Death of a salesman

How AI can help you pitch your best design work

My first boss said “It’s not enough to be right, you’ve gotta take people with you.” He was a charmer. The type of person who could have delivered a compelling keynote aged 8. Smart and creative, but the real magic happened when he shared his thinking; the whole thing was a performance. He’d start softly, appearing slightly unsure. He’d disarm and draw people in, just so they’d be listening intently. Then he’d switch gears and surprise them with his intensity. At various points he’d have them laughing—sometimes roaring with laughter to release the tension. It was a sight to see.

That first boss set the standard for me. A standard I’ve continually failed to meet. So much so that I’ve often thought of him before any big presentation. He’s the metaphorical salesman in my pocket. The problem is, I think AI just killed him.

The first cut is the deepest

A few weeks back, I wrote about how I often use AI tools like extra RAM in my brain. I outsource something I’m working on to the AI, then come back to it. With presentation writing, I’ve found myself adopting a pretty compelling pattern I wanted to share.

I’m working on something (or reviewing something) in Figma. I take a screenshot. Give it to the AI, and then ask it to draft a general structure for my presentation. Here’s an example of the type of prompt:

[I wish I could share the mock I included with this prompt. I’m sure you can imagine, but including a screenshot is important.]

You can see from this image that we're considering adding a right-hand toolbar that operates as an asset library interaction for event creation. I need to convince a group of senior executives that this is the most appropriate UX approach, can you give me a clear, concise structure for a presentation that persuades them of the merits of a side panel approach to this feature?

There are two things I love about this approach:

1. I get to avoid context switching. I can review designs in Figma—or in many cases continue to work on the more detailed aspects of an interaction—then throw my AI the task of starting to think through how it should be presented. It feels like the equivalent of me sending a quick slack or ping to someone.

2. I get to approach my first draft as an editor. This makes a big difference as it would usually take me a day or so to get to the level of completeness in a presentation where I could review the whole thing. That first boss of mine—he made us print out copies of his presentations and lay them down on huge conference tables. He’d walk the length of the table, silently reviewing, rehearsing in his head. I feel like having AI do a first draft gives me a comparative experience (albeit somewhat less chic). I can direct my energy to reviewing and pacing my way through the story. It means I’m considering the whole of the presentation, right from the start—which makes a big difference.

I’m not saying that the first draft from an AI is ready for prime-time. It never is, right? But this is a helluva shortcut and could be really powerful for folks who struggle to pull together compelling arguments.

Ask your AI to be mean

A few weeks back the concept of AI Glazing got some traction. The danger that chat interface AI can become a self-reinforcing ego machine. I get it. I’ve occasionally blushed when Gemini takes it too far “This is a superb draft!” etc. Perhaps this says more about my personality than I’d like to share on Substack, but I’ve started asking my AI to be mean to me.

Not in general. Being generally mean isn’t helpful, but when you ask an AI to not hold back—to give you both barrels. Well, you get better feedback.

For example, here’s my prompt:

“I'm going to give you the narrative for a pitch presentation. I want you to critique it. I want you to be as harsh as possible. Don't hold back. I can take it. But give me actionable guidance on how to make it better. Here's the draft: [insert draft]”

I thought I had a pretty good draft, but to give you a sense of how spicy Gemini can get when you turn it up to eleven, here’s some of the most constructive criticism:

“This isn't a pitch narrative. This is an internal project update memo that you've tried to disguise as a pitch. It's riddled with jargon, it lacks a soul, and it commits the cardinal sin of pitching: it asks the audience to do the hard work for you.”

I can’t share the draft as it’s too sensitive, but it’s a lot better. Gemini’s directness helped me build a much stronger argument. Even if I had to go to the bathroom for a little cry halfway through.

That first boss of mine could be quite mean. Perhaps it’s a necessary part of crafting any story—the willingness to confront any shortcomings without fear or platitude. I know plenty of writers who regularly hate their work. They read it back to themselves and feel an overwhelming sense that they lack talent and don’t deserve the privilege of putting words on a page—but it’s part of the process. You have to write bad things to be able to write good things.

The new salesman that fits in my pocket might be an AI, but counterintuitively it’s made me more human. My job isn’t to do the first draft and lay out the pages of the presentation anymore. I get to walk the metaphorical conference table and run through the story in my head. I get to focus on the parts of the presentation that make it compelling; I get to think about it as a whole story, rehearse in my head, challenge the weaker parts of the structure, and consider ways to bolster my argument.

Most impressive of all? It’s made it fun.

Something I never thought I’d say about writing presentations.