Working with a Creative CEO

Dec 18th 2018

A 2010 survey of more than 1,500 CEOs found that chief executives believe that creativity is the most crucial factor for successfully navigating this increasingly complicated world.

I take a lot of comfort in that study, as I have a very creative boss. Coupling his creativity with a small marketing staff at a company that is rapidly growing and constantly innovating leads me to more sleepless nights than I’d like to count. The marketing team has a lot to do, and I constantly look for ways to be efficient and get as much work completed as possible. That typically means that I’m happy to leave the most creative, time-consuming ideas on the floor for some magical day when we’ve got time.

The David Steinberg

But if you’ve met David Steinberg or heard him speak, you can guess that my master plan doesn’t always work out. I’m not buttering him up to approve my 2019 budget request (hint, hint) when I say this, but Dave is a creative genius. He’s the innovative force behind our sales intelligence platform, Foureyes, and the resulting products, Tap and 20/20. He’s a phenomenal speaker. And as our marketing director, I want to be sure he’s recognized for his exemplary leadership. That story is where our struggle over creativity began.

In the midst of founding a marketing department, rebranding Adpearance, and better defining Foureyes, the deadline for a CEO of the Year award came up. I budgeted a few quick hours to fill out the requisite forms, so I could get back to my “real” job. One of the questions was, “Three words that describe Dave’s leadership style.” I think I suggested innovative, generous, and quirky. All accurate with a whiff of awkward, kinda like Dave.

I passed it by his desk for approval, fully expecting a rubber stamp, believing he didn’t want to spend time on an award application any more than I did. 

But classic Dave: He crossed out my three words and wrote, “not in box.” He thought it was hysterical. I said no and over-ruled him, not realizing the sleeping giant I awoke.

Dave adopted “not in box” as his rallying cry.  Like Braveheart, he took up the cause with gusto. From then on, marketing was under a full-out assault, proving that not just he, but the entire company, was “not in box.”

First, there were the puns. Dave showed up outside my office with a giant box. He wasn’t in it. To every conversation he found a not-in-box way of casually dropping “not in box.”  Instead of answers to questions, I would receive an empty box as Dave’s not so subtle way of saying, “be more creative.” 

Empty Amazon packages piled up outside my office.   

But this is where the rub with creativity comes. Things that were standard procedure for the marketing department suddenly became exercises of not-in-box thinking. From our holiday gift, to our NADA plan, to our upcoming Foureyes website refresh. Dave was in a campaign against my approach of efficient-and-professional-but-not-wildly-creative marketing.

“Not in box” became a transitional rallying cry to reexamine the status quo everywhere and anywhere. I won the battle but lost the war. (Don’t believe me? Just wait until you see our NADA booth.) I’m not going to lie – it’s been a stressful transition. But now that I’m on the other side of it, I’m loving it.

It’s why I’m laughing instead of crying as I type this out this next part: I assigned Dave an article last week. For our marketing campaigns, the team wanted an educational piece that explained Dave’s philosophies that lead to the development of our latest product, Foureyes 20/20. I brainstormed it with him. Wrote out the skeleton of the article to ensure he hit the big strategic imperatives. I got the “Dave Steinberg Guarantee” he would get it done before he left town. 

But I made an in-box assumption that we would be efficient and logical in how to distribute the said article. Oh no.

Dave is insisting that his article is to be published as his out of office vacation autoresponder. That’s right. The only way you can read his article is to send an email to his inbox. (I mentioned his love of puns, right?)

So, here’s my request. Please email with an email titled, “Not in Box” now until December 30, 2018. And when his email fills up? When he’s back from vacation with endless, pointless emails he has to clean up? We can laugh together that he might need to get a bigger box. 

Seriously. Do it. It’s a pretty good article.

And if you are currently struggling with your own creative CEO, a few quick tips I picked up on the journey: 

  1. Don’t waste the calories fighting it: It’s not just that your creative CEO is your boss and you have to do what s/he says. It’s that creativity is the right choice. If you want some inspiration, check out creativity on Harvard Business Review.   
  2. Ensure you get time for alignment: Dave and I both realized that a more creative, on-strategy action plan takes more time. We brainstorm and circle back far more in this new world than we ever did in the past. Both parties have to make time for creativity to drive the work.
  3. Appreciate the upsides: If you are someone who values solid strategy and achieving business objectives, creativity is going to help you. First, you’ll get further faster, even if individual initiatives take longer. And second, creativity and an appreciation for failure go hand-in-hand. You’ll learn to take risks, be open to new ways of thinking, and have more grace in stressful situations. 
  4. Be specific with strategic requirements: Help your creative other half understand the full situation and problem that needs to be solved. Recognize that a bad idea is usually just a sign that they didn’t understand the requirements fully. Try “Yes and” strategies rather than “No” to get it where you need it to go.
  5. Remember to laugh: Creativity is fun. It will surprise you and catch you off guard. It will do the same for your audience. Enjoy it!

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