Impact Opportunity had the chance to speak with Kristin Brennan, Executive Director, Career Exploration and Development at Bowdoin College, to get her advice on conducting successful informational interviews when exploring a career or job change.
Kristin Brennan: The first question I would ask is, do you know what you're looking for? It can be relatively easy to replicate a version of the same job you have had, just at another organization. When people are changing jobs and looking for advice, it's often because of a sizable shift. Either something has come along to surprise them, something has come to an end, or they're in a different life stage, making them reevaluate what they want. Or maybe they want to do something different, and they're not sure how different.
The best piece of advice I remember receiving early on in my career was to make sure you know what you're good at and what you like. Now that I'm a career services professional, I realize that question is all there is. What are you good at, and what do you like? I suggest spending a lot of time paying attention to your favorite project, favorite moment, favorite boss, those times that you felt like "this is me doing my best work." It's one of the best things you can do, and keep track of those insights as you go. You may find that you zig and zag as you shed things you don't like to do or dig in to get really good at things you do.
The second great piece of advice I received was in a book by a woman named Herminia Ibarra called Working Identity. It's for people making a pretty significant shift in their career, where the job they had was part of their identity. "Oh my gosh! If I'm not a lawyer anymore, who am I?" The book does an excellent job of describing what it feels like to go through a moment like that, which I really like about it. Years before the book Designing Your Life by Edwards and Burnett, Stanford talked about prototyping careers. This book said nobody figures out a career shift in a vacuum. You don't sit on the floor in a closet having a meditative moment that results in a new revelation. People find this out by trying stuff on. And there are lots of different ways to try jobs on.
If you're lucky enough to be a college student, one way to try on a career or organization is to do an internship. If you are a full-time working person, you can do informational interviews, a lot of reading, volunteering, or a side gig. Each of those counts as prototyping the person you could be. While the side gig can be a way to try on a career change, it's hard to find time to do two jobs well simultaneously. You have to be in a particular moment in your life to take that on, but it can work really well. A more practical option for many of us is the informational interview, which is probably the easiest way you can figure out whether you would like that particular position or not.
If you enjoy meeting other people who have jobs adjacent to yours, you're already doing informational interviews. That is one way to make it seem less daunting. It is in the process of meeting someone at a conference, thinking they're interesting, and deciding to have coffee that you can be trying on other people's jobs without even knowing it. But the truth is that most of us do not make time for that kind of stuff unless we don't like what we're doing anymore, think there's a change on the horizon, or we're in the middle of the change and actively job seeking. So, the best time to do informational interviews is when you can summon up curiosity about what you might want to do next.
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I always tell my college students that it's tough to get out there and network for the first time. I'll acknowledge that it's hard because sometimes we're called upon to do informational interviews when we feel the least cheerful. Networking calls upon you to be your best, most shiny self, and your best, most shiny self is not always available on a Tuesday when you are job searching. You have to take breaks sometimes, for a day or a week. Be kind to yourself, do something else that makes you feel good. The best time to conduct an informational interview is when you're genuinely curious, and you can bring forth a cheerful, curious version of yourself to meet and have a conversation with a stranger.
It could go a couple of different ways, depending on how much of a vocabulary you've created for the position you're seeking. If you have a good vocabulary for your next thing, if you're able to say, "I think it's social impact, it's probably externally facing, so maybe it's marketing or fundraising," you can begin to identify people to meet. Sometimes when you're just learning about a field or trying to take a new direction, it's like building a map of what that might look like and all the adjacent fields or jobs. Picture one of those bubble maps where you start with, "I think it might be X." Then you meet someone, and you realize you can expand that in a slightly different direction.
If you're interested in something that feels amorphous to you, a good place to start is to find at least one organization or a person who does it and ask them some good questions; they almost always lead you to another person. If you're comfortable conducting research, you can also do that. The organization that you found always belongs to an ecosystem. For example, that first organization might lead you to discover that a number of the leaders there have attended a couple of graduate schools with certificates or degrees in your area of interest. Reading up on that first organization or those graduate schools could lead you to funders in that space or a conference with speakers who do that work. You can start building a picture of what that ecosystem looks like and identify its people. You can start with a person or start reading to develop a map of who works in that field.
You find potential informational interview subjects in three ways. One is the research we just talked about—all those graduate programs, funders, and conferences have people attached to them. Another is that just as soon as you have even a bit of vocabulary for what you're looking for, tell everyone you know. You never know when your best friend's aunt works in the field that you are interested in. You have to be careful about this if you are still employed. Still, even then, you can be choosier about whom you tell, or you could use really long-term language that doesn't indicate an immediate departure, like "oh, someday, I always thought I might like to be a nonprofit COO." You can often find at least one person that you're connected to. It's easier to start with someone you have at least some tangential connection with. When someone can make an introduction for you, it feels less frightening. And it's also a little less high stakes.
