The Strategy Reality Tension
Updated: 1 day ago
The future asks something of every organisation.
There is something wonderfully optimistic about a strategic planning session. For a few hours, sometimes a few days, an organisation is given permission to look past the demands of today and imagine what it could become. New markets, better systems, a different way of operating. The energy is real, and it should be.
I have been in many of these rooms. What stays with me afterwards is rarely the ambition. It is the more difficult questions, too frequently brushed over, that recalibrate the excitement and connect it with reality. Questions like these:
What condition is this organisation in as it stands up to leave the room?
Is that condition strong enough to carry the weight of what the future needs? Or is there readiness work that will have us behind schedule before we have even started?
What else are we already trying to do, and is this genuinely doable alongside it?
What is, or could be, coming down the track that will compete for resources or priorities?
And how do all of these affect one another?
Strategy chooses the future. Transformation reshapes today’s organisation into one capable of it. Between what the future demands and what the organisation has prepared to carry sits a gap. I call it the Strategy Reality Tension.
Two rooms
I have seen this play out in many ways, and whether in Australia or around the world, similar patterns seem to repeat. I don’t underestimate what teams face in these situations. The change often has to happen, and standing still is rarely an option. The complexity is real, and so are the pressures. What I wonder about is whether the learning is ever consolidated enough to change the approach, so the avoidable problems stop coming back.
Two rooms, drawn from real experience across different environments, show how that learning gets lost.
The first room
The strategy was solid and the team was motivated. Complexity got the airtime it deserved. Legacy and competing priorities were acknowledged, then waved through, because each function was comfortable with its part. What none of them could see, or had planned for, was how much each part depended on the others.
The program stalled at its first stage gate, then fell further and further behind as the complexity grew and the real scale of the ask became clear. Each function had built its part, and built it well, but not in a way that fitted the needs of the parts depending on it. The misalignment had been there from the start. It only showed once the pieces had to join up.
Comfort is local. Risk lives in the connections. Everyone owned a part, and nobody owned the whole.
The second room
This one went the other way. It had pace, a fixed date and a team genuinely expert in transformation. It also had distance from the business. Bringing the business closer was debated, and the answer was that it was too busy and too embedded in its legacy ways to drive the change. That wasn’t entirely untrue.
But the business held what the program lacked: the customer, the industry, and the truth about what could and couldn’t be negotiated. The program held the method. Each had what the other needed, and the decision was to keep them apart.
From then on, the date was the only fixed point. Bad news stayed local, so the program moved ahead in whatever state it was in. By the time the implications were clear, there was no attractive way back. The organisation found its way through with remarkable effort, and the objectives were met. The cost nobody talked about outlasted the program.
I can’t say how different it would have been had the business been in the room. I can say it was not for lack of skill. What was missing was a way to put the two kinds of knowledge in the same conversation, and someone whose job it was to keep them there. Which is why I keep coming back to whether the learning is ever consolidated. Ownership of a transformation tends to sit ambiguously between the central function that leads it and the many people who deliver it, and learning that belongs to everyone can end up belonging to no one.
The transformation before the transformation
A business case speaks to the big problem. In reality, that problem is a thousand smaller ones.
The organisation arrives at the planning table carrying every decision that came before. Most were reasonable when made: a workaround to keep a customer served, a legacy system extended instead of replaced, a process that depends on the one person who knows how it really works, and why. Over years they became the shape of the business.
In my experience, the longer a business runs on that legacy, the more complex and risky it becomes to move off it. What drives the complexity is less its age than how little of it can still be seen.
Before the transformation can begin, there is often a prelude, and it is a piece of work in its own right. A foundation can carry today’s business without complaint and still fall short of what a transformation laid on top of it will ask. Working out how far short, and bringing the foundation to a stable baseline, takes real effort: investigation, testing and change, and the people inside have to learn their way through it too. Too often that work is missing from the business case, or underestimated when it is there.
