The 7 toughest questions (and how to handle them)

By Jerry Weissman

In the professional world, tough questions are as fundamental as paper clips and staples. Starting with the employment interview and ranging through staff meetings, management reviews, informal briefings and formal presentations, almost every business encounter has the potential to draw dangerous crossfire. And in many circles, inquisitorial grilling is as much a part of the business ritual as a handshake to seal a deal.

Why do business people ask tough questions? Because they are mean-spirited? Perhaps. Because they want to test your mettle? Maybe. More likely it's because when you make a presentation, you assume the role of a solicitor. In that role, you ask those you solicit (i.e., opposite parties, target audiences) to change. Most people are resistant to change and so they kick the tires. You are the tires.

How then to avoid damage from the kicks? How do you survive slings and arrows unleashed? How do you handle tough questions in the line of fire?

The savage seven
During my 40 years in the communication trade, which has ranged from control rooms in the CBS Broadcast Center in Manhattan to the boardrooms of some of America's most prestigious corporations, I have heard — and have asked — tens of thousands of tough questions. But all of them can be distilled into just seven types:
1. Hostile
2. Negative



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3. Irrelevant
4. Multiple
5. Statements that are not questions
6. Presented material
7. Guilty as charged

Let's look at each of type of tough question and ways to handle it. The operative word here is handle, which goes well beyond providing an answer. Effective handling of tough questions requires a broader strategy, one that both controls the intent behind the question and manages the outcome of the exchange.

Tough question type 1: Hostile
"Wait a minute! You tell me that your product is going to save us money, then you give me a sticker-shock price that's twice as much as your competition asks. That's outrageous! Where do you get off charging so much?"

The standard sales answer to this kind of question goes something like this: "When you consider the total cost of ownership of our solution, you'll see that our product will cost you less money in the long run."

Unfortunately, answering this way is tantamount to telling your potential buyer that he or she is wrong. After all, the clear implication in the question is that you are charging too much, and the clear implication in your answer is that you are not charging too much. If you answer in that way, your customer will perceive that you're contentious, an inference that is highly unlikely to induce them to do anything.

Another conventional answering approach is to repeat the question. However if, immediately after the above question, you repeat it — "Where do we get off charging so much?" — your echo tends to validate the potential buyer's inference that you're overcharging and you are then perceived as admitting guilt.

What's worse, when you answer your own question, you'll most likely start out with the defensive "When you consider the total cost of ownership…" In essence, you are carrying forward a negative balance.

Therefore, when you get a hostile question such as this one, do not answer it directly and do not repeat it word for word. Instead, listen for the key issue, and when you identify it, paraphrase it. Repeat the question in another form; deflect the challenge and control the meaning.

To paraphrase the original question, begin with an interrogative word — such as what, why, how, does, can, is — and conclude with a question mark. These beginning and end points serve to bracket the core idea of the original question — the key issue.

Now, please look at the original question again and define the key issue in one word. If you say "overcharging," "high price," "expensive" or "costly," you are focusing on the questioner's feeling or emotion about the price of your product.

The key issue, simply, is "price." Now incorporate the word price in a paraphrased question, such as:"What is our pricing rationale?""Why have we chosen this price point?""How did we arrive at the price?"Notice that when you strip the charged phrases sticker shock, twice as much, outrageous and so much out of the original question, you neutralize the hostility. When you begin your answer, you only have to address the price itself, and not whether it is too high or too low.

Tough question type 2: Negative
"This is the age of mergers. Banks are consolidating. Manufacturing and pharmaceutical companies are joining forces. Everybody's throwing their lot in with others. Instead of going out there and trying to be the Lone Ranger, why don't you throw your lot in with one of the larger companies in your sector? You can either get acquired, merge or partner."

The subtext of this question is: Why don't you do what the questioner thinks you should do, instead of what your presentation told the audience you will do (which, in this case, was to go it alone and aspire for market leadership).

The key issue in this question has to do with independence.

If you, as presenter, spend any time dealing with "Why don't you?" questions, answering them directly or defensively will only invite more negative questions, and you'll be swatting flies all day. Instead, turn the negative into a positive, by addressing only why you intend to do what you said you'd do. The paraphrase you'll start your answer with is, "Why are we remaining independent?"

Tough question type 3: Irrelevant
"How come your logo doesn't have a space between the two words?"

