In the Line of Fire: How to Handle Tough Questions When It Counts

In the Line of Fire: How to Handle Tough Questions When It Counts

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by Jerry Weissman

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Jerry Weissman has made a career of coaching nearly 500 execs on their IPO roadshows, the most critical presentations of their lives. Now, he's written an indispensable guide to answering the toughest questions you'll ever face. Using compelling examples from Presidential debates to stock analyst meetings, Weissman teaches how to respond with perfect assurance


Jerry Weissman has made a career of coaching nearly 500 execs on their IPO roadshows, the most critical presentations of their lives. Now, he's written an indispensable guide to answering the toughest questions you'll ever face. Using compelling examples from Presidential debates to stock analyst meetings, Weissman teaches how to respond with perfect assurance. Discover how to avoid the defensive, evasive, or contentious answers that have destroyed political careers and ruin credibility. Learn to control your entire exchange with a hostile questioner: the question, answer, interactions with questioner and audience, timing, and above all, yourself. Whether an executive, politician, fundraiser, interviewee, teacher, student -- or even a family member at Thanksgiving dinner -- you're judged on how you handle these moments. Get this book: handle them brilliantly.

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FT Press
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In the Line of FireIntroductionAgility Versus Force

During my 40 years in the communications trade ranging from the control rooms of the CBS Broadcast Center in Manhattan to the boardrooms of some of America's most prestigious corporations, I have heard...and have asked...some highly challenging questions. One of the most challenging I ever heard came during Bill Clinton's presidency when he was engulfed in the firestorm ignited by the revelation of his extramarital affair with Monica Lewinsky, a White House intern.

Despite intense public and media pressure, Clinton continued to fulfill his presidential obligations, among them hosting a state visit by the Prime Minister of the United Kingdom, Tony Blair. On the afternoon of February 6, 1998, after the two heads of state made their customary prepared statements to the press, President Clinton opened the floor to questions from an audience packed with reporters. At that point, he became fair game for nonstate questions on the subject that was uppermost in the minds of the media and the public. One question in particular came from Wolf Blitzer, the senior CNN political correspondent:

Mr. President, Monica Lewinsky's life has been changed forever, her family's life has been changed forever. I wonder how you feel about that and what, if anything, you'd like to say to Monica Lewinsky at this minute?

The stinging question brought a few scattered titters from the other reporters. Looking straight ahead, right at Blitzer, Clinton smiled and bit his lower lip, an expression that had become his trademark.

Then he said,

That's good!

The crowded room erupted in laughter. After it subsided, Clinton continued:

That's good...but at this minute, I am going to stick with my position and not comment.

Blitzer had nailed the acknowledged charismatic master of communication skills at his own game, and the master acknowledged it publicly for all to hear. Fortunately for Clinton, he was able to default to his legal situation and not answer.

Very few people on the face of this planet have the expertise, the charm, the quickness of wit, or the legal circumstances to respond so deftly to challenging questions. Yet very few people on the face of this planet sail through life without being confronted with tough questions. The purpose of this book and its many real-life examples is to provide you with the skills to handle such questions, and only such questions. If all the questions you are ever faced with were of the "Where do I sign?" variety, you could spend your time with a good mystery novel instead. Forewarned is forearmed.

One other forewarning: All the techniques you are about to learn require absolute truth. The operative word in the paragraph above, as well as on the cover of this book, is "handle," meaning how to deal with tough questions. While providing an answer is an integral part of that "handling," every answer you give to every question you get must be honest and straightforward. If not, all the other techniques will be for naught. With a truthful answer as your foundation, all those techniques will enable you to survive, if not prevail, in the line of fire.

Challenging Questions

We begin our journey of discovery by understanding why people ask challenging questions. Journalists such as Wolf Blitzer ask these kinds of questions because, being familiar with the classical art of drama, they know that conflict creates drama. Aristotle 101.

Why do people in business ask challenging questions? Because they are mean-spirited? Perhaps. Because they want to test your mettle? Perhaps. More likely it is because when you are presenting your case, which is just the case in almost every decisive communication in well as in all walks of are asking your opposite party or parties, your target audience, to change. Most human beings are resistant to change, and so they kick the tires. You are the tires.

In the most mission-critical of all business presentations, the Initial Public Offering (IPO) road show...a form of communication I have had the opportunity and privilege to influence with nearly 500 companies, among them Cisco Systems, Intuit, Yahoo!, and Dolby Laboratories...presenters ask their investor audiences to change: to buy a stock that never existed. In fact, when companies offer shares to the public for the first time, the U.S. Securities and Exchange Commission mandates that the companies specifically state their intentions in print. The SEC requires distribution of a prospectus containing a boilerplate sentence that reads, "There has been no prior public market for the company's common stock." In other words, "Invest at your own risk." Caveat emptor. As a result, when the companies' executive teams take their presentations on the road, they are inevitably assaulted with challenging questions from their potential investors.