It goes unsaid for ordinary reasons. The business is busy running today, and to the people running it, the foundation holds. The transformation team, at arm’s length, plans on assumptions that sit too far from the front line. Boards and executives are further away still, too far to challenge the gap. The readiness work is lost between them, and in the meantime people make up the difference with effort.
The condition of a business and its performance are not the same thing. Strong performance can hide a weak condition for years.
This is not an argument for fixing everything first. It is an argument for knowing what the path depends on before committing to it.
The business in between
We treat strategy, transformation and operations as separate disciplines. The organisation experiences all three at once, with the same people running today’s business while helping build tomorrow’s.
That is why the pathway matters as much as the destination. A phased transformation is easier to absorb but slower. A concentrated one is faster but asks more of everyone at once. The right choice depends on what the organisation can carry.
Strategy is not something an organisation moves to in a single clean step. It is something it becomes while still operating.
And when the connections come into view, so do the earlier decisions: who said they were comfortable, who signed off the plan, who backed the date. A question meant to understand can land as a question about who got it wrong. Leaders who expect that keep people solving the problem together, not defending their parts.
Where you land
On paper, the program in the second room succeeded, and the people who saw it through deserve full credit. Bringing an organisation out of a position with no attractive way back is a genuine achievement.
Transformation is hard on its best day, and some of the complexity is unavoidable. Extraordinary effort tells us it was hard, but not which parts of it did not need to be. Even the best people can carry a transformation only so far. Beyond that, the organisation has to carry it, and where it can’t, the cost shows up somewhere else: in reputation, in people, in whatever was put off. Rescuing a transformation is a different achievement from delivering one well, yet too often we celebrate the two as though they were the same. When the rescue is celebrated as the plan, the organisation learns to admire the recovery, and attention moves away from what made it necessary.
So I now ask of any transformation not only whether it arrived, but in what condition. What was strengthened on the way, and what was spent? What did the organisation learn about itself, and whose job was it to reconcile what was promised with what it took? Without someone holding that job, the lesson stays with the people who lived it, and leaves when they do.
Before the next plan is approved
Asking is a start. Proving is better. There is one question I would put to any plan before it is approved: what truths is this plan quietly relying on that we haven’t tested?
Most plans can say what each function must deliver. Fewer can say who owns the places where the work meets. So look at the plan from six perspectives, and ask of each who has actually seen the evidence. No single one is enough, and any one of them can change the plan.
Condition. What shape are we really in, according to the people who run it day to day, and is it strong enough to carry this?
Capacity. What else are we carrying, and what will this ask of us at the same time?
Horizon. What is coming that could compete with this or derail it?
Connections. Where will our decisions meet, and who owns those connections?
Tolerance. What are we prepared to strain, and what must not be damaged?
Arrival. How will we know we have arrived in good condition, and whose job is it to learn from it?
If the answers come mostly from the top of the organisation, that is an answer too.
I find it difficult to imagine an organisation where the Strategy Reality Tension is entirely absent, and I haven’t encountered one. But the size of that tension is not fixed. It can be narrowed through preparation, sequencing, stronger capability or reconsidering the ambition itself. The first step is recognising it. The next is deciding who owns it.
Organisations should keep imagining better futures, and the rooms where they do it should stay optimistic. But a strategy is chosen in the room and paid for everywhere else, by the organisation we are today, with its history, its workarounds, its competing priorities and its capable, stretched people. They are the ones who absorb the journey.
So when the next planning session ends and everyone stands to leave the room, ask the more difficult question. What is this organisation about to carry, and in what condition will it get there?
A transformation does not end on arrival. That is where it starts to earn its return, in whatever condition the journey has left the organisation.
The two rooms are a collation of real experiences from different environments, not accounts of any one organisation. Some details have been deliberately altered for confidentiality.
About the Author:
Tracey Harris is the founder of BackPack Executive, working alongside founders, CEOs and boards navigating complexity, governance, strategic clarity and performance momentum.
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