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How AI Helped Me Deliver the Best Presentation of My Career

Using AI and simple techniques to overcome presentation anxiety and deliver a powerful talk at an analytics conference.

Author

Matt Greene
May 02, 2025

In partnership with

The Pivot

The AI x Sales deep dive. Where we break down frameworks, tools, and systems to help you move smarter and faster through the enterprise deal cycle.

This past week in Chicago, I gave the single best presentation of my career at a packed event.

The difference? I prepared in a completely new way, leveraging AI to boost my confidence, sharpen my messaging, and reduce stage anxiety.

Let me rewind for context. Earlier in my career, I joined an elite leadership development program that pushed me and 19 other top-tier university grads to the brink. (Honestly, coming from a public school without an engineering background, I often felt like a complete imposter.) Every six months, we faced intense "Jack Welch-style" reviews from executives demanding airtight presentations backed by tangible results. These sessions were brutal: high-stakes, high-pressure, and survival-of-the-fittest mentality. The bottom 10% of each rotation got fired, and even today, the thought of presentations gives me serious anxiety due to this experience. But man, did it help me.

Despite drastically improving over the years, big presentations still leave knots in my stomach, cloud my thinking, and take several awkward minutes before I finally find my rhythm. But this presentation felt different, and here’s exactly what I did and why it worked so well:

First, I storyboarded my talk and created my PPT, which was accessible on my phone. Then, on a sunny weekend day in Colorado, I took a long walk along a river path to get into a clear, positive headspace. With my AirPods in, I recorded myself casually "freestyling" the presentation using my go-to app, Clipto.AI (talk to transcription). My casual run-through timed well at ~42 minutes, just right for my 45-minute slot. Clipto made sure to catch all my ‘uhms,’ and ‘uhs’ during my dry run. But that didn’t matter. The ingredients for the meal were starting to come together. Now it was time to create the dinner.

Next, I uploaded this raw transcript into ChatGPT, paired with my slides. I gave ChatGPT explicit instructions to critically assess my content and flow (via my narration), pushing it to highlight both strengths and weaknesses. After a few rounds of precise calibration, I had a highly refined script filled with compelling insights I wouldn’t have otherwise considered - like comparing the financial impact I discussed in my talk to the GDP of the Netherlands, a point that resonated with the audience.

Here was my full prompt:

🧠 Full Dry Run Review & Optimization Prompt

You are an elite executive communications coach specializing in refining high-stakes presentations.
Your task is to analyze the following two inputs:

1️⃣ The transcribed dry run of my presentation (provided below)

2️⃣ The presentation PDF (uploaded separately)

🔵 Your Workflow:

Step 1: Clean the Transcript

Review the transcript in context of the slide deck.

Remove filler words, hesitations, and disjointed phrasing.

Tighten language to sound confident, clear, and aligned to each slide's key point.

Ensure each cleaned section matches the intent and messaging of the corresponding slide.

Step 2: Deliver a Full Presentation Analysis
Analyze the dry run and presentation across these dimensions:

Strengths: What was delivered especially well?

Confusions: Where might the audience get lost, misinterpret, or tune out?

Improvements Needed: What content, flow, or delivery elements must be improved?

Effectiveness Prediction: How will this presentation likely be received? (Give a 1–10 effectiveness score with short justification.)

Step 3: Rewrite for Optimized Delivery

Based on your analysis, create a stronger version of the presentation script.

Keep the same slide flow/order. Maintain the presenter's natural voice and tone but improve clarity, authority, and engagement. Highlight any places where delivery style (e.g., a pause, emphasis, anecdote) could further elevate impact.

🔵 Output Format:

📜 Step 1: Cleaned Transcript

(Organized slide-by-slide)

📊 Step 2: Presentation Analysis

Strengths

Confusions

Improvements Needed

Effectiveness Prediction: [Score]/10

🎤 Step 3: Optimized Presentation Script

(Organized slide-by-slide, tightened and improved)

🔔 Important: Be detailed but concise — no extra fluff. Preserve slide structure and logical flow. Use clean, executive-ready language throughout. Do not invent new content — work within the ideas/messages already presented.

Finally, I fed the polished script into Speechify.com, a text-to-speech tool, and listened repeatedly to the narration during my three hour flight to Chicago. By combining relaxed speaking practice (walking outdoors), visual reinforcement (reading the improved script), and passive auditory repetition (listening during my travel), I engaged multiple cognitive pathways, dramatically reducing my speech anxiety!

The result? I stepped onto the stage calm, prepared, and in full control. I had extreme pattern recognition and went into autopilot. The room filled with 60+ attentive executives and it then went swimmingly.

