5 Informational Interview Questions with Substance

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About a year out of college I was meandering the magazine aisle at Barnes & Noble in Seattle when a cover featuring the CEO of a local book publisher caught my eye. I recognized the name from a book my roomies and I loved. It was filled with questions, and we'd choose one to talk about before going on a run (to distract us from the pain...). On a whim, I emailed the CEO and asked if he'd like to have dinner with us. Six weeks later, he replied "yes."  

There's a remarkable vehicle for connecting professionals with recent grads who have big dreams, lots of motivation, and a desire to sit humbly and learn from someone else's journey: It's called an informational interview. 

(If you've never heard of an informational interview, this blog post is not for you...yet. First, sign up for FREE access to nine Career Experiments, then download "Talk to an Expert.")

If you have heard of informational interviews, you know this is one of the quickest ways to gather lots of great insights about a career path or industry. But, questions like “What are the best and worst parts of your job?” and “How can I stand out as a great candidate in this field?” only scratch the surface.

When you’re lucky enough to be speaking to a seasoned professional with experience, connections, and deep knowledge of their field, why not take advantage of it?

Sure, some friendly chit chat helps everyone settle in. But once that formality is taken care of, these questions will help you move from a high-level conversation to something with substance - so you leave with not just good information, but insider’s information too.

  1. What are some of the hot topics being discussed in your organization right now, or in your field? What’s at stake on both sides of the discussion?

  2. How would I recognize a great opportunity in this field? What danger signs would suggest that an organization is struggling, or that I should avoid the opportunity?

  3. What organizations in this field should I be keeping an eye on? Who’s driving change, shaking up business as usual, or standing out to you for any reason?

  4. Where does the tribe for this field hang out? Are there any specialized networking groups, online communities, professional associations, or other hubs that I should be connected to?

  5. To my understanding, ___(fill in the blank with an assumption you’re making about the field or have heard to be true, like “only candidates with master’s degrees are taken seriously, even for entry level roles.”)____. From your experience, would you agree? Why or why not?

A few days before your informational interview, send the professional you’ll be meeting a few of your questions along with a confirmation of the meeting time and location. This will give them a bit of time to think about their answers, since they just might need it!

Career Experiments: Madison

I was introduced to Madison by way of a mutual friend who loved her design style. Our initial emails about project ideas grew into lively brainstorming/editing sessions, where Madison would do her magic in real time, editing behind the scenes as our conversation progressed and then voila! - something better than I imagined would refresh on my screen. Her fun personal site is about as upbeat and friendly as she is. 

Madison is a true creative, dabbling in projects that build new skills while she investigates her interests. I'm impressed with her skill-building drive (Which is essential...the more skills you have, the more opportunities you have access to!) but I'm floored by her focus on building a community. We talk a lot here about "learning from your tribe," but she's taking it up a level and uniting her own. Wow. 

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Who: Madison, 27

What: Graphic designer, artist, serial encourager

What career interest(s) are you currently exploring?

I’ve always had a passion for supporting local businesses - specifically artists and local makers. I live in a small town. We have tons of makers and creatives, but we don’t really have a place to make sales and gather with community. We kind of have to go into the city for that. Nothing against Atlanta, but I think that’s a real bummer! It’s all right here. We just don’t know each other yet. I have been thinking about creating a maker’s place - think retail shop and workshop space for classes alongside private artist studios. There are several wonderful models for this in the city, but not out here! (Yet!)

How did you discover that interest?

I think it’s always been in the back of my mind. I worked as an office and community manager for a while and I loved creating a welcoming environment. I worked with an arts nonprofit and enjoyed coordinating with artists and nonprofits to do workshops and art events. I worked as a brand manager for a blog and enjoyed connecting with large brands for sponsorships and paid posts. I enjoy making my own little line of greeting cards.

Through all these experiences, I was able to take what I learned and apply that to the next project.

Everyone has so much to offer and receive. So much to teach and learn. We just need to be mindful about putting the pieces in place. I really like putting the pieces in place.

What are you doing to investigate?

I am really trying to be gentle with the maker’s place idea and see if it’s a good fit. I am working with another small town evangelist, Small Town Creatives, to coordinate their first maker’s pop up shop at our local brewery. Pretty cool and special! It’s my own mini career experiment!

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I also started working part time at a local yoga studio to see if I enjoy being in a place at a certain time every day. Turns out, I do! The routine and consistency are so nice after 2 years of dry shampoo and #freelancelife. I’m learning a lot about customer service, about business operations, scheduling and how to solve problems. The owner of the shop is a very smart and thoughtful about her business, and I really enjoy learning from her.

What has surprised you most about your investigations so far?

While I’m in the experimental stage, I have been slowly whittling down the design projects I take on.

