Writing It Out First: My Ultimate Strategic Sales Cheat Code

️ ️⚡ Today’s level up ⚡

Today’s edition focuses on one skill that has helped me more than any other in sales (and retiring from corporate selling)–writing.

Let’s go!

“Who me?”

Five and a half years ago, I was asked to give a presentation in front of a room full of C-level executives.

I was terrified of public speaking and thought if I screwed up my new career as a strategic seller was sunk.

Every year, Skift—a leader in global travel research, holds an event in NYC. CEOs from major airlines, hotel chains, and tech companies are in attendance. It’s the conference for business leaders in the travel industry and the tech companies that want to partner with them.

I was only eight months into my role as a Strategic Account Director when my employer, LivePerson, asked me to deliver a presentation at the event after one of our executives had to drop out.

I only had three days to prepare for it.

There were some heavy hitters who were slated to speak at the event, including Ed Bastian, CEO of Delta Air Lines, Christine Duffy, President of Carnival Cruise Line…and me (yelp).

After a few hours of panicking, I got to work, and my game plan was built around a simple principle—write it out first.

No, not the speech. I first wrote a LinkedIn article on the topic I was going to speak about: How to delight guests with Conversational AI.

Here’s why it was so helpful:

• Writing allowed me to work backward to create the presentation

• It solidified all of my talking points, helping improve my confidence

• It also had the bonus of living on as an expert piece beyond the event

I was set up in The Patron’s Lounge off the main stage. It was filled to capacity. Luckily, no one could see my sweaty palms.

I ended up nailing the presentation.

I know, because a handful of executives of major brands came up to me after to ask questions. I was able to collect twelve business cards…which they all volunteered to give to me.

A part of my follow-up?

I sent a link to the article I wrote. Seven of them responded and complimented my deep expertise in the space (frankly I didn’t have any, other than being a heavy traveler myself…shhh).

The key to the article being helpful for me and a hit to the audience was writing it from the perspective of their customers…because I was one. I then married that with what I knew our solution could solve for and learned so much about our product in the process.

That confidence shined through while I was at the podium and after.

This exercise showcased and proved to me two important things:

1. How effective writing is as a sales skill

2. How efficient it was at helping me learn complex topics

I was hooked.

Writing the story first makes everything that follows easier

I’m not alone with this line of thinking.

Watch below how Graham Weaver, famed Stanford Business School professor and successful VC talked about the importance of writing a new story when his firm was on the verge of collapse during the financial crisis of 2008 (that part starts around 16:15):

From that point on, I got into the habit of writing stories on LinkedIn and Medium about LivePerson’s technology and solutions. But I did it in my voice (as opposed to LivePerson’s Marketing voice).

Let’s snag another example from those days, and I’ll break down the key components of how to incorporate this in your own sales motions, and hopefully you’ll expand it into other areas of your life: I Cheated With Rose in Vegas, and I’m Not Sorry About It.

First, let me provide a little context.

The Cosmopolitan of Las Vegas was one of our clients at the time, and their chatbot, Rose, was a great example we wanted to showcase for other prospective clients.

As I was often in Las Vegas, I wanted to showcase my own personal experience with Rose, and then use the story as a way to a.) get better with my talk track (of going conversational as a brand), and b.) use it as an alternative to LivePerson’s marketing material to land meetings or send as a leave-behind after a meeting.

Here are the five core components that were helpful for me when it comes to producing long-form pieces:

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