The Informational Interview: unlock new opportunities (and snag 25 questions to ask!)

Two people with coffee cups at a wood table with text overlay the informational interview: unlock new opportunities, ask these 25 questions by Rikki Goldenberg, Executive Leadership Coach, Career Coach

The Informational Interview is your magic sauce

When you’re making a career transition, one of the best tools in your arsenal is the informational interview. Even if you have deep clarity around your next role or organization, it’s essential to have deeper conversations in an informal setting to make sure that your instincts are right.

If you don’t have clarity, the informational interview will change your path. By connecting with people in a low-stakes environment you’ll have the golden opportunity to learn more about roles, organizations, or industries. And, you’ll get a chance to learn the truth of it.

In a job posting, or during an interview, we get nervous. We’re focused on making sure the hiring manager likes us. We get tongue tied, caught up in making a good impression.

In an informational interview, we’re able to ask open questions, be curious, all with the final say in what happens next.

These conversations help you understand the deeper details of a potential path - the true risks, rewards, hurdles, and struggles you’ll go through.

They give you power to make a decision from knowledge, not desire.


How to snag the interview - and then have a good one:

There’s three main steps to an informational interview (some of these may seem obvious, but they’re good to remember):

  1. The initial ask - finding the people you want to talk to and reaching out to them directly, or indirectly

  2. The interview - asking the burning questions while being respectful of their time

  3. The follow-up - making sure every door stays open


So let’s dive into it.


The initial ask:

If you aren’t quite sure who you want to talk to, start by thinking of companies you like, and roles that might interest you.

Hunt for people who work at those companies (even if it’s a different department), or have a title similar to that.

Once you have a list of 10 people, take action. Why 10? Because if you go one at a time, all of your energy goes into that one person. They might be too busy for you. They may not be interested in helping. Maybe they’re on mat leave or in the process of switching teams. Whatever it is, by having a group of folks to reach out to rather than just one all-important individual, it helps take the pressure off of everyone - you included.

Reach out to the folks, or friends of those folks and ask for an introduction.

Be clear about what you’re asking for: if you’re learning about their company, say that. If you’re learning about their role, tell them.

Include one or two sentences about your background and where you’re at in your journey. This is essential. If you’re trying to make a switch right now, these conversations will take on the flavor of more formal interviews. If you’re information gathering and curious, they’ll be more informal.

Offer times, days, and be respectful of their schedule.

Don’t forget. People want to help. They might be too busy right now, but if you’re clear about what you’re looking for, even if they’re too busy, they might be able to point you to someone else.


The interview

Be prepared. You’ll want to have questions prepared that are tailored to that person.

Be comfortable. Remind yourself that this is a sharing of knowledge, a chance to hear from the source.

Be flexible. Folks are busy. They may need to end the call early, or you won’t get through all of your questions.

Be you. This doesn’t have to be the time to posture. You’re allowed to create a connection with this person - after all, they may know someone else who you could talk to who’s hiring right now.

Be direct. This is the time to get answers to your questions. If you’re trying to break into a new role or industry, ask about the lingo or education you’ll need to demonstrate expertise. If you’re curious about their organization, find out about hierarchy, culture, opportunities for growth. This is your chance to really ask those questions.

Be grateful. They’ve given you a blessing. Thank them for their time, their information, their willingness to share.

My favorite 5 questions?

  • What is your favorite part of your job?

  • What does it take for someone to be successful (at your company/ in your role)

  • What is the worst part of your job?

  • When you think back, what advice would you give yourself to ensure your success?

  • Who else do you think I should talk to?

    ^ This last question is my absolute favorite - it helps you create continued discussion. Because who knows, your next role might come from not this first chat, but the third chat removed from it.

Want to get even more questions ready? Grab my 25 questions to ask in informational interviews - right in your inbox.

The follow-up

You’ll want to thank them for their time, of course. Reference specific moments to that conversation. If they offered to connect you with someone else, close the loop.

Follow-up with them every once in a while - when something changes in your situation, when you see they’ve been promoted or their company was in the news (for good things.)

Let them know if you see a position or person that they’re connected to - they may give you the personal recommendation to the hiring manager.

Give back - if you see that they’re hiring, or making a change, think of who might be a fit for them to hire, or to talk to.

Reflect. Take time to write down what you learned, what you want to do with this information. If this changed some of your expectations, note that too! Sometimes an informational interview can be exhilarating, pumping you up. But, sometimes it can be upsetting when you discover a company or role that sounded perfect probably isn’t perfect for you.

One of the best parts of these conversations is they’re openings. So often, a simple chat can turn into another chat, into another chat, into an interview. Frequently you’ll get access to someone who doesn’t even have the job posting written yet - and you get to help them write the perfect one (for you!)

Once you’ve made the shift? Don’t forget to help others who’ve asked.

Struggling to figure out who you even want to talk to, and about what? Reach out.

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