The Road Less Stupid: Advice From the Chairman of the Board by Keith J. Cunningham - Summary & Notes

Business success comes less from doing brilliant things and more from avoiding stupid mistakes. The central thesis of this book is that most business failures stem from emotional decisions, poor thinking, and avoidable errors.

Key concepts:

Thinking Time - A disciplined approach to creating and answering high-value questions about your business
The 5 Core Thinking Disciplines - Finding the unasked question, separating problems from symptoms, checking assumptions, considering 2nd-order consequences, and creating execution plans
The 4 Hats of Business - Artist/Creator, Operator/Technician, Owner, and Board roles
Culture Development - Creating rules of engagement that define how people work together
Clarity & Execution - Removing generalizations, creating specific plans
CEO Responsibilities - The non-delegable duties of leadership
Consistency - The power of ordinary things done consistently
Customer Focus - Finding what customers want and delivering it
Structure & Organization - Creating frameworks for opportunity
Adaptability - Recognizing when the environment changes and evolving accordingly
Excellence - Understanding that everything counts in business
The 3 Pillars of Success - Writing down major outcomes, planning each day, and accountability
Business Development - Strategies for growth, enterprise value, and optimization

The book emphasizes rigorous thinking over action for action’s sake and provides frameworks for making better decisions to avoid the “dumb tax” - the price we pay for poor decisions.

Don’t Be Stupid

This is the overarching theme. It’s not about being a genius; it’s about consistently avoiding dumb mistakes.

It turns out that the key to getting rich (and staying that way) is to avoid doing stupid things. I don’t need to do more smart things. I just need to do fewer dumb things. I need to avoid making emotional decisions and swinging at bad pitches. I need to think!

Skill Acquisition and Mastery

Business ownership isn’t innate. You need to learn.

There is no such thing as a natural business owner. Successful business owners and entrepreneurs are not born with an innate set of skills that produce business excellence and success. Great business owners work hard, practice, study, test, think, correct, and practice some more. None are infallible or perfect, but all are committed to excellence and mastery of the game.

This isn’t something you’re born with. You need to put in the work to learn the necessary skills.

Avoid Trial and Error Learning

Don’t try to learn things through brute force. Use other people’s experiences.

Attempting to win the game of business by trial and error is about the stupidest way to learn anything

Seek Guidance and Coaching

Get help, coaches, and mentors. You don’t have all the answers.

Running the wrong direction enthusiastically is stupid. It does no good to practice the wrong thing. Practice does not make perfect. Practice makes permanent. To excel, we need a coach or an advisor to watch our swing and provide candid advice about what we are doing wrong and how we can do better.

Continuous Improvement

You can’t get a new result by doing the same thing. Always look to improve, grow, and learn.

If you want to do better, you must get better. People do not do better because they want to do better; they do better because they get better. You cannot achieve a new outcome without learning something new and practicing what you learned (probably outside your comfort zone). A commitment to mastery (improving) is essential for excellence.

Making Good Choices

The better your options, the better your life.

The people with the best life have the best choices. People with a lousy life have lousy choices

To achieve new outcomes, we must learn new approaches. The quality of our life is directly tied to the quality of our choices.

The Need to Adapt and Accelerate

Answers that were useful in the past are unlikely to work in the future.

Things tend to change at an astonishing pace; yesterday’s answers rarely solve tomorrow’s problems

Thinking Time and Asking Powerful Questions

One of the most valuable practices Cunningham describes is his “Thinking Time” ritual—30-45 minutes of uninterrupted concentration focused on answering a high-value question.

Over the last twenty-five years or so, I have practiced “Thinking Time,” which is a thirty- to forty-five-minute session of uninterrupted concentration. I start by preparing a high-value question before the actual session begins. The better the question, the more insightful and robust the answers and possibilities created.

