Last week’s KJR introduced 20 ways of thinking something through, beginning with Outline Thinking and wrapping up with the satisfying but unilluminating Ridicule.

Honesty requires this disclaimer: While I’m quite sure none of these are original, I’m even more sure I didn’t plagiarize someone else’s list. The only credit I can claim is that of the numismatist: I don’t know who stamped these coins, and the only credit I can claim is that I’ve collected them.

Some of you asked for a deeper look at the 20 ways. And while I might stop at 19 – I doubt the world needs techniques for creating better ridicule – I figure starting with Outline Thinking – the first item on the list and arguably the most useful of the bunch – is a safe, if dull bet.

Outlining is top-down decomposition. It’s tempting to stop there, making this the shortest KJR ever posted. But that would be wrong.

Outlining is the tool of choice for documenting your understanding of a subject – of the details and how they fit together.

A successful outline begins with a good subject. It then breaks that subject down to between three and maybe nine topics that are of the same type, and which, taken together, fully encompass the top-level subject as viewed from that perspective.

For example, the subject of your outline might be a project you need to organize. You’ll have to address a number of different topics. For example you’ll have to think through the project team’s composition … that is, the roles you’ll need on the team to do the project’s work. Then there are the work products its team will have to produce to accomplish the project’s objective and goals.

And, not to be ignored, you really ought to figure out the tasks the team will have to execute to create those work products.

To figure out what these tasks are, the project manager will need to outline them. The project management buzzword is “work breakdown structure,” but don’t let that throw you – it’s an outline. So far so good.

You start the process of organizing project tasks by answering the question, “What are the tasks that make up the project?” That results in a top-level view of the project task outline, as shown in the box at the top left in the figure below, taken from the demonstration project used in Bare Bones Project Management – implementing a warehouse management system.

Figure: Outlining is progressive decomposition

Next, you ask the equivalent question about each project task that you asked about the project: “What are the sub-tasks that make up this task?” The figure’s middle box shows the result for the “Gather data” task, re-casting Gather data to Gather information requirements to help clarify what will be needed. In a real project you would ask the same question about every other top-level task, too.

The figure’s lower-right-hand box shows the result of taking the Conduct interviews sub-task to one more level.

Then you would continue until you run out of sub-sub-sub etcetera tasks. Or, if you’re smart (and lazy, but that’s just saying the same thing twice) you’d delegate the rest of the outlining to the experts on your project team best-suited to do so.

Bob’s last word: As you can see, outlining is an excellent tool for thinking a subject through to understand it better, whether the subject is project tasks, the components needed to assemble a piece of Ikea furniture (pro tip: yes, an Allen wrench is a necessary component, but no, it isn’t a sufficient one), or a meal.

What makes it such a useful tool is that it lets you understand the subject you’re figuring out at whatever level of depth you need, without having to keep all that depth in your head all at once.

Outlining, that is, is a terrific way to keep your head from exploding.

Bob’s sales pitch: Speaking of thinking, The Cognitive Enterprise, which I co-authored with my colleague Scott Lee, is, so far as I can tell, the only business book with “cognitive” in the title that isn’t about applying artificial intelligence to business situations. It asks what we think is a more profound question: What would an enterprise that acts purposefully look like – one that has more in common with predators than with ecosystems – and how would you build one.

The neural pathways humans use to, say, recognize a friend’s face are different from those we use to understand why the square of the length of a right triangle’s hypotenuse is equal to the sum of the squared lengths of its sides.

As Daniel Kahneman explains in his mind-blowing Thinking, Fast and Slow, the former is, for us, quick and effortless (thinking fast) while the latter is a lot slower and takes much more effort (thinking slow).

This disparity of effort is one reason some people accept some profoundly wrong ideas while rejecting others that are correct beyond any reasonable doubt: The attractive-but-wrong ideas rely on the thinking-fast pathway, requiring minimal effort. Meanwhile … if you had a million bucks riding on the outcome, could you, on your own, with just pencil, paper, and a five-minute deadline, prove the Pythagorean Theorem?

Anyway … while thinking-slow is intrinsically hard, it doesn’t have to be quite so hard. It’s possible to jump-start the process through what we in IT might call patterns – pre-defined approaches to thinking through different sorts of situation.

Over my accumulating years I’ve collected quite a few of these, and as they’re the backbone of Keep the Joint Running I figured you might find my compilation useful.

What follows is the list. The extent to which I elaborate on anything in it in future posts will depend on the feedback I get from the KJR community (that would be you). So without any further ado, and in no particular order:

Outline Thinking: Top-down decomposition. Outlines may be taxonomic (breakdown at all levels is based on the same dimension of analysis) or attributional (different outline levels are based on different dimensions of analysis).

Mind Mapping: Like outlining, but with many-to-many relationships.

Systems Thinking: How different components interact and relate to each other – process flows, algorithms, rules, feed-forward and feedback loops.

Stochastic Thinking: How randomness influences and accounts for outcomes.

Anti-anecdotal Thinking: Recognizing that a single event does not represent a trend. Related to Stochastic Thinking.

Narrative Thinking: Connecting the dots in story-telling format to see if everything hangs together.

Geometric Thinking: Step-by-step logic, from premises to conclusions. Similar to Narrative Thinking but more rigorous.

Editorial Thinking: knowing what to leave out; clarity vs completeness. Similar to Narrative Thinking but with less nuance and more emphasis on ease of comprehension.

Causal Thinking: Keeping means and ends straight; keeping correlation vs causation straight.

Proportionality perspective: Placing metrics and measurements on a defined scale; insisting on the denominators that turn numbers into ratios.

Metaphorical Thinking: How an unknown circumstance resembles a known one; what our knowledge of the known one suggests about the unknown one.

Fractal / Recursive Thinking: Metaphorical thinking applied to observations at differing scales.

Pattern-based Thinking: Like Metaphorical Thinking, but more rigorous.

Trade-off Thinking: Recognizing that sometimes, better is the best you can achieve, and that an improvement in one dimension can cause deterioration in other dimensions.

Scientific Thinking: Having increased or decreased confidence in a proposition based on whether reliable evidence fails or succeeds in falsifying it.

Models and Thought Experiments: Exploring how a situation would play out by putting someone or something in a defined situation and applying what we know about how they would behave in that situation to predict what the results would be.

Political Thinking: Choosing what ideas to accept and reject based on what you think those in power prefer, or that members of your peer group will like.

Empathic Thinking: Imagining how others might feel if presented with the idea. Similar to Political Thinking, but nicer. Similar to Thought Experiments, but emotional.

Plausibility testing: Assessing whether an explanation passes the don’t-be-ridiculous test, keeping in mind that quantum physics doesn’t pass it.

Ridicule: When you don’t like an idea but can’t find anything wrong with it. Akin to Plausibility Thinking, but malicious.

Bob’s last word: The point of this list isn’t for you to decide which ones you like the best (hint: as a card-carrying member of Sarcastics Anonymous, Ridicule is my favorite). No, the point is to choose the thinking mode best-suited to the situation you’re dealing with.

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Bob’s sales pitch: Want to be a great leader? I can’t help you. I doubt anyone else can help you either.

But if what you want is to be a better leader tomorrow than you were yesterday, get yourself a copy of Leading IT: <Still> the Toughest Job in the World. According to one reviewer, “This should be mandatory reading for any IT manager and above.” And as one executive told me after attending my leadership seminar that’s based on Leading IT, “I’ve attended at least a dozen of these, and this is the first one that wasn’t utter B.S.”