I am also a real fan of LinkedIn for searching purposes. It's quite useful. Again, if you have a vocabulary, particularly an organization in mind, you can figure out how you're connected to it. If you're a graduate of an institution, you can log in and find your school and then search alumni, and you often have 20,000 people at your disposal. You can then search by geography or sector. If you can find any point of commonality, begin with that person.
I like to know as much about the person as possible. It's helpful to know something about the organization or the part of the ecosystem they sit in. Often the person has a bio that's available online, or LinkedIn will show you their last few jobs, or they might have a connection to you through someone you know in common. At the end of the day, you're talking to a person and taking their time—the more that meeting can be fun and interesting for them, the better. I often think even more about researching the person than I do the industry.
Sample Networking & Informational Interview Questions
Kristin Brennan, Executive Director, Career Exploration and Development at Bowdoin College, shares questions you might ask during an informational interview or networking opportunity.
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And then think about what you're genuinely curious about. There are many good standard sets of questions you can ask in an informational interview, but they boil down to: Who is this person across from me? How did they get where they are? What do they think about it? What advice do they have? The rest of it is just follow-up questions.
One of the first things to get over is this: you have something to bring this conversation, and it's you. You're an interesting person. Even your interesting questions add value to their day, make them think, and make them remember they have a cool job. There's probably also something you can offer them in return because you're a person in the world with your own connections and background. If there's anything I can do to put it on equal friend/colleague footing, I do. That might sound like, "if you are ever interested in X that I know about, please let me know."
The other thing to know is that the informational interview may lead to absolutely nothing. It might just be a conversation and a thank you. That is one of the things you have to be prepared for. You might do 20 informational interviews, and three possible job interviews come out of it. And a lot of interesting conversations that lead to something, that leads to something else. It all pays off eventually because you will know all these great people.
If you can be specific in your thank you, that's always very helpful. "I am still thinking about the perspective you offered on where the field of XYZ is going." Or "I will follow up with that person you suggested." The more specific the thanks, the more authentic and appreciated it will be. And follow up! People think, "oh, I've already used their time once; I can't take any more." But on the other side of the table, it can be so rewarding to hear how it turned out for the person who asked your advice. There are several great opportunities ahead when you could update them and appreciate them again or even ask an additional question—walking out of a conversation with someone they suggested you meet, seeing a job open up at a place they suggested you check out, and the moment you land a job.
How likely the informational conversation is to convert into a job opportunity is a lot about the conditions on the ground that you don't have control over. So often, if something has come up and someone happens to know of an opportunity, it may come up in the conversation. "It's funny that we met today because we just posted this job over here in my department." That could happen. Or "now that you have told me what you're interested in, it makes me think of my friend who just forwarded this job description to me." If there's something live and in play, it will likely surface in the course of the conversation.
If something doesn't surface, then you're not going to convert that into anything at that moment besides a lovely conversation that you learned something from. At that point, you can say, "if this conversation makes you think of something down the line, I'd love to know. If something crosses your desk and you think of me, I'd love to hear about it." But that's about as far as you can go if there isn't anything live.
People have different points of view about this, whether to attach an email to a networking request or bring one to a meeting. Some recipients find it a bit pushy; some will ask you for it if you didn't send it. I'd advise that whether you share a resume right away is less important than the intent behind it. When sharing your credentials, it's all about the intent you convey (via the rest of the email that goes with it, or your body language and tone if you're in person). What makes people uncomfortable is being asked to give something they cannot provide. The more the informational interview feels like, "here I am, hire me," the more that person is put on the spot. But people are generally happy to provide advice and time and keep you in mind if they have something that you might be great for.
People will often ask for a resume after the interview. In advance of the conversation, I prefer to include your LinkedIn profile—explicitly or casually below your email signature, along with your cell phone number. It's an excellent substitute for a resume because the recipient can click, or not click, to their heart's content.
My final word of advice is it really is all about mindset: This person is a new colleague or friend. I am not an imposition. I bring something to the table just by asking good questions and reminding them they have a cool job. I'll get to return the favor someday or pay it forward. This is going to be an interesting conversation.
In my experience, those of us who don't come from privilege but who acquired it by going to a fancy school or working for a fancy organization also struggle with the way networking seems (and is) steeped in privilege. I've worked with people born into privilege, too, who struggle with this from a slightly different angle, so it applies to all of us. Who am I to have access to these people with fancy titles? Is it wrong for me to take advantage of this when not everyone has it? Everyone has to find their own equilibrium with this question, but I think most of us, especially in social impact roles, come to a place of owning our discomfort with privilege and committing to pay it forward.
My favorites are Working Identity by Herminia Ibarra, Designing Your Life by Bill Burnett and Dave Evans, and anything by Tim Butler. Tim Butler researches career development at Harvard Business School and is a teacher and mentor of many other coaches. He's an amazing person. He's got some fascinating work on culture too. And he has a new book called the Four Elements, which is super interesting.
Impact Opportunity would like to thank Kristin Brennan, Executive Director, Career Exploration and Development at Bowdoin College for sharing her insights and in the development of this article.