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There’s no such thing as a stupid question

I once asked a real estate broker whose client was looking to buy warehouses why the client had chosen to invest in that type of property. The broker said he’d never ask such a question. He seemed to feel he’d be prying. I found his response odd. Presumably his client had many potential business opportunities, but had chosen to gamble his money on warehouses. Since the broker’s job was to help him find the right investment property, wasn’t he in a better position to help him make a sound investment if he probed his client’s reasons for making that choice instead of guessing about them or holding back out of politeness or fear?

The same principle applies to pitching. Whether you’re responding to an RFP or doing a proactive pitch you should always start by assuming that you don’t know what you don’t know and then ask questions to fill in the blanks.

That may sound obvious, but I often encounter clients who skip this step entirely. Sometimes they do so out of habit. They’ve never asked questions before. They’ve always just guessed about their client’s needs and assembled a pitch by cutting and pasting from previous pitches. Why poke the tiger? Sometimes they think they’ll bother the client or never gain access to them. Sometimes they’re simply afraid they’ll sound dumb or show their ignorance.

But that’s crazy. You’ll always gain an advantage over your competitors if your understanding of the client’s needs is more thorough than theirs. Besides, clients like to be asked questions (as long as you don’t ask ones whose answers you could easily have found by scrolling their company website). Asking questions makes them feel that you have a genuine interest in understanding their needs. It tells them you want to get it right.

Just be sure to use your time wisely by asking questions that are strategic in nature and preparing them carefully beforehand. I like to focus mine on three main areas: client priorities, desired outcomes, and potential roadblocks that might prevent me from winning their business.

Once I’ve formulated my questions, I pick up the phone. That’s right. You heard me. I call the client. It’s one of the great paradoxes of our age that while we’re fixated on our cellphones, we avoid using them to talk to a real person. If you’ve done your homework, though, you’ll be surprised at how much valuable information you can pick up in a ten-minute phone call. Often you can learn enough to change the entire direction of your pitch.

Once I’m talking to the client, I work from my prepared questions but tend to improvise from there. I start macro, go micro, and use the information I glean as a springboard to narrow my focus even more. I target the client’s rational needs by focusing on the practical considerations driving the decision. Then I zero in on the client’s emotional needs by probing other less measurable factors. If you were buying a new car, for instance, you’d probably have a list of concrete considerations (size, quality, price), but you’d likely have emotional considerations as well (status/cool factor, design). It’s essential to target both types of needs. I also pose hypothetical questions. I might ask ‘If you had a wish list of all the features of a great system, what would be on it?’ I avoid leading questions because they set the client up to give me answers I want to hear instead of honest answers that will actually be helpful in formulating my pitch. And I always probe for barnacles under the water. For instance, has the client had a bad experience with a consultant in the past that might color their decision to hire me?

Finally, remember that asking questions isn’t simply about gleaning crucial information. It’s about developing strong strategic client relationships, which always lie at the root of a successful pitch. Without those, you’ll fail, even if you show up with the world’s slickest presentation.

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