From introvert to interviewer
Everyone is interesting, you just have to ask the right questions. I came to this realization about 20 years ago when I joined what seemed to me at the time a huge software company of around 150 people. Over the decade that I worked there, I was their sole internal communication specialist, newsletter writer and resident interviewer of everyone from the mailroom to the CEO.
By the time I left the company, they had around 250 employees and I had interviewed over 400 people... yes, there was a lot of turnover in that time! With very few exceptions, I interviewed one person every week for the internal newsletter. The interviews were called "11 Questions" and the entire company eventually came to look forward to reading them and getting to know their colleagues. We had a diverse staff of software engineers, designers and sales people from nearly every corner of the world, including China, Argentina, Columbia, Belarus, Pakistan, the Netherlands, every province in Canada, all over the US and everywhere in between.
My first week on the job, I was given nearly free reign to remake the newsletter how I saw fit, as long as all the corporate stories and sales announcements people submitted were taken care of. I quickly decided that I needed to get to know people in the company and, as an introvert, I needed a good excuse. What better way than interviewing a different person every week?
I began with a literal sheet of paper printed with everyone's names, cut out and put in a hat so I could pull names at random. Eventually I migrated to a spreadsheet so I could keep track of who I had interviewed, who I had invited and been rebuffed by, who had said maybe later, etc. Very few people said no outright, and sometimes they would say no a few times but eventually break down and let me interview them.
The questions started out like you would expect... Where did you grow up? What's your educational background? That kind of thing. Then I started asking things I really wanted to know. What was the last good movie you saw or the last good book you read? If you weren't in your current job, what would you want to do for a living? One sales coordinator from Brazil responded to this question, "I would be a doctor because I love blood!"
Then we delved into more esoteric realms. If you could time travel and witness or participate in any event in history, what would it be? If you could spend a day with anyone living or dead, who would it be? (As an aside, one of the most memorable answers I ever received to this question was a day with Salvador Dali and a night with Marilyn Monroe. Perfection!)
4,000 Questions for Getting to Know Anyone and Everyone
I invested in a book by Barbara Ann Kipfer called 4,000 Questions for Getting to Know Anyone and Everyone, which I highly recommend for anyone who struggles to make conversation or is tasked with interviewing people for any reason. The book is organized into categories like childhood and school, fun and sport, love and sex, politics, spirituality and work. Flipping through at random we find intriguing questions like, what is your worst nightmare and how often do you have nightmares? What has been the most difficult decision or series of decisions where your integrity was at risk? Do you obey rules you consider unfair or ridiculous? What is the best thing about growing older? For this assignment, I steered clear of the politics and spirituality categories but they contain a multitude of gems (e.g., what is the most regrettable event in US history? Would you make a good politician? Discuss!).
One of my favorite questions was, what's the worst job you've ever had? With the rare exception of employees fresh out of college who had never held a previous job, this one almost always elicited a funny or poignant story and more than a few rueful chuckles, after a brief moment of staring into space, lost in reverie. One guy talked about working in a meat packing plant; more than a few mentioned briefly working at a call center, which elicited some hilarious responses from our actual tech support team members. Another question was about a job you'd never want to do, to which a lot of people also responded either tech support or anything to do with accounting.
After a few years, I was brainstorming ideas with the CFO for ways to recognize his team, and shine a spotlight on what they do, similar to "11 Questions" but on a group level. I thought about it for a few seconds and then suggested a "Day in the Life" feature, where I would spend an entire day with a particular team; finance, sales, the software developers, etc., interviewing as many people as possible about what they do on a day-to- day basis. I would then go back to my desk and weave it all into a photograph-laden, long-form deep dive into each department and all the personalities, projects, cubicle decor, inside jokes and whatnot that comprised their work lives.
