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Ten questions to quickly self assess your organisations transformation maturity
By Mark Caddy profile image Mark Caddy
2 min read

Ten questions to quickly self assess your organisations transformation maturity

Think your organisation is setup for success? Here's ten questions you need to be able to answer in 60s or less each to feel confident you're on the right path.

Think your organisation is setup for success? Here's ten questions you need to be able to answer in 60s or less each to feel confident you're on the right path.

  1. Who really owns delivery?
    Can every major strategic initiative be traced to a single accountable executive, with no ambiguity or diffusion?
  2. Who owns the strategy and is it being protected?
    Is the strategy function genuinely shaping long-term priorities, or is it being dragged into day-to-day delivery firefighting?
  3. Is the distinction between strategy, delivery, change and operations clear to everyone?
    Could your senior leaders confidently describe the purpose of each, and how they interact, in under a minute?
  4. Are operational leaders truly accountable for benefits realisation?
    Or is the organisation still expecting the strategy or change team to "make the benefits happen"?
  5. Do reporting mechanisms give you real insight or just tidy dashboards?
    Can you see progress against strategic objectives, not just activity? Are risks and constraints genuinely surfaced? Are the right people owning them when they are?
  6. Are change roles positioned as enablers rather than hidden delivery leads?
    Does the naming, placement, and expectation of change roles reinforce neutrality and challenge – rather than quiet ownership?
  7. Where does capability genuinely need to sit?
    Are you building programme and delivery expertise in the right places, or defaulting to putting roles where it feels safe and using blanket training that adds noise, not value?
  8. Is the organisation mature enough to stop masking problems?
    Are strategy and change teams unintentionally compensating for weak leadership, unclear ownership, or under-resourced teams?
  9. Are your governance forums doing real work?
    Do they clarify decisions, escalate issues, and confirm accountability – or do they simply review updates and move on?
  10. Is your culture ready for the transformation you’re asking for?
    Are leaders modelling new behaviours? Are teams empowered to redesign their work? Or is the organisation clinging to old habits while asking for new results?

These questions aren’t a checklist; they’re a diagnostic.
Work through them honestly, and you’ll quickly see whether your organisation is designed for strategic delivery or simply hoping for it.

Want to know how to address these areas then be sure to check out other articles by Collectively Better or reach out directly to us for a consult.

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