Last week, while reading Bent Flyvbjerg’s article “Heuristics for Better Project Leadership,” something clicked. Here was a renowned Oxford professor validating what many of us have learned the hard way – simple rules often work better in complex environments than elaborate frameworks.
This got me thinking about the rules of thumb I’ve collected over the years – not the polished principles you find in management books but the battle-tested heuristics that actually work when reality hits.
“The more complex the world becomes, the more we need simplicity”
Gerd Gigerenzer
Take the moral compass. In an age where AI accelerates everything and tech transforms society at breakneck speed, having an ethical framework isn’t just nice to have – it’s survival critical. Too many leaders optimize for short-term efficiency while overlooking the human cost. When team members burn out or lose their work-life balance, no project savings can justify that cost.
Or consider what I learned from Jim Collins about “getting the right people on the bus.” It sounds simple, almost obvious. But how many of us have tried to fix broken teams with better processes, fancier tools, or more detailed plans? As Daniel Kahneman might say, we’re substituting an easy question (“How do we fix the process?”) for the harder one (“Do we have the right people?”).
James T. Brown’s advice to “kill what is ugly while it is young” resonates with anyone who’s watched minor problems grow into crisis-level challenges. This advice aligns perfectly with Gary Klein’s research on how experienced leaders spot potential failures early—not through formal analysis but through pattern recognition born of experience.
One of my favourite heuristics is: “Create flow, not exploitation.” It challenges our intuition about efficiency. We pack calendars to 100%, then wonder why innovation suffers and stress levels soar. Herbert Simon would call this “satisfying”—accepting good enough over theoretical perfection. Sometimes, having slack in the system isn’t waste—it’s wisdom.
However, perhaps the most crucial rule is about transparency. When Rubenstein and Josephs say, “Be rigorous on failures of transparency,” they’re pointing to something more profound than communication. In my experience, lack of transparency is rarely about information – it’s about trust and psychological safety.
These simple rules might seem obvious. However, as Charlie Munger often said, the gap between knowing and doing is usually wider than the gap between ignorance and knowledge. The challenge isn’t understanding these principles—it’s having the courage to apply them when pressure mounts.
“In preparing for battle I have always found that plans are useless, but planning is indispensable”
Dwight D. Eisenhower
For the intellectually curious, here’s where you can dive deeper:
📚 Further Reading
- Thinking, Fast and Slow by Daniel Kahneman – On cognitive biases and decision-making
- Risk, Uncertainty and Decision-Making by Gerd Gigerenzer – The power of simple heuristics
- Sources of Power by Gary Klein – How experts make decisions
- Good to Great by Jim Collins – Including the principle of “First Who, Then What”
- Administrative Behavior by Herbert Simon – On bounded rationality and satisficing
- Poor Charlie’s Almanack by Charlie Munger – Mental models for decision-making
Next week, I’ll dive deeper into the moral compass and why it matters more than ever in our AI-accelerated world. What leadership heuristics have you found most valuable? I’d love to hear your experiences.