Both Sides

I once worked with a friend who would drive me crazy in meetings.

In the first five minutes of a meeting, he would argue fiercely for a viewpoint and set the tone for the conversation. Once the meeting was going, and the tide was turning in his direction (after much effort and mind-bending on the part of the rest of us), he would begin to change his tone and would shift to the opposite viewpoint! Suddenly, he was arguing against everyone else in the room, and worse, against the idea that he’d so vigorously fought to win the rest of us to adopt.

One day, I pulled him aside and told him that I found his waffling ways frustrating.

“Todd, I’m not waffling,” he told me, “I’m refining. I want to make sure I’m not missing something.”

He went on to explain that the reason he would shift back and forth was to ensure that all sides of the idea were being discussed with equal effort.

“If I don’t do that, especially as the leader, then I am not doing my job to make sure that we’re getting to the best idea, not just the most convenient.”

It is challenging to argue against yourself. Once you’ve determined a course of action, it’s much easier to jump into execution mode and figure it out as you go. However, in the effort to “ship fast” we often fail to lay a sturdy foundation for our work, and the results can be disastrous. Shipping early shouldn’t be equivalent to thoughtlessness. You need to ensure that you are respecting the work by giving it your best mental effort.

When you come up with a great idea:

Spend time thinking about the opposite viewpoint. If you were going to make an argument against it, what would it be?

Find someone to play “devil’s advocate”. Ask them to challenge you with questions that provoke doubts and poke holes in your idea.

Pause – just for a moment – before execution. Why? Because the initial excitement over an idea can lead to ignoring obvious blemishes and result in substandard work.

I am not advocating being overly negative or pessimistic, especially when you are leading others. Don’t be the person no one wants in the room.

Rather, I’m encouraging you to have a fully-engaged, well-structured look at the idea before jumping into execution mode. An ounce of preventative action now is worth a pound of corrective action later.

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