Cunningham’s Thinking Time sessions typically revolve around five core disciplines:

Finding the Unasked Question - Creating questions that generate clarity and better choices
Separating Problems from Symptoms - Identifying real obstacles blocking progress
Checking Assumptions - Distinguishing facts from the story you’re telling yourself
Considering 2nd-Order Consequences - Clarifying risks and potential costs of being wrong
Creating the Machine - Developing executable plans and identifying required resources required to solve the real (core) problem and make progress

Peter Drucker’s wisdom applies here: “Most serious mistakes are not being made as a result of wrong answers. The truly dangerous thing is asking the wrong question.”

Identifying the Root Problem

Most people mistake symptoms for problems.

Most people, when asked to pinpoint their biggest problem, erroneously identify their problems as the gap between where they are and where they would like to be

When identifying problems, we often mistake symptoms for causes. Not having enough customers is a symptom, not the root cause. The real issue might be poor marketing, bad conversion rates, or product-market misfit. We must dig deeper to find the underlying causes.

Cunningham offers three questions to clarify root problems:

What are the possible reasons I’m noticing this symptom?
What isn’t happening that, if it did, would cause the gap to narrow or disappear?
What is happening that, if stopped, would cause the gap to narrow or disappear?

Another powerful question to add: “What don’t I see?” This helps identify blind spots in our thinking.

The Power of Reframing

A thought I had while reading this:

Your story is your story

It is the story you tell yourself. And your story is just a story, not the story. There are other ways to perceive the situation. Choose the frame that provides the greatest utility.

The Cost of Poor Decisions

Small bad decisions can be just as harmful as big ones. As Warren Buffett says, “Stupid in small things, stupid in big things.”

Even minor errors in judgment can reveal patterns of thinking that lead to larger failures.

Cunningham introduces the “Power of 3” questions to evaluate decisions:

What is the upside? (Most people are good at seeing this)
What is the downside? What could go wrong? (We often need help seeing this objectively)
Can I live with the downside? (Few consistently consider this)

A valuable golf analogy illustrates the danger of compounding mistakes: “A double bogey is a bad shot followed by a stupid shot.”
The initial error is often less damaging than the poor decisions that follow as we try to recover. Thinking about 2nd-order consequences helps us avoid this trap.
Often it’s those rushed decisions after an error that get us.

Another gem: “Shoes that don’t fit are not a bargain at any price. A good idea that can’t be executed is a bad idea.”
Implementation is everything.

Questions from Thinking Time

Where are we compromising by looking for the door marked “WOW!”?
What shortcuts are we attempting to take that are not really shortcuts but rather mirages of greed, laziness, or impatience?
What skills do I need to master to attain the success I want?
Realistically, how much additional time and practice are required for me to attain my outcomes?
Who can I hire as a coach or mentor to help guide me and hold me accountable?
Where do I need to practice to improve my game and thus deserve the success I want?
Where do we need to pick up the level of intensity in how we are playing this game?

If my business could talk, what would it say?
Which hat has been my comfort zone and which hats are not getting worn often enough? For that matter, which hats do I not even own, and how can I acquire them?
What, specifically, have I been ignoring about my business, and what specifically needs to be corrected?
What skills or tools do I need to learn (or who do I need to hire) to help me overcome the obvious obstacles that are restricting my growth, sales, and profitability?
What areas of my business could be delegated (or outsourced) to someone else (who is competent and has execution intelligence) to free me up to do the things that would add the most value?
Artist Hat: What needs to be created?
Operator Hat: What needs to be done … today?
Owner Hat: What needs to be structured? Measured? Planned? Delegated?
Board Hat: What could go wrong? How can I mitigate the probability of that risk occurring and, if it does occur, reduce the cost?

