K3 Insights

In my previous article, Why Diagnosis Matters, I explored the importance of ensuring accurate diagnosis before embarking on Operating Model or Organisational Design efforts. A critical next step is to surface and articulate the organisational or cultural dilemmas that, if left unspoken, can silently undermine execution.

Approaching these as dilemmas rather than problems shifts the conversation from deficit-fixing to future-focused evolution. It encourages leaders to embrace complexity, accelerates decision-making, and helps focus on the capabilities needed for the next phase of growth.

Here are three reasons why identifying organisational and cultural dilemmas delivers strategic value:

• Expose the Hidden Tensions That Undermine Execution

The most significant barriers to strategy execution are often cultural and behavioural—not structural or financial. These underlying tensions (e.g. customer understanding and personalisation vs. efficiencies through scale) sit beneath the surface and, if left unspoken, create cycles of frustration, misalignment, or inertia. By surfacing these dilemmas, leaders can have more conscious conversations and make better-informed choices that avoid reactionary or superficial responses.

This also helps avoid the trap of assuming leadership teams are aligned simply because they agree on the strategy. Unspoken differences in cultural assumptions or operating norms can still derail progress. Naming these dilemmas creates a shared language and unlocks more honest, forward-looking conversations about the real shifts the organisation needs to make.

• Support More Balanced, Empathetic, and Sustainable Change

Dilemmas, by nature, require leaders to navigate complex trade-offs rather than default to binary decisions. It’s not about abandoning a deep customer connection or being myopically focused on scale efficiencies – it’s about finding the balance point that enables both.

Framing tensions as dilemmas rather than problems invites empathy over blame. It acknowledges that the strengths that brought success to date are still valued – but now need to evolve for the next stage of growth. This mindset shift also grounds change efforts in the authentic DNA of the organisation, reducing the risk of fatigue, rejection, or failed transformations.

By recognising these tensions explicitly, leaders foster a more human-centred approach to change, enabling teams to move forward with respect, humility, and shared ownership.

• Accelerate Decision-Making, Focus, and Capability Development.

Once dilemmas are visible and named, leadership attention becomes sharper. It becomes easier to prioritise interventions, focus capability-building, and direct attention to the tensions that will unlock real progress. For example, recognising a ‘role clarity vs. collaboration’ dilemma can lead to focused work on decision rights and organisational design.

Framing dilemmas in this way also accelerates decision-making by shifting the narrative from “what is wrong” to “what must evolve”. This positions the organisation as proud of its strengths but ready to embrace its next chapter with clarity, speed, and confidence.

In summary, by explicitly identifying organisational and cultural dilemmas, leaders can avoid being trapped in backward-looking problem-solving and instead create a forward-looking agenda that enables sustainable, impactful transformation.