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 […]

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 […]

PMC 2025: The Spirit of Massachusetts, the Best of America, & Collaboration on Steroids! By Craig Hall Underwood, August 22, 2025 On Sunday morning, August 3rd, at 3:45 a.m., I stood in the pre-dawn glow watching hundreds of volunteers serve breakfast to thousands of riders before the final leg of the Pan-Mass Challenge (PMC). I […]

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: […]

Summary: I recently completed Google’s Coursera course on prompt engineering to continue sharpening my use of AI—for both work and play. Like many of you, I want to get better, faster, and more reliable outputs from these powerful tools. To help me remember the core principles, I’ve adopted and modified a fun and memorable mnemonic […]

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 […]

Waffle House Logic – My Thoughts on the 2024 Election and Actions to Fight Back Now Net: I spent the last 5 days of the 2024 presidential campaign doing GOTV work in Allentown, PA for the Harris/ Walz campaign.  I believe Trump won because – as the manager of the Allentown Waffle House explained to […]

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: 1. Keep smart, fight Russian disinformation and propaganda, and share with others. 2. Contribute to Operation Support the Front Lines in Free Ukraine. 3. Patronize Ukrainian artists and businesses. 4. Help Ukrainian refugees. 5. Write elected officials and candidates.

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 […]

5 “NO REGRETS” ACTIONS YOU CAN TAKE RIGHT NOW TO HELP UKRAINE Originally Published March 7, 2022 Last Updated March 9, 2022 This is a photo of Yaroslav Mudriy [for critical security concerns, his real name cannot be revealed at this time], with his niece Mariya and sister-in-law Olena taken in the strikingly beautiful 1600+ years old city of Kyiv when I visited […]

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 […]

Last weekend I rode CHUBike 160 miles in my 3rd Pan Mass Challenge along with 60 of my Year Up TEAM DMITRI! colleagues and thousands of other like-minded cyclists. The PMC is the world’s most successful athletic fund raiser, having raised over $450 million dollars for cancer research. It may also be the best example […]

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 […]

I have had the great fortune to be a small part of the extraordinary success of Year Up over the past 16 years.  Year Up is the innovative workforce development organization started in 2001 by Gerald and Kate Chertavian that recruits, trains and places underserved inner city young adults in living wage careers with Fortune […]

On the Monday before Thanksgiving [2008] my father, Cecil H. Underwood,  passed away.  The date was November 24th, nineteen days after his 86th birthday and twenty days after Barrack Obama was elected President.   My father was born two days before Election Day in 1922, elected the youngest Governor of West Virginia two days after he […]

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 […]

  Summary: While the Starbucks App is cool and makes buying coffee and food quick and easy without dealing with cash, credit or debit cards, the company appears to have developed the app without fully considering the impact on their employees. The app doesn’t offer users the option to tip baristas when making a purchase.  […]

Net: Coalition loyalty programs are among the most successful and fastest growing businesses created over the past 25 years, with flourishing coalition programs currently operating in many countries around the world. The one glaring exception – the U.S. market. Why? It certainly isn’t for lack of trying. Over $1 billion has been lost by companies […]

Net: Realizing that our son had no dedicated places to skateboard in our town of Brookline, Massachusetts, my wife Patty organized a group of young skate boarders and parents, teachers, nonprofit and other leaders to advocate for the creation of safe places to skate in our community.  Although we have a lot of work to […]

Net: Obama’s failure to leverage the collaborative efforts of others, consider and include good ideas from his opponents and provide the requisite and timely leadership contributed greatly to congress’ inability to pass heath care reform.  Will the rhetoric and approaches of the last two weeks be enough to revive it or are they too little […]

Two weeks ago while on vacation in Washington, DC, Patty and I found D’Acqua, a great seafood restaurant on yelp and left two happy kids with room service and movies at our hotel.  We were seated a few tables away from David Axelrod, President Obama’s senior political advisor.  I was about to ask our waiter for a […]

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 […]

Net:  On a recent day trip to Toronto which could have been “travel hell,” several USAir and Air Canada employees worked together to get me there and back painlessly.  Air Canada’s Connie Hughes went the extra mile to help me look for a lost Kindle.  These businesses should make it easy to tell their CEO’s […]

Just noticed this response from Dell manager. Bonus points for finding this new blog and post and for the very candid response on how Dell’s culture is still evolving to embrace customer and customer service collaboration. His comments: Good points on social media in the enterprise as a whole. Thanks for the write-up. While we […]

One of the great byproducts of Web 2.0 is that I often hear from friends and colleagues I have lost touch with.  I am sure you too receive the “I found you on the internet, Facebook, Linked In, …” email from time to time, hopefully from people you actual want to talk to. Last week […]

When 2 former Bain consultants and one recently minted Harvard MBA started AIR MILES Canada, we knew a lot about the economics of customer loyalty and how to quickly understand and model the profit drivers of almost any business. We also knew almost nothing about database marketing other than a few buzzwords one of us […]

this post was also posted on Social Sphere Strategies For the past six months, we have been recommending to clients, potential clients and anyone unlucky enough to sit next to one of us at a dinner party that all businesses need to do the following: 1. Get smart – find a way to get senior […]