Field Notes: A Day at the O’Connor Group Executive Summit
We spent the day at The O’Connor Group Executive Summit, What’s Keeping CEOs Up At Night, and left with a full notebook and a few new ideas to chase. We also left so energized that it is what is keeping us up writing this.
Starting with the economy
The day kicked off with an economic forecast from Anirban Basu of Sage Policy Group, and it was easily the most interesting session. The major forecasters landed in a tight range of roughly 2.1% to 2.4% U.S. GDP growth for 2026. That is modest growth, but with real risks attached: inflation pressure from tariffs, immigration policy and war, interest rates staying higher for longer, and consumers who are running low on steam. Consumer sentiment is sitting near its lowest levels in three decades.
One number stuck with us: U.S. layoffs attributed to AI have climbed from about 4,200 in 2023 to more than 121,000 through October 2026.
AI: most are still figuring it out
The peers we met are using AI in some genuinely creative ways, but the common thread was that leaders are still working out how it all fits together and are looking for a clear return on investment. Our gut says only a small few have figured some things out, and the rest are still working on it. Our take is that a lot of that frustration comes from where people start. The returns show up when you automate from the bottom up, taking the repetitive drudgery off your people first, instead of chasing a big top-down transformation. Look for the friction and grease it away, so people can get back to people work instead of data processing. Our clients also have access to AI acceptable use policy templates and prompts in our knowledge base to help them get started.
Insurance: broken, and likely to stay that way
The other topic that dominated the day was skyrocketing insurance costs. Most agreed the system is broken, but few have the incentive to fix it because of the sheer amount of money at play. That is a hard place to sit as a business owner and few are sure how to fix it.
The people made the day
A huge thank you to the team at The O’Connor Group, our awesome HR partner. They put on a first-class event, and we are lucky to have them in our corner. It was also great to spend time with some of our clients and meet so many new people. The reassuring part is that we are largely looking to solve the same challenges and share our experiences along the way. Those challenges even showed up in real time, with a major Microsoft outage during the summit. The room was chill about it, maybe even a little relieved for the moment. We will be considerably less chill if it’s still happening when we wake up.
Key takeaways
- Start where the friction is. Automate the repetitive work first, from the bottom up, and let the return follow.
- Do not wait for the economy or insurance to get easier. Neither is likely to fix itself, so plan around them.
- Compare notes with your peers. We are largely facing the same challenges, and sharing what works is the fastest way through them.
If AI return on investment or automation is on your mind, we would love to compare notes with you too.
FWIW, Rocky IV was the best Rocky, and Demolition Man is the best Stallone movie nobody mentioned.
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