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Writing It Out First: My Cheat Code For Improving All Aspects Of My Sales Game

⚡️ 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!

Read time: <7 minutes

“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 writing a first draft and reminding myself that I’m simply shoveling sand into a box so that later I can build castles.” - Shannon Hale

I’m not alone with this line of thinking.

Watch below (for about five minutes) 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:

video preview

“Don’t write a story about what happened. Write your story, then make it happen.” –Graham Weaver

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 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:

1. Write in a public space

In one engagement with a major new logo, I had someone who I had falsely labeled a detractor, compliment me on this very article. Had I not written it in public, she would’ve never found it and we would have missed an opportunity to bond on creating a similar experience at her company.

You never know who’s reading so go ahead and write in public spaces!

2. Make it personal

You have a unique voice. Let that voice shine through by writing your story…not a regurgitation of your Marketing’s voice. Writing from personal experiences is a great way to do this.

You also gain the benefit of positioning your product in a more unique way, especially helpful if you're selling consumer-facing technology.

3. Ensure it’s helpful and relevant

Ultimately, you need to teach your audience something. I've found four effective ways to do so:

  • Keep it focused to 3 - 5 bullet points. The human brain cannot retain more than this, so limit your main takeaways to just a handful of key ideas.
  • Keep your writing simple. Does it pass the 5th grader test? Removing jargon and talking in natural language will help your audience understand what you’re trying to say.
  • Keep it in a narrative format. Don’t forget you’re telling a story, not writing a boring article. That means you need to keep things flowing in a way that encourages them to read further.
  • Keep it novel and share examples. Educating your audience doesn’t mean your personality can’t shine through. In fact, this is what will make it (and you) memorable. Use real examples and tie it all together (Teach → Share → Shine).

4. Keep it interesting with visuals

To pull readers in, it’s important to break up the chunky text with images or visuals. With visuals providing anchor points, the reader can see the pieces of the overall structure with more clarity at a single glance.

This is like a warm invitation to read it and reinforces your message.

5. Show them you know your stuff

Instead of hard-selling them at the end of the piece, I liked a softer approach - give them VIP knowledge that is above and beyond the core pieces of information I want them to know while also highlighting key aspects of our solution that only we could deliver.

This leads them to naturally exploring further with you and positioning any competitor to the insights you shared. Win-win!

YOU MAY ALSO ENJOY READING: Become a Category of One Seller Through Effective Writing

That’s a wrap. See you next week!

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