Be more Socratic.

It took me years to realize I was doing the whole CSO thing wrong.

Imagine you're a strategist on the team; consider the "math" of a typical meeting between you and me.

You’ve spent hours/days/weeks researching, thinking, and interrogating a problem.

I have an hour.

You’ve gone deep, have already tried a few things, reversed out of some dead-ends.

I am probably hearing things for the first time (and, let's be honest, there’s much you're leaving out).

You’re accountable to the day-to-day politics, process, and whatever happens next.

I'm not.

With such asymmetry, I’d be a fool to tell you what to do. (Yet, a fool I was.)

Because whatever I may have in experience, you more than surpass in specific, subject matter expertise.

Yet, the reflex for CSO's is to tell you what to do because the expectation is he/she is always “the smartest person in the room.”

Surely, a meeting is an opportunity for the CSO to tell you the right thing to do.

But in reality, any attempt to do so is uninformed babble masquerading as helpful feedback.

I realized this was the wrong way because:

1. It creates an impression that your work always needs to be "approved." And may not matter until it’s given some kind of higher endorsement. This is absurd.
2. This dynamic doesn't scale. It's bad for both of us when you stall, hold back or second guess until we meet. Meetings become rare gates instead of focused moments for discussion. What happens when you are I not in a meeting is much more important than when we're are in a meeting.
3. Last, and most importantly, I’m often wrong. In the volatile space that is marketing/advertising, problems may rhyme, but almost never have identical solutions. By definition, whatever may have worked for me then probably won’t work for you now. At least, not in a predictable enough way for me to simply declare what you should.

I've found it's more effective to be Socratic.

CSOs should embrace that the more senior they get, the less it's about what they know and the more it's about how they know.

It's less about knowing what the "best" strategy is and more about recognizing the signs of a good strategy as done by you.

My most useful contribution isn't better answers-- it's better questions.

To consistently provide lines of open-ended inquiry that tests your assumptions, compels you to defend or expand your position, reveals possible blind spots, and in the process, helps you to either pivot or gain confidence-- without an inherent bias from me to do either.

Being Socratic means reasoning together, side-by-side.

It's a delicate art, though.

If nothing else, seniority distorts the honesty of conversations.

That's why the onus is on me to:

1. Temporarily separate you from your work. Strategists can get emotionally attached to their work, but being Socratic should never feel personal.
2. Explicitly remove any implied pressure my questions create. Leaders often disguise direction as innocent questions. "Did you think about doing X?" as a way to say "You should do X." It's important that I consistently remind you that I'm actually asking because I don't know or I want to understand your thinking-- there's no ulterior meaning.
3. Never take credit but always take blame. A safe space is required to have an honest debate.

When all is uncertain and there are no right answers, only logic reigns supreme.

And yours is as good as mine.

And ours, interrogated together, is best of all.

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