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.

Draw a Venn diagram. Label one of the circles “What I’m good at.” Label the next “What I enjoy doing.” The third reads, “What someone will pay me to do.

Where the three intersect? That’s your career, if you want one. It’s also the core  framework hiring managers have in the backs of their minds when trying to staff their organizations.

They’re accustomed to hiring employees. They bring in contractors – independent workers, also known as members of the gig economy – for situations that call for individuals with a well-defined “sack o’ skills” for a finite duration.

Contractors are, that is, members of the workforce who have decided they won’t scratch their circle #2 itches through their careers. Their numbers appear to be increasing, very likely as an offset to those who prefer the traditional employment/career approach to earning a living.

Managers generally think of their organization as a social construct. When staffing a role, hiring an employee is their default, and for good reason. They want someone who will do more than just a defined body of work. Beyond that they want people who will pitch in to help the society function smoothly, who will provide knowledge and continuity, who find this dynamic desirable, and whose attitudes and approaches are compatible with the business culture.

Bringing in a contractor is, for most open positions, Plan B.

Which is unfortunate for hiring managers right now. The trend appears to be that if they want enough people to get the organization’s work done they’re going to have to make more use of contractors … and not only contractors but also employees who have no interest in pursuing a career, just an honest day’s pay in exchange for their honest day’s work – who want jobs, not careers.

A different approach to staffing to what we’ve all become accustomed to is evolving, one that’s more transactional and less interpersonal. Culture will be less of a force because contractors will spend less time acculturating than employees; also, the ratio of time working independently than in the team situations where culture matters most is steadily increasing.

In some respects it will be more expensive. Contractor turnover will be higher than employee turnover because that’s built into how the relationship is defined. The ratio of onboarding time to productive time will increase.

Managers who don’t want to head down this road do have an alternative: They can compete for those members of the workforce who don’t want to become independent. The law of supply and demand suggests that this approach will cost more. It will also mean thinking through how to make the work environment as desirable as possible.

One more factor, as if one was needed: The security ramifications of a more transient workforce are significant.

Bob’s last word: “Digital” refers to changes in a company’s marketplace that call for changes in a company’s business strategy in response. Digital is all about products and customer relationships.

The current restructuring of traditional staffing practices is the result of digitization, the rise of the remote worker digital technologies have enabled, and COVID-19, which accelerated it all. It’s the next digital marketplace transformation to which businesses must adapt, only this time the marketplace in question is the one that trades in labor.

Adapting to this nascent transformation of the employment marketplace is less familiar territory, but it isn’t different in principle. Strategists have always had to think in terms of where their organizations fit into an overall business ecosystem. Staffing has always been part of this overall ecosystem. It’s just that few business leaders, not to mention those of us who engage in punditry and futurism … anticipated how quickly and dramatically this ecosystem would morph.

Bob’s sales pitch: Ten years ago, when I published Keep the Joint Running: A Manifesto for 21st Century IT, “Digital” was still an adjective, “everybody knew” the rest of the business was IT’s internal customer, and “best practice” was a phrase people tossed around when they had nothing better to say.

Oh, well. You can’t win ‘em all. But even though Digital has been noun-ified, this book’s 13 principles for leading an effective IT organization are as relevant as the day the book was published.