The Hidden Flaws in Strategic Planning
We have the privilege of working with a wide range of organisations, and across sectors and leadership teams, we see similar patterns in how strategy is approached.
Capable people.
Strong intent.
A genuine desire to do good work.
And yet… sometimes not much really shifts.
Not because strategy doesn’t work, but because the way we’ve been taught to approach it is being stretched by the world we’re now operating in.
There’s a question that sits underneath it all:
What happens when the same people, in the same room, think about the organisation in the same way, and hope for a different result?
This isn’t about getting strategy wrong.
It’s about recognising that strategy needs to evolve, and that invites something different from us.
A shift:
in how we think
in how we see the system
and in how we come together to make sense of what’s possible.
Some organisations are already evolving how they do this, and we’re seeing the results that are unlocked when they do.
Here’s a list of the top 5 flaws and what’s being done differently:
1. Same thinking = Same results.
It’s natural to bring a group of leaders together and expect something new to emerge - sometimes it does.
At the same time, when the same people, shaped by the same system, come together - thinking can stay within familiar boundaries.
We may find ourselves:
Reinforcing what we already believe
Staying within what feels known and comfortable
Refining what exists, rather than reimagining what’s possible.
What we’re seeing work is a simple but powerful shift: expanding thinking before strategic planning starts.
This might look like:
Bringing in new perspectives
Engaging with data and trends
Surfacing and exploring hidden fears and assumptions
Learning from within and beyond the system
Drawing on insight that is not only analytical, but also experiential and collective
So that by the time people come together, their thinking is already beginning to shift.
Coming together then becomes something different. Not the starting point - but a space where thinking is stretched, deepened, and brought together in new ways.
2. Looking Inward, not Outward.
It’s natural for strategy conversations to focus on what’s happening inside the organisation: our priorities, our performance. And these things matter.
At the same time, organisations are part of a much larger system, one that is constantly shifting.
When we widen our lens, we start to notice things like:
Changes in how society is thinking and behaving
Shifts in policy and governance
Increasing uncertainty and disruption
The question becomes not just about what we want to do, but also
What is changing around us, and what might that make possible?
This is where strategy can easily slip into familiar patterns. Traditional tools tend to categorise the environment and organise what we know.
And while that can be useful, it often keeps us at a distance.
Contemporary approaches help us explore outwardly what we don’t yet understand, by:
Exploring patterns and relationships, not just categories
Identifying key uncertainties, not just known factors
Engaging with multiple possible futures, not just one predicted path
It becomes less about completing an analysis, and more about making sense of a living system.
When strategy engages with this broader context in this way, it becomes more grounded, more responsive, and more connected to reality.
3. Setting Strategy in Stone.
There has long been comfort in creating a clear plan and following it through (I love a good plan!!)
And in some contexts, that still holds.
But many organisations are now operating in environments that don’t unfold in predictable ways.
In complexity, what tends to work is less about rigid planning, and more about experimentation, learning and adaptation.
A good strategy in today’s environment is a living approach that is:
Strong enough to provide direction
Flexible enough to evolve as reality unfolds
In this way, strategy becomes less about getting it “right” upfront, and more about staying responsive over time.
4. Strategy stays on Paper
Strategy traditionally tends to take one two forms:
A concise summary that doesn’t quite guide action
A detailed document that’s hard to bring into everyday work
Both are created with good intent. And both point to an important opportunity.
At its best, strategy serves a simple and powerful purpose:
It helps people make better decisions - especially in the noise and busyness of everyday work.
When strategy is working well, it brings clarity to:
What matters most
Where we choose to focus
And what we are willing to say no to
It becomes something people can return to - a steady guide that supports confident, aligned choices.
5. Playing it Safe in the Conversations
Even with the right people and the right process, strategy can struggle to take hold if the conversations don’t create the space for it.
We often notice patterns like:
Defaulting to the most senior voice
Keeping things comfortable rather than exploring difference
Holding back what might feel difficult to say
And this is completely human.
At the same time, strategy benefits from multiple perspectives, thoughtful challenge and honest reflection. When these are present, something shifts.
Clarity deepens. Understanding expands. And better decisions become possible.
Creating these conditions is less about forcing outcomes, and more about:
Slowing things down
Inviting different perspectives
Making it safe to explore and respectfully disagree
Noticing the handbrakes and patterns within the group and gently shifting them
Asking thoughtful, powerful questions of ourselves and each other
Because ultimately, the quality of the strategy is shaped by the quality of the conversations that create it.
Conclusion
At its core, strategy isn’t a document.
It’s how an organisation moves from where it is, to where it wants, and needs, to be.
That movement is shaped by how clearly we can see the system we’re in, the environment around us, and the assumptions we’re making.
And how we respond - by expanding our perspective, staying adaptive, and making clear, focused decisions about what matters most.
That’s the shift we’re interested in.
Not just better strategic plans, but more thoughtful, adaptive, and grounded strategic thinking - the kind that helps organisations move toward where they want to be, and where the world is asking them to go.