At the Uncertainty Project, we highlight tools and techniques for strategic decision making that are either thought-provoking, applicable, or both!

Every other week we package up our learnings and share them with this newsletter as we build the Uncertainty Project!

And yes, we typically don’t post on Sundays, but today is a special day!

1. 🔮 We’re looking back at the first 6 months of the Uncertainty Project with some highlights

2. 🚀 Today we’re launching on Product Hunt!

Uncertainty Project in review - looking back at the past six months

It’s been six months since we launched the Uncertainty Project in January of this year and looking back, we covered quite a bit of ground.

Looking back at some of these earlier posts, I’ve seen how much my own perspectives have changed - and I hope I look back at today’s post and feel the same.

To celebrate this half-year milestone, the list below is an attempt to summarize what seems to be a few common themes with the relevant posts referenced for each:

The importance of making the implicit → explicit

Every individual, team, and organization has an implicit model for decision making - often comprised of deeply seated beliefs, assumptions, and cultural norms that subconsciously drive everyday decisions.

Much of the friction we face with others in the decision making process is actually due to some disconnect at this level - not about the individual decision. Whether we do ‘A’ or ‘B’ is less about the information we have, and more about how we interpret and synthesize that information - how it filters through layers of predefined individual and collective preferences that are different from person to person and company to company.

Decisions are more difficult when ‘how we decide’ is implicit. Principles are ignored, misinformed beliefs and assumptions fester, mistakes are repeated, and decisions get lost in opaque ownership and accountability.

We can only improve what we can see and challenge.

• Designing a Decision Architecture

• Chronos and kairos time in strategic decision making

• Communication starts well before a decision is made

• What makes a good decision, good?

Complacency and premature convergence

Many of the self-reinforcing mechanics of biases and heuristics become systemic problems. Companies seem to be intoxicated by the idea of ‘innovation’, when the problem doesn’t seem to be identifying and incubating ideas as much as it’s just the natural entropy of decision making.

Companies naturally evolve to reduce volatility and trend towards homogeneity. As observed in groups, the more ambiguous the decision making environment, the more we lean on others to shape our perspectives.

Groups tend to amalgamate and force out contrarians. Zero risk bias limits the ability to identify asymmetric bets. The status quo prevails on the self-reinforcing effects of anchoring, confirmation bias, and commitment bias.

• How 'collective illusions' influence decision making

• ‘Divergent thinking’ and ways to facilitate it

• What is the right amount of ‘Strategic Ambiguity’?

Conviction, overconfidence, and the seduction of certainty

Speed is hindered by the empty pursuit of certainty. Uncertainty is uncomfortable - and certainty is an emotional state that we crave in the same way we want safety or acceptance.

That said, Daniel Kahneman and others attribute overconfidence and hubris (the false sense of certainty) as the primary enemy of effective decision making. So how do we navigate this minefield?

In between the guardrails of ‘thinking we know what we don’t know’ and ‘thinking we need to know’ is the balance of a coherent narrative and conviction. This isn’t unfounded confidence, it’s an evidence-based explanation for ‘what’s going on here?’ that also accepts some level of ‘I don’t know’ - conviction holds the narrative together until it either breaks due to new information or calcifies into overconfidence.

• The role of conviction and narrative in decision making

• Our dangerous tendency to overcommit and tools to mitigate overconfidence

• Are we any good at planning?

The power of (productive) discourse

We expect everyone to draw the same conclusions and make the same judgments given the same information, and though this might make sense in high validity environments (actuaries, judges, games of chance), in radically uncertain environments, this is how we navigate uncertainty - it’s the way we draw tacit knowledge from others.

This kind of collective intelligence has been studied by Tetlock’s decades-long work with super forecasters outperforming experts and used in techniques like the Delphi method, crew resource management, and psychological safety - and it comes from disagreement, not consensus.

If we’re looking for ways to improve decision making, the biggest bang for the buck is creating space for disagreement.

• Making space for decision discourse

• ‘Psychological Safety’ and embracing discomfort

• How a tweak in team psychology helped define modern airline safety

Help us make the next six months better!

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