While the stakes in an IPO road show are exceedingly the tens of millions of dollars...the character of the challenge is no different from that of potential customers considering a new product, potential partners considering a strategic relationship, pressured managers considering a request for additional expenditures, concerned citizens considering a dark horse candidate, or even affluent contributors considering a donation to a nascent, not-for-profit cause.

The inherent challenge in these circumstances is compounded in presentation settings where the intensity level is raised by several additional factors:

  • Public exposure. The risk of a mistake is magnified in large groups.

  • Group dynamics. The more people in the audience, the more difficult it is to maintain control.

  • One against many. Audiences have an affinity bond among themselves and apart from the presenter or speaker.

The result is open season on the lone figure spotlighted at the front of the room, who then becomes fair game for a volley of even more challenging questions.

How, then, to level the playing field? How, then, to give the presenter the weapons to withstand the attack? How, then, to survive the slings and arrows unleashed in the form of questions?

The answer lies in the David versus Goliath match, in which a mere youth was able to defeat a mighty giant using only a stone from a slingshot. This biblical parable has numerous equivalents in military warfare. History abounds with examples in which small, outnumbered, under-equipped units were able to combat vastly superior forces by using adroit maneuvers and clever defenses. Remember the Alamo, but also remember Thermopylae, Masada, Agincourt, The Bastille, Stalingrad, The Battle of the Bulge, Iwo Jima, and The Six-Day War. All these legendary battles share one common denominator: leverage, or the use of agility to counter force.

Martial Arts

For our purposes, the most pertinent modern equivalent is the martial arts, in which a skilled practitioner can compete with a superior opponent by using dexterity rather than might. Bruce Lee, a diminutive kick boxer, became an international star by virtue of his uncanny ability to prevail over multiple and mightier armed opponents using only his flying feet and hands. Evolved from Asian philosophy and religion, the martial arts employ these critical mental and physical skills:







A solitary presenter or speaker facing challenging questions from a hostile audience can deploy these same pivotal dynamics against a sea of troubles and, by opposing, end them. This book will translate each of these martial arts skills into Q&A techniques and then demonstrate how you can apply them in your mission-critical encounters. The objective is to put you in charge of those sessions and enable you to win in your exchanges when it counts.

This objective can be stated in one word, although it will take 168 pages to present them in full. That one word is control. When you are confronted with tough questions, you can control

  • The question

  • Your answer

  • The questioner

  • The audience

  • The time

  • Yourself

Effective Management Perceived

A synonym for the verb "control" is "manage." Therefore, the subliminal perception of a well-handled question is Effective Management. Of course, no one in your target audience is going to conclude that because you fielded a tough question well, you are a good manager. That is a bit of a stretch. But the converse proves the point. If your response to a challenging question is defensive, evasive, or contentious, you lose credibility...and with it the likelihood of attaining your objective in the interchange. If your response is prompt, assured, and to the point, you will be far more likely to emerge unscathed, if not fully victorious.

This concept goes all the way back to the first millennium. In Beowulf, the heroic saga that is one of the foundation works of the English language, one of the lines reads: "Behavior that's admired is the path to power among people everywhere."

In the twenty-first century, that same concept as it relates to tough questions was expressed by David Bellet, the Chairman of Crown Advisors International, one of Wall Street's most successful long-term investment firms. Having been an early backer of many successful companies, among them Hewlett-Packard, Sony, and Intel, David is solicited to invest almost daily. In response, he often fires challenging questions at his petitioners.

"When I ask questions," says David, "I don't really have to have the full answer because I can't know the subject as well as the presenter. What I look for is whether the presenter has thought about the question, been candid, thorough, and direct and how the presenter handles himself or herself under stress; if that person has the passion of 'fire in the belly' and can stand tall in the line of fire."

Baptism Under Fire

I, too, was once in the business of asking tough questions. Before becoming a presentation coach for those nearly 500 IPO road shows, as well as for thousands of other presentations ranging from raising private capital to launching products, seeking partnerships, and requisitioning budget approvals, I spent a decade as a news and public affairs producer at CBS Television in New York. As a student of the classical art of drama and with the full knowledge that conflict creates drama, I became an expert at asking challenging questions.

My baptism under fire came early in my tenure at CBS. In 1963, I was assigned to be the Associate Producer of a documentary series called Eye on New York, whose host was the then newly hired Mike Wallace. Although Sixty Minutes, Mike's magnum opus, would not debut for another five years, he came to CBS largely on the strength of the reputation he had developed on another New York television station as an aggressive interrogator on a series called Night Beat. Mike had regularly bombarded his Night Beat guests with tough questions and was intent on maintaining his inquisitorial reputation at CBS. He fully expected his Associate Producer to provide him with live ammunition for his firepower. Heaven help me when I did not.

Fortunately, I survived Mike's slings and arrows by learning how to devise tough questions. In the process, I also learned how to handle those same questions. This book is a compilation of those techniques, seasoned and battle-tested for nearly 20 years in business with my corporate clients.

