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Getting More Information from Your Informational Interviews

The informational interview. A well-intentioned idea that’s often poorly executed.

(TL;DR If you ask the same scripted questions as everyone else you're getting the same information as everyone else, not the most relevant information to YOU.)

It makes sense to talk someone who already works in an industry or position you’d like to be in. A conversation with someone who has ‘been there are done that’ can be helpful in planning your own success 

I know how valuable those conversations can be because I’ve counted on informational interviews throughout my career as a sports broadcaster and business owner.

These days I’m frequently asked to participate in informational interviews. As someone who’s benefited from them I want to help others and provide valuable information.  

But the information you get is only as good as the questions you ask.

I’m happy to answer a wide range of questions, but what I really want to do is provide helpful insight and perspective. I want you to feel more confident in choosing your next career steps. I want you to feel capable and inspired to make your next decision. I want you to feel like our conversation was worthwhile and most importantly I want it to be about YOU.

It’s hard to make the conversation about you if you’re asking the same questions everyone else is after consulting the internet and finding the list of “5 Questions to Ask During Your Informational Interview.”

When you ask the same questions everyone else is asking you are going to get the same answers everyone else is getting.

Here’s the alternative: getting answers that resonate with you and the information you need to make better decisions. 

You do that by being intentional and strategic with the questions you ask. I’m going to show you how upgrade and customize standard information interview questions so you can get better information.


Ditching the same ol’ interview questions

Generic question #1: Can you tell me more about how you got to where you are today?

If you’re hoping to get a detailed timeline of everything I’ve done in the last 25 years related to my broadcasting career or business this is the perfect question to ask.

No? Not what you were looking for? Then ask me what you really want to know.

I could tell you any number of stories from my career but that doesn’t mean they’re helpful for you. In my experience when college students and young professionals ask this question, it’s not curiosity about my career it’s related to self-doubt about their own. Everyone (that includes college students, CEOs, business owners and veteran sports broadcasters) is looking for confirmation they’ve made the right decisions and they’re on the right path. 

If that sounds like you, here are few ideas of questions that get you closer to what you really want to know:

  • Has your career path gone according to plan?
  • What’s the job you were scared to take but glad you did?
  • Was there a moment that confirmed you were on the right track?

If you still want to know about all the stops in my career you can find them on LinkedIn and in my bio. That’s true for many professionals these days too.


Generic question #2: How did you get interested in this field?

Why do you care? I’m not trying to be rude, but it doesn’t really matter.

You’ve already determined you’re interested in this field which makes my interest irrelevant. Conventional wisdom leads us down the wrong path in conversations all the time. I don’t need to or even want to talk about myself. I want to be as helpful and insightful as I can to you.

The purpose of an informational interview is not for me to sell you on the merits of being a sports broadcaster. Anyone asking for an informational interview is looking for answers that confirm they’re on the right track or taking the right next steps.

Let your doubts drive the questions. Being vulnerable leads to honest conversations and more insightful answers.

  • I’m starting to second-guess myself, did you ever feel like that?
  • How did you know this job/career was a good fit for you?
  • When did you know you were on the right track?

If you want to know why I went into TV instead of print journalism ask that question up front to keep the conversation moving in the direction that’s most helpful for you.


Generic Question #3: What does a typical day look like?

I hope you get excited hearing about meetings, emails and the time I spend at my desk writing scripts. 

Oh! You were hoping to hear about the fun parts of my job? Then ask the question.

My job on the surface is nothing but fun because you see me on the sidelines and interviewing players after games. That’s definitely the most fun part of my day, but the reality is that’s a very small part of my day. You know what’s not fun? Detailing all the boring stuff I do the rest of the day. And spoiler alert, every job includes something that’s boring. Very few people I know get excited to talk about the boring parts and even fewer people get excited to hear about them.

Ask specific questions. If you’re curious about how many hours I spend at the ballpark on game day, ask the question. If you’re concerned about getting weekends and holidays off, ask the question. If you want to know what makes the job worthwhile, ask the question.

You take a big risk in asking a broad question and hoping you get the answer you needed. Here are a few ways to learn about a typical day for me:

  • When do you show up to the ballpark?
  • What part of your job makes the boring stuff worthwhile?
  • What kind of boring stuff do you have to do for your job?
  • How do you manage your time during the day?

If you don’t get the answers you need and still want an hour-by-hour account of my workday, ask the question.


Generic Question #4: What skills do you need to have to do your job?

Would you be surprised to learn you need to have experience working in a circus, walking dogs and selling Girl Scout cookies? Of course you would because it’s not true! You probably already have a working knowledge of the skillset needed for your job. If you don’t, Google will answer any question you have about skills needed for every job in the world. 

A small amount of research or even a cursory glance online can help you prepare a better question that will give you more relevant information to you and your situation than Google ever could.

Here are a few questions that help you dive deeper:

  • What’s the experience on your resume you didn’t think would be as important as it is in your current role?
  • What’s the skill you’ve learned to maximize?
  • What skill do you take most pride in?
  • Is there an emerging trend or skill that’s helpful in your role?

Treat the time you have during an informational interview as valuable because it is. You'll get much more out of an interview when you're prepared than when you try to wing it.  

Generic Question #5: What advice would you give your younger self?

This is a tricky one because it could in fact lead to the answer you’re looking for, but I would encourage you to think strategically about it.

I can answer the question but keep in mind the advice I would give myself could be, and likely is, totally different than the advice you need. I’m also willing to bet that all of us who have been asked the question “What advice would you give your younger self?” give the same response every time because it’s part of the script. We’ve been asked so many times that it becomes our cue to deliver the next set of lines.

It's hard to get the information that’s most relevant to you when we’re all following the same script.

Changing the question can lead to a more engaging conversation. Keep the intent the same but change the focus slightly. Here are a few examples: 

  • What’s the piece of advice you have followed throughout your career?
  • What’s the advice that you shouldn’t have followed?
  • What’s the most useless advice you’ve heard for succeeding in this industry/position?

 Here’s what this all boils down to – YOU.

Every professional I know wants to help and is happy to be part of an informational interview. Conversational norms ensure you can ask any question you want and you’ll get an answer. People answer lazy and boring questions all the time. The real question is “Are you getting the information you need?”


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