When ‘I Don’t Know’ Is the Most Strategic Answer
Direction Beats Pace - Every Time!
A keynote speaker recently silenced a room with three words. Someone asked how long a major programme would take, and he said: ‘I don’t know.’
There was a brief pause. A few people probably read it as evasion. But then he leaned in, and what followed was one of the more useful pieces of thinking I’ve heard in a leadership setting for some time. He reframed the question entirely: have you built the right foundations, and are you making consistent, meaningful progress in the right direction? If the answer to both is yes, the timeline will take care of itself. If the answer is no, no timeline will save you.
That moment is worth sitting with.
The Pressure to Look Like You’re Moving
We operate in an environment where visible progress is frequently valued over meaningful progress. Leaders feel the pull to point at milestones, get things launched, and show the board something tangible is happening. That pressure is understandable. But when it starts driving decisions rather than informing them, you begin skipping the slower, less visible work that determines whether any of it actually holds.
The speaker was doing something deliberate: putting the pursuit of outcomes ahead of the pursuit of optics. That takes a certain clarity of purpose, and it reflects a view of strategic leadership that is well worth examining.
One important distinction, though. When I talk about this kind of change, I am referring to large-scale organisational transformation and cultural shift. The kind of work that unfolds over five, ten, sometimes fifteen years. Defined operational programmes, by contrast, absolutely require clear milestones, realistic timelines, and demonstrable progress at every stage. That is just good management. The territory I am exploring here operates on a much longer horizon.
What ‘Foundations’ Actually Means
The word gets used loosely, so let me be specific. In a leadership context, foundations are not a strategy document or a vision statement on a wall. They are a genuine clarity of purpose: knowing why you are doing what you are doing and being able to connect that to the people around you in a way that actually lands. The human core has to be secure before you build anything on top of it.
When leaders skip this, a recognisable pattern follows. A new initiative launches with energy, resources, and a communications plan. People get trained. Systems get procured. Then, about eight or nine months in, the whole thing quietly loses momentum. Not because the strategy was wrong on paper, but because nobody did the slower, harder work of anchoring it to something real. There was no root system. So when the pressure came, as it always does, things did not hold.
Pace Is Not the Same as Performance
There is a particular anxiety that runs through large-scale change: the anxiety of visible activity. Transformation programmes are expensive and disruptive, and people want to see returns. But when that anxiety starts making decisions on your behalf, you end up rushing implementation, launching phases before they are ready, and jumping to the parts that generate the most visible activity. You skip the unglamorous preparatory work. And almost always, you end up doing that foundational work later, under more pressure, with less goodwill.
In Enhanced Leadership, I describe what I call the ‘bolted-on trap’: the tendency to layer new tools or processes onto existing structures rather than genuinely redesigning from the ground up. The same logic applies to pace. Moving too fast usually means bolting change onto a structure that is not ready for it. The speed feels productive. The results often do not last.
Demanding a fixed end date for cultural transformation is a bit like demanding a fixed date for when your organisation will fully trust new leadership. The conditions have to be right. The work has to be real. Rushing it typically produces a performance of change rather than the thing itself.
What Disciplined Progress Actually Looks Like
I want to be precise here, because this is not an argument for slowness. Purposeful progress and cautious inaction are very different things.
A two-way door is a reversible decision: you can try something, learn, and step back if it does not work. A one-way door locks you into a path that is much harder to undo. Disciplined incremental progress is fundamentally about being honest with yourself about which type of door you are walking through, and applying the appropriate level of scrutiny to each.
Under pressure to show momentum, leaders tend to lose that distinction. Everything starts to feel like it needs to happen at the same speed. People stop tracking which decisions are reversible and which are not. Before long, you have walked through several one-way doors without adequate thought, simply because the pace of the programme swept you past them.
The leaders I have seen do this well share a particular quality. They are comfortable with ambiguity in the timeline. They can hold ‘I don’t know exactly how long this will take’ without it undermining their clarity about direction. They know where they are going. They know the next right step. And they trust that doing each step well matters more than doing all the steps quickly.
The AI Dimension
The pace problem is felt most acutely right now in the AI and digital space. No sooner have you started implementing one solution than something better arrives. That is not a temporary condition; it is the landscape for the foreseeable future.
So how do you lead a long-term transformation in a structurally and persistently unstable environment? The answer, I think, is that you decouple your strategy from any specific tool. Your direction of travel, your ‘why’, your long-term outcomes: those need to be durable. They need to survive the next release cycle, the next platform, the next vendor update. The cultural capability you are building in your people, the trust between you and your team, the ethical guardrails you have put in place: none of that becomes obsolete because a new model dropped on a Tuesday.
What should change is your route. This is where governance earns its keep. Too often it becomes a scrutiny exercise dressed up as rigour. But governance at its best holds the long-term outcome steady while giving you permission to adapt the how. It stops you chasing every new development and losing sight of what you were actually trying to build.
For Coaches: What to Watch For
If you are coaching a leader through a major transformation, watch for the moment when timeline pressure starts to compress their thinking. The questions worth asking are not ‘are you on schedule?’ but ‘do you still know why you are doing this?’ and ‘are the decisions you are making this week reversible?’
Watch also for the ‘bolted-on’ signal: when a leader describes adding new capability to an existing structure rather than redesigning from the ground up. It usually means the foundations have not been properly examined. That is the conversation to have, even when there is pressure to press ahead.
The Question Worth Sitting With
So when someone asks how long your transformation will take, the honest answer might genuinely be: I do not know exactly. But I know the direction. I know the foundations we are building. And I know the next right step. For long-term cultural and organisational change, that is not a gap in your strategy. That is your strategy.
The question I would leave you with: where are you currently measuring pace when you should be measuring direction?
