Everyone knows how to plan. We do it all day, every day, mostly without thinking about it. We plan holidays, dinner, school runs and how to get across town when we have three things to do on the way. Even making a cup of coffee involves a plan.
We instinctively understand what needs to happen first, what can happen at the same time, what resources we need and how to adjust when something goes wrong.
So why, when we walk into a large organisation, does planning a transformation become so difficult? I’ve worked with incredibly capable people who can run businesses, manage enormous budgets and solve complex problems, yet struggle to produce a credible transformation plan.
Thousands of activities. Hundreds of dependencies. Endless workshops. Sophisticated tools, roadmaps, backlogs and capacity models. And still, nobody is entirely confident the plan will work.
I don’t believe this is because people are bad at planning. It’s because we underestimate how difficult it is to plan something we’ve never done before.
We apply approaches designed for work we understand to transformations where hundreds, sometimes thousands, of things remain unknown.
The more uncertain we become, the more planning activity we create, often without getting closer to understanding how we’ll deliver the outcome.
That is what I call The Planning Gap.
Why Building a Skyscraper Is Easier to Plan Than a Transformation
Building a skyscraper is enormously complicated. There are thousands of activities, multiple trades, complex engineering, approvals, dependencies and significant financial risk. But there is one advantage: we know how buildings get built.
The broad sequence is understood. Foundations come before walls. Structural work precedes certain services. Trades have established methods, known dependencies and reasonably predictable timeframes. Surprises happen, but the proportion of knowns to unknowns is relatively high.
Now compare that with a major business transformation. You might be changing the operating model, technology, processes, data, customer experience and how thousands of people work, all at once. You may be implementing technology the organisation has never used, creating processes that don’t yet exist and integrating systems never designed to work together, while the business continues to operate and priorities keep shifting.
You may know the outcome you want, but not how to achieve it. Will the technology work as expected? Will people adopt the change? Which design choices could create unintended consequences? What dependencies haven’t been discovered? One answer can change ten other things you thought you understood.
That is the difference between planning something complicated that we know how to do and planning something complex that we are still working out how to do.
Yet we often approach both in much the same way: break the work into activities, estimate durations, identify dependencies, allocate resources and build a schedule.
When the sequence itself is uncertain, more detailed activities don’t necessarily create a better plan. Sometimes they simply create a more detailed representation of everything we don’t yet know. That is where the Planning Gap begins.
Planning Paralysis: Trying to Plan a Thousand Unknowns
A transformation is launched, the strategy is approved and the investment committed. The next question is inevitable: “What’s the plan?” So the organisation starts planning. Big room planning. Quarterly planning. Roadmaps. Backlogs. Tickets. Capacity allocation. Dependency mapping.
None of these disciplines is wrong. Most are helpful once we understand what we’re planning. The problem is asking hundreds of people to create detailed plans for work the organisation hasn’t yet worked out how to approach.
Teams make assumptions, estimate activities and map dependencies based on what they know. Then the plans come together and don’t quite fit. One team is waiting for a design decision. Another has assumed an unapproved technology approach. A third has built its plan around a dependency nobody else knew existed.
So we plan some more. We add detail, bring more people into the conversation and hold another workshop. Before long, planning becomes an enormous exercise in reconciling uncertainty.
I call this planning paralysis. It isn’t necessarily a capability problem; often the people involved are excellent planners. The problem is trying to solve uncertainty through planning mechanics rather than the thinking and decisions that need to come first.
A thousand unknowns cannot be solved by creating ten thousand activities.
We need to work out which unknowns matter, which choices determine the direction and what can safely wait. That is a different discipline from simply organising work.
The Missing Link Between Strategy and Planning: Execution Strategy
Most organisations have a strategy. Most transformations eventually have a plan. Between the two sits a critical piece of thinking that is routinely overlooked.
The execution strategy.
If strategy tells us what we’re trying to achieve, execution strategy answers how we’re going to achieve it. When the work has never been done before, that question matters enormously.
Imagine implementing a new capability across Australia and several smaller international markets. Do you start in Australia because it is the biggest market and offers the greatest value? Or do you start in a smaller market, prove the solution, learn from the experience and then tackle Australia with greater confidence? Both approaches could make sense.
These aren’t debates about the plan. They’re debates about the execution strategy. What are we optimising for: speed, cost, risk, value, confidence or proof before scale? There is no universally correct answer, but the choice fundamentally changes the sequence, resources, risks, dependencies and plan.
You cannot sensibly plan the route until you’ve decided which route to take.
When we skip execution strategy, we ask delivery teams for detailed plans and hope the right approach emerges along the way. Sometimes it does. Often it doesn’t, and discovering that too late can be very costly.
Finding the Strategic Sequence: Cut Through Complexity
Once the execution strategy is established, the next challenge is the strategic sequence. This is at the heart of Accelerated Planning™, a method I’ve developed and used with hundreds of people to help them plan from the top down rather than disappear into detail. It has become one of Flux’s most popular methods because it helps people cut through complexity.
One common mistake is starting detailed planning from the bottom up. We gather activities, tickets, backlogs and milestones, ask teams what they can deliver and then try to assemble their individual plans into a coherent transformation. Before planning thousands of activities, we work out the essential sequence of things that need to happen to achieve the outcome. Collaboratively and in about two hours to develop the overall roadmap.
What are the major steps, and in what order, to move from where we are today to where we want to be?
