Roles in Task Management

As we work toward our goals, we step into one of three roles at any given time. In order for things to move forward, we have to work in each of these roles, and – in these roles, have to work well together with ourselves. That’s not so much about being nice to each other, but about effectively passing on information — most often in writing — from one role to the next.

Cheers to Gina!

So what are these roles? The first two were described by tech blogger Gina Trapani:

At any point during the workday, you are in one of two modes: thinking mode (that’s you with the Boss hat on) and action mode (that’s you with the Personal Assistant hat on). When a project or task comes up, the steps you need to take start to form in your mind. Now you’re in thinking/Boss mode — the guy/gal who gives the orders. Your to-do list is a collection of those orders, which your Assistant personality will later pick up and do. When you’re wearing your Boss hat, it’s up to you to write down the instructions in such a way that your Assistant self can just do them without having to think — or stress. Taking the thinking out of the acting is one of the best ways to make your to-do list a cinch to finish off.

Gina Trapani, Upgrade Your Life: The Lifehacker Guide to Working Smarter, Faster, Better (Wiley, 2008), Chapter 3, “Hack 22: Make Your To-Do List Doable” (p. 80).

The same text is also available online:

  https://lifehacker.com/how-to-make-your-to-do-list-doable-270404

Whether you read the article or the book, Trapani’s concept of switching between “Boss” and “Assistant” modes remains a powerful framework for anyone serious about productivity.

Found on pexels.com – photo by Andrea Piacquadio

There's one more

When I first discovered her approach years ago, I was instantly hooked. To this day, when I talk with colleagues or friends about personal productivity, I find myself coming back to her “different hats” metaphor. It’s simple, practical, and fundamental.

But over time, I’ve realized that for me a three-role model works even better. Maybe I’ve simply split Trapani’s “Boss” into two distinct functions. Or maybe I’ve just added a new layer of my own. Either way, here’s how my model looks:

  • The Worker (Trapani’s “Assistant”): gets the tasks done. This role thrives in a calm, well-equipped environment, free from distractions. Success here is measured in boxes ticked and tasks completed by day’s end.
  • The General (akin to Trapani’s “Boss”): manages importance and urgency, schedules tasks, updates plans, and keeps the to-do list organized and realistic. He gives the Worker clarity, puts the work on rails — which might even involve, in my expericene, some degree of preparation. Success means a clean, actionable list and confidence that the Worker’s time is being spent on the right things. It is the General who assigns and names tasks — so that the Worker knows without a doubt what needs to be done and what is to be achieved, whether on the same day or two weeks later. Some people — and your author is one of them — believe that the exact choice of words and grammar used plays a key role in this.
  • The Visionary: looks beyond the tasks and toward the bigger picture. What am I working for? Where do I want to go? Who do I want to become? This role demands quiet, space, fresh mornings, a good view, and often coffee. Success here isn’t measured in tasks but in clarity, perspective, and the ability to *feel* the goals ahead.

Stay in character

  • The Visionary should manage to stay at his altitude and not get sidetracked by considerations of concrete steps, feasibility, timing, and capacities—he can do that another time, in another role: as a general.
  • The General should not yet consider how exactly individual work steps are to be carried out, and certainly not get carried away by “quickly taking care of something.” Instead, they should remain in a mode of work allocation and distribution – as if the worker doing the work were someone else.
  • The Worker is “not allowed” to leave their ranks of order fulfillment. It is not up to them to revise decisions made by the general – which can also be a relief – like to do certain work later, or not at all. Instead, he follows instructions precisely, just like an employee with a strict boss, or a service provider with a very well-paying customer.
  • And the General, again, organizes the achievement of the visionary’s goals and visions – but while doing so, he does not come up with any further goals or change previously set goals.

Here is another example that does not involve a to-do list, but is still relevant to our topic. Have you ever been in a situation where you had a complicated conversation with a craftsman or an important doctor’s appointment, and you decided beforehand to discuss these three questions in detail and “bring home” a satisfactory answer? Do you remember how difficult (and unnatural) it was, in the turmoil of the conversation, which may have gone in a completely different direction due to the other person, to nevertheless insist on your questions and demand answers?

If you have already experienced this, then you were, when deciding on the questions,  the General. And the Worker when in the situation with the craftsman or doctor. With all the temptations of the worker to deviate from the plan (the questions), to make concessions, to settle for less “because it just went in a different direction.” I hope you stood firm!

If a person can establish all of the above roles within themselves and can work smoothly and seamlessly “with themselves” in these roles, then something wonderful happens: what the person sees in moments of clarity will actually be implemented. And, respectively, a large proportion of the work that the person does in everyday life flows into the projects that they recognize, in moments of clarity, as important and valuable – and that move them forward.