What I Learned Crafting Strategic Narratives for 100+ Companies

5 lessons from helping CEOs align their teams around a story

Andy Raskin
The Startup


The most Japanese of Japanese proverbs, to my mind, is “Three years, even on a rock” (石の上にも三年). The literal meaning is that even a stone is worth sitting on for a long time because it will eventually heat up. In other words, persistence begets rewards.

A little over three years ago, I perched myself atop a rock called “Helping CEOs align their teams around a strategic story,” and there are still plenty of chilly moments. Every time I kick off a new engagement with a CEO and leadership team, I feel nervous: Will I really be able to align these smart, driven people around a simple, powerful story?

But overall, the rock has gotten a bit toastier. Now, hardly a day passes when a CEO doesn’t reach out to me saying, “I’ve realized that a huge factor in our success will be how we tell the story” or some version of that. I’ve worked with leadership teams around the globe, learning from all of them what works and what doesn’t.

A few weeks ago, my database of consulting clients (mostly VC-backed startups) hit 100 companies, so it feels like a good time to reflect on what I’ve learned so far. Here are the five biggies:

#1. Conversations about messaging are really conversations about strategy.

If you’ve been following me from the beginning, you might recall I made exactly the same point, two years ago, in What I Learned Crafting Messaging for 15 Startups. But it’s still my biggest learning, so I’m calling it out again.

Think about it: how is strategy communicated? You can write up complex plans or sketch out diagrams of Porter’s famous five forces, but those things can’t be conveyed throughout a large organization. Ultimately, the only way to get strategic alignment is with a simple story. I still think Ben Horowitz, of Andreessen Horowitz, put it best:

“The company story IS the company strategy”

— Ben Horowitz

#2. The sales narrative is the core narrative.

Early in my career, I was on the receiving end of a lot of messaging and positioning work that sat on a shelf once the consultant left the building. It was usually delivered as either a positioning statement (“For customer with problem X, our product Y is a …”) or a generic positioning presentation. Those positioning assets were supposed to guide the messaging everything else—in CEO keynotes, sales decks, website copy, content, etc.—but it never worked that way: the positioning assets were just too different from what we had to build.

A little over a year ago, I decided to abandon positioning assets and make the sales deck the primary instrument of my strategic narrative engagements. It was a risky move: not every CEO believes he or she should be bothered with authoring the sales presentation. (And, of course, many salespeople hate using them.)

But it’s turned to be a great decision. The sales narrative (as I defined it in The Greatest Sales Deck I’ve Ever Seen) has all the “pieces” of the story. When you get it right (after testing and refining it in actual sales calls), your website messaging, content themes— even your investor deck—practically flow right from it. Even salespeople who never use the deck can learn its narrative flow to better create urgency and engagement.

And when a team tells me their CEO doesn’t have the time to take the lead in drafting the sales narrative—even with handholding from me and support of their leadership team—I politely decline to get involved.

#3. Aligning is the hard part.

Three years ago, I thought my most valuable skill I brought to the table was a knack for boiling down complex ideas into simple narratives. While that’s important, I’ve learned that what CEOs value even more is getting their teams bought in. As the CEO of a San Francisco tech company that’s raised over $56 million in VC cash told me last month:

I realized we needed a narrative, so I wrote one I thought was pretty good. But my VP of sales didn’t like it, so I changed it a little for him. But then my VP of marketing didn’t like it, so I had to change it for her. What I realized is that the hard part is the aligning, not the crafting. That’s why I called you.

I’ve heard that sentiment from so many CEOs over the past year that I changed how I describe my engagements in proposals:

#4. Customer input is SO not optional.

One of the biggest mistakes I made early on was making customer interviews optional. After all, teams I work with boast millions of dollars in revenue. Aren’t their leaders a reliable enough proxy for customers?

I’ve learned that the answer is often no. Even when teams have already done customer interviews, they’ve usually been asking what customers think of the company and/or its products. To build a story that truly drives urgency, we have to shift the focus to what’s happening in customers’ lives: What is changing that gives rise to stakes?

Earlier this year, in the following post, I shared the questions I ask customers to build the narrative:

#5. A strategic narrative can be a powerful execution tool.

In the last few months, several CEOs have asked if we could extend our work together beyond narrative crafting and alignment. As one put it:

Now that we’ve aligned around the story, can you help us make it come true?

It follows that if “the story is the strategy,” it should be a guide for execution. Next year, I’ll be working with these CEOs to see how I can support them as they deliver on the story, not only in sales and marketing but also through product, recruiting and fundraising. As the rock heats up around that stuff, I’ll report back,

About Andy Raskin:
I help CEOs align their leadership teams around a strategic story — to power success in sales, marketing, fundraising, product, and recruiting. 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. To learn more or get in touch, visit http://andyraskin.com.

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Andy Raskin
The Startup

Helping leaders tell strategic stories. Ex @skype @mashery @timeinc http://andyraskin.com