Originally published January 3, 2005.

It’s pretty rare that you find an intersection between information design, interaction design, politics, and war but as James Fallows writes in the December 2004 issue of The Atlantic Monthly, such an intersection most surely exists in the form of Microsoft PowerPoint. In his article, “Will Iran Be Next?”, Fallows describes a war game organized by the Atlantic Monthly. The war game was basically an exercise in role-playing, with the participants discussing the various options available to the U.S. President if and when there is incontrovertible evidence that Iran is on the verge of creating a nuclear weapon.

Although the results of the game were disturbing enough (simply put, Iran is most definitely developing a nuclear weapon and there is no military option for stopping them), perhaps even more disturbing for those of us aware of the inherent limitations and weaknesses of PPT-think, was Fallows’ observation about the role of PowerPoint in military planning.

Case in point are these two paragraphs, separated in the original article by a few pages:

His commitment to realism extended to presenting all his information in a series of PowerPoint slides, on which U.S. military planners are so dependent that is is hard to imagine how Dwight Eisenhower pulled off D-Day without them. PowerPoint’s imperfections as a deliberative tool are well known. Its formulaic outline structure can over-emphasize some ideas or options and conceal others, and the amateurish graphic presentation of data often impedes understanding. But any simulation of a modern military exercise would be unconvincing without it.

When the exercise was over, I told David Kay that an observer who had not often seen such charts remarked on how “cool” they looked. “Yes, and the longer you’ve been around, the more you learn to be skeptical of the ‘cool’ factor in PowerPoint,” Kay said. “I don’t think the President had seen many charts like that before,” he added, referring to President Bush as he reviewed war plans for Iraq.

It is, to put it mildly, extremely disturbing to learn that the most powerful military in world history is heavily reliant on PowerPoint — a tool which so easily affords the dangerous combination of engaging graphics and sloppy thought.

If time is indeed money then managing your calendar is not so different from managing your investment portfolio. Where are you going to allocate your time and how are you going to tactically manage that on a day to day basis?

One strategy to dedicate each day to a particular focus; a single type of meeting; a specific cognitive mode. This not only reduces the friction of context switching between different mindsets but also provides each day of the week with a distinct tone, a certain complexion.

The specifics obviously vary depending on role and environment but for me it looks like this:

  • Mon :: Status & 1:1s
  • Tue :: Cross-Functional Design Reviews
  • Wed :: Networking, Internal & External
  • Thu :: Exec Creative Reviews
  • Fri :: Exec Product Reviews

Although life invariably gets in the way and rarely does an entire week conform to this tidy pattern, the structure yet withstands and my meetings and days — indeed the entire team’s meetings and days — generally comport to this rhythm.

As with my 401K, this allocation will necessarily change and rebalance over time. For now however, it’s proving to be a lucrative approach.

The One-Question Interview

And so there you are. Ten minutes late for a thirty minute interview. With a glance at your calendar you confirm once more that you have a hard stop on the half hour – Executive Creative Review. Non-optional.

A handshake, a smile, you’re seated and you’re ready. Having already experienced the morning’s portfolio review and the afternoon’s messages with the other interviewers, you know that the candidate before you is someone the team wants and given the demand for talent, indeed someone the company needs.

But it’s your job to be sure for you know from experience that a bad hire is far more costly than no hire at all.

With only a few minutes to evaluate, to process, to decide; you find yourself with time for only one meaningful question. And that question is this:

“Let’s imagine for a moment that you get this job and choose to join us.

The one thing I am absolutely certain you will do is the one thing that everyone in every job eventually does. You will quit.

So now imagine that you and I are back in this very room some three to five years from now only instead of an interview, you’re telling me that you’re leaving. We’ll be sad and we’ll be bummed but we’ll both know it was time and that will be okay.

At some point after that, you will sit down to update your LinkedIn profile with three to five bullet points encapsulating your experiences and accomplishments here.

What are those bullet points going to say?”

What would yours say?

File -> New

At some point I suppose, you simply have to start –– to start writing, start posting and stop worrying.

I have hung from the side of cliffs, jumped from airplanes, even engaged in public speaking and still, still nothing causes me quite so much stress as the blank page. Over the years I’ve learned to overcome it by working with pen and paper before engaging with modern technology but the anxiety remains and it is only motion, movement, and progress that appear capable of calming it.

It is such a trap to think about arriving when you’ve yet to even begin. Best to close your eyes, put aside your fears and expectations, and get on with the writing.

After all, nobody’s watching.