What is the culture we have now? (Make a list of how people act and treat each other… both good and bad.)
What is the culture we want to create? (Make a list.)
If this were the worst, most toxic place on the planet to work, what would the culture look like? (Make a list so you can start thinking about the opposites.)
What would the culture look like if we were to become the “employer of choice”?
What are the culture deficiencies in our business that are preventing us from being high-performance vs. high-maintenance?
What are the beliefs employees must have that have led to the culture we now have?
What are the new beliefs employees must have to construct our new vision of how we treat each other and work together?
What are the specific rituals we can create which will help reinforce and memorialize our new culture?
What are the difficult conversations I need to have to reset our culture and create a high-performance team?
What are the simple rules of the game we must adopt to create a culture in which our people are truly engaged, committed to excellence, and do their best work?

How do I need to rework our plans and budgets to make them granular and measurable?
What is the specific recipe I need to create to make certain the outcome we have stated is achieved?
What are the specific activities and milestones we must hit in order to stay on track with our stated deliverables?
Who, specifically, is accountable and responsible for achieving each outcome?
What are the dashboards I need to create to make sure we are measuring the critical drivers and making corrections based on our performance?

In light of the seven fundamental jobs of a CEO, where have I dropped the ball and what do I need to do differently to cause us to get better? (Nothing changes if nothing changes.)
As I am thinking about the next 100 days and what I will do differently, what are the things I must do less of to make room for the things I need to do more of?
If my team represents my leverage, what do I need to do or say to ensure their success?
Starting and perfection are rarely simultaneous. What are the three things I could begin doing that would get me 80% of the way there?
What is the discipline I need to adopt to create the outcomes I want?
What is my specific measurable plan to improve our results?
Where have I abdicated my responsibilities as a CEO and what do I need to do about it?
Where have I optimized for easy instead of outcomes?

As I look back at my most significant losses, stupidest decisions, and biggest mistakes, what are the fifty most important lessons I have learned?
Where am I making some of these same mistakes again?
Based on prior lessons learned, what do I need to change (immediately) to avoid the dreaded dumb tax?
What are the rules and disciplines I will put in place to minimize the likelihood of repeating my mistakes?

Trying to figure out how to immediately solve a problem in one fell swoop is stupid. I might not have the final “Holy Grail” solution to all my problems, but what are five things I can do immediately to improve my situation?
Where am I inconsistently executing the right thing?
Where am I not practicing with the level of intensity I know I am capable of?
Where are we practicing but not correcting or getting the coaching that would give us insights about what we can do better?
Where am I consistently executing the wrong thing?
Where have I allowed the need for instant gratification to become a substitute for picking up the business end of a shovel and consistently breaking a sweat?
What are three outcomes we previously set but have abandoned because of unrealistic expectations or inconsistent execution? Should any of these outcomes be resuscitated and reprioritized with the accompanying realistic plans, resources, and time frames?
What are three bad habits/business practices we have tolerated that are undermining our results?
What are the decisions I must make and the hard conversations I must have to break these bad habits once and for all?
How will I adjust my behavior to create the success/outcomes I envision?

What do our customers want and how do I know that this is the right answer?
What is the solution I need to design to meet their needs and address their pain?
Do I have the ability (skill sets and resources) to successfully build this solution?
How will I deliver it to them?
What is the experience these customers want?
What exactly is the gap between where customers are frustrated and what the competition is doing?
Where can we find pockets of target customers who are frustrated with our competition?
Where is the competition weak or deficient in delivering the outcomes, solutions, and value the market demands?
What should we be doing to communicate to potential customers that we are the aspirin for their pain?
What are the three primary problems (pains) my target market has?
Where have I substituted my judgment for what I want to deliver for what the customers actually want to receive?
How could I check in with our customers to find out what new pains they are experiencing or gains they want to achieve?

