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What is the value of the project sceptic?

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It’s late, you’ve just won a 10-year war against the Greeks, and all you want is to get this giant wooden horse off the beach and into Troy – you want to start the party. But here comes Cassandra – ranting something about hidden Greeks. Honestly, why is she always so negative? Still, as a positive, the horse is a lot lighter than one would expect from a solid statue…

We do not like sceptics. We like simple narratives, clear direction and consensus – the exact opposite of what the sceptic brings to the table. Daniel Kahneman, in his seminal work Thinking Fast and Slow, describes some of the cognitive biases that underlie these preferences, which are driven by our instinctive thinking mechanisms.

Seniority can make one more susceptible to these biases, not less. The work done by Professor Bent Flyvbjerg and his team looking at lock-in theory shows how socially and psychologically linked even the most objective leader can become to a chosen path. Scepticism, or ‘negativity’, can quickly be perceived as a personal attack and dealt with accordingly.

So, when that sceptic pipes up time and again, it can be very tempting to shoot the messenger. But what if they’re not just bored troublemakers? What if they’re Cassandra desperately begging the Trojans to look inside the horse?

The example might be mythological, but Cassandra is an all-too-real protagonist for many programme leaders, who would rather just have everyone in agreement and heading quickly towards glory. We hear time and again that programme leadership is about having that single unifying vision, and inspiring the programme to drive towards that vision at pace and in a coordinated fashion. But what if real programme leadership is not about those things? What if it’s actually about building a temporary organisation that can deliver the vision? Suddenly the sceptic stops being a blocker to a unified vision and starts being something far more valuable – a key part of the organisation’s self-correction systems.

This notion of the programme as temporary organisation is a key principle of project/portfolio management theory and, increasingly, of PPM plc. This interpretation allows one to draw on the vast wealth of organisation research to build a well-balanced and robust programme.

A second key notion is the recognition of the fundamental complexity of major programmes and the weakness of traditional prediction approaches to complexity. In the world of major programmes, black swans will occur, things will go wrong and requirements will shift. At this level of complexity, ‘stuff happens’.

Having spent some years at the fulcrum of programmes, I was keen recently to circle back into academia. It was here, as part of the University of Oxford’s Major Programme Management MSc, that we explored these notions. During Janet Smart’s excellent course on requirements management, we looked at developing a heurism or ‘rule of thumb’ to help in these complex, temporary environments. We formulated the concept of ‘Don’t shoot Cassandra’ – that programme leads should actively seek out their useful sceptics. This is a simple idea in itself, but, in my delivery work since then, its value has stayed with me and grown.

We know that good forecasting is not linked to the confidence of the forecaster. Professor Philip Tetlock, director of the Good Judgment Project, a forecasting project that unlocks the wisdom of crowds, has focused his career on measuring and understanding forecasting accuracy (while consistently flagging how poor most of our professional forecasting pundits are). In his book Superforecasting: The Art and Science of Prediction, he identifies the key ingredients of superior forecasting, which include intellectual curiosity, breadth of knowledge and an ability to continually revisit decisions made and update them with new information. The super-forecaster knows that certainty is a statistical impossibility and that good prediction is the ability to consolidate finely balanced opposing perspectives: to ask difficult questions of oneself and of others and to adapt one’s position based on the results. If your sceptic does this and, most important of all, is happy to revisit their own sceptical position when new data is received, you may have a Cassandra on your hands. They will be the first to sense when complexity is getting the better of your programme and should be respected accordingly.

So when looking across your temporary organisation, ask yourself where you have set the dial between a unified team versus a healthy acceptance of scepticism. Who are your Cassandras? Do they know their point of view and approach are valuable and valued? Have you created mechanisms to allow them to feed their healthy scepticism into the mix? Or, like the Trojans, have you taken them away and locked them in the temple of Athena to wait for the inevitable, and predictable, massacre? Don’t shoot Cassandra…


This article first appeared in Winter 18 issue of Project, the official journal of the APM. APM members can read the full issue. Or you can request a copy.


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