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 to keep up.

But that is not what is happening.

AI adoption is not spreading evenly across the United States. It is being shaped by public choices — by whether states are giving government employees secure AI tools, helping educators understand how to teach with AI, investing in public higher education, and making AI training available to residents.

In other words, the next AI divide may not be just between people who use AI and people who do not.

It may be between states that help their people learn AI — and states that leave them to figure it out alone.

That was the hypothesis behind this research. I wanted to know whether states differ meaningfully in their investment in and support for AI, and whether Massachusetts — my home commonwealth — is at or near the top.

The short answer: yes.

The longer answer is more interesting.

State AI readiness evaluation criteria.

For this analysis, we ranked all 50 states plus Washington, D.C. on a 100-point AI readiness index. The index was not designed to measure private-sector AI activity alone. Silicon Valley venture capital, university research labs, and AI startups matter, but they were not the core question.

 

The question was civic and public:

Which states are helping their residents, students, educators, public employees, and institutions actually learn and use AI?

The ranking used four categories:

 

We gave the most credit for concrete implementation: secure AI tools, training programs, statewide public AI portals, public higher-ed credentials, K–12 AI guidance, workforce-development programs, and published use cases.

We gave much less credit for task forces, commissions, executive orders, or legislation unless they were tied to real funding, training, tool access, implementation, or public-facing programs.

We also distinguished among three policy postures:

Policy posture Meaning
Responsible AI enablement The state encourages AI adoption while providing guardrails, training, privacy protections, and human oversight.
Neutral risk management The state is studying or regulating AI but has limited public evidence of broad adoption support.
Restrictive or chilling policy The state’s actions appear more likely to discourage useful AI adoption than to enable it.

That distinction matters. AI governance is not automatically anti-AI. In fact, the most impressive states are not choosing between innovation and responsibility. They are trying to do both.

The top 10 states and jurisdictions

The highest-ranked states are not merely “interested” in AI. They are putting AI into public systems.

Rank State / Jurisdiction Score Tier
1 Massachusetts 91 AI Readiness Leader
2 Utah 88 AI Readiness Leader
3 New York 86 AI Readiness Leader
4 New Jersey 84 AI Readiness Leader
5 California 82 AI Readiness Leader
6 District of Columbia 80 AI Readiness Leader
7 Maryland 78 AI Readiness Leader
8 Colorado 77 AI Readiness Leader
9 Ohio 76 AI Readiness Leader
10 Georgia 75 AI Readiness Leader

Massachusetts ranks first because it appears to have the most complete public AI readiness strategy. The Commonwealth has launched a secure enterprise AI assistant for executive-branch employees, partnered with Google and the Massachusetts AI Hub to offer no-cost AI training to residents, and developed K–12 AI guidance and educator resources through the Department of Elementary and Secondary Education.[1]

Utah ranks second and may be the national leader in education-focused AI readiness. Utah has announced a statewide AI Workforce Credential for public college and university graduates and a statewide partnership to bring Gemini for Education to K–12 schools.[2]

New York ranks third because of the scale of its state workforce rollout. The state has expanded AI training and a secure AI tool, AI Pro, to more than 100,000 state employees, while also investing in Empire AI, a major public-interest AI research consortium.[3]

New Jersey ranks fourth because it has one of the clearest examples of practical public-sector AI implementation. Its NJ AI Assistant has been used by about 20,000 state employees, with more than 300,000 sessions and 1 million prompts as of February 2026.[4]

California ranks fifth because it combines a massive AI economy with state and local government training, K–12 guidance, higher-ed activity, and workforce-disruption planning. But California’s posture is more complex than the top four because it is also heavily focused on regulation and labor-market disruption.

The bottom 10 states

The bottom states should not be described as “anti-AI.” That would overstate the evidence. In many cases, they are better described as states with limited public evidence of broad statewide AI enablement.

Rank State Score Tier
42 West Virginia 42 Limited / Early
43 Wyoming 41 Limited / Early
44 New Hampshire 40 Limited / Early
45 Alaska 39 Limited / Early
46 North Dakota 38 Limited / Early
47 Louisiana 37 Limited / Early
48 Nebraska 36 Limited Public Evidence
49 Kansas 34 Limited Public Evidence
50 South Dakota 32 Limited Public Evidence
51 Arkansas 30 Limited Public Evidence

This is an important methodological point. A low ranking does not prove that nothing is happening. It means I found less recent public evidence that the state is combining AI tool access, training, education strategy, workforce development, and responsible-use infrastructure into a coherent statewide approach.

That distinction matters because the AI landscape is changing fast. A state could move from the bottom tier to the middle quickly if it launched a statewide AI training portal, gave public employees secure AI access, published K–12 guidance, and used community colleges to scale workforce credentials.

The map tells the story.

The lead map shows a striking pattern: AI readiness is not evenly distributed.

Some states are already treating AI as a public-capacity project. They help people learn, practice, and use AI responsibly. Others are still closer to the study-and-watch stage.

National research supports this uneven picture. Code for America’s 2026 Government AI Landscape Assessment concluded that states are at different stages of AI adoption, ranging from readiness and piloting to implementation and impact.[5] The National Conference of State Legislatures has also tracked a surge in state AI activity, reporting that all 50 states, Puerto Rico, the Virgin Islands, and D.C. introduced AI-related legislation in 2025, while 38 states adopted or enacted around 100 measures.[6]

But legislation alone is not the same as readiness.

The leading states are doing more than passing bills. They are creating tools, training people, building public infrastructure, and giving educators and public employees permission to experiment within guardrails.

What the K–12 comparison adds

We also compared each state’s AI readiness rank with its K–12 education rank, using WalletHub’s 2026 public school system ranking as the K–12 comparison source.[7]

The result is one of the most interesting parts of the analysis.

Good schools help, but they do not automatically produce AI readiness.

Some states have both strong K–12 systems and strong AI readiness. Massachusetts is the clearest example: it ranked first in both our AI readiness index and the WalletHub K–12 ranking. New Jersey, New York, Maryland, Virginia, Connecticut, Rhode Island, Wisconsin, Pennsylvania, and Utah also appear in the high-education / high-AI zone.

These states are in the strongest strategic position. They have educational capacity and are beginning to convert that capacity into AI readiness.