Where have I done a poor job of posting the speed limit (explicitly stating expectations, deliverables, and outcomes)?
Who are the people in my organization that seem to require repeat conversations about the same issue?
What is the “belief coaching” they need to get clarity around the correct beliefs that will enable them to do and keep their job?
What is the deliverable that is missing? What is the outcome I want that isn’t being delivered?
Where am I frustrated because an employee is not performing at the standard I expect (and set)?
Is the problem that I haven’t set a clear standard?
Is the problem a lack of specificity about what I want it to look like? A lack of training? A lack of consistent coaching (calling it tight) when the problem arises? A lack of understanding about why this is important and why it needs to be done correctly every time?
Where have I created (or tolerated) a culture of mediocrity, an absence of accountability, a fear of saying what needs to be said, and an inattention to results, measurements, and periodic correction?
What is the belief my employees must have for this problem to persist and what belief needs to be substituted for my employee to excel?
Who needs to get an apology from me?
What is the coaching I need to deliver to make sure the problem gets fixed and stays that way?

What is the structure we need to create the progress I want?
What are the missing structural components required to produce consistent execution on our critical drivers?
When I look at my business, where are the opportunities for me to tighten up the structure, processes, and efficiency of what gets done?
Where do we have disorganization, inconsistent execution, slippage, and chaos?
What are the obvious choke points in my business that continue to strangle the smooth operational flow of serving customers and supporting the back office?
What specifically needs to happen to put some structure into place to address the turmoil?
Is there an opportunity to hire someone (even part-time) to help fill some of our gaps or to support us in getting a process in place?
What needs to happen to the workflow, back office, accounting, and support processes so my business functions smoothly and efficiently?
Where is the structure of my calendar slipping that is preventing me from taking consistent action on my major initiatives?

What is the real problem I am facing and exactly how is this problem different from the one I thought I had? Or used to have?
What are the poleaxes, shovels, and backpacks I’ve been lugging around that are no longer useful in helping me solve my immediate problem?
What are the tired, worn-out strategies and plans that are no longer supporting us to solve the problem we face?
What are the existing models of behavior we need to drop because they no longer work?
What existing knowledge, training, or experience needs to be abandoned?
What are the new, fresh ideas and solutions we need to create to get us past this problem and back on track to our desired outcomes?
Survivors and successful people are always learning, innovating, and adjusting. If this statement is true, what do we need to learn and where do we need to adjust our performance to succeed?
Who around me is screaming an alternative solution, but I am ignoring them because I don’t see the problem or the need to shift strategies?
Under the broad heading “What got me here won’t get me there,” who do I need on my team, who is excess baggage slowing me down, and what do we need to start doing differently?

When I think about the outcomes (goals) we have set for the coming quarter or year, where do I need to get clarity about my starting point in terms of environment, resources, competition, etc.?
Who can I ask to help me think through our reality so that I minimize the likelihood of tricking myself about our starting point or current capabilities?
What is the specific path/plan we have designed to move us from here to there, and what additional color or specificity do I need to add to this path to make it executable?
What would it take to transition our plans from “shoulds” (wouldn’t it be nice if…) to “musts” (failure is not an option)?
What are the hard decisions and actions I have been postponing in the irrational hope I can “goal” it away?
What are the nonnegotiable standards we must establish?
What am I tolerating in my business that is sabotaging my results or that is incongruent with my standards?
How do we build in the accountability required for the critical driver standards and outcomes we have committed to achieving?
What is the specificity I need to add to our plan so that everyone on the team has a clear, measurable metric (target) they are shooting for?
What are the specific causes I must identify that will enable the effect I want to happen?
What have we done well and what am I grateful for?
What are the unexpected opportunities that are being presented that might move us in the direction we want but don’t look the way we thought they would look? (Where is there a gaggle of quacking ducks?)

Where has the environment in which we’ve been operating (economic, technology, regulatory, competition, customer preferences, employees, cultural) changed over the last few years?
How are customers’ expectations different today than they were two or five years ago?
What will customers’ expectations be twelve months from now?
Where has our expertise (relevance) as a company lagged or stagnated in the last thirty-six months?
What skills or personnel do we need to add to excel at what we do, shift our direction, and optimize our bottom line?
What is happening competitively that could change what we sell, how it is sold, the price we charge, and where/how/what we message?
Are we learning, training, and evolving as fast as things are changing?
Based on the answer to the questions above, what do we need to learn, who do we need to hire, what do we need to change to remain relevant and competitive?