Post-talk, several people immediately sought me out for further discussion. Their feedback:

  • “Your storytelling was incredible.”

  • “You made a complex topic easy to follow and relatable.”

I also got some love from an attendee as my company posted about it after on LinkedIn.

Most importantly, we now have several qualified leads that will turn into meaningful deal opportunities.

This was not a post meant to boast - simply to articulate another clear, practical win for AI.

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The Locker Room

Let’s be honest - most 1:1s with your manager feel like a pop quiz on your own pipeline.
So instead of walking in cold, read this section and then spend 15 minutes talking sports that you pretend you watched. I’ll give you a sharp take or two and a few relevant insights to break the ice and even a smart comment to say. Then once you’re done talking sports, best of luck on that forecast review.

1. Sanders' Epic Draft Day Nightmare

Quick Highlight: Top QB prospect Shedeur Sanders tumbles shockingly to Round 5 amid bizarre draft-day chaos.

  • Sanders plummeted to the Cleveland Browns at 141 after an embarrassing prank call leak.

  • NFL stunned as teams pass on Sanders despite massive pre-draft hype.

  • Giants star openly criticized league owners for overlooking clear talent.

  • Sanders' draft drama is raising big questions about scouting biases.

What to Say to Your Boss in a 1x1: Interestingly, Sanders is the lowest-drafted quarterback ever to appear on ESPN’s pre-draft “Top 10 Locks” list, highlighting potential blind spots in NFL scouting evaluations.

2. Clippers Upset Nuggets, Force Epic Game 7

Quick Highlight: Harden and Leonard lead Clippers’ gritty comeback, setting up a thrilling Game 7 against Denver’s dynasty.

  • James Harden (28 points) and Kawhi Leonard (27 points) dominated a tight 111-105 victory.

  • Harden dished out eight crucial assists in a dramatic fourth-quarter comeback.

  • Clippers now poised to shake up Western Conference hierarchy.

  • Denver facing unexpected playoff pressure, possibly impacting league marketing and sponsorships.

What to Say to Your Boss in a 1x1: Harden’s eight assists in the fourth quarter marked his highest-ever playoff single-quarter total—an overlooked stat indicating how significantly he influenced Game 6's outcome.

3. Falcons' Draft Leak Costs $250K

Quick Highlight: NFL hits Falcons with hefty fines over leaked Sanders’ prank call scandal, tightening draft-day rules.

  • Falcons fined $250K, coach Jeff Ulbrich personally fined $100K.

  • Leak traced to Ulbrich’s son, exposing draft-day tampering risks.

  • Jax Ulbrich publicly apologized, but damage control might not be enough.

  • NFL expected to overhaul communication protocols for drafts.

What to Say to Your Boss in a 1x1: This incident marks the first instance the NFL has penalized a franchise directly for draft-related communications leaks, potentially shifting the league’s policy enforcement significantly.

4. NBA’s Historic $76M Cap Surge Ignites Free Agency Chaos

Quick Highlight: An unprecedented salary cap leap is set to revolutionize NBA team strategies and star signings.

  • NBA salary cap expected to jump dramatically to $151.1M for the 2025-26 season.

  • Fueled by a massive new $77 billion media deal involving ESPN, NBC, and Amazon.

  • Small-market franchises now positioned to compete aggressively for elite talent.

  • Player contracts projected to reach record-breaking figures amid intensified bidding wars.

What to Say to Your Boss in a 1x1: Interestingly, with this new cap, over 60% of NBA teams will now have room for at least one max-contract player—potentially shifting competitive balance and forcing major strategic rethinks across the league.

5. Scheffler’s Freak Accident Shakes PGA

Quick Highlight: Scottie Scheffler sidelined by bizarre kitchen injury, reshuffling PGA Tour odds.

  • Scheffler cut his hand severely on Christmas Day, requiring surgery and a 3–4 week layoff.

  • Missed the 2025 PGA opener, causing dramatic shifts in betting odds.

  • Hideki Matsuyama benefits most, becoming a new betting favorite at The Sentry.

  • Scheffler’s absence could lead sponsors toward investing in rising talents.

What to Say to Your Boss in a 1x1: Scheffler’s injury caused an immediate 7% shift in betting market odds, highlighting how quickly non-sport incidents can impact financial projections in major sporting events.

Singles and Doubles

Other things I found helpful, smart and witty.

I’m Matt

Enterprise sales leader, systems builder, dad. I write this to show how the best sellers think like athletes: they train for leverage, not hustle. Sales is a game of precision and in today’s playbook, AI is part of the edge.

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