But the scatterplot also reveals two other important patterns.

First, some states appear to be using AI as a leapfrog strategy. California, Georgia, Ohio, North Carolina, Colorado, Oregon, Arizona, Texas, and New Mexico do not rank at the very top on K–12 education, but they show stronger public evidence of AI support and investment than their education rankings alone would predict.

That may be strategically wise. AI training can scale faster than traditional education reform. Community colleges, public universities, workforce boards, libraries, and state agencies can help adults, small businesses, and public employees gain practical AI skills quickly.

Second, some states with relatively strong K–12 systems appear to be underleveraging that advantage. New Hampshire, Nebraska, North Dakota, Montana, Wyoming, Indiana, and Vermont all have educational strengths, but weaker public evidence of broad AI readiness.

That is the danger for high-education states: yesterday’s education advantage does not automatically become tomorrow’s AI advantage.

Four strategic positions for states

The AI readiness vs. K–12 education scatterplot creates four useful strategic categories.

  1. High K–12 / High AI: Compounding advantage

These states have the strongest starting position. They have relatively strong education systems and are also investing in public AI readiness.

Strategic imperative: move from AI readiness to AI advantage.

These states should publish public AI use-case libraries, scale AI literacy expectations, train public employees, support educator professional development, fund public higher-ed credentials, and measure productivity and learning gains.

The risk is complacency. Strong schools and strong universities are not enough. AI advantage requires structured implementation.

  1. Lower K–12 / High AI: Leapfrog opportunity

These states may be using AI as a way to accelerate workforce development and public-sector modernization.

Strategic imperative: use AI as a human-capital accelerator.

These states should focus on community colleges, adult learners, small-business training, teacher productivity, student supports, and accessible AI credentials.

The opportunity is speed. A state does not need to wait 20 years to improve every K–12 metric before helping people build useful AI skills.

The risk is inequity. If AI programs primarily benefit already-advantaged residents, AI may widen internal gaps.

  1. High K–12 / Lower AI: Underleveraged education advantage

These states may have strong educational foundations but less visible statewide AI implementation.

Strategic imperative: convert education strength into AI readiness.

The playbook is straightforward: issue practical K–12 AI guidance, train educators, give public employees secure tools, create public AI learning portals, and use public universities and community colleges as AI training engines.

The risk is losing ground to states with weaker traditional education systems but stronger AI implementation strategies.

  1. Lower K–12 / Lower AI: Double catch-up challenge

These states face the hardest strategic position.

Strategic imperative: start with practical, low-cost, high-leverage AI readiness moves.

They should create a statewide AI learning portal, train state employees in responsible AI use, publish K–12 AI guidance, partner with community colleges on short credentials, and build a public use-case library.

The risk is that AI becomes another driver of regional inequality.

The deeper point: AI readiness is public infrastructure.

The best states are not treating AI as a gadget. They are treating AI readiness as a form of civic infrastructure.

That means giving people:

  • access,
  • training,
  • permission,
  • examples,
  • guardrails, and
  • time to practice.

A state employee who has access to a secure AI assistant can learn by doing. A teacher with practical guidance can move beyond fear and confusion. A community college student with an AI credential can enter the labor market with greater confidence. A small business owner with free training can experiment without hiring a consultant. A resident with access to a public AI learning portal can begin without needing to be part of the technology sector.

That is the difference between AI as a private advantage and AI as a public capability.

Why Massachusetts matters

Massachusetts is a particularly useful case because it already had advantages: great universities, strong K–12 performance, a dense innovation economy, world-class hospitals, and a highly educated workforce.

But those advantages alone are not what made Massachusetts rank first.

What matters is that Massachusetts appears to be converting its existing advantages into public AI readiness.

The Commonwealth is giving executive-branch employees secure AI access. It is offering residents no-cost AI training. It is building a public AI Hub. It is supporting K–12 educators with guidance and resources.

That combination is the key.

Massachusetts is not simply an AI-rich state. It is investing to become an AI-ready Commonwealth.

The policy lesson

The policy lesson is not that every state should copy Massachusetts exactly. States differ in size, economy, demographics, politics, education systems, and fiscal capacity.

But every state can do five things:

  1. Give public employees safe AI access and training.
  2. Publish practical K–12 AI guidance.
  3. Use public higher education and community colleges to scale AI credentials.
  4. Create a public AI learning portal for residents and small businesses.
  5. Measure outcomes and publish use cases.

The first states to do these things well will have an advantage.

Not just a technology advantage. A civic advantage.

Final thought

AI adoption is often framed as an individual responsibility: learn the tools, keep up, do not fall behind.

But this research suggests that public leadership matters enormously.

Some states are making AI learning easier, safer, and more accessible. Others are leaving residents, teachers, workers, and public employees to navigate the AI era largely on their own.

That is the state AI readiness divide.

And it may become one of the most important competitiveness and equity issues of the next decade.

 

 

Endnotes

[1] Massachusetts state AI assistant materials; Massachusetts-Google free AI training announcement; Massachusetts AI Hub; Massachusetts Department of Elementary and Secondary Education AI resources.

[2] Utah System of Higher Education announcement of statewide AI Workforce Credential; Google announcement of Gemini for Education partnership with Utah K–12 schools.

[3] New York Governor’s Office announcement of AI Pro and AI training expansion to state workforce; Empire AI materials.

[4] New Jersey Innovation Authority, NJ AI Assistant project page and 2026 update.

[5] Code for America, 2026 Government AI Landscape Assessment.

[6] National Conference of State Legislatures, 2025 AI legislation summary and AI legislation database.

[7] WalletHub, 2026 public school system ranking.

