THE BLOG
08/07/2014 10:26 am ET Updated Dec 06, 2017

Sales and Storytelling With Craig Wortmann

I came across a job post for a director of sales role on a startup's website, and the required skills and experience section enlisted:

i) emotional intelligence,
ii) self-awareness,
iii) active listening,
iv) conflict resolution.

These are precisely the skills, along with storytelling, that I want to master at this stage of my career, and I am lucky to be in a sales position at LinkedIn. Learning to problem solve, deliver value and communicate effectively as a salesperson will greatly benefit me in any and every professional and personal pursuit in future.

I recently had the opportunity to meet with Craig Wortmann, a three-time star CEO, clinical professor of the award-winning Entrepreneurial Selling MBA course at Booth, and bestselling author of What's Your Story?, a book that looks at how leaders and sales professionals use stories to connect, engage and inspire. Just like my mentors and peers at LinkedIn, Craig advocates for transparency and authenticity while "selling," and because I remain fascinated by the concepts of selling and storytelling, Craig generously let me pick his brain.

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Craig Wortmann

Q: What's your story?

CW: My story really starts in 1989 at IBM. It was the Google, the Apple of its time, and I was very lucky to start my career there. IBM was a place that took the ability to sell and communicate with people very seriously. They would take in a bunch of young people and teach us how to sell and how to communicate, or as we insiders would say, they "dipped us in blue" (the IBM logo is blue)! After several years of working at couple large companies, I tried my hands at entrepreneurship. Through success and failure, I learned over and over again how important stories are to connect with people! My third incarnation as a person is as a professor. The necessity is to not only to transfer "content," but to also help my students see and experience the content. In my three-part journey as a salesperson, entrepreneur and a professor, the significance of effective storytelling has become clearer and clearer over time.

Q: Why does storytelling matter in sales?

CW: For two primary reasons: context and emotion.

1) One mistake we make as salespeople is that we know our product so well, our company so well, that we overwhelm people with this information. Stories take this factual, disparate information and give it context, color and meaning. If you give me a story, I am able to see so much more than when you primarily give me the facts, the details. Don't sell me a computer with only its features. Tell me that Joe bought this laptop because it is light-weight, faster and cheaper and hence, Joe could take it along on his African safari and use it to make movies of his kids. Help me feel what it's like to use that product. Now, I can "see and feel" it and not just understand it from an intellectual level.

2) As soon as you give me Joe's context, as soon as you tell me a story, you connect with me, because I am a human being. I can feel what using your product will be like. If I can feel the joy of using your service, your message will stick with me better and faster. If you just give me facts, I won't be as affected.

I picked up the importance of storytelling while I was at IBM, but I didn't quite consciously identify it until working in my first company and experienced it first hand. I realized the power of what we can do with creating a story, and I wrote What's Your Story? in 2005 and 2006 while still running my first company as a full-time CEO.

Q: What is "entrepreneurial selling"?

CW: ES is that wonderful chaos from the time a company is founded and when the entrepreneur is a salesforce of one, to the time that you have really figured out what your sales process is, when you have won that first critical set of 15 customers (B2B) or 1k customers (B2C). There are over 8,000 books in the market on professional selling, but ES is a different beast! It is the process of getting your arms around how to talk to those first critical customers.

Firstly, professional selling process assumes that you know who your target is. IBM has an established sales process, but an entrepreneur doesn't have that part figured out. You have this passion, you create this product, and then you figure out who do you sell it to- all while you are figuring out 900 other things about your business model and product features.

Secondly, an entrepreneur needs to be incredibly disciplined around the first part of your sales cycle. You have to know if a customer can be good business for you, otherwise you could put yourself out of business. IBM won't suffer if a salesperson has 14 meetings with the wrong client, but you will!

Q: What makes for a successful salesperson? What best practices would you prescribe for Sales?

CW: Top-performing salespeople have two main characteristics:

1) The ability to communicate concisely and clearly, and 2) discipline. The latter is equivalent of exercise and diet for your body. You know what you have to do to have a healthier body, the question is do you do it? High achieving sales stars demonstrate constant discipline and effort to drive the consequent performance.

If you are a rookie, I recommend that you do all the "little" things. Be disciplined, make all the calls, hand-write the thank you notes -- you will not believe what well-written, timely-executed thank you notes can do for you! You need to be disciplined and have tremendous gratitude; thank clients even when they don't want to do business with you. If you plan to be in sales for long, have stories, and learn how to tell stories, and in which situations to tell them. Then, you will be unstoppable.

Q: How can we become better storytellers?

CW: Just practice. Recognize when a story is taking place. For example, if you are on a conference call with a company leader, and they tell a great story, don't let it pass. Write it down and capture it. Then, tell it. Tell it to your wall, to your dog, to your boy/girlfriend, and practice this story. If you say the story aloud or teach it to someone, it will get stored in your memory, and you will be able to pull it out from this storage and use it in the right situation in the future. Obviously, not every story is worth writing, just like not every sales call is worth writing a thank you note for. Use your judgment, and yes, you will develop better intuition for good stories with practice!