Nearly twenty years ago, one of the first companies I worked for out of college decided to hold its annual office meeting outdoors. 

And not just in any outdoor location. To turn up the dial to "11" on the inspirational mood level --to borrow the now classic "metaphor" from the 1980s cult rockumentary, "This Is Spinal Tap" --our company gathering was to happen at a scenic spot situated on the edge of a precipice in the stunningly beautiful Taroko Gorge Park on the eastern coast of Taiwan.

I had volunteered to help our managing partner prepare his presentation, which he ambitiously intended to project on a screen placed outside, with the lush green mountains and roaring waterfalls as an inspiring natural backdrop.

I'll never forget the sense of misgiving I had around his plan. Yes, it was inspiring! But, even though I had only recently joined the firm, I was already well familiar with the technical hiccups we often encountered. Malfunctions that would cripple our presentations, even in the supposedly safe confines of a conference room in our office, or at our client's office--predictable places where we could readily locate someone from the IT department who could fix our problem and get things working again.

So, as a "Plan B," I decided to print hardcopies of the presentation the night before our two-hour train ride the next morning. While everyone else had left the office at a much saner hour, I was stuck in the printing room at 3 am, churning out copies of the presentation. (Just in case, of course.)

The next day, after our cross-country train sojourn and another hour by bus up a ridiculously narrow and winding mountain road, we arrived at the scenic rest spot on the edge of Taroko Gorge.

Sure enough, the projector. 

Did not.

Work.

(Distressed look on managing partner's face.)

(Cue Glenn and his box of printouts!)

(Look of relief and gratitude on managing partner's face.)

I've experienced a lot more surprises, mistakes, mishaps, and, sometimes, utter failures, over the course of my career. Today, unexpected and very unpleasant surprises still happen. Well laid plans get tossed out the window. Things sometimes just go really wrong. 

Here are a few lessons I've learned along the way that have helped me navigate many tough situations:

1. Beware of making assumptions.

Our managing partner's plan was creative and inspiring, but it was also based on several assumptions that turned out to be, well, wrong. Like the projector working. I continue to see people make assumptions that are based on excessive doses of optimism, on misinformation, or on just plain ignorance. You may not be able to eliminate all possible risks, but you can certainly mitigate them, and prepare yourself to deal with them better if you do what I suggest in the next point.

2. Map out potential scenarios and key decisions.

Try to visualize the event you're trying to organize, or the product you're trying to create (this "product" could be a heavily quantitative report, a creative design, a piece of communication, or anything else that you are working on). Then plot out a few possible scenarios and sequences of events that could happen between now and the actual event, or the moment when you're delivering your finished product. In "Scenario A," what could possibly happen? What course of action would you and others need to take? Do the same for "Scenario B" and "Scenario C." Don't do all this, however, unless you also do what I suggest in the next point.

3. Communicate your scenarios--and gain support for them. 

The last thing you want to do is craft a clever set of "What if's?" and key decisions, only to find that nobody else is on board with your plan. Make sure you communicate your "Plan A" and "Plan B" with key stakeholders and decision-makers, so they understand what to expect when things don't go as originally planned. 

4. Don't trust technology (not entirely at least).

Our entire professional and even personal lives are so tightly tethered to technology, we have no choice but to trust in its ability to deliver what it promises to do. 

But we all know that technology does fail, and it fails fast, and it fails hard. Make sure you've got a redundancy plan in place, that you know how to troubleshoot basic problems, and that you have an expert to call on when you need them. Because you will.

Published on: Apr 19, 2018
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