When a transformation fails, the symptoms are easy often easy enough to spot — missed milestones, broken governance, budget overruns, lack of visibility on status or a vision no one can connect to. These are visible and quantifiable deadly sins that with structure, capability and effort can be overcome. Perhaps the hardest of problems, the true silent killer is something less obvious and far more dangerous: the thinking gap.
The thinking gap is the absence of deep, critical reasoning at the moments it matters most. It shows up in early-stage decisions that are made on instinct or politics instead of insight. It’s what happens when people move from problem to plan too quickly, without taking the time to think through what they are really solving for. Or during key moments in Execution when hard decisions are needed and someone needs to craft a thoughtful plan b (or c).
Transformation, by definition, is a fundamental shift from one state to another. It is ambiguous and unpredictable. What starts as a clear case for change rarely ends where anyone expected.
That ambiguity demands careful thought — not just about what to do, but why, how, and when to do it. Yet most organisations skip this step. Agitated and keen to move fast to early results.
At Flux, we coach leaders to pause and ask three deceptively simple questions before they go any further:
- What problem are we trying to solve?
- Why are we trying to solve it?
- How are we going to solve it — and by when?
In my view, if you can’t answer these questions consistently as a leadership and delivery team at any stage of your program, you’re not ready to start or you should pause before going any further.
The thinking gap begins right there.
The Problem with the Problem
What problem are we trying to solve and why? Saying, “we have a cost issue” or “our risk profile is too high” isn’t enough. These are surface statements. Real thinking means interrogating the problem — quantifying it, validating it with data, and proving that the proposed actions will actually address it.
Too often, teams jump into planning without a grounded understanding of what they’re fixing. The political and emotional arguments dominate the conversation while the rational argument — the one based on evidence and logic — gets drowned out.
Winning the rational argument early is essential. It brings clarity and discipline to the process and forces leaders to confront whether the issue they see is the one they actually need to solve. We have all done it after all. Convinced ourselves of a course of action, even though there is a nagging doubt on whether it is the right thing to do, and later lived to regret it.
The missing thinking on the “How”
Even when leaders understand the “what” and “why,” they often underinvest in the “how.”
Execution strategy — how a transformation will actually unfold — is one of the most overlooked areas of critical thinking. Execution strategy can save years of effort and millions of dollars.
Think of it this way, you don’t just book a flight to Byron bay for holidays. You consider your options, your needs and your budget carefully first. Do you need a car? Can you afford to fly in the school holidays? Can you stomach the drive? Is it in the end ACTUALLY faster to fly end-to-end etc. etc. That’s execution strategy, and if you try to plan without one you are planning in a vacuum.
Leaders must consider early choices about their approach:
Will change happen incrementally, or as a coordinated, large-scale shift? Should it be driven from within the organisation or outside it, free from legacy constraints? Is the goal to stabilise cost first or accelerate growth? If the answer is do it all – do they have the capacity to do it all, really, or is that just ambition overtaking reality.
Developing a hypothesis of the right way to approach the problem as a leadership team increases the chances of success tenfold.
The cost of not thinking early is always paid later.
Why Thinking Can’t Be Outsourced.
One of the most common — and damaging — leadership missteps is mistaking delegation of thinking for empowerment. Leaders believe that by handing responsibility to teams, they are empowering them to own the work. In reality, they are outsourcing thinking to where it cannot be performed.
Teams can deliver, analyse, and execute — but they rarely hold the organisational context, experience, or authority to make the trade-offs that sit at the heart of a transformation. That perspective belongs to the leadership group.
When leaders step out of the thinking, the organisation loses its compass. Programmes become exercises in activity rather than progress. The hard questions go unanswered, because the people now tasked with answering them can’t see the whole system.
Critical thinking in transformation is not a task to be delegated; it is a responsibility that must be owned at the top. The best leaders don’t just sponsor transformation — they stay in the conversation, using their experience to help the organisation navigate complexity and make deliberate choices. To help as teachers and mentors to their teams. Helping them look around corners.
Thinking as a Continuum
Thinking isn’t a workshop or a planning phase — it’s a discipline that should run through every stage of the transformation lifecycle.
As delivery takes over, thinking is often replaced by process. Teams become experts at filling templates, updating dashboards, and producing reports. It all looks like progress, but most of it is motion, not movement.
Every milestone will bring decisions — and decisions require options. Teams should always be able to articulate alternatives: What’s Plan B? What happens if the market shifts? How do we pivot if our assumptions no longer hold?
When thinking continues throughout the journey, transformations stay flexible, resilient, and focused on outcomes rather than process.
The Call to Think - Bridging the Thinking Gap advice for Leaders
- Pause before you plan—Never approve a transformation until the executive team can clearly and collectively answer the core questions — what, why, how, and by when. If the answers are unclear, you’re not ready.
- Ground every problem in evidence—Make data your first filter. Challenge opinions and assumptions. Ensure every problem statement is quantified and validated before it becomes a business case. Politics and emotions are important but not the most important argument at this stage.
- Design your execution strategy early—Choose the approach that fits your context — incremental, staged, or full-scale. Debate trade-offs upfront and revisit them regularly as the world changes.
- Own the thinking, don’t outsource it—Delegation is not empowerment when it comes to strategy. Stay engaged in the reasoning and trade-offs. Thinking at scale belongs to leaders, not the project team.
- Reward quality thinking over process compliance—Progress isn’t measured in templates filled or reports produced. Celebrate the people who connect dots, anticipate risks, and challenge assumptions to move the organisation forward.
Final thought
The best transformations aren’t driven by process compliance — they’re led by leaders who reward clarity, curiosity, and courage over comfort. In the end, the call to think is the call to lead. — Conibear