Day in the life
The CFO wholeheartedly agreed and I started with the Finance team, spending one day with each of the sub-groups under finance, including Legal, Accounts Payable and Accounts Receivable, the mailroom and the Executive Assistant to the CEO. One of the most interesting things that came out of that last interview was the fact that the CEO and CFO were never booked on the same plane if they had to go on a business trip together, just like the President and Vice President of the United States, for reasons of succession. I almost couldn't believe it when she told me, but it gave me an insight into the level of importance that even the most banal duties like booking flights, can entail.
Towards the end of my day with Accounts Receivable, I was sitting in the middle of their open office space, surrounded by Finance workers and their spreadsheets filled with inscrutable and off-putting data. One girl turned around as I was scribbling notes and asked, what exactly are you doing with all these questions? I told her I was going to go away and turn all their answers into a story about the Finance department and she looked at me blankly and a bit horrified, then impressed. She said, "Wow, you have to turn this into a story?" I realized at that moment that while I considered what they do to be impossibly complicated and daunting, to them, the idea of taking what they do and turning into a compelling story seemed just as impossible and daunting. Perspective!
Some of the departments were much happier to open their arms to me than others. One particularly grumpy IT guy almost revolted at the idea of "babysitting" me all day and answering my pointless questions... and yes, of course I included that delightful exchange in my article!
At first, the Sales team acted like they were way too busy to talk to me, but in the end, many of them opened up and shared moments of fun, failure and triumph that peppered my story, greatly humanizing one of the least understood teams in a company characterized by coders and engineers. One seasoned sales rep even wrote me a poem about what it's like to sell software! It was filled with humor and pathos and was actually quite touching and beautiful. I closed my article with his poem and the news that one of the girls I had interviewed made the biggest sale of the fiscal year right at the end of the day. I captured a picture of her, face flushed, grinning from ear to ear, and then she continued running around the office hugging her teammates.
The software developers, by contrast, scheduled me to sit with a different person every 30 minutes each, between team Scrum meetings. I barely had 20 minutes to type out my notes over a hasty lunch break. They were probably the most eclectic team of all, though, representing people from all walks of life before they came to the company.
To my surprise, one of the best days I spent was with Tech Support, a very international team of mostly guys and one girl, hailing from all over the world... Germany, Chile, India, Columbia and China among other places. They told me some of the funniest stories about the bizarre questions callers ask and, although I wouldn't say any article "wrote itself," that one came the closest. All I had to do was quote them verbatim to get several guaranteed laughs out of my audience.
The Fulfillment team was a merry band of pranksters who posted their Myers-Briggs personality types on their cubicle walls and shared hilarious tales about one-upping each other with practical jokes, like covering a manager's office in tin foil, or filling every inch of another's office with balloons. Probably the best prank involved one team member Photoshopping an incredibly realistic parking ticket and leaving it on the hood of another team member's car. When the guy found it, he was outraged because he was sure he had parked in a legal spot. He was ranting about it to everyone in the room, so worked up he didn't notice their barely-contained laughter. Someone finally urged him to call the phone number on the back and when he dialled it, the phone on the desk next to him rang and his teammate picked it up, saying the name of the parking company. Pwned!
After I left that company, I worked for a much larger company, orders of magnitude larger; in fact, the size of a modern city. One of my favorite parts of that job involved interviewing people who had moved from one department to another about their new job. It was part of a campaign to increase internal hires and reduce attrition. It was less hands-on since all the interviews were conducted on paper, and there was none of the humor or irreverence of my previous interviews, but I still loved being able to shine a spotlight on a different person every month and give them their 15 minutes of fame within the company.
Podcaster
In 2013, I began podcasting with Alison Price (you can find our old episodes archived here) and after a several year hiatus, we picked it up again last year. We've done over 100 episodes so far and I love being able to converse and explore different astrology-related topics every week with her and our other guest participants. One day maybe I'll start my own podcast interviewing people on a wide variety of subjects. I think Joe Rogan has the best job in the world and I would love to somehow craft a third act career doing what he does!
Me and Alison Price, celebrating our 100th episode of Starzology.
