The Story Matrix

Having the right story — the one that creates context, has an impact in that meeting, and creates a magnet by which you can draw people toward you — can make the difference between winning and losing a deal. You have to have them.


Your ability to tell a compelling story as an entrepreneur is a critical skill and discipline. We all have to have a pallet of compelling stories by which we can engage and draw customers, investors, new employees towards us and towards our businesses. But do you have the stories? Do we have that metaphorical quiver on our back with the red arrow, blue arrow and the green arrow? And those arrows are marked for specific purposes when we need them? They are sitting right on our back when we need them. I think the answer is no, I don’t think we do. I think, in fact, when we think about stories as a tool or an asset at all, we think about well, I’ll just tell a story it will sort of be‑‑ I’ll pull out an arrow and let it fly wherever it lands. Let’s just hope it’s an engaging story. You know what, I think that’s fine. That’s one way to tell stories. But when we’re entrepreneurs, when we’re in business we need stories for specific reasons. We need a tool that will capture our stories, categorize them, categorize them by type. And then allow us to pick that story and not that one, the red arrow and not the green arrow. Because from what I know about this meeting I’ve got coming up next Thursday with that woman who’s going to make a decision on my business, I think the blue arrow will be better. That story will be better context for her. She’ll get a better understanding of who I am, who we are, what are the skills and abilities we’re bringing to the table. And that one is better than this one over here. That’s the type of telling stories that we’re talking about here. But you need a tool. And I call it The Story Matrix.

The Story Matrix is an incredibly simple tool. It’s got rows and it’s got columns. Let’s start with the columns. Every entrepreneur story matrix should have four columns across the top representing types of stories we tell as entrepreneurs; success, failure, fun, and legends. All four of those types of stories are obvious.

Let’s start with success stories. Success stories are you made a set of decisions, things went your way, great, it turned out, success.

Failure stories, very similar except it didn’t go your way. So you hired someone, you decided to build a product in a certain code, things didn’t go your way and you had a failure. Failure stories are not “look what a moron I am” stories. They are just failures. They happen to all of us, mishap, circumstances, failure.

Fun stories are very obvious, fun. I want to tell you a funny story. I want to tell you about something that happened, some mishap, anything, something with fun to it.

And legends have a two‑part definition. Legends are sort of the way we think about legends is the once upon a time story, they come from history, they come from culture. And then there’s another definition of legends. We all know stories about Steve Jobs at Apple. We all know stories about the growth of Anita Roddick’s, The Body Shop. Those type of legendary stories that we all, because we all swim in the same business culture, we share those stories. So those are your four types of stories across the columns at the top of your story matrix.

Now there are also rows. The rows are the categories, the types of stories you have. You might have a type of story that you need to tell to win investment dollars. You might have a type of story to tell to hire new people, to sell. And you might even get more granular. And you might say well, I have qualification stories. Or I have stories that I would tell to help people better set and reset expectations in the sales process.

One of my‑‑ my first company, three‑four months in, I went and sold a pharma company, a big pharmaceutical firm. And I was patting myself on the back and feeling great until I realized that unintentionally I had overpromised them. And their expectations were here and my ability to deliver was here. And it was a huge problem. It quite literally could have put my first business out of business. And I had to backpedal to the point where I had to fire my, one of my first customers. That was my own fault.

That’s a story that I would pull from the failure column and the expectation setting row. And that’s the key to The Story Matrix. The key to The Story Matrix is building it and then the discipline is I need to select that story about the pharma company and not that other story about hiring someone or failing to raise investment dollars or succeeding over here because I think that story will be most powerful in this situation. That’s the way we use The Story Matrix.

Now here’s another question, of those four columns; success, failure, fun, legends, what is your most powerful type of story? I think most people say success. I actually disagree with that. I think your most powerful stories are your failure stories. Your ability to tell a compelling failure story is engaging, and magnetic. Those are your most compelling types of stories because they demonstrate humility. They demonstrate the ability to learn, the ability to process, the ability to move quickly and adjust and pivot. Failure stories capture so much about us that go beyond the other three types, success, fun and legends.

