Strategic Thinking

Tools for reading situations, finding pressure points, timing moves, and thinking in systems.

Pattern Recognition

Read a situation for the forces and players that aren't being named.

Set aside the stated aim. What does their behaviour reveal?

Someone's behaviour doesn't match their stated intentions, or you're in a multi-party situation where motivations are unclear.

Find the Incentive

Show me the incentive and I'll show you the outcome.

Someone's actions seem irrational, a system is producing bad outcomes despite smart people, or an organisation keeps making the same mistake.

Find the Unseen Player

Who's affected that I haven't thought about?

You're making a decision in a complex environment — organisational, competitive, political — with multiple affected parties.

Check If History Rhymes

Where have I seen this movie before — and how did it end?

You're in unfamiliar territory and need a starting framework for thinking about what might happen next.

Separate Signal from Noise

What information here would actually change my decision? Everything else is noise.

You're drowning in data, opinions, or updates and can't identify what actually matters for the decision at hand.

Positioning & Power

Find the position where small effort produces outsized, durable advantage.

Seek the Asymmetric Bet

Is the upside many times the downside? And is the downside survivable?

You're evaluating an opportunity, investment, career move, or strategic bet and need to assess whether the risk profile justifies commitment.

Create Optionality

Does this open doors or close them? When in doubt, keep options alive.

You're facing uncertainty about the future and need to make a decision without full information.

Find the Bottleneck

What's the one thing that, if it broke, would stop everything?

Progress feels slow despite effort, or you're investing resources across multiple areas without clear improvement.

Find the Pressure Point

Where's the smallest move that shifts the most?

You're deciding where to invest limited time, money, or attention for maximum strategic impact.

Check Your Moat

What stops someone from copying this tomorrow? Be honest.

You're assessing the durability of a competitive position — your own or someone else's.

Timing & Tempo

Decide not just what move to make but when — early, late, or not yet.

Move Early or Move Late — Never Middle

Am I early enough to lead, or late enough to learn? Don't get stuck in the middle.

You're considering entering a market, joining a trend, adopting a technology, or committing to a strategic direction.

Use Patience as a Weapon

Not every situation needs action right now. Sometimes the best move is to wait.

You feel compelled to act but can't articulate what specifically would be lost by waiting another week or month.

Force the Clock

I'm ready. They're not. Compress their time.

You're in a negotiation or competitive situation where you're better prepared and the other side benefits from delay.

Spot the Inflection Point

What's the force building beneath the surface that could change everything?

Things feel stable but there's an underlying shift you sense but can't quite articulate — or your industry is experiencing unusual turbulence.

Know When to Withdraw

Would I enter this position today if I weren't already in it?

You suspect you're overcommitted to a losing position but the thought of withdrawing feels like failure.

Systems & Second-Order Effects

Trace what happens after what happens — the loops, dependencies, and downstream effects.

Ask "Then What?" Three Times

That's the first effect. What happens after that? And after that?

You're about to make a decision that affects a system — an organisation, a market, a relationship, a process.

Check the Feedback Loop

Does this amplify itself or correct itself? Know which loop you're in.

You're operating in a system where effects compound — growth, conflict, reputation, debt, team dynamics.

Escape the Local Optimum

Am I climbing the right hill, or just getting better at climbing the wrong one?

Progress has plateaued despite continued effort, or you sense that you're getting better at something that might not matter.

Impose a Constraint

Remove the obvious resource. What would I do then?

Innovation has stalled, thinking feels predictable, or you suspect you're solving problems with resources instead of creativity.

Map the Dependencies

What has to be true for this to work? And what if it isn't?

You're about to commit significant resources to a plan and want to stress-test its weak points before launching.