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Know the Lay of the Land (Intentional Leadership, Part 2)

A Businessman Jumping Off A Cliff

Ah, geez. There it is. Right there on his presentation slide. And right up there in front of the CEO. I start silently counting in my head to see how many seconds it will take before the CEO blows his top.


Walking into any engagement (a presentation, meeting, negotiation, or even a 1:1) without understanding the lay of the land is putting an awful lot in the hands of chance. And chance tends to be pretty crazy. Yes, it will lead you to a great opportunity from time to time, but it can also run off with your opportunities in a dozen different directions, many of them directions you’d rather not go.

You might find yourself falling off a cliff. Not fun.

I know that you know preparation is a good thing. But like all high achievers, you are BUSY. You don’t feel you have enough time to do the pre-work that will guarantee your best outcomes. And you are really good at “winging it” in the moment, right?

So, why take the time to proactively understand the lay of the land?

Lay of the land: the general state or condition of affairs under consideration; the facts of a situation


The obvious answer is that the amount of time you invest in understanding the situation you are walking into is usually dwarfed by the amount of time you spend later trying to correct, clean up, re-engage, or start all over after your presentation, pitch, proposal, or discussion goes less than wonderfully.

And the hard truth is that people tend to over-estimate their “winging it” abilities. Not because they aren’t smart or talented, but because they aren’t clairvoyant.

Trial lawyers know this well. They are taught to never ask a question to which they do not already know the answer. The notoriously famous example of this basic tenet being violated was when OJ Simpson was asked by a prosecutor to try on “the bloody glove”. We all got to see the prosecutors’ case blow up right in front of our eyes.

This happens far too often in the work setting also. People come to meetings with a clear intention to accomplish something, and then proceed to walk right off a cliff because they failed to anticipate a reaction or tough question, or they present info or data in a way that hits someone’s hot button.

They did not take the time in advance to understand the lay of the land.

The worst news is that failing to understand the situation you are walking into in advance can not only hinder your efforts in your particular engagement, it may also irreparably destroy your chance of success of your entire project, proposal, or presentation…and even potentially harm your career.

…8…9…10…thar he blows!

Our CEO was a data nerd with a super human focus on numbers. A sure way to get on his bad side was to present data that was out of context or (God forbid!) inaccurate. This was not a huge corporate secret. A question or two to the right people could have told the presenter that important fact in advance.

What a shame. I hope his singed eyebrows have grown back by now.

Take the time to understand the lay of the land before your next engagement: do a little research, ask questions, do your homework, and plan your approach accordingly.

Don’t rely on “Leadership by Chance.”

Go get ‘em, tiger.

P.S. In case you missed Part 1 of Intentional Leadership, see it here.

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