Starting a business is so freeing, but sometimes it can feel a little prison-like too. (Just me?) It can be tough to see how to grow beyond what you’ve built. It’s actually quite scary to think about pivoting or changing your business, “just when you’ve got it figured out.” Saying no to new work feels impossible because you’ve created this momentum and you don’t want to waste it! (While I totally get that - that’s a scarcity mindset and it has no place here!)

This experiment has created a much healthier balance of work and play for me. I've been working on my photography, my writing and illustration. I've been reading a lot. It's been fun! I’m excited to see where this goes!

If your career doesn't happen "according to plan," you're in GREAT company

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When you ask people how they got into their careers, you hear some crazy stories. 

Kat Cole, CEO of Cinnabon, got her start at Hooters. She was just planning to waitress to earn money for college. Her talent landed her on the radar of management, and then other opportunities began coming her way...including traveling internationally to train new staff members. By 26 she was promoted to VP of Training and Development. 

Her story might be on the "extreme" end, but the truth is that finding a job you love rarely happens "according to plan" for any of us. More often, the path becomes clear as you walk it.

My favorite tool for creeping on the surprising twists and turns that ended up shaping the career paths of other professionals is...

The Roadmap

(Check it out. I'm pretty sure you'll have fun.)

How to use your stories to write sparkling cover letters

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After you've collected all your unique, hands-on experience, it would be to shame to waste it in a generic cover letter. 

Here's what I mean. Many cover letters include stupendously boring body paragraphs like this one:

Working in laboratory settings has been a passion for many years. From the moment I stepped foot into the AP Chemistry lab I knew this was where I wanted to be. In college, I spent many hours learning how to be a valuable lab assistant, ensuring that I developed the skills to become highly competent, detail oriented, and able to take preventative actions to minimize any safety hazards.  The focus of these efforts has been to become a qualified candidate for a crime lab such as yours.

Paragraphs like this are problematic because they don’t include evidence. They expect the reader to simply believe the claims that are being made, rather than proving their skills or competence with compelling proof.

This is where your own, unique experience comes in. You can use it here to make your cover letter interesting!

For example, this body paragraph backs up a specific claim about the writer’s skill with a story from their real life experience. Most importantly, the story includes concrete evidence, which makes it much more impactful and relevant to the position:

My work in the Montana State University’s BioDesign Institute challenged me to develop the attention to detail necessary for assisting in a fast-paced laboratory. For two years I have given hands-on assistance to six PhD students, supporting their research while managing my time independently to give each project the attention it required. These projects involved extracting RNA, PCR reactions, and creating, running, and analyzing gel electrophoresis. This experience has prepared me to prioritize tasks and work efficiently in the Gilman County forensic lab.

Let's break that story down into a simple structure. You can use this skeleton to fit a lot of quality information into a small space, so your body paragraphs get right to the point while featuring the experience that makes you special.

1) Make a claim. After you’ve thoroughly read the job description and decided which desired skills, competencies, or experiences you want to feature, make a claim:

Coordinating logistics in a swiftly changing environment is a skill I have mastered through supporting a 3-person executive team.

2) Back it up with a short story illustrating how you modeled the skill or competency in one of your experiences.

This position required me to maximize the impact of our organization’s leaders by ensuring they that were always prepared to be productive. In an ever shifting startup environment, this meant changing priorities at a moment’s notice to prepare travel itineraries, update slide decks to reflect the latest product developments, anticipating needs and preparing to meet them in advance. On my departure, my ability to pivot with grace was rewarded with a special gift - gold pointe shoes.

3) Project the skill forward. Help the reader connect the dots by clarifying how the skills you developed in your experience can be applied in the new position, or how it might benefit the organization.

As an Operation Lead, my experience proactively identifying needs will ensure that Sandbox Cowork is always appropriately staffed and stocked, so members can focus on doing what they love.

The best thing about featuring your own stories, from your own experiences, is that NOBODY ELSE will have exactly the same ones. Your experience is what separates you from other candidates, so show it off!

If you've never written a cover letter before (or if you have but you used one of those awful templates from Google) there'e more to learn. My guide, How to Write a Resume and Cover Letter that Gets You Noticed, is a good place to start. 

Career Experiments: Celestine

The first thing that impressed me about Celestine was her number of interests, ranging from mastering languages to the great outdoors. The second thing was her determination to take advantage of all the opportunities that came her way.  

This is HUGE. I just read the brilliant Herminia Ibarra's article "Women Rising: The Unseen Barriers" about how leadership experience creates leadership identity. The way to become a leader is to do leadership stuff, just like how Celestine co-led a wilderness expedition with her class. Not only does action help you see yourself as a leader, but others start to see you that way, too. 

Nature might not be your thing, but if Celestine's experience of learning alongside others inspires you, consider Finding Your Tribe. A "tribe" unites people from different backgrounds around a common interest. A strong tribe connects you to people who are already rooted in the field, so you can benefit from their advice on getting started, getting ahead, and what to expect on the road ahead.

