If you’ve ever had an informational interview request go unanswered, you know just how crushing it can be. It wasn’t long ago that I was in similar shoes, reaching out to media industry veterans whose footsteps I wanted to follow in. And it’s a roller coaster of a ride: The anticipatory glee of finally tracking down someone’s email, quickly followed by a sinking feeling that your outreach has gone into the ether, only to be ignored.
To increase your chances of having a successful connection, you’ve got to be up on the latest professional etiquette and be prepared to make the most of your facetime once you finally land the meeting. Take it from someone who turned two informational interviews into job opportunities ahead of my college graduation—it truly is all in the approach.
To help set you straight, we tapped Karlie Everhart, a career and life coach who after years of climbing the advertising industry ladder pivoted to working with millennial women on everything from career transitions to how to find more confidence on a professional and personal level. Ahead, she delivers a step-by-step guide to securin a meeting with a potential mentor or employer, plus a few helpful conversation starters to keep in your back pocket along the way.
How to nab an informational interview with just about anyone
Do your research
According to Everhart, everything starts with finding inner and outer peace within a situation. In this instance, the outer piece of it is making sure you’ve done your research.
“If you’re looking at a specific job, make sure that you’ve done your research. Look at the company’s core values and what their mission is.”
“When you’re first starting, I always encourage people to cast a wide net. Reach out to people who are on your same level and then extend the net from there. The more individuals you reach out to, the merrier.”
Choose your platform
While there are different rules of engagement for each platform, Everhart encourages people to try to reach out via email or LinkedIn. “I think Instagram (and social in general) lends itself to a more casual conversation. And when you’re reaching out for a job, you want to be taken more seriously. Ideally, I’d use email. If you can’t track down someone’s address, go for LinkedIn.”
Know your intention
As far as the inner piece of the puzzle goes, Everhart always recommends setting a clear intention. “Know what you want. When you’re reaching out to people, be really specific and don’t be afraid to ask for what you want.”
Start with a compliment (and curiosity!)
“In the outreach, you want to keep it short and sweet,” Everhart says. “Let’s say you found their profile on LinkedIn. Open with, ‘I really admire your career trajectory.’”
Another point of entry? “Let them know that you’ve done your research. People like to talk about themselves. And knowing that you’ve invested in them before you’ve reached out makes people feel good. Then, cut to the chase and ask for what you want—whether you’re interested in a specific career opportunity or looking to connect to learn more about what made them successful in their role. Get really curious about the other person.”
“When someone asks you about yourself, it makes you think ‘oh wow, they’re really interested in what I have to share.’”
Know that you have something to offer, too
If you go into the conversation with the mindset that you’re the only one receiving value from the connection, you’re not going to have as rich an experience as you could. Instead, reframe your outlook. Everhart stresses knowing deep down inside that you’re inherently valuable and that you have something to give, as well. Reverse mentorship is real and it’s valuale—so think about how you make this exchange feel like a two-way street.
IRL is always better
“Because you’re better able to showcase yourself in person, always go for the in-person meetup,” Everhart says. “It’s more personable and you can make a deeper connection in that way.”
And try to keep it on the shorter side, she adds, no longer than 30 or 45 minutes. “If they come back with feedback that that’s too long, suggest 15 or 20 minutes.”
“The goal is to get in front of them, have specific questions ready, and really make a connection—because you can always follow up later once you’ve made the connection and start to build a rapport.”
If you can’t secure an in-person meeting, don’t fret. A phone call can work, too!
Have your questions ready to go
It’s expected that the initial meeting might feel a little awkward—you’re meeting someone new for the first time, after all. To ease the tension, have your conversation-starters and questions ready to go, so you can avoid awkward silences as much as possible.
Shivani Siroya, founder and CEO of Tala, (who unsurprisingly is frequently sought out for informational interviews) offers this pro-tip: “I always recommend that students send questions ahead of time so that the 30 minutes can be used productively.”
If you’re chatting with a hiring manager for a specific role you’re interested in, Everhart recommends starting with something like: “So I saw that you’ve been at this company for over two years now. I’d love to hear about some of the projects you’ve been working on.”
Another idea: “Can you share a few of the challenges you’ve faced, along with some of the bright spots of working here?”
Everhart says it’s important to get the other person talking about themselves and their experience. To keep the conversation moving, use phrasing like, “Oh, tell me more about that.”
But beyond just keeping the conversation going, don’t forget to ask for specifics that will help you become a better candidate. “What kind of person are you looking for? What qualities would make someone successful in this role?” Use this time to gather intel that will make your application stronger.
Skip the coffee, if you can
If you’ve asked someone to meet for coffee, you should always offer to pay. But to avoid this potentially awkward scenario at the cash register altogether, try to land an in-office meeting so you can suss out the workplace culture while you’re at it.
And if there’s any doubt about what to bring, always have your resume on hand. It’s wise to have a pen and notebook as well, so you have the option to jot down any notes. And don’t forget to give them some way to get in contact with you in the future, such as a business card.
Be prepared to get in the hot seat25>
While it’s a good strategy to head into the conversation without expectations, you want to be prepared in case you start getting some of the questions. If you’ve already done the inner work of shifting your mindset to a place where you know you have something valuable to provide as well, you won’t be caught off guard if the person starts inquiring about your work history and what you’re looking for now. After all, you know your story better than anyone else, so you should feel nothing but confidence in telling it. Everhart says, “Being yourself and being authentic in the conversation is the most important thing.”
Follow up and follow through
If you already had the in-person meeting, send a follow-up thank you note within 24 hours. If you haven’t gotten the in-person yet and you’re still trying to get ahold of them, be persistent. “My rule is I’ll reach out three times,” Everhart says.
“Once you’ve reached out three times, in two months or so, try to reach back out again, because it’s all about trying to stay top of mind.”
When you try to pick the conversation back up, it can be helpful to say something like, “I noticed it might not have been a good time to connect a month ago, but I’m wondering if now is a better time.”