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How To Ask Probing Questions in Social Settings

Detroit—“I hear you loud and clear about socializing with clients and centers of influence during the holidays,” Linda said in a tone oozing of skepticism. “But how do you initiate a business conversation without coming across as salesy?”

“Very carefully,” was my response. Linda wasn’t amused, but I was not making an attempt at humor. I felt obligated to walk her through some opening questions that can be natural door-openers for a brief business conversation. The following is what I spent 15 minutes explaining to Linda.

The mantra for any type of social prospecting is strategic intent, and holiday schmoozing is tailored made for this. In simple terms, this means that you approach every social activity during the holidays with a game plan. You know who will be attending, whom you will know, whom you want to meet, and whom you’re targeting to romance into your pipeline.

As I explained to Linda, social prospecting isn’t a science because you’re never absolutely certain of the opportunities you might or might not encounter. However, if you know that you’re going to be introduced to a colleague of a client, you want to get some information about the person. This can be as simple as asking your client a few questions regarding family, hobbies, interests and the like, reviewing their profile on LinkedIn and Facebook, or conducting a Google search.

Armed with this information, you can begin a conversation very naturally by referencing your client with the bit of personal information you learned, followed by a question. A perfect example occurred last week with an advisor attending a law firm’s holiday party. One of the law partners was a client and an internal advocate of this advisor. He invited the advisor to the party with the promise of introducing him to a law partner who he thought could become good client. With a brief query, Bob discovered this partner was a diehard Boston Red Sox fan.

Here’s how it began…

Client Tom:“Jack, I wanted to introduce you to Bob. He’s the guy I told you about—he’s a pro’s pro.”

Advisor Bob: “Tom’s too kind. Incidentally, he tells me that you’re a big Red Sox fan. They’re my top American League team. What do you think of the Bobby Valentine hire as their new manager?”

This prompted a serious discussion about the Red Sox year-end meltdown (they missed the 2011 playoffs), the team’s personnel needs, and a general baseball discussion that led to Jack, the attorney prospect, inviting Bob to participate in his fantasy baseball league. This common interest was such a natural rapport builder that Jack brought up business by referencing the positive things his law partner Tom, Bob’s client, had said about him.

This provided Bob a window of opportunity to play humble with a planned,“Shucks, I’m just working hard, making the adjustments, and protecting clients amidst all this volatility.” Then, with Jack fully engaged in the conversation, Bob asked, “Has your advisor crafted a recovery strategy for your portfolio?”

Bingo! As was reported to me by Bob’s coach, Jack had a blank stare, and Bob simply proceeded—“In this environment, this is really something that should be done. If you’d like, I’d be happy to review it for you.”

Bob doesn’t have Jack’s business yet, but he met with him the following Tuesday. There’s over $2 million involved, and he has no financial plan. Bob plans on turning Jack into a client at their upcoming meeting scheduled for the following week—the week before Christmas!

In this instance, Bob got himself invited to his client’s office party. With the help of his client, he identified a prospect he wanted to be personally introduced to; he did his homework, and then turned the initial introduction that began by asking questions on a topic of great interest (Red Sox) into an opportunity to deliver a second opinion on the prospect’s investments.

Going into the holiday season, we recommend doing your homework. Your conversations can take the form of:

• Family—“I hear your daughter’s on the traveling soccer team. That’s impressive; how long has she been playing?”

• Hobby Questions—“Tom tells me that you’re an avid cyclist. How far do you generally ride, and what type of bike do you have?”

• Business—“It seems as though your company is handling this recession better than most. How have things been over the past year?”

• Interests—“Bob tells me you’re a big Champion’s League fan. Me, too; I like Barcelona, what’s your team?”

The list of topics is endless. The idea is to approach every holiday social event, whether it’s a simple lunch or an office party, with strategic intent. Which means that you’ve done your homework, zeroed in on a topic from which you plan to build rapport, prepared a few simple questions, and you’re off; dumb like a fox, dressed to professionally impress, and ready to make it rain. The secret is to be able to conversationally ask probing questions.

By the way, whenever anyone asks you about the markets, you must be prepared to redirect the conversation into a brief summation of what you’re doing with clients—not investment details— that can segue into recovery strategy questions. If you get sucked into a conversation about the market, you short-change your social prospecting opportunities. Remember, the less business you discuss, the more business you’ll get.

By the time I finished, Linda, with a smile of understanding said, “And I thought you were being a wise guy. Thank you, this has been quite helpful.”

If you are planning to conduct an off-site retreat for year-end, make sure you download a copy of our sample agenda click here.

Also, if you haven’t already - join The Oechsli Institute’s Group on LinkedIn!

Once again, we want to thank all of you who have e-mailed comments and questions to us. We will continue to do our best to answer each one. If you would like to learn more, please visit

If you have any topic suggestions or special requests, please contact Rich Santos, publisher of Registered Rep. and Trusts & Estates magazines, at [email protected].

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