You will find the techniques illustrated with a host of examples from the business world, as well as from the white-hot cauldron of debate in the political world.* In that world...unlike business and other areas of persuasive endeavor where facts and logic are at stake...the issue is a contest of individuals pitted one against the other in mortal combat: Only the winner survives. Although the lone presenter or speaker pitted against the challenging forces of an audience is not quite as lethal as politics, the one-against-many odds raise the stakes. Therefore, analyzing the dynamics of political debate will serve as a tried and tested role model for your Q&A skills. The following pages will provide you with an arsenal of weapons you will need when you step into the line of fire.

Expanding upon David Bellet's observation, the objective of this book is not so much to show you how to respond with the right answers as it is to show you how to establish a positive perception with your audiences by giving them the confidence that you can manage adversity, stay the course, and stay in control.

*For a companion DVD of the original videos of these examples, please visit

© Copyright Pearson Education. All rights reserved.

What People are saying about this

Ray Dolby
"Jerry Weissman helped prepare my management team for our recent IPO. I sat in on some of the sessions and was most impressed with Jerry's innovative ways of teaching and optimizing effective executive communication methods. This training, encapsulated well in his new book, In the Line of Fire," paid off handsomely during our numerous road show presentations."
Founder and Chairman, Dolby Laboratories, Inc.
Leslie Culbertson
"Jerry's book is a must read for any presenter facing tough and challenging questions from their audience. This book provides the fundamental foundation on how to prepare, be agile, and take charge no matter how difficult the question."
Corporate Vice President Director of Corporate Finance, Intel Corporation
Po Bronson
"In an era where businesspeople and politicians unfortunately have proven their inability to be honest with bad news, I believe this book should be prescribed reading in every business school, and for every management training session. In fact, I hope it is read by a far wider audience than that. It's just what our society needs right now."
author of the bestselling What Should I Do With My Life?
Sue Bostrom
"In my role at Cisco Systems, I am confronted with challenging questions from customers, government leaders, press, and analysts on a daily basis. The techniques used in this book, In the Line of Fire, are spot on; providing straightforward ways to be on the offense in all communications situations."
SVP Internet Business Solutions Group and Worldwide Government Affairs, Cisco Systems
Scott Cook
"Jerry Weissman tells the tales of the makings of presidents and kings, the dramas of the dramatic moments of our time, and in each episode he uncovers the simple truths behind what makes great leaders like Ronald Reagan and Colin Powell loved and trusted. Great truths made simple and compelling for any leader to use."
Founding CEO, Intuit
Mike Wallace
"I've been asking tough questions for half a century and listening to variously brilliant, boring, evasive or illuminating answers. Jerry Weissman's book will help anyone...anyone...answer even the toughest questions."
Senior Correspondent, Sixty Minutes, CBS News
Tim Koogle
"Have you ever been faced with a tough question? Jerry Weissman shows how it's not necessarily what the answer is. It's how you answer that will allow you to prevail and win!"
Founding CEO, Yahoo!
Sky Dayton
"During one of the most important periods of my career, Jerry used the concepts in In the Line of Fire to prepare me and my team for the EarthLink IPO road show. He helped us field tough questions from the toughest possible audience: potential investors, but the same skills are necessary for every audience."
Founder EarthLink and Boingo Wireless, CEO SK-EarthLink

Meet the Author

JERRY WEISSMAN, the world's #1 corporate presentations coach, founded and leads Power Presentations, Ltd. in Foster City, CA. His private clients include executives at hundreds of the world's top companies, including Yahoo!, Intel, Cisco Systems, Intuit, Dolby Laboratories, and Microsoft.

Weissman coached Cisco's executives before their immensely successful IPO road show; afterward, the firm's chairman attributed at least two to three dollars of Cisco's offering price to Weissman's work. Since then, he has prepared executives for nearly 500 IPO road shows, helping them raise hundreds of billions of dollars.

Weissman is author of the global bestseller Presenting to Win: The Art of Telling Your Story (Financial Times Prentice Hall, 2003).

In this book, you'll find many examples of Q&A sessions and political debates in the public arena. The original videos of these sessions are available on a DVD that you can obtain by visiting

© Copyright Pearson Education. All rights reserved.

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In the Line of Fire 3.5 out of 5 based on 0 ratings. 8 reviews.
DrNabilMajid More than 1 year ago
In the Line of Fire is all about you... to control the Q&A session, to control yourself, to control the follow. Therefore, you learn to manage effectively. Although the vast majority of examples were about public servants' debates, you can easily realize that if you can understand and apply their techniques to your life situations you can succeed. After all, the techniques are learnable I recommend this book highly especially after reading more compelling titles such as Presenting to Win and the Power Presenter. The first is the best of the trilogy I learned a lot and you can too...
Anonymous More than 1 year ago
First of all I would say this book deserves four stars but I gave it an extra to counter the previous review that had not even read it. This book looks at the dynamics of question and answer sessions and has some great insights and ideas. It is very nuanced and my only criticism is that some of the lines he draws would still be hard for me to find on my own. But I learned a lot.
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Teenylion More than 1 year ago
Haven't read yet