The Executive AInxiety nobody’s talking about.
From AI to talent retention, here’s what I learned about tech in MKE last week.
I meet with people building, funding, running, and wrestling with technology in Milwaukee. From coffee shops to Teams calls and happy hours around the city, here’s what last week taught me.
NOTE: This first one is a freebie but I’m considering doing these in future weeks only for paid subscribers. Just a heads up.
The one thing keeping manufacturing leaders up at night.
I recorded a podcast this week about the state of manufacturing in Wisconsin, what role tech is playing, what’s working, and what’s not.
Near the end I asked about what keeps manufacturers up most at night?
The answer arrived without hesitation: talent. Specifically, finding and keeping people in Wisconsin.
Emphasis on that came from a couple of other conversations this week while working on an idea to bring college journalism students into Experience Milwaukee. Yes, reviving a thesis from my first company, Spreenkler to give students real work, real bylines, real reasons to stay in Milwaukee.
One conversation opened a door deep into a major local university.
Another, with someone who sees this through an economic development and talent retention lens, helped me focus on how I should carry the idea forward.
Same problem even through different conversations: how does Milwaukee, or Wisconsin for that matter, retain its up-and-coming talent?
Lead with their pain, not your idea.
That economic development conversation gave me the single most useful piece of advice I got all week: when you walk into a room with an idea, don’t open with the idea. Understand the pain first. And let that tee up what you’ve brought.
It sounds obvious, I know. But I’ve watched hundreds of pitches (and made a few myself) that started with the solution and hoped the problem would surface later.
This was such a great reminder that I’m taking curiosity on the road with me.
I’ll be out West at the end of the month meeting with economic development, business, and tech leaders and I’m going with questions, not answers.
For executive leaders, the AI conversation brings a hidden, complex layer of anxiety.
Conversations this week, from two different vantage points, ended eerily similarly.
One was with someone leading the AI charge inside one of Milwaukee’s legacy professional firms. They’re early in the journey of figuring out how to bring AI in at scale.
The other was an early-morning phone call with a former Fortune 500 CTO talking about what enterprise technology leaders are feeling right now.
I shared what I’ve been hearing and seeing in tech executive conversations for some time. It’s that underneath all the AI strategy decks, pilot programs, and POCs there’s a real insecurity.
CIOs / CDIOs / CTOs and the leaders who report to them aren’t entirely sure if they’re doing the right things, doing enough things, or heading in the right direction.
My former CTO friend didn’t hesitate. He’s hearing and seeing the exact same things across his national network.
It’s one thing to sense anxiety in a conversation. It’s another to have someone who spent years at the top of a global enterprise tell you the anxiety is everywhere.
The goal I’m taking into next week.
If the smartest, most experienced tech leaders in our region are privately anxious about AI, what does this ecosystem owe them?
More case studies and vendor pitches clearly aren’t it.
Is it permission to say “I don’t know?”
Maybe it’s time to take the performance pressure off.
Let’s do what we do best in Milwaukee: grab a brewski (A or NA), a seat at the table, and sit down with friendly, honest folks and talk it out.
After all, I believe AI anxiety, like a lot of business problems at the moment, is that every leader thinks they’re the only one who feels unsure or that they’re falling behind.
And that, my friends, is b***s***.
It’s also part of why I said yes to a new role at Xorbix (I announced here earlier this month). I believe the work I’m doing can meet leaders where they are, somewhere in that anxiety.
So, the goal I’m carrying into next week is continuing to build trust that lets leaders admit what they don’t know. Whether that’s about AI or anything else. Sometimes professional things, sometimes personal. And likely over a brewski.
Love you, Milwaukee.