Think about making a coffee. I need to boil the water, and while the kettle is on I can get the cup, coffee and milk. Some activities happen in parallel; others have unavoidable dependencies. I can’t pour boiling water until it has boiled. If the kettle breaks, I need another route, but the outcome remains clear.
Transformation follows the same basic principle. The difficulty is that the logic isn’t always obvious; we have to discover it. What must be true before something else can happen? Which capabilities need to exist first? What can happen in parallel? Which unknowns could fundamentally change the sequence?
Once we understand the strategic sequence, we can break it into enabling activities and delivery steps, identify the critical path for the near term and map the dependencies that matter. We cannot credibly plan the critical path for the entire transformation end to end when so much remains unknown.
We must hold the longer-term sequence at a higher level and plan the near term in greater detail. This is necessary whether you are delivering in agile, waterfall or any one of the hybrid methods that sit in-between.
The strategic sequence doesn’t remove complexity. It turns an overwhelming collection of unknowns into a coherent journey that leaders and teams can understand, challenge and progressively work through.
Leaders bring organisational context and decision-making authority. Delivery teams bring detailed knowledge of the work. We need both. The art of transformation planning is bringing strategic intent and delivery reality together before either becomes locked into a plan that doesn’t work.
Not All Unknowns Need to Become Known
If transformation involves hundreds or even thousands of unknowns, should we resolve them all before starting?
Absolutely not. That would be impossible and create another form of planning paralysis.
The skill is knowing which unknowns matter now. Which decisions determine the route? Which assumptions could invalidate the plan? What must we understand before committing significant time or money, and what can safely remain uncertain until later?
Some unknowns need analysis and design before we proceed. Others can be tested through prototypes, pilots or early delivery. Some simply don’t matter yet.
We need to resist creating artificial certainty about things we cannot reasonably know. A plan that describes every activity eighteen months into the future may look reassuring, but that doesn’t make it credible. The goal isn’t to know everything. It is to know enough to move confidently while creating opportunities to learn what we need to know next.
Capacity Is a Constraint, Not a Strategy
Capacity planning matters. There is no point creating a plan that requires 100 people when you have only 20. But capacity is a constraint on the plan, not the thing that should determine the execution strategy.
If we start by asking every team what it can fit into the next quarter, we risk building a plan around available capacity rather than the work needed to deliver the outcome. We end up optimising for keeping people busy instead of delivering value.
Establish the strategic sequence first, then confront the constraints. Can we execute it? Which capabilities are scarce? What must move? What can happen in parallel? Where do we need more resources, and what should we stop doing?
The answers may mean slowing down, investing more, growing some teams or capabilities deliberately changing the sequence or reducing scope. Those are leadership decisions, and they should be made with a clear understanding of what we’re trying to achieve and how. Knowing how many people are available doesn’t tell you the right plan. It tells you what constraints the plan must work within.
Planning Is a System, Not an Event
Perhaps the biggest misconception is that planning happens at a particular point in time. Annual planning, quarterly planning and big room planning can all be useful, but they are moments within the planning system, not the system itself.
In a transformation full of uncertainty, planning must be continuous. Start with the outcome. Translate it into an execution strategy. Establish the strategic sequence. Progressively break the sequence into work, test it against capacity, dependencies and risk, and execute.
Execution is also where we learn. Something expected to take six months takes six weeks. A technology behaves differently than expected. A hidden dependency emerges or a constraint disappears. As the balance of knowns and unknowns changes, the plan should change too.
If a motorway closes, we don’t keep driving towards the roadblock because it was on the original route. We find another way. We still know where we’re going; we adapt how we get there.
Maintain a clear longer-term strategic sequence, but create detailed plans only for the period where you have enough knowledge to plan with confidence. Refresh that detail as execution progresses. That isn’t a weakness in planning. It is how planning should work when the future is uncertain.
The Call to Leaders: Closing the Planning Gap
If you’re leading a transformation and struggling to get confidence in the plan, challenge the assumptions behind your planning approach before commissioning another round of detailed planning.
- Recognise that transformation is different. Don’t assume that being good at planning known work means you can plan transformation in the same way. Design your approach around uncertainty.
- Make the execution strategy explicit. Before asking for detailed plans, agree how you intend to achieve the outcome, what you are optimising for and which choices will shape the journey.
- Establish the strategic sequence before drowning in detail. Identify the essential steps, early critical path, major dependencies and unknowns that could change the route. Build the detail progressively.
- Bring strategic thinking and delivery reality together. Leaders own the major execution choices; delivery teams test and challenge them. Good planning is a continuous conversation between the two.
- Build a planning system that learns. Maintain strategic direction, plan in detail where you have enough knowledge and refresh the plan as unknowns become known. The goal is not to stick to the original plan; it is to keep finding the best route to the outcome.
Final Thought
I find it extraordinary that something we do so naturally in everyday life becomes so difficult when we apply it to transformation. But perhaps we’ve been asking the wrong question.
True Transformation is different. In a world of AI and constant innovation, transformation is becoming a permanent condition. We are planning a journey where the destination may be clear, but the route, dependencies and sometimes even the means of getting there are changing every day.
That requires a different kind of planning mindset and system. Because the real challenge of transformation planning isn’t organising a thousand activities. It’s navigating a thousand unknowns.
And the answer isn’t simply to plan harder. It is to think more carefully about what we know, what we don’t know and what we need to learn next. Then build a planning system that adapts.
That is how we close the Planning Gap.