Source links for the article endnotes

Massachusetts has an official enterprise AI assistant page, and Google announced no-cost AI training for Massachusetts residents through the Massachusetts AI Hub and Grow with Google. (Massachusetts Government)

Utah’s higher-ed system announced a no-cost AI Workforce Credential for more than 50,000 public college and university graduates, and Google announced Gemini for Education access for every Utah K–12 school beginning in the 2026–2027 school year. (Utah System of Higher Education)

New York announced expansion of AI education and AI Pro to more than 100,000 state employees, while New Jersey reported about 20,000 state employees using its AI Assistant, with more than 300,000 sessions and 1 million prompts as of February 2026. (Governor Kathy Hochul)

Code for America’s 2026 Government AI Landscape Assessment evaluates state AI adoption across readiness, piloting, implementation, and impact, while NCSL tracks AI legislation across states and reported that 38 states adopted or enacted around 100 AI-related measures in 2025. (Code for America)

For education context, Playlab reports that 36 states plus Puerto Rico had official K–12 AI guidance or policy frameworks as of May 2026, and FutureEd tracked 71 AI-in-education bills across 27 states during the 2026 legislative session. (learn.playlab.ai

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 not a software platform, productivity app, or universal template. It is a weekly paper-and-Google-Sheet discipline I use to manage work, family, relationships, health, values, commitments, follow-up, and focus. The specific system is mine. The larger point is universal: every serious leader needs a system.

Why I Built CHUMS

I originally developed what became the CHU Management System during the seven years I founded and led The Loyalty Group, that created, launched and grew the AIR MILES Canada shopping reward program and database/ internet marketing business. Like many entrepreneurs and CEOs, I had too many priorities, too many people depending on me, too many ideas, too many meetings, too many relationships to maintain, and too many chances for something important to fall through the cracks.

Later, in 2016, I began using the system again while working at Year Up, where my work involved roughly 60 internal colleagues, more than 100 external partners, and 12 locations. That was the kind of operating environment where “I’ll remember that” is not a system. It is a fantasy.  It also served me well when I used it in 2020 as Vice Chair of Alan Khazei’s congressional campaign in Massachusetts 4th District.  I have described well-funded competitive political campaigns are like an “internet start-up on speed.”  Personal management systems are a life saver in these environments.

CHUMS is heavily influenced by Stephen Covey’s The 7 Habits of Highly Effective People, David Allen’s Getting Things Done, Jim Loehr and Tony Schwartz’s The Power of Full Engagement, James Clear’s Atomic Habits, conversations with friends and colleagues, and a lot of agile trial and error. It is also influenced by a simple, humbling reality I have learned repeatedly in my life: when I use my system, things get done. When I don’t, things fall off my plate, and I drift into a growing pile of “urgent and important” crises.

The “triple-infinity” symbol represents the need for leaders to keep the most important things, actions, tasks, and priorities among your business, your family, and yourself in balance.  This was something emphasized for me personally during the many years I was a member of The Young Presidents Organization, while CEO of The Loyalty Group in Toronto.

The name is slightly tongue-in-cheek: CHUMS stands for CHU Management System. But the point is serious. CHUMS is a personal operating system for self-leadership.

And for senior executives, self-leadership is not optional. If you cannot manage your own attention, energy, values, relationships, commitments, and follow-up, you will eventually transfer your internal disorganization to the organization you lead.

The Big Idea: Senior Executives Need a Personal Operating System

Most executives already have organizational systems. They have strategic plans, dashboards, CRM systems, board packets, financial models, Slack channels, calendars, and performance reviews. But many do not have an equally disciplined personal system for deciding what deserves attention this week, what must happen today, who needs care and connection, what values must be lived, and what can safely wait.

That gap is dangerous.

Without a personal operating system, leaders become reactive. They chase whatever is loudest. They answer the latest email. They respond to the most anxious stakeholder. They spend too much time in Covey’s “urgent and important” quadrant and not enough time on the important-but-not-yet-urgent work that actually builds a life, a team, a strategy, and an institution.

CHUMS is my attempt to solve that problem for myself.

It has 11 parts:

  1. Daily and weekly self-monitoring
  2. Personal must-dos
  3. Weekly to-do list
  4. Strategic priorities and relationships
  5. Calendar blocking
  6. Must do today before I sleep
  7. Rolling discussion lists, house list, and someday/maybe
  8. Live your values
  9. Feedback is a gift
  10. Weekly must-do / three priorities per day
  11. The 86,400 reminder

Here is how each part works.

1. Daily and Weekly Self-Monitoring

What is it?

The first section of CHUMS is a simple weekly tracker. It includes the people and practices I want to stay connected to each week.

For me, the initials and abbreviations on the left-hand side are personal:

J = Jordan, my oldest child.
M = Myles, my youngest child.
LEZ = my wife, Laura.
X = exercise.
S/G = spiritual practice and gratitude.
SSU = my sister Sharon.
CUF = my sister Cecilia.

This section is influenced by Stephen Covey’s “Sharpen the Saw” habit — the idea that we must renew ourselves across the physical, mental, emotional/social, and spiritual dimensions if we want to remain effective.

How do I use it in practice?

Each week, I track whether I have engaged with these people or practices. Did I connect with my kids? Did I connect meaningfully with Laura? Did I exercise? Did I do anything spiritual or gratitude-oriented? Did I check in with my sisters?

This is not meant to be a guilt machine. It is a visibility tool.

A senior executive can easily spend the week serving clients, employees, donors, investors, board members, political allies, or external stakeholders — and then realize that the people and practices that matter most personally received the least intentional attention.

This section makes that visible.

Why include it?

Because what gets tracked gets attention.

Executives are usually very good at tracking business metrics. Revenue. Margin. Retention. Pipeline. Fundraising. Cash runway. Employee engagement. Customer satisfaction. But we often fail to track the personal relationships and renewal practices that keep us grounded and human.

This section reminds me that productivity is not just doing more work. It is living the right life while doing the work.

If I say my family matters, my system should reflect that. If I say health matters, my system should reflect that. If I say spirituality, gratitude, or reflection matters, my system should reflect that.

Otherwise, my stated values and my calendar can be in conflict.

2. Personal Must-Dos

What is it?

This is the short list of the most important personal things I must get done this week.

Not someday. Not eventually. This week.

These are not necessarily the biggest strategic projects. They are the personal commitments that matter enough to deserve explicit weekly attention.

How do I use it in practice?

When I update CHUMS on Sunday night, I ask: what personal things must happen this week for me to feel I have honored my commitments to myself and the people closest to me?

That might include a family follow-up, a personal finance task, a health appointment, a home issue, a difficult conversation, a commitment to Laura, a call with one of my kids, or something I have been avoiding.

