Gators, Golf, and the Executive Decision-Making Process...

Go for it... Drop... or Negotiate?

On a recent family trip to Florida, I had a beautiful drive off the tee. Perfect arc, nice roll… and then it kept rolling… all the way up to a sunbathing alligator.

Yes, a real one. Big. Lazy. Sunbaked. Smiling like he knew I’d have to make a decision. I was golfing with my father-in-law, who has seen me in high-pressure business situations and now—apparently—about to see what I’d do under a very different kind of pressure.

He looks at me, deadpan as if to say: “Well… you going for it?”

Now listen, I’ve made a lot of tough decisions in my career. I’ve launched my own company, built campaigns on tight deadlines, pivoted entire strategies mid-flight, moderated rooms full of execs with strong opinions and stronger Wi-Fi connections.

But nothing quite prepares you for staring down a gator who may or may not be guarding your Pro V1.

In that moment, I had a few options:

➜ Go for it – risk my hand (and my pride) for the sake of the shot.

➜ Drop a new ball – lose the stroke, but keep all my limbs (even though most of them are metal these days).

➜ Try to negotiate with the gator.

I chose option 2. Why? Because sometimes leadership is knowing when to take the risk—and when to walk away with your arms still attached.

We talk about calculated risks all the time in business. But the key word is calculated. Just because you can go for it, doesn’t always mean you should.

So here’s the takeaway from my brush with golf course wildlife:

➜ Great leaders know when to swing big…

➜ And when to drop the ball, smile, and say, “Let’s play the next one smarter.”

Also: Florida golf is always an adventure

What’s the wildest “leadership decision” you’ve had to make under pressure—business or otherwise?

And golfers: would you have gone for it?