Find The Person Who Has The Job You Want, Then Ask Them These Questions

Get The Most Out Of Your Informational Interview

Within the first five minutes of my meeting with Clarissa, I suspected that I had made a mistake. And by the ten-minute mark of this informational interview, my suspicions were confirmed; Clarissa—a recent graduate—offered to buy me coffee in exchange for picking my brain. And as usual, I was happy to oblige. We booked an hour-long chat at a nearby coffee shop and I came prepared to give her every possible insight I had into making the successful transition from post-secondary to a dream job. But when we met, for ten minutes straight, all this young lady did was talk about herself. However, this wasn’t the reason I abruptly ended our discussion. To be fair, I would’ve gladly chalked up Clarissa’s monologue to nerves had it not been for her brazen answer to my one and only question: “Why exactly did you want to meet with me?” To which she replied, “Because I want a job at Student Life Network. Are you hiring?” Flustered, I recommended a few resources and wished the young job seeker the best of luck on her hunt. And with a 50-minute gift of time, I went back to my office and wrote this post.

One of my mentors once told me, “If you ask for a job, you’ll get advice. And If you ask for advice, you’ll eventually get a job.” Several times a week, I eagerly answer the questions that students and young professionals ask me about how to reach their goals. It’s a debt that I’m only too happy to repay, as it continues to be instrumental to my own success. In fact, according to a survey conducted by the U.S. Bureau of Labour Statistics, 70% of professionals found their job through networking. And informational interviews not unlike the ones I’m regularly engaged in are, in my estimation, the most effective way to increase your odds of success. “Informational interviews are essential to helping you find out more about the type of industry, company, or role you’re interested in,” says Dorie Clark, author of Stand Out Networking. “You may think you already know all about a certain position, but speaking to someone directly gives you the opportunity to test your assumptions.”

When exploring a new career path, it’s smart to go out on informational interviews. But who should you meet? And what should you ask when you’re actually in one? My experience has taught me that to make the most of an informational interview, find the person who has the job you want. Then tease out their blueprints for personal and professional success. To that end, I’ve compiled a list of 14 tried-and-tested questions that I have either asked or been asked over my career. They help you to unlock rare industry insights and professional pathways (including secret shortcuts) that will prove invaluable compared to the job you won’t land by foolishly shooting your shot like Clarissa did.

Here they are, in the order I typically ask them:

1. What is your North Star?

Successful people tend to be driven by a strong, often singular purpose. This question will help you to understand what truly motivates your interviewee and empowers them to push through adversity.

2. What do you love most about your job? What gets you up out of bed every morning?

Those who ascend tend to be emotionally connected to their work—either to their people, their product, or the end result of their output. Or all of the above. This link enables them to transcend the trials of the day-to-day.

3. What are your leadership superpowers? Specifically, what are the soft skills you’ve relied on to get you where you are?

In asking this question, listen carefully to the stack of soft skill strengths (such as compassion, empathy, creativity, etc.) that your interviewee shares with you. Then consider investing in the development of these skills.

4. What are the technical skills you’ve relied on to get you to where you are? And what skills will be important 5–10 years from now?

Don’t shy away from asking them where and how they learned these technical skills. Get specific—ask for course details, learning outcomes, and reviews of their experience. After your interview, seek out the skills you’re missing.

5. What book is currently on your bookshelf? What ebooks/audiobooks/podcasts are you currently listening to?

Get a sense of how they’re investing in their ongoing professional development through media consumption. Then head over to Amazon and fill up your cart with what they suggested.

6. What book was a game-changer for you?

Buy this book, and read it cover-to-cover. In addition to helping you better understand the ideas in your interviewee’s head, it will serve as amazing talking points for follow-ups and future meetings.

7. How do you continue learning and growing as a professional? What are some of your habits aside from reading/listening?

You’ll want to know how your interviewee is continuing to learn outside of their media consumption. Are they in any professional organizations? Do they engage in high-level informational interviews themselves?

8. Who inspires you? Who are your mentors?

Find these people on social media and follow them. And begin the gradual campaign to one day interview them. Analyze what they talk about. Look for clues that further explain your interviewee’s success.

9. What’s the best piece of advice that you’ve ever received?

There’s a good chance that in this interview you’ll receive some game-changing advice. Multiply its effectiveness by learning what piece of game-changing advice your interviewee received when they were in your shoes.

10. What are some industry trends that you’re keeping an eye on?

Peer into the crystal ball owned by your interviewee. Their answer will be the synthesis of the time, energy, and attention they’ve invested in becoming successful at what they do.

11. What was the lowest point of your life/career? What did failure look like, and how did you bounce back?

Successful people tend to have a strong resilience muscle. That’s to say, they’ve experienced hardships and had to overcome them. Over and over again. Try to understand what feelings your interviewee is trying to get away from, and store their process for escaping it. You may need it some day.

12. What was the highest point of your life/career? And how do you continue to recreate that feeling?

Understand how your interviewee views their own success. And prepare to be surprised—very rarely have my interviewees given me an answer that has to do with their professional accomplishments.

13. What advice would you give to someone like me who one day wants to be in your shoes?

This question will drive home the point that you’re interested in emulating their success (but in a non-threatening way). It will reassure them that they are someone who is extending the runway of what’s possible for you.

14. When all is said and done, how do you want to be remembered by the people whose lives you’ve positively affected?

The million dollar question. It will put into perspective the end game of your interviewee, and help you anticipate their next career moves. You need to know this, because if all goes well, you’ll be following suit.

Now, a few things will happen when you ask these questions. Like clockwork, the interviewee will admire the thoughtfulness of your questions. And then eventually they’ll realize they’ve been doing all of the talking and naturally ask you about yourself. This is your opportunity to shine. Use it to position yourself as someone eager to learn more from them. And then make an ask that is considerably more valuable than asking for a job: “Can we do this again in a couple of months? And if possible, could I bounce some ideas and ask you some questions over email?” And if you feel that the meeting went really well, hit them with this: “I would be honoured if you would consider being a mentor to me.” By the way, if you want to create your own questions, go for it. For maximum effectiveness, just make sure that they don’t end with a “yes” or “no” answer.

If you’re looking to dramatically improve your chances of landing your dream job, you’ll find the most effective approach will be to pick the brains of people who currently have the job that you want. Why? Because chances are, they’re thinking differently than you. Frankly, it’s one of the reasons why they have the job and you don’t (yet). So when you manage to land a meeting with them, don’t ask for a job—ask them about their mindset, their practices, their outlook, their rituals. Deconstruct your target’s path to success and emulate their practices.

At best, you’ll walk away with a job offer and/or mentor. What’s most likely is that you’ll have made a great impression, made a new connection, and placed yourself on their radar for future opportunities. At the very least, you’ll have download their blueprint for success.

All of that and more, for just a cup of coffee.