The key is that it gets written down in a place I will see all week.

Why include it?

Because personal obligations do not become less important because they are not professional.

Many senior leaders unconsciously privilege work commitments over personal commitments because work commitments come with meetings, deadlines, assistants, board pressure, customers, and money attached. Personal commitments are often quieter. They do not always send calendar invites.

But neglected personal commitments create stress, guilt, friction, and emotional drag. They also erode integrity. If I repeatedly fail to do what I told myself or my family I would do, I become less trustworthy to myself.

This section protects my personal credibility.

3. Weekly To-Do List

What is it?

This is the classic weekly capture list, heavily influenced by David Allen’s Getting Things Done. Allen’s GTD method emphasizes capturing what has your attention, clarifying what it means, organizing it where it belongs, reviewing it regularly, and then engaging with the right work.  Allen advises against keeping a long daily to-do list, as spending time on most nights moving things that did not get done that day to the next can become energy sapping.

In CHUMS, this becomes a weekly written list of work and personal to-dos.

How do I use it in practice?

The list is organized along the right-hand side of the matrix roughly by my most important clients, projects, and people.  CHUDOW – stands for CHU (to) Do Other Work related and CHUDOP – for CHU (to)Do Other Personal.  IC/ AI is a bucket to make sure I build intellectual capital every week and AI to remind me to keep up with the latest developments in artificial intelligence.

The point is to avoid what I call the “four-year-old soccer problem”: every kid chases the same ball.

Organizations do this. Leaders do this. I do this. The urgent issue gets the ball, and suddenly every person, meeting, and ounce of energy is chasing it while other important areas are neglected.

During the week, whenever something comes up, I write it down. I do not rely on memory. I do not assume I will magically remember it after the meeting, after the bike ride, after walking Izzy, or after the next call.

On Sunday night, I update the system in Google Sheets, print it, and carry it with me. Yes, I am trying to eliminate paper from much of my life. But for this, paper still works. I can fold it in half and keep it in my jacket pocket.  A few more folds and it fits in my jeans or cycling jersey pocket.  If something occurs to me while walking the dog, riding my bike, sitting in a meeting, or thinking through a client issue, I can write it down quickly and get it out of my head.

Why include it?

Because the brain is a terrible office.

It is wonderful for creativity, empathy, pattern recognition, judgment, and strategy. It is not wonderful as a storage facility for 73 unrelated commitments.

David Allen’s core insight is that unprocessed commitments create mental residue. The more open loops we carry in our heads, the less fully present we are for the task or person in front of us.

For senior executives, this matters enormously. Your attention is one of the most valuable assets in the organization. If your mind is cluttered with unrecorded obligations, you are spending executive attention on memory management instead of judgment.

Writing things down is not clerical. It is strategic.

4. Most Important Strategic Relationships and Priorities

What is it?

The last two columns force me to list 1-3 relationships in appropriate areas of focus that I must invest in during the week and to whittle down the many to-do items under each to the 1-3 that simply must get done by the end of the week.

How do I use it in practice?

I use the categories to force a broader scan.  The most important relationships and priorities in each category ensure that I narrow down and prioritize those actions and people that are most important for the period.

What needs attention in each major area? What am I ignoring? Which relationships need follow-up? Which strategic priority is quietly drifting? Which area has become too dominant? Which important work is not urgent enough to scream yet?

This section turns my week from a random pile of tasks into a portfolio.

Why include it?

Because executive work is portfolio work.

A CEO or senior leader is rarely responsible for one thing. You are responsible for strategy, people, capital, culture, customers, operations, governance, risk, external relationships, and often your own health and family system at the same time.

If you only manage the loudest category, you will underperform in the quieter ones.

This section creates balance. It forces me to ask: am I paying attention to the whole field, or am I chasing the ball?

5. Calendar Blocking

What is it?

I use this section to block out my calendar, identify major client and board meetings, presentations, and color-code travel dates. It gives me a high-level overview of the most important personal and business events that will require major prep work or personal planning over the next two months.

How do I use it in practice?

At the beginning of the week, I look at the major events and commitments coming up over the next 8 weeks and make sure the requisite pre-work is somewhere on the list above or elsewhere recorded in the system.

Why include it?

This section helps me connect intention to time. It also helps me see overcommitment before it becomes failure. If I have 30 hours of meetings and 50 hours of work I claim must get done, the math is not going to work. Pretending otherwise does not make me ambitious. It makes me irresponsible.

Calendar visibility is a form of honesty.

6. Must Do Today Before I Sleep

What is it?

This is the daily hard-stop section: what must I do today before I go to sleep?  With all due respect to David Allen, this is my daily to do list.  I use an erasable pen to fill it in each morning before starting my day and clear it by the end.

This includes any true Covey Quadrant I items — things that are both urgent and important. But it is not limited to crisis work. It can also include one or two actions that simply cannot be allowed to slip another day.

How do I use it in practice?

Each day, I identify the small number of things that must happen before I sleep. Not 20 things. Not everything. The real must-dos.

This is the section that confronts the day directly.

At the end of a long day, when I am tired, distracted, or tempted to postpone something uncomfortable, this section asks: what did I promise myself would get done today?

Why include it?

Because weeks are won or lost in days.

A beautiful weekly plan can still fail if there is no daily commitment mechanism. This section turns the system into action.

It also helps distinguish between “I was busy” and “I did what mattered.” Senior executives can be busy every minute of the day and still avoid the one conversation, decision, note, workout, apology, or follow-up that actually mattered most.

The phrase “before I sleep” creates useful pressure. It makes the commitment concrete.

7. Rolling Discussion Lists, House Perfect List, and Someday/Maybe

What is it?

The right side of the front page is a set of rolling lists.

I use it to track topics I need to discuss with team members, client contacts, consultants, family members, friends, and collaborators. Instead of immediately calling or texting every time a thought occurs to me, I write it down under the relevant person or project.

This section also includes ideas for articles, my “House Perfect List” — smaller or larger things I need to do around the house or yard — and a “Someday/Maybe” list, borrowed directly from David Allen’s Getting Things Done framework.

How do I use it in practice?

When I think of something I need to discuss with someone, I put it in that person’s box. Then, when we meet or talk, I have a ready-made agenda.

