Success is often a combination of preparedness, opportunity, and work. Scott Hanselman's presence at a local user group last week proved this.
Inspiration
I discovered an opportunity when my friend Michael Blumenthal emailed me that Microsoft Vice President Scott Hanselman was scheduled to deliver a keynote presentation last week at the Chicago Accelerate conference, to be held in the Willis Tower. Michael suggested we organize a community event the same week and invite Scott as the featured speaker. I immediately recognized a great idea and leaped into action.
I emailed Scott the next day. If he was willing to speak at a community event, I was happy to organize one. He agreed, and we settled on Tuesday, June 23. We went into action, planning, promoting, and executing on the event.
In this article, I will talk about the evening, Scott's presentation, and how a group of volunteers made it happen.
Scott's presentation
I will begin at the end with Scott's excellent presentation.
He titled his talk "AI for Normal People Who Aren't Totally Bought In" and covered a variety of topics, including Artificial Intelligence, Apprenticeship, and Knowing How to Drive a Stick Shift.
It was entertaining, thought-provoking, and full of memorable analogies.
Scott described himself as an "AI vegan." He uses AI extensively but has little interest in image or video generation. He also pointed out that AI-generated websites and content often have a recognizable look and feel. In one example, he joked about LLMs' apparent love of text gradients.
He illustrated the importance of clear communication. Scott also referenced research showing AI can optimize for passing tests without actually solving the underlying problem. One example involved fixing a race condition by adding a sleep statement that made the test pass while leaving the real issue unresolved.
A recurring message was that software development with AI is becoming less about writing code and more about sculpting it. The engineer's role shifts from authoring every line to shaping, validating, and refining what AI produces.
My favorite analogy compared AI to Uber and engineering fundamentals to driving a stick shift. Uber is convenient. But knowing how the machine works is what helps when something breaks. The engineers who matter most in the future won't be the ones with the best prompts. They'll be the ones who understand what's happening beneath the surface and can recognize when AI is confidently wrong.
One theme that resonated with me was Scott's distinction between mentorship and preceptorship. Mentors give advice. Preceptors work alongside less-experienced engineers and pass along judgment, context, debugging instincts, and engineering taste. As AI takes over more routine coding tasks, this transfer of knowledge becomes more important, not less. Scott argued that AI will not eliminate the need for junior developers. Instead, we'll need better systems for helping both people and AI agents become trusted contributors. Junior developers and AI agents share one thing in common: both can be capable and confidently wrong.
Scott closed with a personal note: he announced that he has 941 days until retirement and wants to use that remaining time effectively. Despite grouping himself with an older generation of IT professionals, he peppered his presentation with Gen-Z jargon. "AI output is mid," he quipped, indicating that LLMs gravitate toward the average, while humans are more likely to explore ideas outside the norm.
Preparing for the Event
We pulled this event off in a short period of time, thanks to the hard work of a small group of individuals.
Scott, Michael, and I are all passionate supporters of the tech community. In fact, I know the two of them because of my involvement in this community. I emailed Scott the day after hearing from Michael.
Eric Boyd and I run the Chicago Cloud Computing Meetup Group, which meets once a month at the Microsoft office in downtown Chicago. We had already scheduled a June meeting, so we decided to hold a rare second meeting during the month. I reserved the Multipurpose rooms at the Microsoft office for Tuesday, created a registration page, and began promoting the event.\
Promotion proved to be a challenge because the event was not far off and because I was helping to organize two other events within a few days of this one: our group's regularly scheduled monthly meeting (June 18) and JuneteenthConf (June 19-20). Recognizing that oversaturating a message can yield poor results, I left some time between promoting each event. I promoted via the following channels: Social Media posts; word of mouth; emails, texts, and private messages; and internal Microsoft Teams channels. Some of those who heard from me spread the word to others. The strategy worked: over 80 people attended a meetup despite the short notice.
Money was another challenge. Because our user group meetings take place in the evening, we always supply dinner - typically pizza and salad. Food is the primary expense for our meetups, and Eric's company, ResponiveX, has been great about covering our food costs at most meetings. Not wanting to burden them with another large expense, we reached out to potential sponsors. Progress stepped up, agreeing to buy all food and drinks for the meeting. In exchange, we displayed Progress's logo prominently, thanked them multiple times during the meeting, and played a 5-minute video at the start of the meeting.
The Meeting
The meeting was excellent.
We began with Progress's video and a lightning talk from one of our members. We allow members to give a 10-minute presentation at the start of each meeting to gain experience in public speaking.
I introduced Scott by telling the audience, "They say you should never meet your heroes, but I have very real evidence that this is not true," before explaining that I was a fan of Scott Hanselman for years before we finally met. I learned what a genuine person he is and how much effort he puts into helping others.
The Aftermath
I attended Scott's keynote presentation the next morning, where he gave a talk similar to the one he delivered at my group. When it was over, he flew back to Portland - two more presentations in the books. He will soon be on the road for another conference, another keynote, and another audience. But this one will remain with me. It is an example of how a talented speaker and a group of passionate individuals can quickly put together an event that provides value to the community.
NOTE: Pete Rodriguez contributed to this content
In 1943, the Allies hatched a plan to fool Adolf Hitler and Nazi Germany into believing they planned an invasion of Italy through the island of Sardinia - the real plan called for invading Sicily. Britain's MI-6 agency executed this ruse by concealing false papers on a dead body and washing that body ashore off the coast of Spain, where the papers would eventually make their way to Hitler. The plan was dubbed "Operation Mincemeat."