This kind of question usually elicits a smile, a snicker or a frown from the presenter, each of which may be perceived by the questioner as disdain. When you're presenting, there is no such thing as an irrelevant question. Every question from every audience member is relevant and appropriate. If they ask it, you must answer it.

Replace the snicker or frown with a paraphrased question, "What's behind our logo design?" or "Why the logo style?"

Tough question type 4: Multiple questions
"How much did you spend on R&D last year? What percentage of your revenues does that represent? And what is your R&D model going forward?"

You'll probably have no difficulty answering multiple questions that are related. In this example, any financial presenter could easily handle all three because they have a common thread.

The difficulty comes when one of the questions in the set is from left field, another from right field and another from the moon. What many presenters do in these circumstances is to dive in to answer one of them, then lose track of the rest. At that point, the presenter often turns to the questioner and asks, "What was your other question?"

The audience's perception? You weren't listening.

Don't burden yourself with having to remember someone else's ramble. Instead pick only one of the questions to answer: the easiest, the hardest, the last, the first, the one that surprised you or the one you were expecting. Paraphrase this question, answer it, and then turn back to the person who asked and, using the declarative, say, "You had another question."

The audience member will then either repeat the other questions, and you can answer each one succinctly, or the questioner might say, "That's all right, you covered it." The latter response is common in Q & A sessions because most people can't remember their own questions, especially if they ramble.

Tough question type 5: Statement
"Your new solution appears to be very effective, but you've only just released it. You don't know if it has any kinks. I'd like to see it field-tested, before I commit. It's not for us at this time."

This statement, made during the Q & A session, is not really a question. But if you are trying to land a sale for the early release of your new product, you certainly don't want to leave it at this. Instead, paraphrase the statement as a question: "Why adopt our new product now?" Then follow with your answer about why your prospective customer wants to be the first kid on the block to enjoy the many benefits of your promising new product.

Tough question type 6: Material previously covered
You've probably witnessed this common occurrence: A presenter delivers a thorough explanation of a new product, only to have someone in the audience ask a question about one of the product's features — a topic covered thoroughly in the presentation. At an internal company meeting, this usually results in audible groans from other members of the audience. At an external meeting, other audience members, being discreet, stifle their groans.

Most presenters, being both discreet and respectful, also stifle a groan, but all too often will begin their answer with, "As I said…" This seemingly innocuous phrase telegraphs impatience with the questioner as well as condescension.

Instead, move directly into the answer as though you hadn't covered the subject in depth earlier: "Absolutely! Our new product performs this function better than any other product on the market." Take advantage of this opportunity to briefly recap the main features of your new product. Resist the temptation, however, to go into the material in as much detail as you did in your original presentation. Answer succinctly and move on to the next question.

Tough question type 7: Guilty as charged
Your startup company is entering a sector dominated by a larger, longstanding competitor. An audience member stands up: "There are dozens of little start-ups doing exactly what you're doing. Then there all those big guys, with their entrenched market share. It's a jungle out there, and you're only just getting off the ground. What on earth makes you think you can survive?"

This final question type is perhaps the toughest of all, as it concerns a difficult issue about which you or your company are "guilty as charged." The underlying issue posed by the question is true. Startups do have a difficult challenge, but you don't have to plead guilty and surrender the point.

Here are a few more productive ways to respond:Start by paraphrasing: "How will we compete? …"Agree with the point: "You're absolutely right; it is a jungle out there. …"Don't agree too long; step on the brakes and make a sharp U-turn: "But that doesn't mean that there isn't room for a new entrant. …"Supply evidence: "Those large companies are top-heavy and have multiple interests, while our agility and sole focus have netted us 15 major customers in our first year of operation. …"Conclude positively. "So we're confident that we not only can compete effectively, but will succeed in this market."Master these techniques for handling the tough questions, and you'll never again have to feel like you're in the line of fire.

(See also 7 basic tactics for tough questions)

This article is based on excerpts from In the Line of Fire: How to Handle Tough Questions…When it Counts by Jerry Weissman (Pearson Education, Prentice Hall, 2005) and its companion DVD, In the Line of Fire: An Interactive Guide to Handling Tough Questions, featuring video clips of major political debates, press conferences and media interviews. Both products are available at www.powerltd.com.

Originally published in the October 2005 issue of Presentations magazine.

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