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👨‍🏫 AI’s Analysis of my Blindspots

Despite years of trying to be a “good” leader, I realized there’s only so much self-reflection I could do inside my own head. So, on a whim, inspired by someone I met on LinkedIn, and maybe a little anxiety I asked my AI assistant to tell me the truth:

What are my biggest leadership blind spots?

The results? A mix of brutal honesty, surprising accuracy, and, thankfully, real actionable steps.

We all have blindspots.

To ignore the potential for blindspots is to immediately limit your growth. Full stop.

We all have blindspot. It’s part of being human.

Our big ol’ brains naturally interpret the world through the lens of our own experiences, no matter how much we try to combat bias or grow our empathy.

This is one of your greatest obstacles to professional growth.

As aspiring technical program managers and leaders, this becomes a real challenge: to reach the next level, we have to grow beyond the habits and paradigms that once served us.

AI Prompt for Blindspot Monitoring

The prompt itself is not complicated. It isn’t fancy. But that’s the point.

I’m sharing this to all of you as a potential direction to explore with AI.

Here’s the prompt:

Now that you know everything I’ve typed, tell me my top 5 blind spots. 

Prerequisites for this prompt

For this to work, the AI needs long(ish)-term context about you.

In my case, I’ve been using ChatGPT almost daily across every corner of my life for months.

I’ve used AI for everything from:

Learning:

• Researching random topics

• Translating talks across languages

• Finding strategies to beat my son’s video games

Life Admin:

• Protesting my property tax assessment (results pending!)

• Running my LLC and side projects

• Creating family dinner recipes

Work Productivity:

• Jira and Google Sheets troubleshooting

• Daily task management (minus any proprietary info)

• Researching domains to ramp up quickly on projects

Needless to say, it has replaced any other search engine that may have been my go-to just a year ago.

My Blindspots, per AI

The feedback felt uncomfortably accurate.

(But again, what should I expect after oversharing my life with AI?)

Before I share the results, a reminder: Growth is not a race.

There will always be people ahead of you and people behind you. This applies to every Technical Program Manager you meet. This is a journey, not a competition.

So with that said, hang with me as I open up with some vulnerability for where I’m at with my growth as a Technical Program Manager

Now, onto what the AI surfaced about my leadership pivot.

As AI performed this analysis, it pointed out the top 5 blindspots that led to the high level summary of being a Hero Operator rather than a Strategic Multiplier.

1. Over-Optimization at the Expense of Delegation (ie, despite having a great solution for something, I can accidentally make myself a bottleneck)

2. Passion-Led Diversification vs. Strategic Focus (lots of ideas, not executing on enough. Mostly related to my LLC.)

3. Excellence Masking Simplicity. (ie, wanting a perfect solution rather than an 80% “good enough” solution).

4. Guarding Energy for Family Might Delay Personal Scaling. (this one hit hard! But it had a good point: I equate growth with more time while ignoring that growth can be experienced with the right growth “levers”)

5. Leading Through Competence vs. Influence (I may lean to hard on my skills rather than organizational influence to rally around an idea and vision)

Fixing my Blindspots, per AI

Thankfully, AI didn’t just stop at critique. It gave me a roadmap to grow past these blindspots.

The first recommendation were a series of mental models to shift:

Moving into a Staff TPM role has already started facilitating these shifts, but making them second nature is still a work in progress.

But there’s still so much growth to take place if I want these mental models to become a habitual way of working rather than feeling like I’m going outside my normal knee-jerk reactions.

After the mental model suggestions, it recommended tactics to begin practicing these shifts:

A note of caution: I do not fully agree with every tactic.

Sometimes in technical program management, you have to roll up your sleeves. Sometimes you are simply the fastest way to unblock progress.

But the real danger is letting that mode of working become your default.

When “just getting it done” becomes a habit, you rob others (and yourself) of bigger growth opportunities.

Blindspot Challenge

Gaining this insight was valuable. No, not because I believe AI is infallible in its advice-giving, but because it forced me to pause and ask:

Is the way I’m working today aligned with the future leader I want to become?

So here’s my challenge to fellow Technical Program Managers:

• Use one AI tool daily across life and work.

• Let it observe your patterns over time.

• Then, when ready, ask it: “What are my blindspots?”

You might be surprised (or even a little humbled) by what you learn. And that’s exactly the point.

Your Thoughts

🤔 Have you used AI for professional growth?

I’m always happy to chat with folks who have found AI useful in professional growth. Feel free to respond to this email directly! Or DM me on LinkedIn.