On Strategy: the Power of WITDO

It’s fine to look for answers, but often you don’t find them. Instead, if you’re lucky, you wind up with better questions. WITDO is one of them.

Before we get to today's main topic, some miscellaneous goodies…

• I’m dedicating this issue to my friend David Cooperstein, who will find his influence below and who combines smarts and kindness in ways I admire.

• Don’t miss Rishad Tobaccowala’s latest issue, “Messiah Karma,” where he takes the straw of our collective rubbernecking about different media and business implosions and spins it into actionable business insight gold.

• I have nothing to say this week about the current owner of a certain social media service. If somehow you aren’t exhausted by this story, Casey Newton and Kevin Roose have an excellent account in the latest episode of their Hard Fork podcast.

• Regardless of your politics and emotions about the current election, one thing we should all agree on is that we are still way too polarized a society, still too ready to demonize people who disagree with us, and that we need to focus on the many thing we have in common rather than what tears us apart.

• R.I.P. Kevin Conroy who was the animated voice of Batman for decades and who died young this week at 66. I rewatched Batman: Mask of the Phantasm, my all-time-favorite Batman movie, on HBO Max in his honor.

• Gosh this New Yorker piece about Emma Thompson is delightful, but it never mentions one of her best early performances in The Tall Guy. It’s not streaming (alas!) and this trailer entirely misses what is lovely about the movie, which was written by Richard Curtis. If you ever have a chance to see it…

• There are lots of annoying things out there, but the latest spam headline trend of calling a pitch a “confirmation receipt” is getting on my last nerve. Why would I ever give my money to a business that tries to initiate a relationship with an outright lie?

• My latest ear worm is a nice one: Paul Simon’s Once Upon a Time There Was an Ocean. If you don’t know it, you should.

• Please follow me on LinkedIn for between-issue insights and updates.

On to our top story...

On Strategy: the Power of WITDO

One of my first corporate gigs was as the digital editor at EarthLink, an early dial-up Internet Service Provider (ISP). We scrutinized every move that AOL and Microsoft made. They were our closest competitors selling identical dial-up products. AOL was the biggest; when AOL raised prices so did Microsoft and EarthLink. It was an apples to apples world, and we were all selling apples.

We kinda/sorta saw broadband coming (DSL and Cable), but we thought our members would value their @earthlink.net email addresses and the EarthLink software package enough to stick around and buy their broadband through us. This did not happen. Broadband was selling customers a five-course gourmet meal while we were still selling… apples.

We no longer live in a world where apples to apples comparisons make sense much of the time. The problem is that business thinkers love to overfocus and break problems down to fruit on fruit comparisons even though doing so misses crucial context.

One powerful way to dodge this problem is to get in the habit of asking different questions, questions that change the context of your endeavor and let you focus on the things that matter rather than the things that happen to be in front of you. This is the difference between focusing on what’s urgent versus what’s important, a.k.a. the Eisenhower Matrix.

Here are three of my favorite change-the-conversation questions:

#1: What Business Are We Really In?

Although that precise phrase never shows up in the classic 1960 Harvard Business Review article “Marketing Myopia,” this idea comes from Theodore Levitt. His example was that Amtrak thought it was in the business of trains rather than transportation. The other classic “Good Heavens do I really need to hear this again” example is Kodak, which thought it was in the pictures-on-film business rather than the pictures business.

You’d think that 62 years after Levitt we would have figured out this question, but we haven’t. Auto manufacturers didn’t understand that people needing to get around would see Uber and Lyft as viable alternatives to car ownership (particularly when those services were subsidizing the cost of most rides). Newspapers and magazines didn’t see that the internet—and particularly social media—would be the primary point of access for their product.

Never focus on containers: focus on behaviors, which are liquid and can easily be poured into new containers. This is particularly true in our age of digital disruption and transformation.

#2: What Job is the Customer Hiring this Product to Do?

“Jobs to Be Done” theory comes from Competing Against Luck: the Story of Innovation and Customer Choice by the late Clayton M. Christensen and co-authors Taddy Hall, Karen Dillon, and David S. Duncan.

The classic example here is about morning commuters “hiring” milk shakes to have something to drink during a long drive that wasn’t messy and wouldn’t be gone too soon. Powered by that insight, Christensen’s clients could develop a line of morning shakes different than the afternoon treats people might have on the ride home. Christensen observed:

For me, framing innovation challenges through the lens of jobs customers are trying to get done was an exciting breakthrough. It offered what the theory of disruption couldn’t: an understanding of what causes customers to pull products or services into their lives (10).

#3: WITDO: What is the Dream Outcome?

This one’s mine: I developed it working on boards and with consulting clients as a way of helping people to think more strategically but also more practically.

The power word in the question is “dream.”

If I just ask “what’s your goal?” or “what do you want to achieve?” then I get back tactical, short-term answers. But when I ask “what is the dream outcome?” it helps to break people out of their workaday concerns.

One person’s eventual answer was, “I want to sell the company.” That changed our conversation around the next year’s worth of endeavor. Another’s was, “I want to use the power of this platform to help the homeless.” That changed who I brought into a new group of advisors. Another’s was, “I want to get advertisers to invest more in DEI because it has a high ROI, not just because it ticks a diversity box.” That changed who the company approached for partnership.

Don’t get me wrong, dreams don’t always have to be noble, highfalutin, Gandhi-esque “be the change you wish to see in the world” ideas.* It’s not the sentiment of the dream that makes WITDO a powerful question: it’s the expansiveness of the thinking it catalyzes.

Once you know your dream you can take a first step toward making it real.

Here are two corollary questions that I find productive:

Is my product merely a feature of somebody else’s bigger offering? You don’t want to be in the camera business in a smartphone world. (Likewise, I always think of the Dennis Duffy character from 30 Rock: the Beeper King in a world where nobody carried beepers anymore.)

Who are my counterintuitive competitors? For example, Netflix co-founder and co-CEO Reed Hastings famously quipped that his company’s chief competition isn’t other streaming services: it’s when his subscribers sleep (or play video games, or read a book, or play cards, or….) There are more fruits than apples in the grocery aisle.

Thanks for reading. See you next Sunday.

* By the way, Gandhi never said “be the change you wish to see in the world,” although he did say equivalent things. See this explainer from Quote Investigator for details. (Gandhi, Churchill, and Twain get credit for lots of smart things they never said.)