In the last year, how many people tried us and never came back?
How much did that lack of repeat business cost us in incremental revenue and profitability?
If everything counts and nothing is neutral, where are we missing the mark on delivering on our promise and meeting our customers’ expectations?
How can I be certain that our team is performing to our standards?
How can I make sure we are consistently executing and meeting our customers’ expectations?
What is our commitment to training and how can I be sure the training we offer is getting the traction and implementation I expect?
What can cause our customers to not come back and what are we doing as a management team to prevent customer defection?
What can we do to get the honest assessment from our customers about their experience so that we can minimize the likelihood of a customer firing us because of substandard performance?
What are our “cold eggs and untoasted English muffin” that are sabotaging our customers’ experience?

What are the one or two major outcomes and deliverables I am prepared to commit to achieving this quarter? This year?
What are the business outcomes and results I am prepared to make nonnegotiable?
What would prevent me from finding an extra five minutes every morning (before I turn on my computer) to write down my major outcomes and plan my day before it starts? How could I create a ritual for this so that I didn’t miss for ninety days?
What are the specific priorities and executables I must focus on and get on my calendar to create the momentum and results I have planned?
I know that guardrails and rules help me avoid feeding every kitty scratching at my screen door. What are the most frequent reasons my calendar gets hijacked, and what guardrails do I need to build to keep these intruders from sabotaging my day?
Who have I given permission to tell me the truth and hold me accountable?
How frequently will I check in with this person?
Am I willing to tell this person the truth so that he has the opportunity to coach me?
Am I ready to play this game to win, or do I want to keep dabbling … hoping to get lucky? What does that look like, specifically?

Who do I want to buy from me?
What must happen to cause them to buy?
What must happen to keep them coming back?
What could happen to cause them not to buy?

The 4 Hats of Business

Cunningham describes four distinct roles in business:

Artist/Creator - The visionary who creates new products, services, or opportunities
Operator/Technician - The person doing the daily work and executing tasks
Owner - The leader who structures, measures, plans, and delegates
Board - The protective oversight that anticipates risks and ensures longevity

These seem similar to The E-Myth Revisited framework.

Most businesses start with someone who’s either passionate about an idea (Artist) or skilled at a particular trade (Operator). However, long-term success requires all four hats.

While the Artist creates and the Operator executes, the Owner leads, structures, and leverages the business, and the Board protects it and keeps it alive.
Knowing which hat you’re wearing—and ensuring all hats get worn—is crucial for business health.

Culture Is King

Culture isn’t about mission statements on the wall; it’s about how people actually behave. As Cunningham emphasizes, “You get what you tolerate.” Culture manifests in how people treat each other, communicate, handle conflict, and whether they trust one another.

Culture is not values or mission statements; those are ideals, not disciplines. Culture is how we treat each other, how we talk to each other, whether or not we trust each other, and how we handle conflict. Culture is about accountability, measuring, a bias for urgency, a focus on solutions, calling it tight—saying what needs to be said—being kind and generous, acknowledging one another, and expressing appreciation.

It’s about what you tolerate. What behaviors are acceptable? What is the standard of conduct?

Here it is on a bumper sticker: The key to a great culture is creating and fostering a never-ending conversation about the “rules of the game.” The rules define the boundaries or guardrails so that everyone knows exactly how to act, how to communicate, and how to treat each other. Culture, not a value statement, is the key to high performance and becoming the employer of choice. (Enron’s Value Statement was Respect, Integrity, Communication, Excellence. A plaque on the wall is not a substitute for culture, and neither are nap rooms.)

