To what extent should we avoid relying on inference regarding the attitude of others? There is a business strategy book that warns against relying on inference regarding other people, especially the clients or leaders you’re working for. This is very sensible advice for technology consultants and project managers who can get too immersed in systems-thinking. They wind up assuming wrongly that every situation in their environment can be understood through a systems analysis, including other people. The book advises that you can overlook the need with human beings to simply ask them about their motivations, falling into a trap of further analyses of your own models of them. But this advice can have it’s own pitfall, because it still assumes that we can ultimately avoid or do away with inference and interpretation by simply finding better ways of taking in information more accurately from the environment.

This advice pins its hopes on the idea that ‘someone else’ has the answers, perhaps someone in a position of authority who ‘ought’ to have the answers, we just need to ask them to tell us. From the perspective of work in ‘creative’ industry, I would argue that the hardest problems and the deepest challenges people face go to a level where there is no external information to answer a question – nothing. Empirically-minded people tend to have a hard time accepting this possibility, but for most creative types it’s simply a fact of day-to-day life. We’re faced constantly with how to come up with original responses to problems. That is, a creative worker is judged by how their work innovates on and deviates from a precedent template.

Where must this ‘originality’ and deviation come from? It can’t come from tracking more and more closely to information that already exists ‘out there’ in the environment. According to existential philosophers like Heidegger and Sartre, it comes from an encounter with the nothing — das Nichts — at the bottom of the well. They advise that the nothing need not be a moment of despair, but can allow us to gain true clarity and insight into the human condition, and that is of supreme value when it comes to understanding leadership. Leadership depends on being able to face up to the fact that hard problems and deep challenges do not have ready-made answers ‘out there’ waiting for us to find, we have to do a lot of hard, creative thinking to lead in the face of ambiguity.

Authentic leaders recognize and respect others who convey an understanding of this deepest challenge they face. If you go to a leader simply to ask them for more information to do your work, they will naturally assume you are ‘a good follower’, perhaps useful to them, but unable to help with the deepest challenge they face: making decisions for the future in the face of an intrinsically ambiguous reality without complete information.