You’ve had your eye on a company for a while. And after doing some LinkedIn reconnaissance, you realize that a connection of a connection works in HR.
So you reach out about setting up an informational interview.
If you handle it right, this could lead to your dream job—if you ask the right questions.
“If you spend as much time as I do hosting meetings at Starbucks, you’re privy to a lot of informational interviews gone bad,” says Tara Goodfellow, a former career development instructor and director of Athena Educational Consultants in Charlotte, N.C. “There have been times I’ve had to stop myself from giving unsolicited advice.”
So what sage advice would she impart?
Read on to see what Goodfellow and other career experts say are the best—and worst—questions to ask in your next informational.
“This is the worst question,” says Adrian Granzella Larssen of career site The Muse. “If you ask something that you can easily find online, you’re wasting your time and the other person’s time.”
Instead: Make it clear you’ve done your research by asking nuanced questions that convey your interest and professionalism. You might say, “I see you moved from a small boutique agency to a very large one. Was it difficult to make that transition?”
Another example that Granzella Larssen suggests: “You spent six years at the same company but had multiple, varied roles. What would be your advice for someone who wants to do the same?”
“People like to be helpful, and they’ll feel much more helpful if you do some digging beforehand to take the conversation beyond the surface level,” she adds.
You’re trying to build a rapport during an informational interview, and this type of probing question can be a conversation stopper.
“In a first interaction, [it] sets you up for an awkward dynamic,” says Todd Horton, a 15-year HR veteran and founder of KangoGift, a company focused on employee recognition.
“I was once in a group interview with a major oil and gas company when my friend asked about environmental damage and subsequent fees the company faced. The interviewer curtly responded, ‘I’m not authorized to comment,’” Horton recalls. “It changed the tone for the rest of the group chat—and my friend did not advance to the next interview round.”
Instead: Take an open-ended approach by simply asking what kind of challenges may lie ahead for the company. This way, you give the other person the chance to interpret the question.
“The interviewee may answer with a remark about competition, the marketplace, or a big internal initiative,” Horton explains.
Based on the response, he says, you then have the opportunity to share which of your skills could help the company overcome that challenge—keeping the interaction focused on what you bring to the table.
It’s natural to be curious, but this type of point-blank inquiry comes across as inappropriate and off-putting.
“When you ask what another person has in their bank account, it can feel like a violation of privacy,” says New York–based career counselor and executive coach Roy Cohen. “I can guarantee that the mood of the meeting will shift.”
Instead: Pose a more general question about gauging the industry’s going rates.
“Say something like, ‘I’m wondering if you can give me a sense of what the salary range for this sort of position might be? It would be enormously helpful as a benchmark as I begin to officially interview for jobs,” suggests Cohen.
After all, Cohen says, the goal of an informational interview is to gather data.
If you’re becoming fast friends, it’s a sign that the informational interview is going well—but it doesn’t mean you should send a Facebook request.
The employee may be reluctant to connect personally with someone who primarily wants to talk to him about his company, cautions Philip Blackett, founder of Magnetic Interviewing.
Besides, he points out, if everyone who requested an informational interview Facebook-friended him, it could become overwhelming.
Instead: Focus on forging a connection, and express interest in staying in touch.
“Take a genuine interest in your interviewee,” recommends Blackett. “Try asking, ‘What initially attracted you to this company when you were job searching like me?’”
This line of questioning lets the person share his story in a more natural way. And once you’ve hit it off, continue the dialogue by sending a thank-you note and, perhaps, a LinkedIn request.
Personality fit is a big determinant of job success, so you’ll want to take this question seriously.
“I think people often say this just to ask a question, rather than to actually listen to the response,” says Denver-based career coach Jenn DeWall. “Be an active listener—and hear what’s not being said.”
Bringing up office culture also creates a positive impression twice over.
“You are showing your interest in finding success in their culture, and you are demonstrating big-picture thinking about the variables that can impact your success within the company,” DeWall says.
“Often in an informational interview, the employee is able to speak more freely,” says Angela Copeland, a career coach and founder of Copeland Coaching. “They’re able to share what’s going well, and be honest about what’s not going well.”
In other words, the answer to this question could help you envision yourself in a potential role, with its day-to-day ups and downs.
Copeland gives the example of a recent client who wanted to move away from retail management. She went on four informational interviews: with a corporation, a nonprofit, an advertising agency, and a startup.
The informational with the corporation came first.
“When we met afterwards,” Copeland says, “My client said, ‘They sit in cubicles all day long.’ So we took corporate jobs off her list, and she ended up finding a great job at an advertising agency—one that suits her personality and plays on her strengths.”
Any informational interview should be just one in a series of conversations on the road to your next job. So you’re not overstepping with this question—you’re keeping the momentum going.
“It allows you to expand your network,” says L.A.–based career and business coach Crystal Marsh, citing the example of a client of hers who was looking to work at a small marketing company.
“She had a stellar informational interview with an executive who simply did not have an open position,” Marsh explains. “So I advised her to ask this question, and he thought of someone right on the spot—a college friend who did the same work but at a larger company.”
An email introduction led to an interview and then a job offer.
“You just don’t know what the possibilities are until you ask,” Marsh says.
Ending your conversation with this question shows your willingness to give back.
“If you say it sincerely, this question takes some of the emphasis away from, ‘What’s in it for me?’” Goodfellow says.
It also demonstrates that you’re willing to work on your side of the future relationship, treating networking as it should be treated—a mutually beneficial relationship developed over time.
“Then, if after an informational interview you determine you’re not a good fit, you can offer to send along a contact,” suggests Goodfellow. “When this question isn’t asked, it’s really a missed opportunity for both parties.”
This article originally appeared on LearnVest and is reprinted with permission.