CEO Leadership Insights - June 2026

“A man should never be ashamed to own that he has been in the wrong,

which is but saying, in other words,

that he is wiser today than he was yesterday.”

Alexander Pope

1688-1744

English poet and satirist

Checking Out of the C-Suite

The youngest members of the Boomer cohort are turning 60 this year and if they haven’t retired yet they know it’s imminent but may not know what retirement will look like.  For C-level executives this is particularly important as a life of above average challenge, opportunity and learning may be hard to replace.

The former CMO of United Airlines saw the challenge early and decided to design a life.  In this short article, Tom O’Toole shares how he designed a “post corporate life”.  As life spans lengthen, a 65-year-old C-Level executive may well find that they have a good 20 years ahead of them. 

Mr. O’Toole devised a concept he calls a “portfolio life “to describe the set of activities in which a senior executive decides to engage after stepping out of the C-suite."  If you know that you’ll be checking out of the C-Suite soon, Mr. O’Toole offers 5 Tips to Chart Your Post-Corporate Life

A Mythos Primer

By now you may have heard about Anthropic’s new AI offering “Mythos” that among other things has an unprecedented capability to identify IT system vulnerabilities.  This may be a defining moment in AI’s evolution so take a moment to familiarize yourself with Anthropic ‘s Mythos: What It Is and What It Is Capable of

The Limits of Unlimited Vacation

Summer is upon us, and many employees’ thoughts turn to vacation, and many employers’ thoughts turn to how to get the work done and whether their vacation policies encourage new employees to join and current employees to stay.

Vistage Employment Law Speaker Hunter Lott shares his own expertise and some data from SHRM in a 4-minute video “Unlimited Vacation”, that may help you determine if your vacation policies are what they should be.

The State of AI for CEOs

A colleague of mine asked AI for “Best general article on AI for a C-Level Executive published in the last month for a small to medium size business" (i.e. the Vistage Community) and it picked AI Consultant and former CEO Glenn Gow’s post “The State of AI for CEOs (June 2026)”. The article and accompanying video that summarizes 19 interviews Mr. Gow had with CEOs that he breaks down into four segments: “The Pilot Era”, “The Talent Equation”, “Automating the Back Office” and “Governance and Risk”

One real gem from the post is a vital question to ask AI after it’s returned an answer to a complex prompt… and how often AI will modify its answer.

Econ Recon:

Will productivity save us?

Our history with inflation tells us that we cope with it by increasing interest rates and or productivity.  Interest rates don’t appear to be headed down anytime soon, so many are hoping that AI will be the productivity answer that pushes inflation back down or at least moderates it. 

Economist Brian Wesbury explores this question is a one-page post “Is Productivity Growth Picking Up?.”

A Note from Scott:

Friends,

As you navigate these chaotic times, who are you turning to for advice?

Why not ask successful, growth-minded CEOs and senior executives what they've tried? What has worked, and what hasn't worked for them?

My CEO peer advisory group provides a confidential forum where 18 high-performing, non-competing business owners share their experience, identify blind spots, and hold each other accountable.

As a result, members grow faster, are more profitable, and have less stress.

Contact me if you are interested in exploring membership in our group. Typical members are growth-minded CEOs/business owners in southeastern New England with revenues between $10 million and $200 million.

Don't go it alone. Don't suffer from being 'lonely at the top'. Contact me to see if you'd be a fit with this group.

Warm regards,

Scott