The State AI Readiness Divide: Which States Are Actually Helping Their People Learn and Use AI? An Underwood Partners Collaboration Evangelist White Paper By Craig Underwood in collaboration with ChatGPT Artificial intelligence is often discussed as if it were a single national wave: ChatGPT appears, companies scramble, schools debate cheating, workers worry, and everyone tries […]

by Craig Underwood | June 22, 2026 Net / Summary / Abstract Massachusetts now has one clearly universal free AI training offer for all residents: the Massachusetts AI Hub + Grow with Google partnership, which provides no-cost access through December 31, 2027 to Google AI and career certificate programs. The clearest free AI tool-access benefit […]

Summary / Net Most senior executives do not have a productivity problem. They have an overload, attention, energy, relationship, and prioritization problem. The CHU Management System — CHUMS — is my personal operating system for getting shit done without letting the loudest, most urgent, or most emotionally reactive issue take over my life. CHUMS is […]

One of the most common questions I hear from nonprofit leaders, educators, students, and executives is deceptively simple: How do I get started with AI? My answer: start with prompt engineering. That phrase may sound technical, but the basic idea is very practical. Prompt engineering is simply the skill of designing and refining instructions so […]

FOMAT & THE AI PRODUCTIVITY TSUNAMI: WHY AI ISN’T MAKING SOME OF US WORK LESS By Craig Underwood | collaborationevangelist.com Net/ Summary: Artificial intelligence can absolutely make us more productive. But for executives, consultants, entrepreneurs, nonprofit leaders and other ambitious “power users,” increased productivity does not necessarily mean increased leisure. It can mean more ideas […]

CHU RECOMMENDS: 4 Books, 1 Novel, & 3 Podcasts to Learn About & Keep Up with AI Net/ Summary: The Books: The AI Driven Leader by Geoff Woods AI First by Adam Brotman and Andy Sack The Experimentation Machine by Jeffrey Bussgang Human + Machine by Paul R. Daugherty & H. James Wilson The Novel: […]

CHU Recommends: The Experimentation Machine, by Jeff Bussgang   I am fortunate to have known Jeff Bussgang for over 25 years and can honestly say that he is the perfect person to have written this book (and perfect is not a word I use often!). Jeff studied AI in the late 80’s as a computer […]

Net/ Summary: If it feels like AI came out of nowhere, is suddenly everywhere, and you somehow missed the bus—you’re right about the first two, and dead wrong about the third. While AI adoption has skyrocketed—faster than any technology in modern history—actual usage still varies widely by industry, age, and education. I’ve recently taken a […]

Net/ Summary: When on-boarding new team members or meeting new peers during my second tenure at Year Up leading national accounts like GE and Nielsen, I always scheduled two sessions with my colleagues. The first meeting had nothing to do with strategies, performance metrics, or deliverables. It was about connection.  These are the 8 questions […]

DEMOCRATS (USED TO) SUCK AT MARKETING. 3 IDEAS THAT DON’T.  Net/ Summary:  I absolutely LOVE the Harris Walz positioning “Freedom, Opportunity, and The Promise of  America.” It’s tight, brilliant, positive, and even better, in my opinion, than Jon OssofF’s “Jobs, Justice, Healthcare.” The team’s consistent use of the 3-point slogan also relieves years of personal […]

Summary/ Net: Boomers, please stop believing that you “can’t do” things you never mastered before – or better yet – tried without success in the past.  Use “The 5 T’s” to overcome your lack of confidence: Try, Training, The Right Tools, The Requisite Time, and Trial and Error. I wrote this for three reasons: Few […]

Today is the 103rd Anniversary of my beautiful mother’s birthday.  At her 2004 memorial service, I spoke about 6 of the most important lessons she taught me by the way she lived her 85 years.  Recently, I have thought a lot about the Leadership Lessons I learned from her words and actions: Take care of […]

LEADING BY LISTENING – A LESSON FROM COACH K Near the end of Duke’s Sweet 16 victory over Texas Tech, Coach K (Mike Krzyzewski), one of the winningest coaches in college basketball history listened to his players – who asked him to let them change from zone defense to play “man to man.”  He agreed […]

Summary: We drove over 3,000 miles last week from Boston to Atlanta, Jonesboro, Ellenwood, McDonough, Riverdale, Montgomery, Griffin, Lagrange, Oxford and Covington, Georgia and back home.  We travelled south to work door-to-door canvassing to help the Reverend Raphael Warnock and Jon Ossoff win their runoff races to represent Georgia in the US Senate.  The bulk […]

Net: CEO’s and other company leaders with a enterprise view of their operations are uniquely positioned to identify and share best practices in all areas.  This opportunity can be greatest in organizations that operate in multiple locations with a lot of entrepreneurial flexibility to pilot new ideas, especially in sales and marketing. One way to […]

Net: One of the most important roles of leaders and managers is to “look for people doing things right and tell them.” Like most companies, The Loyalty Group (now the LoyaltyOne division of Alliance Data) had Operating Principles.  Ours were: Work together Be at cause Respect & challenge each other Teach & learn Have fun […]

My brilliant friend Morra Aarons-Mele, creator of the podcast “Hiding in the Bathroom” and author of a book by the same name subtitled “An Introvert’s Roadmap to Getting Out There (When You Would Rather Stay Home),” recently posted the poignant question “How do you stop obsessing over a f-up?” on Facebook. I responded to her […]

Net: A Year Up student recently asked me if I had any favorite any motivational words or slogans.  I told her about the 4 T-shirts we wore at Sports Loyalty International: Carpe Diem; Never, Ever Quit, No Regrets & Breakthrough.  After speaking with her, I realized they applied to my current role at Year Up […]

During the time I was CEO of The Loyalty Group, we grew from three entrepreneurs in a Toronto hotel room to over 600 employees when we sold the business to Alliance Data System (NYSE: ADS) in 1998.  Throughout this period, I thought a lot about both leadership and how to help our people develop the […]

Although you wouldn’t know it from the 50 degree weather we have had the last three days, it is spring in Boston, which means my 9 year old son is playing baseball again.  Helping coach his little league team reminded me of the leadership model we developed at the Loyalty Group that others have found […]