Winning new clients is key to growing a business, but quickly establishing a rapport with a stranger is no easy feat. Moving the conversation from silence to deep engagement is a challenge, and one that requires verve and skill on the part of advisors.

For new and prospective clients who might be ill at ease when discussing money and finances, some advisor may find that they need a few tricks up their sleeve.

In honor of Valentine's Day, we've collected a roundup of advisors' best tips for chatting up new or prospective clients -- strictly for business purposes. These icebreakers run the gamut from eye-popping questions to clever desktop props.

See what some of the best practices are below, or click here to see a slideshow version. And if you've got a good idea that's not here, please share your tips in the comments below. -- Andrew Welsch, Maddy Perkins & Andrew Shilling

'What's Your Top 5?'

Janet Nichols, an advisor at Raymond James & Associates, says she almost always asks prospects or new clients what their top five bucket list goals are.

"People love to have that conversation, and by listening to their answers I tend to learn a lot about them," she says via email.

"For most people it involves some type of travel (which I make a note of, so that I can forward them articles about, say, Prague or Costa Rica as I come across them).  For some people it involves athletic achievements, or writing a book, or living for a year on a sailboat, or getting all of their kids through college. Some people have not identified them yet, but even that can be a revealing conversation as they muse out loud about some hopes and dreams, and try to rank them in order of importance.  I find that by asking that question and then staying quietly attentive for the next 15 or 20 minutes, I can get a pretty good feel for what makes this individual tick, what are his or her values."

It's also a good way to kick-start a conversation at a dinner party, Nichols said.

'Got a Guilty Pleasure?'

"My main goal in a first meeting is to build rapport with the prospect," says David Lyon, head of Main Street Financial.

A good way to find some commonalities with that prospect is to ask them what their favorite decade is and why, Lyon says via email. He also suggests asking them about their favorite guilty pleasure.

"If I am finding that it is hard to get the prospect to open up about what is important to them. I like to ask questions just to get them to talking and get a sense of what is important to them," said Lyon, who is based in Chicago. "If you could eliminate one thing that you have to do every day and never do again, what would it be? If you had one extra hour a day, what would you do with it?"

'Check Out My Legos'

Darla Kashian, an RBC broker in Minneapolis, keeps her best client ice breaker on her desk at all times: a Lego calculator.

"I have this calculator because I love Legos, and because, to me, the work I do should be fun. Every single person I sit down with says, 'Wow is that real?' 'Yeah, it's real,'" says Kashian, 51.

It not only puts clients at ease, she says, but also serves a kind of symbolic purpose, emphasizing that clients' dreams and goals come first. "From my perspective, we always start about you and your life and what you love and do. The investment piece is really just the tool to solve for the desire," Kashian says.

New and returning clients often play with the calculator, which Kashian got for her birthday. "And then they want to see if the Legos come off," she says. "They do."

In addition to Legos, she also keeps a box of crayons in her office. Kashian says she'll ask if clients' kids have seen any movies recently -- because she keep movie-themed coloring books at the ready. (Think Frozen.)

These tricks create the right atmosphere for clients, she says: "I do think we can sometimes make it more difficult for people to walk in through the door. My job is to make it easier and more comfortable," Kashian says.

'Tell Me About Yourself'

Vaughan Scott, a broker at Wells Fargo, says he gets the conversation started by conducting background research in advance, keeping the first conversation focused on the client and asking the right questions.

"So many times advisors script things religiously," he says. "They want to say the right thing at the right moment. We have the tendency in this industry to dive into financial questions. In reality, people want to have a genuine connection to the person they are talking to."

More successful conversations, he says, "focus on things that are relevant to them and their background and their history."

Scott says his approach has helped form connections with many hesitant clients. He says he was once referred to a prospect who owned a machine shop. Scott was warned he was a "tough character."

At first, the prospect dismissed Scott, saying that any money he had left over would be better spent on a machine to put someone else to work than a wealth manager.

"I said, if everyone in America had that attitude, the world would be a better place and I'd be happy to be out of a job," Scott says. "I told him, 'Investing in your business is the most critical decision you could ever make.' ... It went from a confrontational situation to a completely different one in no time at all."

'Which Way Are You Headed'?

Richard Morrow, a broker at Wunderlich Securities, finds meeting on the potential client's home turf provides a comfortable atmosphere to get things started.

"I ask where they want to end up and what they want their money to do for them," Morrow said. "I think that's a lot better way to invest people's money than saying, 'Hey, I think this asset class is undervalued; you should buy.' It may not serve their needs.

"Some people can't afford to lose their money. If you know where they want to end up, and if they want to just end up debt free with enough money to pay for their funeral, that's going to be different than, say, a guy with an ultrahigh net worth that may need a few million dollars to go on with the rest of his life. His major goal might be to provide a big estate for his kids."

Too much information can also distract prospects or new clients, he says. "They know what you do. They know why you're there. And they really don’t care that the emerging market's p/e's are 25% lower than the developed European market p/e's, or whatever. And trust me: Six years ago I was that guy that thought people cared about that. They don’t care one whit within reason."

'Are We a Good Match?'

Michael Wall, president and founder of Palm Beach Gardens, Fla.-based Wall Financial Group, says his initial conversations with clients are about evaluating whether the relationship is a good fit.

"We know we're not right for everybody, and not everybody's right for us," Wall says. "And that's OK. The whole purpose of [the conversation] is to evaluate the situation and figure that out."

He says not rushing into product or strategy discussions takes the pressure off significantly. "I see it all the time: Once I tell them I'm not here to sell anything, their guard goes down," he says. "The thing is, I don't know what's right for [the client] yet. To offer something to them right now is like giving a haircut over the phone."

'Let's Talk About Me'

David Adams, an independent Raymond James advisor in Nashville, Tenn., finds that he can eliminate any "uneasiness or stiffness in the room" by telling his own story about why he got into the business. He does follow that, though, by posing some open-ended questions to the clients.

"We want to get them telling us about why they are here, and what experiences they have had in the in the past with financial advice, and what they hope to gain by choosing a financial planning team," he says via email.

Adams says once the conversation has started, it's much easier to get clients to discuss the ways they gauge financial freedom and success: "You would be surprised by how easily the ice is broken once you get clients talking about their experiences, goals, and fears."

'Ask Me Anything'

Anna Behnam, an independent advisor at Ameriprise, says she connects with reticent new clients in part by asking them to pose any question to her that they want.

"I share a little bit about me -- that I'm married, I have a kid, I have another on the way here right now," she says.

Behnam says that clients can sometimes be nervous, just as if they were going to the dentist. By bringing her personal side into focus for a client, Behnam has been able to form long-lasting connections. "I really, really try to bring out the human side of me."

If the client is still reticent, she'll switch tactics.  For example, Behnam recalls meeting with two new clients who were sisters. One of the two was extremely introvert and would only answer questions with a simple yes or no.

"Turns out she's a watch addict, and she collects watches and jewelry. So I ran with that," says Behnam, who began asking questions about what the client liked and didn't. "I even took off my own bracelet and necklace and asked 'What do you think about these pieces?'"

But new conversations can often be challenging, she notes, citing the old cliché that you should never talk about three topics: money, sex and politics. "And I happen to work in one of those three," Behnam says.