The key to great culture is an ongoing conversation about “rules of the game”—the boundaries that define acceptable behavior. These conversations create clarity around expectations and standards. As Cunningham points out, Enron had a value statement of “Respect, Integrity, Communication, Excellence,” which clearly didn’t reflect their actual culture.

Generalizations Kill Clarity

Whenever there is weak, ineffective, or no action, it is usually a result of a lack of clarity and/or accountability.

Weak or ineffective action usually stems from a lack of clarity or accountability. Generalizations are the enemy of execution. A proper plan should be specific and measurable, breaking down targets into concrete steps, timelines, resources, and personal commitments.

How to Create an Actionable Plan

Cunningham presents a clear example of what specificity looks like:
“Here are the specific, measurable steps I’m taking (broken down by week) and the milestones, timelines, resources, and personal calendar time I am committing to reach $2,000,000 in revenue this next quarter. These are the names of each lead in our funnel. This is who and how many I will call on this quarter. Here is the conversion percentage I will achieve. This is the monetary value of each transaction.”

A truly effective plan is always executable—like a cookbook or Google Maps. It answers How, What, and Who questions with precision.

This is the level of detail and specificity required for a truly effective plan.

Key Questions for Building a Plan:

How will we achieve this outcome?
What specific activities are required?
Who will perform them?
What are the standards of performance?
What are the critical drivers?
How frequently must these be measured and reported?
Who owns this outcome?

These questions provide a strong framework for plan creation.

A CEO Should Never Delegate…

Leaders have core responsibilities that should never be delegated:

Clarity on Starting and Ending Points - Defining where you are and where you want to go
Identifying Gaps and Obstacles - Pinpointing what’s blocking progress
Allocating Resources - Ensuring resources are directed toward overcoming obstacles
Top-Grading for A Players - Hiring exceptional talent and creating conditions for their success
Building the Organization Chart - Defining who’s responsible for what outcomes
Creating Culture - Establishing how people work together and treat each other

Regarding A players, Cunningham identifies six common characteristics:

They have clear scoreboards showing whether they’re winning or losing
They possess a high internal drive to succeed
They love being measured and held accountable
They have exceptional technical skills
They’re humble enough to ask for coaching
- What else can I do?
- Where can I get better?
- What do I need to do or learn so that I can continue to grow?
They see opportunities where others see only problems

How to hire and retain A players:

Interview rigorously
Compensate generously
Onboard effectively
Measure consistently
Coach continuously

A Crisis Is a Terrible Thing to Waste

You do not have to swing at every pitch that is thrown

Do less, better. Focus on the right opportunities.

Ordinary Things, Consistently Done, Produce Extraordinary Results!

Excellence doesn’t come from occasional heroic efforts but from consistent execution of fundamentals. As Cunningham writes, ordinary things consistently done produce extraordinary results.

The challenge isn’t finding miraculous solutions but identifying the right ordinary actions and performing them with consistency. This means avoiding two common traps: inconsistently executing the right things or consistently executing the wrong things.

O Baby! (Attracting Customers)

The core idea:

Find Out What They Want (FOWTW): Understand customer needs and pain points.
Go And Get It (GAGI): Design and build solutions.
Give It To Them (GITT): Deliver the solution effectively.

While the acronyms are forgettable, the concept is vital: figure out what customers want, create it, and deliver it exceptionally well.
Focuses on solving real pain points rather than pushing unwanted solutions.

Help Me Understand (Setting Clear Expectations)

Clear expectations are like speed limits—they tell people what standards they need to meet. Problems often arise when leaders fail to explicitly state expectations or when they tolerate performance that falls below those standards.

When performance issues arise, Cunningham recommends the phrase “Help me understand…” This opens a non-confrontational conversation about gaps between expectations and performance.

The question “What is the belief my employees must have for this problem to persist?” helps identify underlying mindsets that need addressing.

