Introverts, Failed Graduation Speeches, and the Loo: Doug Kessler Spills His Writing Secrets

doug-interview-featured-imageThere are a lot of people in the world who want to be thought leaders. They probably say they're one in their Twitter bios. They send out generic platitudes and half-baked ideas into the world, just to try to build their "tribe."

In reality, it's really hard to be a thought leader -- you have to earn it by consistently creating awesome, thought-provoking, insightful, engaging pieces of content. There's only a handful of people in marketing that do that well. 

One of them is Doug Kessler, Creative Director and Co-founder of Velocity and hands-down one of the best B2B marketing writers out there.

You've seen his work. Remember that SlideShare presentation about the crap in content marketing? That's Doug's. It's smart. It's poignant. And best of all, it's chock-full of humor. 

Recently, he released another SlideShare presentation on searching for meaning in B2B marketing, and it resonated with marketers all over the world. (Check it out below if you haven't seen it yet.) Like his other SlideShares, it was smart, thoughtful, and funny -- and I couldn't help but wonder: How does Doug create home-run content over and over again? 

To get to the bottom of this, we chatted with Doug about his writing process, staying inspired, and getting over his fears of hitting "publish," among other things. If you want to get the inside scoop on how one of the most successful B2B marketing writers became that successful (and take away a few tips for your own writing), keep on reading. 

Q: Who do you create your best content for?

Doug: When it's for clients, of course, it's for their target audiences.

When it's for Velocity, we're lucky because, as Pogo said, "We have met the audience and it is us": fellow B2B content marketers.

What's cool about this moment is that the entire market is on this massive, steep learning curve together. Marketing (especially B2B) used to be a sleepy world. Not a lot changed for decades. Then three huge things came along: the internet, the digital incarnation of content marketing, and marketing automation. 

Now the entire industry is learning to reengineer the discipline around these big changes. And no one is much further along than anyone else! So I like to write for fellow explorers.

Q: Is there someone specific you think about when creating your best content?

Doug: The best content always comes when you're looking someone in the eye, empathizing with them, and working hard to sell your ideas to them. So I always need to have the target super-clear in my mind before starting. 

Sometimes, other people creep into the audience -- like my wonderful dad (no longer with us) or my fantastic brothers (thankfully very much with us) or even my rotten kids (all-too-with-us). Knowing (and loving) some folks in the virtual audience can open up new things. We're people long before and long after we're personas.

Q: How do you think of ideas?

Doug: Quiet times. Late at night. Early in the morning. On the loo (sorry for that image -- I know, you're thinking this is where the "Crap" deck came from). Being an introvert seems to be an advantage. Being receptive to ideas feels really important. 

I took a class in the psychology of dreams in college, and we had to keep a dream diary. For the first few days, I'd only get a few dream-scraps. After a week or so, I was filling notebooks with dreams. The key was to be open to capturing them instead of letting them disappear.

Same goes for content ideas. Once I'm in the writing mode, the ideas are everywhere and I'm grabbing them in Evernote. If I'm not in that receptive mindset, I struggle. 

Writing all the time keeps me in the receptive mindset. I try to always have two or three big Velocity pieces on the go and two or three blog posts -- backed up by a few dozen ideas for posts. That keeps me in the writing frame of mind.

If I go too long without writing, I start to dry up a bit. Fortunately, client work keeps the keyboard smoking 'round the clock, too.

Q: What's your writing and editing process like? 

Doug: Sometimes, I just start writing to grope around a subject and find out what I think about it. 

But mostly, I have a really good idea about what I want to say and to whom before cracking open a fresh Word doc. Then I like to plunge in and write without stopping until the credits roll. When I over-think a piece during the first draft, the piece suffers. That (admittedly constructed) spontaneity and momentum is really important for me. 

Writing anything usually takes an hour. I don't know why. A blog post, an ebook, a shopping list … an hour. Actually getting to the desk with a clear hour and an idea can take weeks. Then I might sit on a draft for days, months, or (as with "The Search for Meaning in B2B") a year.

Brutal scrutiny during rewriting is also important. I think I'm ruthless about self-editing but I'm sure many would say not ruthless enough. I do think putting a piece aside for a while and re-reading it with fresh eyes invariably makes it better.  

Q: Your tone is strong in each piece of content you produce, but it's not always the same. How do you tease out the right tone for each piece?

Doug: Voice is the second most important thing in writing (after the idea) -- and tone is a key ingredient. But, weirdly, I don't consciously adopt a tone of voice for any piece.

If you asked me, "What tone of voice will this piece take?" I know I could tell you in precise detail. But I rarely sit down first and say, "Okay, go for angry with a hint of insult and a sprinkling of wit."

The tone seems to emerge from the combination of topic, audience, point of view, time of day, and blood-caffeine level. In rewriting, I do attend to tone more consciously -- editing out or sanding down tone clashes -- but for the first draft, I just go for it.

Q: Are you ever afraid to publish content? How do you decide to hit "publish" or not?

Doug: Terrified. I'm always worried something meaningful to me will fall flat with others. (Flashback: High school graduation. Worst. Speech. Ever. Still blushing 35 years later.)

"The Search for Meaning" piece was the scariest yet because it's personal -- outside the chain-link fencing of the Introvert Comfort Zone (I tend to stay well inside the ICZ except for mad dashes to the bar at parties).

For me, a fork in the road is when I ask the designers to take the piece and make it fly. Once I do that, I feel I owe it to them to publish. We have AMAZING designers who always treble the value of our pieces -- so once they've put in the talent and the work, I know I'll have to publish. That makes me more reticent to send it over to Jim, of course (Jim Harrison, Head of Design. Don't even THINK about poaching him).

If I'm really not sure about a piece, I share it with friends I respect and trust. I'm REALLY lucky in that some amazing people have become willing and honest readers for me -- and me for them. If the piece isn't quite right, they'll say so. Occasionally I go with my gut anyway -- but usually, I listen and respin the piece.

It helps to put the fear in context, too. No one is going to die if I get it wrong. A piece of content that fizzles off and dies is nothing to be ashamed of. Happens to us all. 

Q: What do your best pieces of content have in common?

Doug: Gosh, false modesty forbids …

Oh, okay: Our best pieces hit a timely issue that people are silently obsessing over right now (consciously or not). Then they attack that issue with some attitude and energy. Taking a stand is way more compelling than calmly analyzing an issue. Of course, confidence is the magic ingredient (as we say in "The Other C Word"). So I try to fake that before writing.

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