This improves the quality of meetings and reduces the number of interruptive one-off communications. Instead of spraying texts, emails, and half-formed thoughts throughout the week, I batch topics for the right moment.

For the Collaboration Evangelist articles, House Perfect List and Someday/Maybe list, the same principle applies: capture without overcommitting. Not everything belongs on this week’s must-do list. Some things simply need a trusted parking place.

Why include it?

Because not every thought deserves immediate action.

This is especially important for senior leaders. Executives generate a lot of ideas, questions, concerns, and follow-ups. If every thought becomes an immediate interruption for someone else, the leader becomes a chaos machine.

A rolling discussion list creates discipline. It respects other people’s attention. It makes meetings better. It lets me remember without reacting.

The Someday/Maybe list is equally important because it gives ideas a place to live without letting them hijack the week. That is a critical distinction. A good idea is not always a current priority.

8. Live Your Values

What is it?

The left side of the back page is my values reminder. It lists the personal values and commitments I am trying to live.

The emphasis is on trying.

This section is not a declaration that I am fully living these values every day. It is a reminder of who I want to be and how I want to show up.

For me, this includes being the best father I can be, being a good brother, honoring my parents by how I live and work, being respectfully and graciously honest, taking care of myself physically, emotionally, intellectually, and spiritually, using my experience and resources to help others, fighting for justice, being conscious of the impact of my words and actions, not judging others, being the best partner to Laura and best human to Izzy I can be, and passionately promoting what I believe in.

How do I use it in practice?

I keep it on the back page so I see it repeatedly. It is not a framed statement on a wall. It is part of the weekly system.

That matters. Values should not be separated from execution. They should shape execution.

When I review my week, I am not only asking, “What do I need to get done?” I am also asking, “Who am I trying to become while I get it done?”

Why include it?

Because productivity without values can become efficient selfishness.

Many senior executives are extremely productive by conventional measures. They clear inboxes, make decisions, hit numbers, raise capital, close deals, and move fast. But speed and volume are not the same as leadership.

This section forces me to connect action to identity. James Clear’s Atomic Habits argues that lasting behavior change is connected to identity — not merely what goal we want to achieve, but what kind of person we believe we are becoming.

For me, CHUMS is not just a task system. It is an identity system. It reminds me that the goal is not simply to get more shit done. The goal is to get the right shit done in a way that is consistent with the person I am trying to be.

9. Feedback Is a Gift

What is it?

This section captures some of the most important feedback I have received from supervisors, mentors, colleagues, friends, and role models.

It includes short reminders — phrases that mean something specific to me. Some are blunt. Some are cryptic to anyone else. Some are deeply personal. The point is not that the phrases would work for everyone. The point is that they work for me.

How do I use it in practice?

I keep the feedback visible so I cannot conveniently forget it.

Most of us say feedback is a gift. But in practice, we often treat feedback like a gift we would like to return, exchange, reinterpret, or bury in a drawer!

This section makes feedback operational. It turns lessons learned into recurring prompts.

Why include it?

Because leaders repeat avoidable mistakes when feedback is not converted into practice.

Senior executives often receive a lot of feedback, but not always honest feedback. The more senior you become, the more people manage you, flatter you, fear you, or soften the message. So, when you do receive real feedback, you should treat it as valuable data.

But insight fades. A hard lesson learned in March can be forgotten by June. This section keeps the lesson alive.

It also reinforces humility. No matter how experienced I am, I still have things to work on. The system reminds me of that every week.

10. Weekly Must-Do / Three Priorities Per Day

What is it?

The top right side of the back page can be used to list three priorities per day for the week. I have also used it as a blank note-taking space or as a place to list annual goals.

The three-priorities structure is intentionally simple.

How do I use it in practice?

For each day, I write the three things that would make the day successful.

Not 12. Not 27. Three.

This creates focus without pretending the day is clean, predictable, or fully controllable. It gives me a simple way to answer: if everything goes sideways, what are the few things that still matter?

Why include it?

Because constraints create clarity.

Executives are vulnerable to over-listing. We confuse ambition with volume. We put too much on the list and then feel behind before the day starts.

Three priorities force choice. Choice is the essence of strategy.

This section also creates a bridge between weekly planning and daily execution. The weekly system sets the field. The daily priorities define the play.

11. The 86,400 Reminder

What is it?

The final section is a visual reminder: 86,400; Be The Buffalo: Make The Next Best Choice; Proverbs 3:27.

There are 86,400 seconds in a day. Something I learned from my Pastor and Spiritual Entrepreneur friend Ray Hammond. For me, this symbol is a reminder to make the most of each day, confront challenges directly, not dwell endlessly on mistakes, and help others when I am able.

How do I use it in practice?

I do not use this as a productivity hack. I use it as a perspective hack.

Some days go well. Some do not. Some include progress. Some include mistakes. Some include conflict, disappointment, fatigue, or frustration.

The 86,400 reminder helps me reset. It says: this day is finite. Use it. Do not waste it in avoidance, resentment, self-pity, distraction, or fear.

Why include it?

Because time is the only non-renewable leadership resource.

Money can sometimes be raised. Staff can sometimes be hired. Strategy can sometimes be revised. Reputation can sometimes be rebuilt. But the day is spent once.

This does not mean every second should be optimized. That would be exhausting and inhuman. It means the day should be honored.

For a senior executive, the question is not merely “How do I get more done?” The deeper question is: “How do I make choices worthy of the time I have?”

Why the Whole System Works

CHUMS works for me because it integrates five things that are often separated:

  1. Tasks
  2. Time
  3. Energy
  4. Relationships
  5. Values

Most productivity systems over-focus on tasks. They help you capture, sort, and complete work. That is useful, but incomplete.

Senior executive effectiveness is not just task completion. It is sustained judgment, emotional regulation, strategic focus, relationship management, physical and mental energy, and values-based action under pressure.

That is why The Power of Full Engagement is such an important influence on CHUMS. Loehr and Schwartz argue that managing energy, not just time, is central to high performance. A leader with a perfectly organized calendar but depleted physical, emotional, mental, or spiritual energy is not operating at full strength.

CHUMS also works because it is reviewed weekly. A system that is not reviewed becomes clutter. A system that is reviewed becomes trusted.

