Chapter 16. The Importance of Challenge

Marcus Guest
4 min readApr 15, 2024

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In 1558, Venetian nobleman Nicolò Zeno published a map he found in his family’s archives. It was created by his ancestors during their expeditions to the North Atlantic and Arctic. The “Zeno map”, as it became known, became very influential among early cartographers. However, Zeno’s ancestors had mistakenly thought that southern Greenland was a separate island, which they called ‘Frisland’. This phantom island was replicated on all other maps for 100 years, until later explorers proved it didn’t exist.

Fig.49: The Zeno map

“Frisland” can be seen bottom left

The phantom island of Frisland shows that maps can be imperfect representations of a Landscape. But it also illustrates how maps make assumptions visible (“we think there’s a island here”) which allows others to see and challenge them. This process of examination and questioning is how we deepen our understanding of the world and correct any errors along the way.

Yet, in many organisations, assumptions often go unchallenged. People continue to follow outdated practices simply because that’s ‘how things have always been done’. This is captured in an apocryphal tale from World War II involving Winston Churchill:

During the second world war, the British Prime Minister, Winston Churchill, was observing an artillery unit conducting a firing drill. Churchill expressed his satisfaction with the speed that the four-man team loaded and fired their large gun. But he also noticed a fifth man, uninvolved in proceedings, standing off to the side.

— “What’s his role?” Churchill asked the artillery officer.

— “That’s the fifth man, sir” replied the officer, but could offer little more.

— “Fifth man’s always been there, sir” he added, somewhat unhelpfully.

That evening, the insatiably curious Churchill took a book from his library on the Crimean war, where this artillery unit had first been deployed 90 years earlier. He found a sketch of the artillery team dressed in similar, though now dated, uniforms and firing a similar, though now antique, gun. And off to one side was the ‘fifth man’ — holding the horses they had to use to transport a large gun around a century before.

This story illustrates how organisations accumulate “fifth men” — people continuing to perform roles long after their value has passed — simply because these processes have never been challenged. By mapping how your organisation creates value today, you can identify these inefficiencies — the equivalent of asking: “Do we still need someone to hold the horses?” And, once identified, these people and resources can be re-directed to create real value by focusing on how to satisfy users’ needs today.

Despite the benefits, challenging assumptions remains uncomfortable for many organisations. Many leaders especially struggle with this. They’ve been taught that great leaders are great storytellers, so invest heavily in crafting compelling narratives to mobilise people. But if these narratives are challenged, it can feel like an attack on their leadership itself. Therefore, out of fear of giving offence, people refrain from voicing legitimate concerns, which denies the organisation critical opportunities for collective learning and alignment. Without challenge, they’re forced to follow assumptions, hoping they’re not setting sail for an island that doesn’t exist.

Challenging Your Map

Maps evolve through collaboration. Someone creates a map based on their best understanding of the Landscape, which allows others to see it clearly and identify mistakes: errors of commission, (like adding an non-existent island); or errors of omission, (like missing an island that does exist). By challenging the map, it improves, becoming a more accurate tool for navigating the Landscape.

The same process applies to Wardley Maps. Invite knowledgeable others to challenge your map by asking three questions, then listen carefully to their answers and improve your map as appropriate:

  1. What’s unclear on this map?
  2. What’s missing?
  3. What’s wrong?

Remember, the aim isn’t to make the perfect map — that would require it to be 1:1 scale, rendering it impractical. Instead, the aim is to make a better map, one that enhances your awareness of the situation and helps you identify smarter moves.

Modern business Landscapes are too complex for any person to know everything. Success increasingly depends on being able to harness the collective intelligence of all your people. Maps facilitate this by encouraging constructive conversations that create and spread knowledge. Maps don’t fall apart when challenged — unlike PowerPoint narratives, which are the end point of a thinking process that has taken place elsewhere and is not open for discussion. On the contrary, maps are ‘anti-fragile’ — improving through challenge, creating alignment around an informed, shared view of the situation. This is how maps help organisations navigate uncertainty and find their way in a fast-changing world.

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Marcus Guest
Marcus Guest

Written by Marcus Guest

Govern the state by being straightforward; And wage war by being crafty. — Laozi, Tao Te Ching marcus@powermaps.net PowerMaps.net

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