Opportunity Without Structure Is…

Opportunity without structure is chaos.

Structure doesn’t mean bureaucracy; it means creating frameworks that allow opportunities to be captured and realized consistently.

Dreams and Demand

About the stupidest thing management can do is to announce some lofty goal for the year (“Our revenue target is $6,000,000 this year.”) without any thought about the working plan to attain it. (In “It’s Not About the Plan,” I actually speak about the value of planning.)

Setting ambitious goals without a concrete plan is a recipe for failure.

H. Ross Perot’s definition of an entrepreneur: “Someone who is grateful for the progress that has been made and simultaneously dissatisfied with the rate they are making it.”

Don’t let your obsession with the dream get in the way of noticing the demand. Or as my friends on Wall Street say, “When the duck quacks, feed it.”

Pivoting can be necessary to keep your business alive. Don’t keep doing the same thing if it isn’t working.

The Big 8 (Controlling Process, Not People)

This is a method for controlling process without controlling (micromanaging) people.

What are the few specific measurable outcomes I am optimizing for? (The clear, measurable target.)
- What am I optimizing for?
What are the specific expectations I have about what these outcomes look like when they are achieved? (What does success look like, specifically?)
- What does success look like?
What is the primary obstacle that is impeding our progress between Point A and Point B?
If this obstacle is so obvious, why haven’t we seen or addressed this obstacle previously? (Is this really the obstacle or a symptom?)
What sacrifices will we need to make or risks we will need to take to overcome this obstacle?
By saying “yes” to solving this obstacle, what are we required to say “no” to?

In evaluating my current team, where have I settled and, therefore, produced mediocrity?

You can’t have everything. But be aware of where you’re falling short, intentionally or unintentionally.

What are the specific measurable standards of performance I have for each critical driver activity?

Establish a Standard of Performance and commit to it.

Under the theory that nothing can change until the unsaid is spoken, what are the hard conversations I know I need to have but have avoided in my misguided desire to keep the peace or minimize the disruption of the status quo?

What conversations am I avoiding?

Something for Nothing… Seriously?

Passive income makes about as much sense as passive health or passive relationships. You would scoff at the idea of a passive weight loss technique or a passive gold medal in the Olympics or a passive marriage. But financial shamans write hundreds of these books every year counting on you to lurch to the door marked “Something for Nothing.” But somehow this concept of passive income has gotten traction. (Here is a pretty good rule of thumb: Never buy anything from someone who is out of breath.)

There’s no such thing as truly passive income (at least, nothing worthwhile).

Where am I looking for the path of doing the least or the door marked “something for nothing” to create the success I want?

To achieve the success I desire, what effort and expertise are required?

What have I been procrastinating on doing that would help us get traction on this project?

What am I not doing that I should be?

What’s the one thing that, if done, would make everything else easier or unnecessary? (Paraphrasing Gary Keller.)

Where have I been active but not productive?

Avoid busywork.

The Only Constant in Business Is…

The only constant in business is change. A good idea three years ago could be a bad idea today. A great idea today could be a disaster next quarter. The answers I have now were answers created in a different environment at a different time.

The business environment constantly evolves, requiring us to evolve with it. Yesterday’s good idea might be today’s disaster.

The reason companies lose relevance, go broke, or fade into the sunset is because they continue to grow, but fail to evolve. They rely on the wrong questions and old answers.

This explains why 87% of the Fortune 500 companies from 1955 are now gone. Companies like Kodak, BlackBerry, Blockbuster, and many others failed not because they stopped growing but because they failed to evolve with changing conditions.

The 3 Pillars of Success

Cunningham recommends three daily practices for 90 days to create substantial progress:

Write down major outcomes every day - Not goals (which have become synonymous with wishes) but non-negotiable standards and objectives.
Plan your day before it starts - Ensure your calendar reflects your priorities and the critical actions needed to make progress.
Be accountable to someone - Have a person who holds you to your commitments and tells you the truth when you’re making excuses.