My Sunday night practice matters. I update the Google Sheet, print the system, and carry it with me. That ritual turns CHUMS from a document into a discipline.

James Clear’s Atomic Habits emphasizes the power of small, repeatable systems. The point is not heroic motivation. The point is designing a structure that makes the desired behavior more likely. CHUMS does that for me. It makes remembering, reviewing, prioritizing, connecting, and acting easier.

It also creates accountability. Even when no one else sees the sheet, I see it. I know what I wrote down. I know what I said mattered. I know what I avoided.

That is powerful.

What Happens When I Do Not Use It

When I do not use CHUMS, my productivity does not collapse all at once. It degrades gradually.

First, I start relying on memory. Then I miss small things. Then I become more reactive. Then important-but-not-urgent work slips. Then relationships become less intentional. Then my day gets captured by other people’s priorities. Then I feel behind. Then I start chasing the crisis of the day. Or, at worst, fall into a state of depression or anxiety paralysis.

Eventually, I end up with exactly what Covey warned about: too much time in the urgent and important quadrant because I failed to invest enough time in preparation, prevention, relationships, renewal, and planning.

When I do not use CHUMS, I also become more likely to confuse motion with progress. I answer emails, create PowerPoint slides, attend meetings, respond to texts, and knock off visible tasks, but I may not be moving the most important priorities forward.

Worst of all, I become more likely to drift away from my values. Not because I stop believing in them, but because I stop seeing them.

That is how it happens for many leaders. They do not abandon their values dramatically. They simply get busy. Then they get reactive. Then they get tired. Then they rationalize. Then the urgent crowds out the important. Then, slowly, the life they are living stops matching the life they say they believe in.

CHUMS is my defense against that drift.

The System Is Mine. The Need Is Universal.

I do not recommend that everyone copy my exact system.

In fact, you should not. CHUMS is highly tailored to my priorities, family, relationships, passions, work, quirks, and flaws. Your system should be tailored to yours.

But I strongly believe every senior executive needs some kind of personal operating system.

It does not have to be paper. It does not have to be a spreadsheet. It does not have to have 11 parts. It does not have to use my language. It does not have to be called anything clever.

But it should help you answer these questions every week:

What matters most?
Who needs my attention?
What must get done?
What can wait?
What am I avoiding?
Where is my energy going?
Am I living my values?
What feedback am I trying to practice?
What must I do today before I sleep?

If your system cannot answer those questions, it is not yet a leadership system. It is just a task list.

A Note for CEOs and Senior Leaders

The higher you rise, the less anyone else can fully manage your attention for you.

An assistant can manage your calendar. A chief of staff can manage your meeting flow. A COO can manage execution rhythms. A board can help set accountability. A coach can ask hard questions.

But no one else can decide, week after week, what kind of leader you are trying to be.

That is your work.

CHUMS is one way I do that work.

It helps me get shit done. But more importantly, it helps me get the right shit done, with the right people in mind, for the right reasons, while trying — imperfectly but seriously — to live the values I claim to hold.

For me, that is the real productivity challenge.

Not just doing more.

Doing what matters.

Building Your Own GSD System

In my CEO coaching and productivity accountability partner (PAP) practice, this is one of the places where I believe I can be most helpful.

Not by handing leaders my system and pretending it will fit their lives.

But by helping them build their own.

A strong executive productivity system should be personal, practical, visible, reviewable, and honest. It should include the work, but not only the work. It should include relationships, energy, renewal, values, feedback, and follow-through. It should be simple enough to use when life gets busy, because that is exactly when the system matters most.

The goal is not to become a productivity robot.

The goal is to become a more intentional leader.

A leader who knows what matters.
A leader who writes it down.
A leader who follows up.
A leader who protects time and energy.
A leader who lives values in practice, not just in speeches.
A leader who gets shit done without losing himself or herself in the process.

That is what CHUMS does for me.

And that is why I still use it.  To paraphrase my son Myles, when I don’t use it, “Shit goes left.”

Here’s a link to the front page google spreadsheet you can edit to start building your own system.

Endnotes

  1. Stephen R. Covey, The 7 Habits of Highly Effective People. CHUMS is especially influenced by Habit 7, “Sharpen the Saw,” and Covey’s distinction between urgent/important work and important-but-not-yet-urgent work.
  2. David Allen, Getting Things Done: The Art of Stress-Free Productivity. CHUMS draws heavily on GTD’s core practices of capturing commitments, clarifying next actions, organizing reminders, reviewing regularly, and maintaining a “Someday/Maybe” list.
  3. Jim Loehr and Tony Schwartz, The Power of Full Engagement: Managing Energy, Not Time, Is the Key to High Performance and Personal Renewal. CHUMS reflects the book’s core argument that sustainable high performance requires managing energy across physical, emotional, mental, and spiritual dimensions.
  4. James Clear, Atomic Habits. CHUMS reflects Clear’s emphasis on systems, small repeatable practices, identity-based behavior change, and designing structures that make desired behaviors more likely.
  5. Gail Matthews, Dominican University of California, research on goal achievement and accountability. The CHUMS presentation cites Matthews’ findings that written goals and weekly accountability increased the percentage of participants who accomplished at least half of their goals.
  6. Craig Underwood, CHU Management System aka CHUMS — Overview, updated June 12, 2026. The structure, 11-part framework, personal examples, and CHUMS descriptions are based on the author’s original presentation.

APPENDIX I – FULL FRONT PAGE (BEFORE FOLDING)

APPENDIX II – FULL BACK PAGE (BEFORE FOLDING)

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 turned 34 and elected the state’s oldest Governor on his 74th birthday.  In my post, Why a Collaboration Evangelist, I wrote:

Perhaps it’s a “nature and nurture” thing, as I have always been a strong believer that teams of smart people with diverse backgrounds and points of view will always have a better chance of solving challenging problems and finding new opportunities to add value to any enterprise than the model where “one smart guy solves all the problems and makes all the decisions.”

