The art of interviewing: 11 tips

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By Caitlin Kelly

I’ve been interviewing people for a living — journalistically — for decades.

These include the former female bodyguard for New York City mayor Rudy Giuliani on 9/11 (global exclusive), a female Admiral, Olympic athletes, an NHL coach, convicted felons and just regular people, aka “civilians”, people who may never before have spoken to a journalist and realized that every word counts.

My 11 tips:

Always start and end with a sincere thank-you for their time and attention.

 

Very few people have to speak to us, and for some, it can feel like an ordeal. The more warm, empathetic and human you are, the better it will go. Yes, some interviews are very tough on the subject, even adversarial. That’s also our job. But being an efficient robot is rarely the best way to elicit great stuff.

 

Prepare, prepare, prepare.

 

Nothing is ruder than waltzing into someone’s home, office, or life without knowing who they are, why you are speaking to them and how they fit into your story. Do your homework! It shows respect and will, always, elicit a deeper, richer exchange as a result.

 

Consume everything you can on this person before you speak so you’re easily able to reference their books, videos, TED talks, podcasts, essays, journal articles.

 

Obviously, if you’re writing 300 or 500 words, you can’t afford to do this. But a story of 1,000 words or more means digging deeper. Few moments are as flattering to an interview subject than letting them realize you’ve really done your prep on them and their ideas and accomplishments. Sometimes I go all the way back to college or high school yearbooks and friends from those years.

It only appears social.

 

A great interview can be conversational or feel like it. There are times I just lay down my pen and stop writing,  preferring just to listen, watch their body language and take a breather. I also, when it feels legitimate, may share a personal detail with them that’s relevant to the story and its focus. This can build trust. Why would anyone just spill it all to a stranger?

 

Allow at least 30 minutes unless you truly only need a very quick quote.

 

My interviews are routinely 30-45 minutes, often an hour, sometimes 90 minutes and (whew!) rarely, two hours. After that I am utterly whipped and so are they.

 

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One of my old notebooks — coffee stains and all!

Tape or take notes on paper or computer — whatever works best for you — as long as you are accurate!

 

Do what works for you. Fact-check!

 

Make sure, whenever possible, no one — pets, children, the mailman, an assistant, your cellphone — intrudes and interrupts.

 

This is a sacred space. Don’t check your phone! Create intimacy and trust. Focus.

 

Allow plenty of time beforehand, certainly when doing this face to face, to find the right place, settle in, use the washroom and steady your nerves.

 

We all have those “ohhhhhh shit!” moments — your kid melts down as you’re leaving the house, you feel ill, the bus/train/subway is slow or late or cancelled. Give yourself plenty of time to get calm. Your subject needs to feel confidence in you.

 

Ask them who else they consider essential for you (and your audience) to understand and explain the story properly.

 

If you’re done your job well, they’ll share some great intel they might not give someone less skilled.

 

 

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What’s the story’s direction?

If this feels comfortable, consider sharing the focus, length and direction of your story, and maybe some of the other sources you’re speaking to.

 

Some journalists totally refuse to do it. I do this, judiciously, for strategic reasons.

 

Ask them, at the end, what you failed to ask.

 

Always.

I also coach other writers to excellence for an hourly fee. Details here!

The deep comfort of seeing old friends

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By Caitlin Kelly

Imagine opening your kitchen door to someone you haven’t seen in 50 years.

That just happened for me and a woman I knew at boarding school in Toronto, with whom — both of us bad girls asked to leave the school at the end of that year — I then, briefly, shared a room there.

She’s an incredibly talented art photographer, with three books to her credit; here’s her website.

After we lost touch, she moved to Ireland, then back home to Toronto, then to the U.S. — as I did, and there married and divorced without children (as I did.) Now she’s back in Canada and we caught up on so many stories! It was eerie how much we had in common and so comforting to feel like it had not been so many years; she, too, had DCIS (early stage breast cancer) and reached out to me on Facebook last year when I was diagnosed, then living in New Mexico — my husband’s home state.

On this trip we also caught up with a man I’ve known since my very early 20s, married for years to his husband, now retired to the country. We met their gorgeous Airedale and enjoyed a great meal together. We hadn’t seen them in a few years and look forward to returning. How nice to know we’re welcome again.

We also spent an evening with yet another friend of many, many years — who I met when he was a tenant in an apartment in a house my father owned. It’s lovely when you’re out on the road for three weeks, most of it working, to sit at a friend’s table and savor their hospitality. (We arrived there with a big box of delicious bakery goodies.)

I finally, after many lonely years there, have several good friends in New York, and one who’s known me for about 20 years — but the depth and breadth of my earliest friendships, the ones who knew me before my first husband, (pre-1986), are so precious to me. They knew me “when” — and, still, gratefully, know me now.

On this trip, I’ve also made several new younger friends through Fireside, and I am really enjoying getting to know them better.

 

Friendship sustains me.

Ten tips for freelancers

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At its best, time for a long lunch out! This is L’Express in Montreal

 

By Caitlin Kelly

Some call it — ugh! — the “gig economy” as if we were all hep-cats pounding some drum-set in the basement.

Freelance life, if it’s your sole income, really means self-employment, running a small business. While freelance sounds hip and cool and breezy — being a small business owner sounds, and is, much more serious.

I’ve been full-time freelance since 2006, but have done it for long stretches before that.

Some tips:

 

Choose your clients very carefully

It’s tempting, especially when you’re starting out, to lunge at every opportunity. It’s not a good habit to develop. People can smell desperation and will, sadly, take advantage of it with low rates, slow payment, awful contracts and abusive behavior. Do your due diligence whenever possible so you can avoid these toxic monsters.

