Insights

Notes on deciding well.

Short pieces on framing decisions, surfacing assumptions and working with an incomplete view. Written for people who have to choose, not people who want to be told.

Note 01 Framing

The question behind the question

Almost every enquiry arrives as one question and turns out to be another. "Should I take the role" is often really "can I afford to leave the one I have", or "will I be forgiven for wanting something different".

Getting to the real question is unglamorous work, and it is where most of the value sits. A well-framed question narrows the field: it tells you which information matters and which is noise. A badly framed one keeps generating options that never feel like progress.

Before a single card is dealt, it is worth writing the decision down in one sentence. If you cannot, the decision is not one decision.

Note 02 Assumptions

What you already know but haven’t said

People rarely lack information about their own situation. They lack permission to say the part they already suspect.

A spread is useful here because it is external. When a card names a dynamic you had been carefully not looking at — a partner’s waning interest, your own boredom, a dependency you built and now resent — it is easier to discuss it as something on the table rather than something about you.

Most of the moments clients describe as breakthroughs are not new facts. They are existing knowledge finally said out loud.

Note 03 Uncertainty

Deciding without enough information

Waiting for certainty is itself a decision, and usually an expensive one. Most consequential choices are made with a partial view, under time pressure, with other people’s interests in play.

The useful move is not to predict the outcome but to describe the terrain: which forces are acting on the situation, which are fixed, which are softer than they look, and what direction things are travelling if nobody intervenes.

A clear map of the landscape does not remove the risk. It tells you which risk you are actually taking.

Note 04 Dynamics

Why the same decision keeps coming back

Some decisions get made repeatedly. A board revisits the same strategic question every quarter; a founder relitigates a hire they made two years ago.

When that happens, the decision on the table is usually not the one that needs resolving. Something underneath it — an unspoken disagreement about what the business is for, an unaddressed relationship, a definition of success nobody agreed to — keeps regenerating it.

Reading the influences around a recurring decision tends to surface that underlying question quickly. It is rarely comfortable and it is usually the fastest route to the decision actually holding.

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