Great Decisions and Process

Greg Skinner
4 min readNov 27, 2020

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What makes a great decision?

The annoying truth is that most great decisions can only be seen in retrospect, after the consequences. That’s because we can’t know the future entirely, we can only make probability-driven guesses at best.

That means that in the run-up to a decision, the effort is to skew probability as much in your favour as possible, where the rewards considerably outweigh the risks.

This can lead to endless prevarication: so-called analysis paralysis, except analysis might not be happening at all. You might be seeking information perfection in an imperfect world.

Gaming the system

Enterprise today would have you believe that deciding, amusingly enough, is rather like making a move in Monopoly, poker, or chess. If you get it wrong, you’ll damage your chances of winning in subsequent moves.

No take-backsies.

That’s because these games, erroneously taken as metaphor for reality, distil the bewildering complexities of real life down into a crisp cause-effect relationship.

With Chess, there are only so many moves that are realistic (unless you’re playing Microsoft’s fun ‘orangutan’ setting from Windows 3.1); a good player assess them against what she or he sees opposite. With poker, the same is true save for probability taking a more active role. The most complex is, maybe, Monopoly, the other players on the board may be pursuing different strategies, all subject to change, move by move.

The consequences of making a move are — at least immediately* — constrained to the game as an in-game result. There’s a direct relationship between cause and effect and it’s fast compared to a real-world decision, such as one on a major project.

The winds of change

The real world isn’t like that. There’s cause and effect, but the connection is less direct. Deciding is more like predicting the weather than a game. By the time you could understand all the factors that would be needed to decide, the event is unfolding before you; you can only understand in retrospect.

Returning to the start, this means people attempt to get as much information about one giant decision as possible, to try and tip the odds in their favour.

We think that once we’ve decided, it’s irreversible… and we’re biased to think in terms of giant, one-off decisions.

Two things can help here: better analysis and better process

Breaking down a decision into much, much smaller parts — analysis — means you can do two things:

  • Remove a great amount of hidden ambiguity, and where you can’t do that, the remaining ambiguous bits can be tackled with small, high-information-yield actions
  • Cut away useless stuff that might have been hiding in your giant mega-decision in the first place.

And what of process?

Decisions — especially those that have been broken into smaller, less risky components — can be evolved. You can change your mind on the presentation of new information, which de-risks a decision substantially.

What is more, thanks to the analysis thing mentioned above, you can do this by parts — changing your mind about some bits, but not the whole concept.

A bird in the hand is worth two in the bush

Taken together, these tightly coupled principles allow you to make decisions with less total information.

And this unlocks the following maxim:

A good decision made today is worth infinitely more than the potential-perfect decision made tomorrow.

How does that apply to projects?

Projects (be they business or personal) all involve major decisions. These decisions are frequently cut into a few phases along a timeline, but not really analysed any more than that as decisions.

If we break down big, vague decisions into tiny clear ones that are mostly reversible, we’ve gotten ourselves a new ability to decide.

Even if it’s a bit rough, you can move forward, comfortable that the consequences of a small decision can be understood, and either reversed or used to progress further.

Deciding things today means clarity, today.

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