Your Plan B's are wrong.

Good strategists consistently plan for best and worst case scenarios.

What does a good scenario look like and what will it require?

What does a disaster scenario look like, how will I know and what mitigations can I enact?

Great strategists, however, plan for 2nd best best scenarios. Or Plan B's.

The real world is wicked.

Things go wrong, randomness pervades, all information is incomplete.

How to navigate Plan B's is much less obvious, much more frequent and much more important to get right, consistently.

The alpha hides in the nuance.

Here are three specific Plan B's strategists get wrong.

The first example, you've likely already encountered: Who to hire.

Obviously, the best case is someone with higher talent with higher character (1) and the worst is (4).

But the best Plan B is (2) not (3).

The output of a single toxic unicorn may be phenomenal but the cost to the team will be irreversible. It'll also drive your (1)'s away.

Have multiple toxic unicorns and you create a system of accelerating adverse selection where only the most toxic stay and survive until they eat each other alive.

You are much better off sacrificing pure talent such that you raise the average collective quality of everyone. More slowly, yes, but sustainably.

(Simon Sinek talks about it in the context of the Navy SEALs.)

The second example: Decision-making.

Again, (1) and (4) are obvious, but the best Plan B is (2) not (3).

Said another way, I do not believe in "fewer, better, bigger" when it comes to decision-making.

In a wicked world, like marketing & advertising, the biggest mistake isn't making too many wrong decisions, it's making too few decisions, too infrequently (I got this from Intel's Andy Grove.)

It's better to make more decisions, see what happens, learn, adjust quickly and continue to make more decisions than to wait for conditions to improve (they often don't), more perfect information (it often never comes) or wait to make a grand plan (too much would have changed by then rendering it obsolete).

Better outcomes are gained by more, more frequent action (and the new evidence derived)-- regardless of how uncomfortable it may be.

Compel yourself and everyone around you to make more decisions.

The last example is the most trivial, but the one I find the most dangerous: Big meetings. A pitch, a multi-day workshop, a creative presentation.

There are few feelings that are as great as the feeling of a good meeting.

The adrenaline, relief, joy, pride released after late nights of collective & compounded anxiety, pressure, fatigue is unparalleled. (If you know, you know.)

"The CMO loved it!"

"Everyone participated!"

"We got so much done!"

The problem is that good meetings often have no lasting, meaningful or tangible outcome.

The tyranny of good meetings is how much they create the (feel-good) illusion of things mattering (when they don't), people committing or agreeing (when they don't) and work making progress (when it's not).

It often all dissipates into nothing 24 hours after the meeting when everyone realized it was all just a great performance. Then nothing happens.

Here's my advice: there's often a moment in big meetings when you have to decide whether to argue, disagree, create conflict (i.e. ruin the good meeting) or go with the flow or remain silent (i.e. increase your odds of having a good meeting)-- always choose to have the bad meeting.

Conflict creates clarity.

Clarity increases the odds of tangible outcomes.

Bad meetings feel bad.

Good meetings that go nowhere feel worse.

Your job is not to have more good meetings.

Your job is to have whatever meetings are necessary to do better work.

Never conflate the two.

In sum, make more Plan B's decisions, more frequently with more high character people in more bad meetings.

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