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Illustration:

Verónica Grech

We’ve all gotten mired in banal small talk at some point. What if there were a way to avoid that conversational quicksand?

If someone says, “I just got back from vacation,” three in four people give a dead-end reply like, “Boy, do I need one of those.” A more inviting question, such as, “What was your favorite day like?” can keep the conversation from dying on the vine, according to research by Contacts Count,​a Newtown, Pa., consulting and training firm that advises employers on networking.

Much of our day-to-day talk is a missed opportunity. The ability to draw others into meaningful conversations can determine whether people want to get to know you, or remember you at all. Failure to learn it can stall your career.

Vanessa Van Edwards

had been attending networking events for several years during and after college when she realized she was having the same conversation again and again. “It went like this: So what do you do? Yeah. Where are you from. Yeah, yeah, been there. Do you live around here? Well, I’d better go get another glass of wine,” says Ms. Van Edwards, a Portland, Ore., corporate trainer and author of “Captivate,” a new book on social skills.

She started trying conversation-openers that jarred people a bit, in a pleasant way: “Have you been working on anything exciting recently?” Or, “Any exciting plans this summer?”

“If I’m feeling very brave, I ask, ‘What personal passion projects are you working on?’ ” Ms. Van Edwards says. She began making contacts who followed up more often.

An End to Small Talk

How you answer at the start of a conversation could make the difference between something boring and something deeper.

OPENER: “I just moved here two months ago.”
SMALL TALK REPLY:
“I’ve been here 10 years.”
BETTER: “What has it been like getting used to a new city?”

OPENER: “I found the speaker so fascinating.”
SMALL TALK REPLY: “Me, too.”
BETTER: “Tell me more about what caught your attention.”

OPENER: “I’m starting a new company.”
SMALL TALK REPLY: “I work for XYZ Company.”
BETTER: “What kind of people are you looking for to help you make a go of it?”

OPENER: “This hot weather is killing me.”
SMALL TALK REPLY: “Me too, I can’t wait until it cools off.”
BETTER: “Do you think the weather affects people’s moods or job performance?”

People are more likely to remember encounters that are emotionally charged, research shows. Opening lines that spark pleasure, such as, “What was the highlight of your day?” tend to spark conversations that are memorable and enjoyable, Ms. Van Edwards says.

Such openers also risk falling flat. Ms. Van Edwards recently asked a stranger she met on a business trip what he was working on that was exciting. The man replied that he hated his job and was going through a divorce. She salvaged the exchange by thanking him for being honest, empathizing and drawing him into brainstorming about what’s it’s like being stuck in a rut and how to escape it.

Only one in four people sees value in asking probing questions of strangers, based on a Contacts Count survey of 1,000 people. Doing so can be risky, says

Lynne Waymon,

the firm’s CEO and co-author of a book on networking. “I’m demanding more of you when I ask thought-provoking questions. I’m making an assumption that you’re in this conversation to make something of it—that you’re not going to see somebody across the room and say, ‘Oh, I need to go talk to Susan or Bob,’” she says. “But the connections you make are going to be much more dramatic and long-lasting.”

A valuable 17-year friendship for

Bill Stokes,

an executive recruiter, began when a woman he met at a fundraiser asked him, “What do you do to relax?” His reply, that he’d been raised on a farm and loved going to horse races, sparked a conversation about her hobby of rescuing retired racehorses in need of a home, and the friendship blossomed quickly, says Mr. Stokes, founder of the Washington Network Group, a Washington, D.C., executive group.

Many people who rely on small talk don’t realize they lack critical conversational skills until they hit a career wall. Employers can hire coaches or trainers to deliver a crash course in conversation to professionals who lack the skills to engage new clients or customers, or middle managers who lack the internal networks needed to rise to executive jobs.

Dianna Booher

coached an attorney several years ago whose bosses wanted to promote her but didn’t trust her to socialize with clients. “She was sharp in her answers” to acquaintances’ opening questions, giving dead-end or one-word replies that made her seem arrogant, says Ms. Booher, a Colleyville, Texas, communications consultant and author. Ms. Booher brought the attorney to her office for coaching and recorded her practicing warmer responses that revealed more about herself. She soon learned to start conversations on a more inviting note.

Among the tactics Ms. Booher suggests is giving mundane topics a serious twist. If an accountant or lawyer says she’s just returned from vacation, ask, “Can someone in a stressful job like yours ever really get away totally and shut down?”

Learning to start deep conversations can be a relief to the people who dread networking the most.

Pamela J. Bradley

says she’s an introvert. Meeting strangers used to touch off an anxious voice in her head. The voice would scream, “I have a terrible time networking, or I have a terrible time remembering names,” says Ms. Bradley, human-resources manager for Keiter, a Glen Allen, Va., accounting and consulting firm. Asking probing questions turns down that voice and puts the spotlight on the other person, she says. Among her favorites is, “What’s keeping you awake at night?” because it encourages clients to explain their most worrisome issues.

Such skills also make you happier. People who have more substantive conversations with others report a greater sense of well-being than those who engage in small talk, according to research led by

Matthias Mehl,

a psychology professor at the University of Arizona. Those findings, first reported in a 2010 study of 79 college students, have recently been replicated in a larger, unpublished study of 500 adults led by

Anne Milek,

a postdoctoral researcher working with Dr. Mehl.

It isn’t clear whether people who are already happier have deeper conversations, or the conversations make people happier, but Dr. Mehl suspects each factor fuels the other.

Work & Family Mailbox

Q: Your column on being a successful No. 2 was timely. I’ve been named chief of staff at a company that was recently acquired by the private-equity firm where I work. Although I’m 26 years old and lack experience, the CEO will be counting on me to oversee projects and people. Any advice?—B.P.

A: Don’t be surprised if older employees who resent your authority don’t welcome you with open arms. Your value to your boss will rest largely on your ability to keep him or her well-informed. This will require you to build trusting relationships with insiders and stay abreast of issues inside the company.

Ask the CEO for a settling in period of two or more weeks. Begin building an internal network by talking with insiders one-on-one about their goals, successes and challenges. Ask questions and listen carefully for problems that need attention. Show humility and admit what you don’t know. Look for key internal allies who can help you identify the most pressing issues. Consider seeking out a trusted senior executive outside the company as a mentor to help you stayed focused on your own goals—to help your boss achieve his or her objectives and avoid negative surprises.

Write to Sue Shellenbarger at sue.shellenbarger@wsj.com