnects between strategic ambitions and operational realities. Let me share three revealing examples from my experience.

1. In one case, I worked with a company that aimed to achieve "digital transformation" within six months while lacking basic digital literacy across 60-70% of their workforce. They hadn't even considered the fundamental requirements of tools and data health needed to work in a transformed way. Furthermore, they were completely misaligned on what products they served customers, roles and responsibilities and had high confidence in their technology stack and project managers to become product managers within 2 weeks following a mandated course. The hard truth – which they initially resisted – was that they needed a comprehensive foundation-building phase before any meaningful transformation could begin. This required a committed investment in technology and skills development.

2. Another particularly illuminating case emerged while working with a leading financial institution. I was brought in to conduct a Product Operating Model alignment session – a workshop designed to help leadership teams understand their current position and what implementing a Product Operating Model truly entails. A telling moment occurred as we delved deeper into the details and the genuine effort required. A director-level participant revealed they had expected this to be a 2-3 month initiative, merely making surface-level changes to satisfy their new CIO's mandate for transformation. This perfectly illustrated the common disconnect between executive mandates and middle-management understanding – or acceptance – of what fundamental transformation requires.

3. I recently witnessed a perfect example of well-intentioned but misguided consulting logic. A consultant insisted on drastically oversimplifying a product operating model transformation, reducing it to a mere "technology department issue" when, in reality, it demanded changes across strategy, product lines, governance, and team structures. Their reasoning was fascinating in its naïvety: "The client is at step 1 of 10, so if we show them the full journey, they'll disengage. Let's just get them to step 2 and then they can build confidence to see what they need to do from there!" What this person failed to grasp was that this surface-level approach would inevitably crumble. You can't deliver level 10 outcomes with level 1-2 effort, and pretending otherwise doesn't serve anyone. The Agile community has seen a great deal of this over the past 2 decades. The irony? In trying to keep the client engaged through oversimplification, they were actually setting up both the client and themselves for a crisis of trust when reality eventually hit. True consulting value comes from having the courage to show clients their full journey while meeting them where they are—then building a pragmatic, step-by-step path demonstrating value at each milestone.
   

The Truth Over Comfort

One of the most challenging aspects of my role is delivering unwelcome news to stakeholders who've invested emotionally and financially in particular initiatives. However, I've learned that sugar-coating findings or avoiding difficult conversations only leads to costly failures down the line. You will satisfy sponsors in the short term but at the cost of the needed outcomes in the long term. This is not a good strategy for repeat business and building strong relationships ahead.

While initially difficult, an honest assessment allowed us to:

• Reset expectations with key stakeholders

• Develop a more realistic transformation timeline

• Identify and address fundamental capability gaps

• Build a stronger foundation for lasting change

• Develop an iterative plan “Think Big - Start Small”, yielding value at each step

Building a Realistic Transformation Plan

Once we've established an honest baseline, we can build a transformation plan that acknowledges current limitations and future aspirations. This might mean:

• Starting with more minor, achievable changes that demonstrate the value and embrace feedback and learnings for the path ahead

• Focusing on capability building before process changes

• Addressing cultural barriers before technical ones

• Understanding the true impact and relationship between culture, mechanisms, governance, people, organisation and technology.

• Setting realistic timelines that account for organizational readiness

I've found that organizations appreciate honesty when coupled with a clear path forward. Rather than promising quick wins, I focus on sustainable progress and value. This might mean telling a client that their 6-month transformation plan needs to be extended by 1-2 years – but with the assurance that the changes will be lasting rather than superficial.

In my experience, successful transformations rarely follow a linear path. Instead, they proceed through carefully orchestrated phases, each building upon the last. This approach allows organizations to:

• Validate assumptions before making major investments

• Build confidence through early successes

• Adjust course based on real feedback

• Maintain momentum while managing risk

Key Lessons from the Field

1. Start with Honest Diagnosis: Don't skip or rush the diagnostic phase – it's your foundation for success. This brings people together with data and is a catalyst for setting expectations, investment and collaboration.

2. Align with Strategy: Ensure every proposed change connects directly to strategic objectives.

3. Communicate Reality: Be prepared to deliver uncomfortable truths when they serve the organisation's best interests.

4. Build Incrementally: Focus on sustainable progress rather than quick fixes.

5. Maintain Perspective: Remember that meaningful transformation takes time and sustained effort. Celebrate successes in the context of value.

Moving Forward

As transformation and operational specialists, our value lies not in telling comfortable stories but in guiding organizations through necessary changes. This requires courage – the courage to speak truth to power, to challenge assumptions, and to advocate for realistic approaches over quick fixes.

The most successful transformations I've led have one thing in common: they started with leaders who were willing to hear and act on difficult truths. When organizations commit to honest diagnosis and realistic planning, they create the foundation for lasting, meaningful change.

Remember, the goal isn't to implement change quickly – it's to implement it correctly. This means starting with a thorough diagnosis, maintaining honest dialogue throughout the process, and staying focused on long-term success rather than short-term comfort.