The higher you go or the better you want to get, the greater the requirement to have someone in your life who will hold you accountable and tell you the truth.

Systems vs. Flexibility

Systems can be helpful tools but aren’t the complete answer to business success. Rigid systems can make a business fragile and unable to adapt. As Cunningham points out, if systems were the key to success, the federal government, United Airlines, and other highly systematized organizations would be the most revered institutions on the planet.

What works for one business (like McDonald’s extreme systematization) won’t necessarily work for another (like Google). McDonald’s succeeds with interchangeable parts and rigid processes, while innovative companies need autonomy and exceptional talent.

The question becomes: what does your specific business need?
Low-skill jobs may benefit from rigid processes, while high-skill roles might scale with greater autonomy.
The goal is balance—enough structure to ensure consistency without stifling initiative and adaptation.

Where do we need to start making exceptions to be exceptional?

Where could I give my employees an opportunity to grow, learn, and contribute their ideas so they would engage in their work at a deeper level?

Where could I allow our employees to be self-directed and in greater control of their processes and outcomes?

Working On vs. In Your Business

Contrary to popular advice about automating everything and removing yourself from operations, Cunningham argues that success comes from being deeply involved in your business—not just working in it (doing technical work) but working on it (performing owner duties).

Regardless of your business, industry, or stage of development, don’t ever think for even one minute that your business would be better off without you.

The key is leveraging yourself appropriately—identifying what you should personally handle versus what can be delegated, always focusing on the highest-value activities.

Where am I confusing activity and sweat with productivity?

What am I currently doing that should/could be outsourced or leveraged to someone else (even part-time) who actually enjoys and is good at the thing that is bogging me down, which would then free me up to do more of the critical, value-add, business Owner activities?

What critical projects are languishing because I simply don’t have the time to allocate to them and get them off the ground?

What could I do in the next week that would improve this situation?

How can I prioritize my calendar to find an additional thirty minutes per day to chip away on the high-value projects?

Planning vs. Plans

Dwight D. Eisenhower said: “In preparing for battle, I have always found that plans are useless, but planning is indispensable.”

The value isn’t in the plan itself but in the planning process. As Field Marshal Helmuth von Moltke noted, “No plan survives contact with the enemy.”
Planning helps us think through scenarios, identify resources needed, establish timelines, and consider alternatives.

If you cannot get clarity on the plan to achieve the outcome, change the outcome. Even with a plan, you probably will not hit the bull’s-eye, but at least you will not end up in a graveyard.

Execution and Implementation

Knowledge without action is just “shelf help.” Reading books and learning strategies is meaningless without implementation. The hard part isn’t setting goals but figuring out what needs to change and consistently executing to reach those goals.

The reality is that most of us would be much farther along if we simply asked ourselves the question, “What can I do today to improve my situation?” and then picked up the shovel and started digging where we are while simultaneously learning new skills and tools.

Cunningham recommends: “Start fewer things, finish more things.” By focusing on the critical few rather than the trivial many, we make real progress.

Cause and Effect and The Great Question

The hard part is not envisioning the outcome or setting the goal. It’s figuring out what needs to change and consistently executed to reach this outcome. If you know what needs to change and get executed, you know what needs to be measured. These are your critical drivers. Execute on the critical drivers and close the gap.

My rule is: Start fewer things, finish more things.

The great question is: “What am I optimizing for?” In other words, what is the one major that, if accomplished, would have the most significant impact on my business?

What one meaningful, specific outcome, if I achieved it, would have a significant positive impact on my business?

What are the three most significant things I could do this week that would kick the can and close the gap by moving me closer to my major priority?

The central question becomes: “What am I optimizing for?” In other words, what one outcome, if achieved, would have the most significant positive impact on your business?

Notes on

The Road Less Stupid: Advice From the Chairman of the Board

by Keith J. Cunningham