From the nature side, I was born the day after my father was inaugurated as the 25th governor of the State of West Virginia at the age of 34.  One of the things he told me about that campaign was although they had only one paid staffer – his driver – the campaign was supported by 3000 volunteers. The campaign put all of their efforts into organizing and energizing their volunteer network to register and get supporters to the polls.  They spent the money they raised on the new technology of the day called TV advertising.  This strategy enabled him to become the first Republican governor in 25 years in a state where Democratic voters outnumbered Republicans   by 2.5 to 1.

The many papers around the world that carried the news of my father’s death described him as “a high school teacher who became a governor.”  While it is true that he started his career as a high school biology teacher and his last formal employment was as a Drinko Scholar at Marshall University, my father was always quietly teaching through his actions to those of us who had the good fortune to know and work with him. At his memorial service, I remembered my father by sharing some of the lessons he taught us by the way he lived and the way he led.  These included:

1. No obstacle is too high to overcome if you believe in yourself and are willing to work very hard to achieve your goals.

My father took on monumental challenges from the beginning of his career.  At the age of 22, he challenged a long standing incumbent to win the first of six terms to the State Legislature.  Twelve years later he was elected Governor.  But at the end of his first term he lost a race for the US Senate (at that time, Governors could not run for re-election) and over the next 36 years he ran unsuccessfully for Governor three times.

1956 Campaigning for Governor at 33 Years Old

1956 Campaigning for Governor at 33 Years Old

During this period, I remember thinking that maybe my father had “peaked too soon” at the age of 34, like an NBA team playing their best ball before the playoffs.   He showed me otherwise in 1996 when he was elected the State’s 32nd Governor.  During his second administration, more jobs were created, more roads were built and more school children and seniors were connected to the internet than during any other four year period in the history of West Virginia.

As I admired his work ethic and the successes of his second term, I thought he was the greatest role model for working hard and beating the odds that anyone could ever have.  But again I was wrong. Not wrong in the role model, but wrong in the act.

The most amazing thing I saw my father do was to come back from a paralyzing stroke he suffered in 2006 at the age of 83.  The entire left side of his body was paralyzed with the exception of his fingers, which he could move slightly if he wasn’t too tired.  At his discharge planning meeting a few months later, my sisters and I told Dad he needed to move to an assisted living facility to continue his rehabilitation.  He was none too happy with our proclamation and wanted to know what he had to do to live at home again. We told him he needed to be able to walk.

So, for the next three months, he did 5 hours of physical therapy a day – riding the stationary bike, lifting weights and doing anything else the PT staff at Charleston Gardens told him to do.  His efforts were rewarded as he indeed did walk again and was selected “Stroke Recovery Patient of the Year.” More importantly, he was able to return home for several years.

Read more

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 requisite skills to advance as far as they wanted to in their careers.

Nothing gives me greater pleasure that seeing those who worked with me do extremely well.  Two great examples are John Scullion and Brian Sinclair.  In 1993, I had to use all of my selling skills to convince John to leave the high profile corporate travel business Ryder Travel and join a company whose balance sheet looked similar to some now defunct Wall Street firms.  John is now President and COO of Alliance Data Systems, with a market cap of several billion dollars.  Brian Sinclair, whose first job out of college was an AIR MILES analyst, is now the Managing Director of Nectar, the wildly successful coalition loyalty program in the UK that recently sold to Aeroplan for $700MM.

After we visited Brian at his London offices last summer, my 12 year old daughter Jordan remarked, “You gave him his first job and now he has a better job than you!”  Although I thought about reminding her that the flexibility of my firm enabled our father-daughter trip to London, my wiser side prevailed and I responded, “That’s right, and nothing could make me happier than seeing people I hired doing really well.  That means I hired great people and hopefully they learned a few things from working with me.”

One of the things I came to understand about leadership and developing executive talent became what I call the “Three I’s of Leadership.”  I realized to build a successful high growth company while delivering on our cultural goal of “doing what others consider the impossible, while treating people with respect and having fun along the way,” we needed leaders with the following skills:

  • Intellectual Leadership – Leaders who had both the raw brain power to identify opportunities and solve challenges and very deep skills in their specific areas of expertise.
  • Implementational Leadership – Leaders who were not just “consulting smart.” Executives who could actually stop thinking, developing models and drawing 2 x 2 matricies and “land the helicopter, get the troops in the field and make things happen”, to quote a former client.
  • Inspirational Leadership – Leaders who could get things done without making everyone who worked for them want to quit.

Over time, I found out two things about this model:

Three I Leadership can be, and usually is, a shared set of skills. Although no senior executive can have below threshold skills in any of the areas, many highly successful companies are lead by “Three I Leadership Teams.”  I first realized this through being involved in YPO (the Young President’s Organization) where I spent a lot of time with other Presidents of successful companies. My original belief was that successful CEO’s had to be “A” players in all three leadership skill sets, but I observed several who clearly were not what anyone would consider “motivate the troops inspirational” and others who were brilliant “idea machines,”  but needed someone to keep them from trying to implement every idea as soon as it burst into their heads.  All I observed were very smart, but not all would qualify for Mensa.

I soon realized that almost everyone had built a “Three I Team” around themselves by hiring direct reports that balanced and complimented their skill sets. There was the collaboration principle at work again.  Once I realized the importance of Three I Teams (and the stupidity of expecting every senior executive to be naturally gifted at all three), I started using the model to help my direct reports work on their weakest areas and to make sure we had Three I Teams leading all of our major groups and strategic initiatives.

I later began using the Three I model in recruiting and would ask candidates to distribute 100 points across the Three I’s to indicate their leadership strengths and weaknesses. One of the funniest reactions I received to this question came from an executive who had worked at American Express during the 90’s when Harvey Golub was CEO.  He responded something like, “That’s a great model.  Harvey is 60 intellectual, 40 implementational and 0 inspirational.” Then he became even more excited and said, “No, that’s not correct.  He is 60 intellectual, 60 implementational and negative 20 inspirational.”  Although the candidate was clearly exaggerating in jest, he was making my point exactly as Ken Chenault was Gulob’s number two at the time. I had the good fortune to spend time with Ken in the late 90’s as he had to personally approve American Express’s deal to  become an AIR MILES Sponsor.  Then and now, there may not be a better example of a “High I Inspirational” leader than Ken.

