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Coaching CEOs to Craft the Story, Rather than Doing It for Them

The beneficial struggle of building your own narrative

Credit: Andreas Selter via Unsplash

In 2016, the CEO of a New York City tech startup that had raised over $30 million (Flybridge, Accel) called me with what initially sounded like a questionable idea.

By that point, I had been helping leadership teams align around a strategic narrative—the high-level story that guides sales, marketing, fundraising, recruiting, everything—for nearly two years. My model was that of an advertising agency’s creative department: I would gather information about a client’s company and products, research its market, and retreat to my cave to create a draft. It was time-consuming, sure, and as word of my practice spread, my lead time for starting new projects ballooned to four months. But that seemed like a necessary price to pay if I was going to deliver great results.

The New York CEO, however, said he couldn’t wait four months. His company was about to launch a new version of its SaaS platform that would support a dramatically more engaging narrative, and he wanted to get started immediately. So he made this proposal:

Listen, my team and I have read all of your articles about structuring the strategic narrative. How about you facilitate us to build the story instead of doing it for us?

My first reaction was that it would never work. For one thing, even if I was just “facilitating,” the result would reflect on me and my reputation. Could I trust this CEO—whom I had never met—to do a great job?

Another concern was the perceived value of my services. As a facilitator, perhaps I’d be able to take on more projects. But how much less value would CEOs feel they were receiving?

On the other hand, it quickly became clear that the New York CEO truly had read all of my articles, and that he was taking ownership of his narrative (in other words, he agreed with me that story is the CEO’s job.) It didn’t hurt that the messaging challenges facing his team were fascinating, and I felt I could learn a lot from working with them.

“OK,” I said, “let’s try it.” To lessen the chance that anyone might feel badly if things went south—and in recognition of the fact that I wouldn’t be doing all of the work—I quoted an engagement fee that was 50 percent lower than what I normally charged.

The surprising results of “facilitated” strategic narrative development

The CEO, his marketing VP and I designed a six-week “facilitated” engagement.

As in previous projects, I still led a half-day kickoff with his leadership team, training them on my framework and eliciting story elements from each executive. I still led weekly check-ins as we boiled down the possibilities and iterated on the story. And I still pushed the CEO to make difficult tradeoffs that great messaging requires (what one recent client affectionately termed “Andy’s shit trimming” services).

To my surprise, the results in many ways surpassed those of any engagement I had done before. Specifically:

#1. The CEO and his team owned the story faster—and more deeply

Within weeks, the CEO and his sales team were telling the new story in sales conversations, and their website had been updated to reflect the new story. The VP of marketing was sending me photos of tote bags and other new swag bearing messages they had crafted.

More significantly, the CEO said prospects were “getting” the story faster. He also shared the new story with his board of directors, who told him they had never seen the company vision presented as clearly and powerfully.

2. The CEO and his team acquired narrative skills for evolving the story

In the year and a half since we completed the project, the CEO and his team have updated their messaging to reflect new learnings and developments in their market. (If there’s one thing I’ve learned, it’s that it’s never “final.”)

Recently, the company’s VP of marketing told me that our work together helped him do that more effectively. As he put it:

You gave us a framework for calling out what’s not working much more quickly. As a result, we’ve been able to iterate on our messaging and it gets noticeably better each time.

#3. They told me to charge more

As I said, one of my fears about being a “mere” facilitator was that the perceived value of my work would suffer. But when we were done, the CEO told me, unprompted, that he would happily have paid 3x the fee I had charged.

Since I had charged him around half my standard rate, he perceived 50% higher value than what I charged when I did the work myself.

That was a pretty big eye opener.

Now, the facilitated model is my only model

Since then, I’ve led dozens of engagements this way, and the results have been so similarly positive that the facilitated model is now my only model.

To be sure, I still torment myself — day and night (in the shower, watching TV, driving) — about how to best structure each team’s narrative. I still lead every engagement, and I still help CEOs incorporate voices of customers and test their new story in conversations with real prospects, investors and other stakeholders.

The difference is that I make it clear upfront that the ultimate owner of the new story is the CEO. (To make that less scary, I commit to being available for the CEO as frequently as she/he wants to meet during my engagements, which usually winds up being 2–3 times per week, even though I charge fixed project fees.)

Of course, the CEO has always been the owner of the story, but I’ve found that it’s best to declare that outright and structure engagements accordingly. Surely one reason that’s the case, as Logikcull CEO Andy Wilson surmised after our work together, is “the age old truism that if it’s your idea, it will stick better than if it’s someone else’s.”

But another, I think, is what any novelist or journalists already knows, which is that struggling with how you structure your story seems to be a necessary part of telling a great one. As Auvik Networks CEO Marc Morin recently told me:

“Working with you was frustrating, infuriating, exhilarating and awesome all at once — and exactly what we needed at Auvik.”

Now that I’ve gotten to work with so many CEOs who are willing to endure the “frustrating” and “infuriating” process of wrestling with their own story in order to get to an “exhilarating” and “awesome” result, how could I work any other way?

About Andy Raskin
I help CEOs and leadership teams align around a strategic story — to power sales, marketing, fundraising, product, and recruiting. My clients include teams backed by Andreessen Horowitz, KPCB, GV, and other top venture firms. I’ve also led strategic storytelling training at Salesforce, Square, Uber, Yelp, VMware and General Assembly.

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