Meet my new executive coach, Claude

Seth Godin shared a post recently about the capabilities of AI platform Claude. I gave it a whirl.

Back in 2011 I was embroiled in a small city scuffle that became known as "Burritogate." It hit the front page of the Boston Globe a couple of days later. A really ridiculous situation, one that ended a previously positive relationship with then Mayor of Boston Tom Menino.

Anyway, I had written about this episode in a writing class in 2015, and brought that piece back up and asked Claude.ai to "please summarize and critique this, looking for strategic errors and inconsistencies," just as Seth proposed.

Per Claude, here is a summary and critique of the scene - TL;DR not super flattering for me.

Summary:

The scene depicts John Pepper, CEO of the restaurant chain Boloco, navigating a series of interactions with Boston city officials. It begins with John committing to donate 200 burritos to a city press event launching a new bike sharing program. However, a health inspector then threatens to shut down the Boloco location making the burritos if they show up at the event without a permit. Since the event is being held by the City, and the food was being prepared on a licensed premises, Pepper felt the threat was unwarranted and sought clarification.

John calls the Assistant Commissioner at the Inspectional Services Department, Thomas Goodfellow, who is rude and unhelpful about the permitting issue. John gets the permit but then later learns the city's position is that Boloco was in the wrong. Frustrated, John tweets criticism of the city's treatment of businesses. He also runs a Boloco Facebook campaign asking people to share messages of thanks to those who contribute to good causes, which goes viral.

John decides that evening that he wants to improve the city's customer service and business relations. He plans to call the Mayor's office in the morning to share his ideas and potentially leave Boloco to lead this initiative.

Critique:

Strategic errors:

• John loses composure on the phone call with Goodfellow, descending into personal attacks rather than resolving the situation professionally.
• The tweets and Facebook campaign, while generating attention, come across as immature and reactionary. Making sweeping generalizations about bureaucracy and union rackets dilutes the legitimate complaint about the specific incident.
• John contemplates leaving his CEO role impulsively without fully thinking through the implications or having a transition plan.

Inconsistencies:

• John wavers on his branding and messaging vision during the logo design meeting, failing to stick to his conviction around themes of empathy and compassion.
• After committed to focusing charitable efforts on Community Servings, John gets distracted by the allure of access and relationship-building with the Mayor.
• John preaches kindness and gratitude but lacks patience and nuance in his criticisms of the city.

In summary, while well-intentioned, John shows reactive decision-making and contradictory behaviors which undermine his goals. Approaching city officials from a solutions-oriented perspective with specific, constructive requests could be more effective.

I must be getting older and wiser because this comes off as sound advice 12 years after the fact. That said, the editorial board of the Boston Globe came out with an opinion piece a few days later essentially telling the Mayor that he owed Pepper an apology. I was right, see?! (which I definitely was relieved to see at the time). But then again, for being right, nothing really positive came of that. There were better ways to go about handling this situation, as Claude so objectively shares.

I'll look forward to reading Claude's thoughts on other episodes or correspondence of mine in the near future.