Teach the Monkey Shakespeare First: Why Good Strategy Starts With the Hardest Question

Why organisations need to identify the hardest strategic challenge before building the operating model.

---

---

I have spent recent weeks helping a charity develop its strategic plan and the operational arrangements needed to deliver it.

It is the kind of work I deeply enjoy because it sits at the point where purpose, governance, leadership and delivery have to meet. A strategy is not just a document. It is a set of choices about what matters, what must change, and what an organisation is prepared to prioritise.

It also reminded me of a principle from X, Alphabet’s Moonshot Factory: if you wanted a monkey to sit on top of a ten-foot pedestal and recite Shakespeare, you would teach the monkey Shakespeare first.

The point is simple: do not start with the easy, visible, measurable activity that creates the illusion of progress.; start with the part that determines whether the whole endeavour can succeed.

If the monkey cannot recite Shakespeare, there is no point building the pedestal.

The comfort of building the pedestal

In organisational life, pedestal building is everywhere.

It looks productive. It creates outputs. It can be planned, measured, reported and shown to others. It gives people the reassurance that something is happening.

None of these things are wrong. In fact, most organisations need them. The problem arises when they are built before the organisation has honestly faced the harder question underneath.

• What are we actually trying to achieve?

• What change are we really trying to create?

• What capability has to exist for that to happen?

• What must be true for this strategy to succeed?

Until those questions are answered, the organisation may simply become more efficient at solving the wrong problem.

Strategy is not the same as activity

One of the most common strategy traps is the belief that more activity means more progress. It is easy to understand why this happens. Organisations are busy. Leaders are under pressure. Boards want confidence. Funders, regulators, partners and stakeholders often want visible signs of delivery.

The temptation is to produce plans that are full of movement. However, movement is not the same as direction. A strategy should not just gather together everything an organisation already does and give it a more polished format. Nor should it become a long list of worthy aspirations. Good strategy requires judgement. It involves deciding what matters most, what should come first, and what may need to stop.

This is where the monkey and pedestal metaphor becomes most useful. It cuts through the polite language that often surrounds strategic planning and asks a wonderfully blunt question.

Which part of this is actually the hard bit?

The North Star comes before the roadmap

One of the thoughtful comments on the original post described this as the need to identify the organisation’s North Star before building the roadmap.

Spot on.

A roadmap is only useful if the destination is clear. Without that clarity, organisations can spend enormous time refining the route while remaining vague about where they are going. This matters particularly because the mission is often broad, ambitious and emotionally compelling. That mission can inspire people, but it can also make prioritisation harder. When everything feels important, it becomes difficult to make choices.

A good strategic planning process helps an organisation move from general commitment to specific direction.

It asks:

• What is our central purpose now?

• Who are we here to serve?

• What outcomes matter most?

• What is changing in our environment?

• Where are we most able to make a distinctive contribution?

• What must we strengthen if we are to deliver that contribution well?

• Only then does it make sense to design the operational arrangements.

Adding more monkeys rarely solves the problem

The comment discussion also brought in a useful parallel from project management: the warning often associated with Brooks’s Law, that adding more people to a late or struggling project can make things worse rather than better.

It is a different metaphor, but it points to the same underlying truth. If the core problem is unclear purpose, weak coordination, poor prioritisation, uncertain capability or unresolved decision making, adding more people may simply create more complexity.

More people. More meetings. More handovers. More interpretation. More routes for confusion.

Sometimes organisations respond to strategic difficulty by increasing effort before improving clarity. Everyone works harder, but the system does not work better. A lack of strategic clarity is exhausting. It creates frustration for staff, uncertainty for leaders, weaker accountability for boards, and poorer outcomes for the people the organisation exists to serve.

Operational plans should flow from strategic honesty

The best operational plans almost design themselves once the fundamentals are clear. That does not mean they are easy. Delivery still requires skill, resource, discipline and leadership. But the work becomes more coherent because the organisation knows what it is trying to make happen.

A strong operational plan should be able to trace a clear line from purpose to delivery.

• Purpose: why we exist.

• Strategic priorities: what we must focus on.

• Outcomes: what change we want to see.

• Capabilities: what must be in place.

• Activities: what we will do.

• Measures: how we will know whether it is working.

• Accountability: who owns what.

• Learning: how we will adapt.

When that line is broken, operational planning becomes a collection of tasks rather than a delivery system.

When it is intact, the plan becomes a practical expression of strategy.

The discipline of doing the difficult thing first

The reason I like the monkey metaphor is that it brings a little humour to a serious discipline. Good strategy often requires organisations to pause before rushing into action. That can feel uncomfortable. It may even feel unproductive at first.

However, it is usually where the most valuable work happens.

• Before the structure, ask about purpose.

• Before the KPIs, ask about outcomes.

• Before the operating model, ask about capability.

• Before the implementation plan, ask what must be true for success.

• Before building the pedestal, teach the monkey Shakespeare.

Good strategy is not about doing more things. It is about identifying the thing that matters most and having the courage to tackle that first.