 Break time: No camera can capture the true golden color of that canyon wall that stood before us. But never mind that, let’s learn how to read a topographic map and find out where we’re going!

Break time: No camera can capture the true golden color of that canyon wall that stood before us. But never mind that, let’s learn how to read a topographic map and find out where we’re going!

Who: Celestine, 20

Where: Kanab, Utah

What have you done recently to explore a career interest?

I recently took a leadership class that was required for my Parks and Recreation Management degree, with an emphasis in Outdoor Education and Leadership. Through that class, I had the opportunity to go backpacking for six days in the Kanab Creek Wilderness.

I went into the trip not knowing what to expect and being fairly confident in my leadership skills. I got to put these skills to the test for two days during this trip.

It was a great setting to get helpful feedback from the group and my professor. I learned that I need to have a stronger voice in my leadership. Previous to this trip, I would have felt too rude to interrupt the group’s conversation and get us all on task. Now I know that as a leader, it’s my job to speak louder and make sure we’re accomplishing our goals. I have to work on being louder and prouder in my voice. 

There were also some things that I did well on the trip. I was recognized as very compassionate, patient, and communicative. So although we may not have stayed on task as much we needed, at least I made sure everyone’s needs were being met, whether it be taking it slow and helping people climb down a dangerous part of the trail, or taking the time to listen to someone if they were having a bad day.

I learned a lot about my own leadership style and observed other peoples’ styles. Now I know where I need to improve as well as what I need to continue doing.

 Look for the big green back back on the bottom left. There she is!

Look for the big green back back on the bottom left. There she is!

Best moment from this experience?

What I loved about being a leader on this trip was my ability to teach others and problem solve. Beyond the leadership aspect, this trip was a good reminder of how simple life can be. Whether you’re teaching a friend how to climb up a rock, sharing a moment of admiration for the natural surrounding beauty, or eating peanut m&m’s, I was reminded that I can find happiness and reward in the little things in life.

Now, I know that sharing the outdoors with others is my calling. I plan on finishing my degree and one day working in wilderness therapy.

Action: It's Your superpower

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“I think I need to Purel my tush.”

So said Alicia, another teenager on a volunteer trip to Bolivia, where expeditions to the bathroom were a multi-step process:

  1. Stuff your pockets with as much toilet paper as necessary, since it doesn’t come free in the stalls
  2. Dig out your headlamp, since the bathroom complex didn’t have electric lighting
  3. Find a buddy to keep you company on the walk across the dark field to the bathroom complex
  4. With a narrow beam of light for guidance, leap across a stagnant puddle to the rotting log sitting in front of the toilet seat, so your feet could be out of water while you did your business
  5. Purel everything

The reflection staring back at me in the mirror that night wasn’t “me.” This girl was streaked with mud, hadn’t washed her hair in days, and had pit stains down to her waist.

I don’t know exactly how this happened, but at 17 I determined I was spoiled rotten and should volunteer in a developing country to get a bigger perspective on life. (I also couldn’t tell you how my parents decided to go along with this whim, sending me off to Bolivia for a month with a highly dysfunctional national service organization I found online.)

Four months later, I found out what happens when you drop a perky prom queen with a love for platform sandals and hygiene into the Bolivian Amazon with no air conditioning, billions of bugs, and a single bathroom to share between 13 teenagers.

Her identity grows.

Until this experience, I would have told you that the “authentic” version of me was poised and put together. Being a teenager, I demonstrated this through fashion: Handbags coordinated with the rest of my attire and perfectly manicured fingernails. Quite quickly, I realized that being "put together" was of no value when aggressively scrubbing spider larvae off of cement walls.

Early on in that month I determined to push through the homesickness and sense of disorientation that came from not knowing how to be successful in a strange new environment and culture. By end of the month I could add another word to that list of "authentic" traits: Adaptable. 

As a teenager, I hit on an insight that Herminia Ibarra calls the "authenticity trap." This is the idea that we tend to use "authenticity" as an excuse to keep doing what's familiar, rather than push into the great unknown. In her words, “Because going against our natural inclinations can make us feel like impostors, we tend to latch on to authenticity as an excuse for sticking with what’s comfortable.” 

The way out of the authenticity trap is by taking action, putting yourself into new situations that draw out your potential. 

These experiences aren't about reinforcing who you already are, but about discovering who you could become next. 

Action is your superpower. It transforms you

Are there any ways that you're letting "authenticity" bind your powers? 

  • If you catch yourself saying "That's not my thing," could it be? 
  • If you decide not to pursue an idea or interest because "I'm not really that type,"...are you sure? 
  • If you turn down an opportunity because "I couldn't do that,"...have you tried? 

This week, why not take one new action and see what happens? If you take this challenge, please drop me a line at Laurah@betterbetter.co with a brief note on what you learned or gained. I'd love to send you a special gift in return.