I advise people who want to engage others through their writing to pretend they’re having a conversation with the person they most want to connect with. As I prepared for a talk at the University of Toronto last night, I figured I would use George Clooney as my personal example. Gorgeous. Smart. A talker.

can George Clooney write?My fantasy involves persuading George to use my book, Write Like You Talk Only Better, to help him write his memoirs. I know that’s an odd fantasy for a woman, but even in my fantasties I know I wouldn’t stand a romantic chance. Besides, riding motorcycles and squeezing into designer gowns are not my style.

But I believe that one day George will take a break from hit movies, pretty girls, racing and protesting to share his experience and wisdom. This won’t be an “as told to” collection of celebrity vignettes. He will want to write the book himself. After all, his father is a respected journalist. Writing must be in his DNA.

Better still, he will inspire people who are not so gifted.

More than a pretty face

To better understand George, I asked the two questions I advise everyone to ask before they start writing: What gets him going in the morning? What keeps him awake at night? Much simpler and personal than all that data mining the online gurus extoll.

What gets George going, his passions, are the movies, pretty girls, racing and protesting. What keeps him awake at night? I’d say that George wants people to know that he’s deeper than the celluloid images.

Too busy for the book?

If George is too busy with movies, pretty girls, racing and protesting, he may instead opt for my upcoming e-learning series, which will take only about five minutes a day for two weeks.  With practice while he works on the book. He could squeeze it in between takes or while awaiting bail.

Better still, private coaching. This fantasy keeps getting better.

George’s warmup

As a warmup, I would coach George to write a 25-word statement that summarizes the main message he wants to deliver. I would ask him who he most wants to connect with. People who share his passions and convictions, George would reply. I would ask George: what gets this kind of person going in the morning (justice and fun) and what keeps him awake at night (the fear that his life won’t amount to anything because he’s not hot and connected like George.)

With that knowledge in mind, I would advise George to pretend he’s having a conversation with this guy. We’ll call him Fred.

Start with the murder

Now that George knows what drives Fred, the book-writing conversation can begin. He’ll start with a story. Not the kind of childhood knife attack story Tina Fey was no doubt advised to lead with in the otherwise enjoyable Bossypants. She admitted the only scar was physical. No, George needs an emotional turning point, that explains why he became the person he is today and sets up the rest of the narrative.

Next, I would encourage George to write the final chapter. That way, he could make sure that Fred, and people just like him, will wind up with an understanding that they share the spirit and principles that make their lives count. Plus writing will be easier because George will know where he wants to finish.

George shows his smarts

I know that George can hire editors, or ask his father, to fix up his writing. But I think he would take pride in handing in a reasonably polished draft. So he would love my tips about how to make his writing unforgettable and concise. He would laugh at the part about the spinach-in-your-teeth mistakes that our over-reliance on spell check has produced. But he would take seriously my advice about remembering to write “its” for possessives instead of “it’s.” After all, George wants people to know he’s smart.

George would open his stories with the conflict that drives the plot, as in the murder in Law and Order and other crime dramas. He would make sure that Fred, and people just like him, can identify with how he feels deep down inside. And he’d make sure that almost every story drives home the point that he wrote during his warmup.

Hollywood endings

Through the coaching, George and I would become close friends, eventually soul mates. I would spend holidays with him at Lake Como. While I’m away, my teens wouldn’t throw parties or overflow the toilet and my aging parents would manage to stay out of the hospital.

George would tweet and rave about my book so much that it becomes a best seller.

Then one day, after a particularly boring conversation with his latest bimbette, George would take a second look at me. I would fling off my glasses, puff up my short hair and melt into his arms. In the background, the sun sets and romantic music serenades. Fred drops by, but we’re too busy to answer the door.

Fade to black.

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What I would teach George Clooney
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