Jim Whiddon’s book, “The Old School Advantage: Timeless Tools for Every Generation,” started out two years ago as a lengthy love letter to his four millennial children.

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Jim Whiddon says old school is new again.

So the 56-year-old financial consultant has written a how-to-communicate guide for millennials who want to jump-start their careers and employers who want to connect with the largest generation in the U.S. workforce.

His book, “The Old School Advantage: Timeless Tools for Every Generation,” released in February by Brown Books Publishing Group, started out two years ago as a lengthy love letter to his four millennial children, who are now ages 17 to 24. He noticed that they and their friends just didn’t have the same observation and listening skills that most boomers learned from their parents.

“Remember those station wagon vacations and listening to your mom and dad talking?” he asks. “Today they sit in the backseat with earbuds on.

“The economic climate all over the planet is going to make things more challenging for millennials than it was for my generation,” he says. “It’s really about equipping them for the future.”

First-time job applicants often face the same rote inquiries.

There’s the ubiquitous ice-breaker: Tell me a little bit about yourself.

“We tell students to pick wow words that best describe them,” he says. “‘I believe in being consistent.’ ‘A lot of people would describe me as being very determined.’ ‘I have common sense.’ ‘I think it’s important to … ’ and then they fill in the blank.

“It’s such an open-ended question. We want them to personalize it with the words that they’ve already determined describes their characteristics.”

Be prepared for: How did you find out about this position?

Do your homework. Say that you like the company’s products or admire its culture and decided to look into its job opportunities.

“The answer has to be true and authentic,” he says. “But just saying ‘I saw your ad online, and I thought I’d call you,’ simply won’t cut it.”

The biggest curveball question is: What books are you currently reading, or who is your favorite author?

That’s one he teaches to corporate clients when they’re working the other side of the hiring equation. “It’s an excellent way for a recruiter to gain insight into not only your habits but also your character,” he says.

The only wrong answer is that you don’t read.

One chapter deals with having a pointed discussion without letting it disintegrate into pointless bickering.

You start with leading questions:

—What do you mean by that?

—How did you come to that conclusion?

—Have you ever considered … ?

The first clues you into any bias.

The second asks for evidence. “Too often my kids and their generation listen to bumper-sticker messages.”

And the third allows you to take the other side offense without being offensive.

“Old School” also teaches power words or phrases that show off your intelligence and improve the way others see you as a person.

“‘First things first’ says you’re organized and a sequential thinker,” he says.

Supplant the mindless “awesome” with “exceptional” or “extraordinary,” which will make you seem wise beyond your years.

Whiddon loves the “ability” words: responsibility, predictability, accountability, reliability and stability. “Anytime a young person uses an ability word, their abilities are seen as greater than they otherwise would be because those words are very positive in the minds of older people.”

But his favorite phrase is “Let’s get to work.”

“That sends chills up the spines of people my age because we love that go-getter attitude,” he said.

He also encourages dialing down your opinions. “Don’t be so declarative. You think you know it all, but you don’t,” he says. “Yeah, you can say what you want, but temper it with ‘In my opinion’ or ‘I believe.’ It’s gentler and doesn’t offend people.”

Whiddon believes the most powerful word in the English language is imagine. “Whatever follows in the fill-in-the-blank has hundreds of millions of meanings. Everybody imagines something different.”

Whiddon, who ran his own wealth management company for 30 years, is now a “national thought leader” for the St. Louis-based company that bought it. The book started out as a handout for clients who wanted to pass along time-tested techniques to their children or grandchildren.

“It’s a way to say to our clients, ‘We know that worries about your money sometimes keeps you up at night. But more often than not, your kids and your grandkids are what worry you most,’” Whiddon says.

But lately, his lessons are gaining traction with educators and employers who want to learn better ways to deal with the distracted social media generation. He’s formed a new company around the principles. He and his team of three consultants go into high schools, colleges and companies and give tutorials about the value of going back to the future.

Whiddon’s children want to go into business with him. He’d love to have them — after they’ve had experience in the real world.

His oldest, Johnathan, 24, is nailing down his first post-college job. He says the most valuable tool his dad has handed him is the handwritten thank you card. “That makes an immediate splash with potential employers.”

A picture might be worth 1,000 words, but Whiddon contends that a story is worth 1,000 pictures. “Nothing is stickier or more memorable than the right story told the right way at the right time and place,” he says. “When people tell you a story, their body language changes, they lean forward and look directly at you.”

The section of the book I liked best is the one on the “reverse interview” — when the interviewer asks the job applicant if he or she has any questions.

“We have a saying that: ‘You are judged by the quality of the questions that you ask,’” Whiddon says. “When they give you the ball, you want your questions to be powerful and impressive.”

Among the arsenal of suggested loaded questions:

What brought you to this company and why have you stayed here?

How would you describe the company’s values?

What’s the biggest challenge your company faces right now?

What are the two or three traits that are most important for an employee of this company to have?

And my personal favorite: Why is this position open?

What if there’s dead silence?

“That’s telling,” he says, “don’t you think?”