The model can apply to the leadership teams of organizations large and small. I recently thought about this model and how it applies to little league baseball coaches.  A coach needs to know the game of baseball, the complex rules, how to catch, hit, run and steal bases, etc.  Knowing how to play baseball is necessary, but insufficient. Someone on the coaching staff needs to know how to teach young kids to play baseball – how to learn the game and improve their skills. What drills are most effective in practice; how to spot a batting stance off balance or throwing motion without follow-through and how to make the subtle changes to correct these errors.  Finally, as all sports are partly mind games and baseball can be incredibly stressful for young athletes, at least one of the coaches has to be able to keep the kids fired up and have a vast vocabulary of positive things to say no matter what happens at the plate!

If this model makes sense to you, try it inside your own organization.  If it applies, consider building it into your professional development systems and recruiting strategies.  Collaborate by letting me know if it worked and what you have done to build upon it.

 

Note:  This post was originally written on November 11, 2008. 

When two 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 picked up from a girlfriend who had launched several magazines.

One thing we felt we did know for certain was that if we could build a broad based coalition of leading Canadian companies who committed to market the program to their customers, we would have the opportunity to create and utilize one of the world’s best marketing databases. All of our friends got that as well; and every one of them thought we would “make a ton of money selling the database.” What they didn’t get was our founding principal of not selling the “list” to businesses outside of the Sponsor coalition (i.e. the companies who paid for the points). We believed we could create the future of database marketing (although we didn’t have a clue as to how we were going to do that), but only if we developed a relationship with our Collectors built on trust.

Before long, we began to talk about the 4 R’s of Relationship Marketing and sketching this diagram on napkins and tablecloths around Toronto, Montreal and Calgary:

The 4 R's

We described our thinking about building relationships like this:

  1. If we recognized that when people showed their AIR MILES card at a retail Sponsor we were rewarding them for both their loyalty to the Sponsor’s business and the fact that they were sharing information with our company (by purchasing the good or service and identifying themselves as an AIR MILES Collector, they were telling us when and where they made the purchase, if they were responding to a targeted offer or coalition promotion, etc.), and…
  2. If we respected the information Collectors shared with us – including demographic and shopping intention information millions shared with us through surveys in return for bonus miles – and didn’t sell or give that information to anyone outside of the AIR MILES coalition (and not even other Sponsors if so requested), and…
  3. If we used the information to present relevant offers to Collectors based on their shopping habits, needs and interests (if a Collector was turned down for an AIR MILES Mastercard, we wouldn’t send them additional bonus offers to apply for one; if we knew there were only guys living in a household, we wouldn’t send them offers for a woman’s magazines; no car, no Goodyear offers, etc.), then…
  4. We would create higher open, read and respond rates to both our basic offers as well as our targeted specific offers and bonuses, which would – in turn – give us the opportunity to continue to reward both loyalty and the sharing of information.

If you think about this simple model, it doesn’t just apply to relationship marketing, but also to basic human relationships as well. If you begin to develop a relationship with someone and share something personal and confidential with them, that relationship will be short lived if they share it with others or otherwise don’t respect your confidence.  We tend to develop relationships with people we have at least something in common with – some point of relevance – be it kids, snowboarding or web 2.0. If these 2 elements are present, the potential for a relationship exits; without them, one probably won’t develop.

The 4R’sl, along with a lot of other parts of the AIR MILES model, appears to have worked fairly well as the program now has over 70% (that’s 9 million) Canadian households as members. More pointedly, while I was CEO, we had open rates for our (snail mail) direct marketing programs of over 70%. Although AIR MILES doesn’t share specific data on email response rates, my understanding is the company still enjoys high open and click through rates for their email marketing programs.

Which brings me to Facebook, Amazon and Eons. Like Jeremiah and many others, I was amused to be served up a banner ad on Facebook last spring for “Thirty Plus and Single” when on the same page I clearly listed my status as “married.”

Facebook was clearly not getting the relevance part and I don’t need to go into all of the respect angles violated by Beacon. Business Week had a good article on the social networking sites’ challenges with developing advertising.

Like many, I use a separate email account for marketing emails. Last week, as I was cleaning them out, I found 2 other examples of online businesses not getting the 4 R’s from Eons and Amazon.

John Della Volpe, the founder of SocialSphere, always thought one of the challenges facing Eons was that many people over 50 aren’t really excited about standing up and telling everyone, or joining a social network for those over the hill. Do people really like to say, “Hey, I’m old?” Partially because I’m in the business, partially because I know Jeff through our work with Year Up, and partially because I was eligible (even before they lowered the age threshold) I joined Eons. But I never really got the value proposition. At least AARP’s mailings tell you right up front about discounts and other offers they bring. Not terribly hip, but getting a deal on anything will always be relevant to me.

So imagine how jazzed I was to open an email only to be greeted with an offer to “get pictures of your grandkids” or something like that. Surely, they have some way of knowing I am probably a couple of decades away from being a granddad. Not relevant and not the kind of email someone like me would open again.

Then Amazon, who has many features I dearly love and admire (Amazon prime may be the world’s best loyalty program – more on that in a future post) sends me an email with a recommendation to buy a case for the flip video I recently purchased.

So what’s wrong with that? Take a look at the user ratings – 2 STARS! This one stood out to me because I had already checked out the product and knew it was a dud. Amazon served up the “people who bought this product also looked at these” content when I was purchasing the flip. After seeing the 2 stars and reading a couple of reviews (e.g. “This pouch is really cheaply made, hard to use, and not worth the money at all”), I didn’t bite.

Back to our core principle – building a relationship requires a foundation of trust. As John Lederer, the longtime leader of Loblaws supermarkets often said, “the consumer has given us their trust to select products for them to be available in our stores.” Although Amazon sells many products through third party retailers and clearly lets you know they are not being sold by amazon.com, it’s one thing to sell products you have little control over and another thing completely to send an email to a highly active customer recommending a product other customers have given a 2-star rating. I have come to trust that Amazon will offer great products and extraordinary service. I have been less enamored with their recommendations and – given this latest example – am even less likely to look at their recommendations or open their emails.

The more time I spend in this space, the more I realize that on-line community builders and advertisers can learn a lot from those of us that also spent time in the traditional direct mail and loyalty space. In true web 2.0 fashion, combining the best of both models will create the most effective strategies.