When I interviewed‑‑ I had run my first company, we had sold the company. And I was interviewing to do a turnaround of a digital marketing agency owned by a big venture capital firm out of San Francisco. I flew out to San Francisco from Chicago. I walked into the meeting with the founder/owner of this venture firm and thus majority owner of this digital marketing agency. We had one hour. I consciously walked in that room and I thought to myself what am I going to tell him. He knows about my last business. He knows what I’ve done. I’m here. I’ve made it here. I’ve made it through the initial phases of this process. I told him my failure stories. I didn’t say I’m a moron. I just said here are all the decisions I’ve made that didn’t go my way, here’s what I learned from them. In that engagement process, I strongly believe that those were the most powerful stories that I could tell him. He didn’t want to hear what a success I was, right? He didn’t care about that. I wouldn’t have been there if he didn’t think I could do the job. What he wanted to understand is does this guy understand when things are going wrong, does he know how to fix it, has he been down that road, has he learned on somebody else’s dime. And the answer was yes. But the only way I can communicate that is through failure stories.

So now you’ve got your columns and you’ve got your rows. You’ve begun to build your story matrix. And you’ve done the most important thing and that is you’ve populated that matrix with stories, your best, most compelling stories. Now imagine you’re looking at your story matrix. You’re looking down into your quiver of arrows. And you can now select with intention what stories you’re going to tell. I’m going into this meeting, and from what I know about this customer, or potential employee, or this potential channel partner, I’m going to pick a failure story, failure to qualify. I’m going to pull that arrow out of my quiver and tell that story. Or I’m going to tell a success story in closing a deal. I’m going to pull that arrow out of my quiver off my story matrix. But you’ve got it. And you’ve got the tool. And the tool is there to support your effort to sell as an entrepreneur. Because at the end of the day your ability to be convincing and persuasive with a customer is your ability to tell stories that create context, have an impact in that meeting, and create a magnet by which you can draw that customer towards you. That’s the key to The Story Matrix.

Suggested Readings

Founders School || Entrepreneurial Selling || The Story Matrix || Impact Guide (PDF).

Isaacson, W.”The Real Leadership Lessons of Steve Jobs“. Harvard Business Review, 2012.

Heath, Chip and Dan Heath. Made to Stick: Why Some Ideas Survive and Others Die. New York, NY: Random House, 2007.

Olson, R. (2009). Don’t be such a scientist: Talking substance in an age of style. Washington, DC: Island Press.

Wortmann, Craig. What’s Your Story? Evanston, IL: Sales Engine, Inc., 2006. Ch. 7-9.

To collect your most powerful stories, grab a journal and at the end of every day, write down something that happened that day that could be told as a story. Think about the characters. Who was there? Jot down what happened in three quick bullet points. And finally, note the “lesson” or “moral” of the story. For instance, if you interviewed a new hire, and that person told you a story about how she had gone above and beyond for a former customer, you might write: “Interviewed Chris. She told about XYZ Company and how they couldn’t make a deadline. She jumped in and went to their office after hours. She knocked out some of the work til 3 a.m., and they made their deadline and won the business.”

Something like that. Then, note the “moral.” In this case, it might be: “We hire ‘above and beyond’ type people.”

Now, you’ve got the beginnings of a story. Next time you are selling a prospect on your value proposition as a firm, you might tell about your hiring process, and use the “Chris” story as a demonstration that you put your money where your mouth is.

Questions for You

Do you write down your stories? Do you practice them?

What are the rows in your matrix? Why?

In any given week, in which kinds of situations do you need strong stories?

Can you think of an example of when you shared a story and it had a profound impact?

Tools and exercises

Story Matrix(℠) (PDF)

Write Your Story (PDF)