 

 

Cultivate a wide, deep network of peers, fellow professionals whose work, work ethic and character you know well.

 

See point one! Without a network, how would you know? With a network, you will be more able to pick and choose which opportunities are best for you and your skills. Once you have a posse, you can safely refer work to them when you’re swamped, and vice versa.

 

 

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Keep at least three months of basic living expenses in the bank or have access to a line of credit.

Very few clients pay quickly. The best will pay 50 percent up front, or one-third, but this varies by industry. Late payments are a huge source of stress.

 

Know your legal rights! Read every contract carefully and amend them whenever possible. In New York State, the law protects freelancers who get stiffed.

 

Some contracts have become virtually unmanageable. Worst case? Walk away.

 

Negotiate. Every time.

 

No one is ever going to just hand you bags ‘o cash. Ask for more money, more time, a larger travel budget, social media boosts, etc.

 

Keep growing and building your skills.

 

Your competitors are!

Attend conferences, take classes and workshops and get some individual coaching. Listen to podcasts and Ted talks and YouTube. Read books. Take a college or university night class. The wider and stronger your skills, the more options you have to earn multiple revenue streams.

Yes, I coach!

 

 

 

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Get out into nature. Slow down. Rest.

Take time off!

 

Without rest, recharge and respite, burnout is inevitable. For all the putative freedom — no commute! work in a T-shirt! — this is often a highly stressful way to earn a living. Some people with “real” jobs, some of whom have paid vacations and paid holidays and paid sick days, get time off.

Freelance? The only people who know when it’s time to take a break is us.

 

Set clear boundaries between work and rest. Keep them!

 

I don’t work nights or weekends. If I do, I take time off in recompense. I keep a fairly standard work schedule, 10:00 a.m. to 5pm. I don’t like early mornings so will only schedule something before 10:00 a.m. if it’s really urgent — like working with someone in Europe (five to six hours ahead of me in New York.)

Get out of your lane!

 

I hate this new admonition — stay in your lane! All it does is ensure we don’t listen to, look at and engage with others who are different from us, in politics, interests and vocation. If all you ever do is talk to other writers or fellow freelancers, you’ll quickly die of boredom! Go to museums and parties and gallery openings and concerts and stuff your kids are into (Fortnite!) to keep your brain open to new ideas and ways of thinking.

 

 

 

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Remember in your heart of hearts that your skills and work bring value

 

Freelancing can be really lonely and really isolating. If you work alone at home for years, and have no kids or pets and your partner or spouse works out of the home, it’s very easy to start to feel feral and ignored. Make an “attaboy” file of every bit of praise and kindness so on days when everything gets rejected you recall why you’re good at this stuff and things will improve.

Here’s a recent interview with an American freelance writer, a woman of color.

Two new stories of American labor

By Caitlin Kelly

Happy Labor Day!

As regular readers here know, how people work and earn their living — and for what pay and under what conditions — is a bit of an obsession of mine.

I’ve had many staff jobs: at three big daily newspapers and at several magazines, (trade and consumer) — and worked 2.5 years selling stuff for $11/hour as a sales associate for The North Face, by far the most difficult job of my life and the most humbling. It became my second book.

Since losing my last staff job in 2006, I’ve remained freelance, which means I am only paid for whatever work I can find, negotiate and successfully complete. Pay rates for journalism are now much lower than in the early 2000s,. when I easily brought home $60,000 a year. Not now.

It’s crazy.

 

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I grew up in Canada — a country with unions! — and moved to the United States in 1988. It is a truly eye-opening experience to live in a land of such brute, bare-knuckled capitalism! No paid maternity leave and very little unpaid. No paid vacation days, by law. At-will employment, which literally means anyone can fire you anytime for no reason at all.

Then, no severance!

Weakened unions at their lowest membership ever.

Stagnant wages — while CEOs “earn” 254 times the pay of their lowest-paid staff.

So, hey — try these!

Former New York Times labor reporter Steven Greenhouse, a friend, has finally just published his new book about American labor, The Big Squeeze.

I can’t wait to read it.

Just one of its many rave reviews…


“The power of Greenhouse’s book lies . . . in its reporting, especially on low-wage workers . . . his best material vividly focuses on the always difficult and often abusive working conditions of low-paid employees. Such stories get far too little airing and rarely are they so well told.” —Business Week

Here’s an earlier book on the same topic, from 2014.

And a new documentary,  American Factory, takes a close look at one American factory taken over by the Chinese.

From The New York Times’ review:

In 2016, Cao opened a division of Fuyao, his global auto-glass manufacturing company, in a shuttered General Motors factory near Dayton, Ohio. Blaming slumping S.U.V. sales, G.M. had closed the plant — known as the General Motors Moraine Assembly Plant — in December 2008, throwing thousands out of work the same month the American government began a multibillion dollar bailout of the auto industry. The Dayton factory remained idle until Fuyao announced it was taking it over, investing millions and hiring hundreds of local workers, numbers it soon increased.

The veteran filmmakers Steven Bognar and Julia Reichert, who are a couple and live outside of Dayton, documented the G.M. plant when it closed. They included the image of the last truck rolling off the line in their 2009 short, “The Last Truck: Closing of a GM Plant.” That crystallizing image also appears in “American Factory,” which revisits the plant six years later. The feature-length story they tell here is complex, stirring, timely and beautifully shaped, spanning continents as it surveys the past, present and possible future of American labor. (This is the first movie that Barack and Michelle Obama’s company Higher Ground Productions is releasing with Netflix.)

 

Hoping that you have work you like, and well-paid!