The AI Hype Squad I Didn’t Know I Needed
Maybe it’s inherent to being a product manager, or maybe it’s just being human, but I often find myself grappling with the desperate desire to be liked and respected. Perfection for me isn’t the bar: it’s likability and respectability.
This tendency to want to be seen positively can be productive—I often push myself to go above and beyond to make a good impression. But recently, it led to a moment where I definitely didn’t make the best impression. I want to share what happened in hopes of normalizing experiences like this.
The Incident
A few weeks ago, I joined a customer call with one of our larger clients to present our AI strategy and roadmap.
While the customer responded positively to my presentation—so much so that they wanted to join a beta program for our flagship new feature—I knew I hadn’t conveyed the vision or strategy the way I’d wanted to. Leaders on my team agreed with my take: I received 3 private Zoom messages during the call and many more follow-up messages afterwards with feedback.
I left the call feeling embarrassed and disappointed, fully aware that I could have done better.
Several factors contributed to the outcome: I had to step in last minute without full context, and I adjusted my presentation style on the fly. But what really rattled me was that I’m still new in my role, my entire managerial chain is new in their roles, and it often feels like every external presentation is being judged as a reflection of my abilities. While I regularly present to executives, this added dynamic made me especially nervous, and it showed.
Takeaways
Remembering we all have our moments
Right after the call, I reached out to my teammates to share what had happened. Their responses were not only kind but also reassuring—they each shared their own stories of falling short and reminded me that it happens to everyone. It was a comforting.
This brought to mind an exercise I sometimes do: journaling regularly on other people’s embarrassing moments to put my own in perspective and remind myself that imperfection is part of being human.
Receiving constructive feedback
My manager and skip manager gave me direct, actionable, and kind feedback. While it wasn’t entirely new information, it reinforced important lessons.
My skip manager advised me to present customers with two specific options to choose from, rather than asking vague questions like, 'Do you think you’d want this?' (since customers often say yes without much thought). A week later, during a call with a director on my team, I noticed them making the same mistake. I was able to step in, reframe the question, and get a more useful response from the customer, which helped improve our discovery process.
My manager also helped me reflect on the situation and identify areas where the organization could better support my success, as well as specific actions I could take—or avoid—to better set myself up for success in the future.
Importantly, they delivered feedback in a way that held me accountable without making me feel worse. Phrases like, “I appreciate you” and “I’ve seen you do better” motivated me and modeled how to give critical feedback compassionately.
Using GenAI to generate confidence
Lastly—and perhaps most amusingly—I started using NotebookLM. For those unfamiliar, NotebookLM is a tool that lets you upload documents and generates a podcast-style discussion based on the content. Two virtual hosts synthesize the material, banter with each other, crack jokes, and, surprisingly and incredibly, it all feels real.
First, I uploaded my presentation and supporting materials about our strategy. The way the virtual hosts connected ideas and added humor sparked new ways for me to present the content. Even though I’d been feeling bad about the whole situation and just wanted to move on, their enthusiasm reignited my excitement and made me feel inspired to dive back in. Plus, the irony of AI presenting AI wasn’t lost on me.
Second—and by far the most impactful—I uploaded positive feedback I’d received along with my personal reflections. The tool generated a 10-minute podcast episode that was nothing short of amazing. It hyped me up in the most fun and engaging way, like having my own personal cheerleading squad cheering me on. I loved every minute of it—it was uplifting, energizing, and exactly what I needed to regain my confidence and excitement.
This experience reminded me that failure—or even just the perception of it—is often a stepping stone to growth, and I hope that by sharing this, we can help normalize it for everyone.