The Brutal AI Report Card That Made Me a Better Leader


ISSUE #72

Welcome to the Forward Obsessed Founder, my newsletter with insights, awesome tools, and real-world advice to grow your business and career.

GO FORWARD THOUGHT OF THE WEEK ➡️

A few months ago, my team told me the truth, and it stung.

Not because they were mean. But because they were honest. And I finally asked the right question.

But first, here’s how I figured out the right questions to ask. I ran my entire communication history through Claude to scan thousands of my messages. I built a free tool called Promptly that saves me hours of time retyping the best prompts and building a report.

The report didn’t just highlight quirks, it gave me a real-time playbook on how I lead (and how I think I lead).

You can get the same. Access the Promptly Library I used to build this report. I also used it to build a real time “Communication Codex” that my team could reference at any time. A bit more about that below, it’s been insanely useful for everyone I work with.

Anyway, what I got back from the AI was brutal:

  • I say "this will be quick" then ramble for 30 minutes
  • I interrupt 3x more than I realize
  • I give direction that feels like "word soup"
  • I ask for "quick updates" and derail them in seconds

Oof.

And by the way… sound familiar?

The AI didn’t sugarcoat anything. It held up a mirror to my actions and I didn’t love what I saw.

But here’s the kicker: when I shared the results with my team, they didn’t deny it. They nodded. Then someone said, “We’ve been waiting two years for you to ask.”

It hurt. And it helped.

That report became a living, breathing guide my team could use to work with me and not around me.

Suddenly, meetings finished on time. Updates were sharper. Feedback got clearer. I stopped pretending I was the leader I thought I was, and started becoming the leader my team actually needed.

By the way, I automate the whole process: pushing call transcripts, email history, and other data to Google Drive automatically so I can analyze my leadership style in one click. This is the “Communication Codex” I referenced earlier. Click to get access to the prompt, no signup required.

We talk a lot about AI for productivity, but this is AI for self-awareness. For leadership. For building companies where people actually thrive.

And in a world where the loudest leaders often lack the deepest self-awareness, that’s a real competitive advantage.

So here’s my challenge to you: Use AI to look at how you communicate. Not the idealized version. The real one. Then ask your team if it matches their experience.

You might not like the answer. But you’ll build trust just by asking.

Because AI isn’t just about doing more. It’s about becoming better. And better leaders build better businesses.

Talk soon,

Pete

💬 Get access to the Promptly Library: getpromptly.ai

⚡ Want to automate your own communication codex? Click here and I’ll show you how I do it with Google Drive + AI.


Please take a second and hit the FWD button ▶️, to share this email with your favorite growth-obsessed peer. I want to inspire 1 million awesome minds like you.

Unsubscribe | Update your profile | 470 James Street, Suite 02, New Haven, CT 06511

Pete Sena

I help founders design demand & business growth, and visionary brands create what's next. Startup Advisor. Founder @digitalsurgeons.

Read more from Pete Sena

ISSUE #79 Welcome to the Forward Obsessed Founder, my newsletter with insights, awesome tools, and real-world advice to grow your business and career. GO FORWARD THOUGHT OF THE WEEK ➡️ I updated my LinkedIn a few months ago. Changed my title to "Chief AI Officer." Added "turn AI into ROI by connecting your story, strategy, and systems" to my headline. I started seeing people reach out. They wanted to talk specifically about AI. At first, I was pumped. Then I got nervous. Here's why: I didn't...

ISSUE #78 Welcome to the Forward Obsessed Founder, my newsletter with insights, awesome tools, and real-world advice to grow your business and career. GO FORWARD THOUGHT OF THE WEEK ➡️ I was stuck in a dead zone yesterday. No internet. No AI. For the first time in months, I had to think without help. It was terrifying. I literally had to remind my brain how to solve the problem. That's when it hit me. We just invented fire. But most people are still rubbing sticks together. Let me explain....

ISSUE #77 Welcome to the Forward Obsessed Founder, my newsletter with insights, awesome tools, and real-world advice to grow your business and career. GO FORWARD THOUGHT OF THE WEEK ➡️ Last week I was showing off my AI setup to a potential client. I gave Claude a simple prompt: "Read my meeting transcripts and extract my core beliefs." Within seconds it spat out a perfect list of my business philosophy. Systems-first thinking Rent it, buy it, then build it Technology amplifies creativity The...