Chapter 16. It’s All About The Challenge

Marcus Guest
6 min readApr 15, 2024

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In 1558 Nicolò Zeno, an Italian nobleman from the Republic of Venice, published a map he had discovered in the storeroom of his family home, together with a series of letters and sketches detailing his ancestors’ exploration in the north Atlantic and Arctic. The Zeno map (as it became known) was extremely influential in the early years of cartography. It showed a separate island, called Frisland, south-west of Iceland that may have been confused with the southern part of Greenland. And this mistake was replicated on other influential maps for 100 years and was only proven not to exist when later explorers charted these waters more fully.

Fig.43: The Zeno map

“Frisland” can be seen bottom left

The phantom island of Frisland shows why maps can be an imperfect representation of a Landscape. But it also shows how maps make assumptions explicit (“we think there’s a island south-east of Iceland”), which can clearly be seen and challenged by others (ex, later explorers who seek to verify if the island is really there). This is how we deepen our understanding of a given space (“this is just the southern part of Greenland”). Therefore, we map in order to share our assumptions so others can challenge them, which help us learn.

Unfortunately, in many organisations, challenging assumptions about ‘the way things are done around here’ is not encouraged. This results in a lot of waste as people continue to do things long after they were useful, merely because ‘this is the way things have always been done around here’. We call this the “fifth man problem” as it’s reminiscent of this apocryphal story involving Winston Churchill:

During the second world war Winston Churchill, the British Prime Minister, was inspecting an artillery unit. The unit was running a firing drill and Churchill was impressed with the speed of the four-man team as it loaded and fired a large gun hitched to the back of a truck. However, he noticed a fifth man, uninvolved in proceedings, standing off to the side. “What’s his role?” Churchill asked the artillery unit’s officer. “That’s the fifth man, sir” replied the officer, but could offer little more. “Fifth man’s always been there, sir” he added.

That evening the insatiably curious Churchill took a book from his library on the Crimean war, where this artillery unit had first been deployed some 90 years earlier. In it he found a sketch of the artillery team, dressed in similar, though now dated uniforms and loading a similar, though now antique gun. And, off to one side was the ‘fifth man’ — holding the horses used to transport the gun around in pre-mechanised times.

Left unchallenged, assumptions about why we do things can linger long after the original (logical) reason for doing them has passed. That’s why an organisation of any size or longevity will have “fifth men” all over the place adding little to no value today. And this is where Wardley Maps come in. Maps enable you to see your entire organisation from end-to-end and ask important questions like, “do we still need someone to hold the horses?” Once you’ve identified such waste, you can re-deploy those resources to more productive areas that create value for the organisation by focusing on what users need today (rather than just doing something because “that’s the way we’ve always done things around here!”).

Challenging assumptions sounds threatening to some leaders, especially those who believe that being a great leader means also being a great storyteller. Leaders who spend time crafting inspiring stories in water-tight PowerPoint presentations can get defensive if anyone challenges their story, because it feels like they’re challenging their status as a leader. When people in an organisation sense this they keep quiet. The result is that no-one challenges the leader’s assumptions and very little learning takes place. The organisation ends up being left with no choice but to go with the leader’s story, wherever it leads them, and keeping fingers crossed it doesn’t involve setting sail for an island called Frisland.

As we can see from the Frisland story, maps are made collaboratively and iteratively. Someone makes a map of a Landscape, based on their best understanding of it, which enables others to explore that space more easily, (as they now have a map of it). Should they find any mistakes — errors of commission (such as adding an island, like Frisland, that doesn’t exist) or errors of omission (failing to add an island that is there) — they can amend the map, creating an even more accurate representation of the Landscape, which others can now use to explore even further and increase their chances of discovering something of value no-one else has yet.

This is the same process with your Wardley Map. You invite others to challenge your map in order to improve it. You can simply ask others — those with deep knowledge of some areas of your map, or different perspectives to your own — the following three questions, listen carefully to what they say, and learn:

  1. What’s not clear to you on this map?
  2. Is there anything missing on this map?
  3. Is there anything you think we’ve got wrong?

The aim, of course, is NOT to make the perfect map, as that would require the map to be 1:1 scale, (rendering it useless as a map). The aim, instead, is simply to make a better map in order to develop better awareness than your rivals have of a given situation. With this clearer vision you increase your chances of identifying new sources of value first — multiple WHERES you can act, which is at the heart of real strategy.⁠[1]

The alternative though, rife in many organisations, are tightly-woven narratives retold in pretty PowerPoint slides that collapse if someone challenges an underlying assumption (ex, “it’s a very detailed plan, but are you sure people want X,Y,Z?”). Most people therefore know the enquiry that follows such presentations — “what do you think?” — is not meant to elicit challenge, but praise and acceptance. The aim of such presentations is to present a narrative so water-tight that the only answer anyone can give is, “Great! Let’s do it!!”. This is why some organisations, (famously Amazon) ban such presentations as they’re the end point of a thinking process that’s been done elsewhere and only meant to dazzle and coerce the audience assembled to listen to it.

Yet the modern business Landscapes are far too complex for any single leader or expert to know everything. To survive and thrive we need to become better at bringing the collective intelligence of all our people online. Merely accepting the presentation of the senior leader (or their preferred consultant) as the final word risks falling into the ‘thinkers v doers’ trap discussed earlier[⁠2] or sailing off in pursuit of a mirage. Therefore, we can use maps instead to enable constructive challenge to bring the collective wisdom of crowds online — creating a deeper awareness of our current situation, how it’s changing and where our options for action are. Maps do not fall apart if challenged — on the contrary, they become even better representations of a given situation — and help create alignment as they become “our map” representing “our collective awareness” of a situation (rather than being someone else’s perspective we’re forced to adopt).

In a complex and uncertain world, organisations that harness collective intelligence can develop potential (shi⁠[3]) over those rivals who continue operate with eyes wide shut, buying into the narratives they’re being sold.

Fig.44: Map⁠4 of the Landscape for XYZ Gym Ready for Challenge (what’s not clear, is there anything missing, is there anything we’ve got wrong?)

1 For a reminder of the importance of WHY in strategic thinking see chapter 12

2 See Book One, chapter 1

3 Seek Book One, chapter 8

4 The map here was created in a Keynote template and it’s just as easy to create a similar template in PowerPoint or a Google Slides template (where it can be worked on by several people at once). For those keen to use a technology for mapping this is the most popular tool (at the time of writing) onlinewardleymaps.com

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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