The time to play devil's advocate...

...is not at the last minute.

We were in the final throes of planning for a national sales meeting.

We’d dedicated months to this thing. Location, theme, agenda, speakers, catering, entertainment. So many details, all wrangled and captured in a massive spreadsheet.

It was our last meeting before we all boarded flights to get there. Our meeting sponsor piped up:

“Are we sure this keynote speaker will really resonate?”

The keynote speaker was a former Olympian with an amazing backstory of overcoming challenges no mortal could conquer. He was engaging, energetic and motivating – just what you want to rev up your salesforce.

We’d locked him down weeks ago.

I felt that special kind of nausea that comes before a full-blown panic attack.

I (calmly) explained that we had all agreed – again, weeks ago – that this speaker was The One. We’d already paid the hefty deposit. All of our pre-meeting communications included his headshot.

“OK, but – not everyone is into sports. I just don’t want to exclude anyone.”

Fair pushback.

That he had not shared before we signed the speaker.

He went on to list a few more concerns that he’d never mentioned before. The former Olympian was American, but we had some Europeans in our audience – would that be a problem? Our new VP was a woman – maybe the keynote speaker should be, too?

Then he looked at my face. Really looked at it.

“I’m just playing devil’s advocate,” he said.

This wasn’t the first time this particular executive claimed that role. I’d worked with him on a few other projects. He spoke often about the value of disruptive thinking.

That wasn’t what this was.

A devil’s advocate raises questions thoughtfully and early enough that the team can digest and act on the feedback.

His concerns were…cosmetic at that point.

This wasn’t disruptive thinking. It was just disruption – at the worst time possible.

These moments made me wonder about the mechanism that drove them. I came up with three possible theories:

1. He hadn’t bothered to put any real thought into the decision at the time we had to make it.

2. When it was in the theoretical stage, it wasn’t compelling enough to really consider. Once it became real, he realized he had a stake in the game and had to step up and contribute.

3. He really enjoyed lobbing a grenade when it would do maximum damage. Wait until the underlings feel comfortable and confident, then sow doubt with an ill-timed question or observation.

Whatever the case, I have since developed a theory of my own: if you want to challenge a decision, do it when there’s still time to make a better one.

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