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Chapter One
Why Organizations Fail at Strategy
Strategy may be the most misunderstood word in business—which makes the art and science of it possibly the largest untapped capability in most organizations.
- Stop outsourcing the core. For over a century leaders have handed strategy development to consulting firms. Three objections: it is the foundation of the business, so why give away the reins; no entrepreneur ever started by hiring a consultancy; and nobody has ever mastered a skill by outsourcing the work. External help with facilitation, analytics or modeling is fine—abdication is not.
- The CEO is the chief strategist. The board approves; the CEO owns. Success depends on how well they harness the collective intellect of the organization rather than how well they present to it.
- Fragmentation dilutes everything. The provider market splits into strategy shops, culture shops, leadership shops and change shops. Specialist delivery is fine—but only if it is anchored to the competitive strategy. Without that anchor, brilliant workshops produce a burst of energy and then everything reverts.
- Democratize it. Competitive strategy can be understood and evolved throughout an organization. Until it is, the firepower stays locked up.
A dinner party with people, chairs, food and plates—but no table. The table is what makes all the other parts meaningful.On strategy work without competitive strategy at the center
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Chapter Two
Strategy Is Messy
Strategy is born in what the Harvard Case Method calls a wicked environment: patterns may or may not exist, feedback is delayed or wrong, and there is no guarantee. Trying to force it into a tidy linear process is how potential gets left on the table.
- Speed with substance. Moving fast is not rushing. Speed forces you to let go of control over the content, which is what allows unhelpful assumptions to surface and break.
- Three ways to stand out. Product leadership (Apple—dictating to the customer rather than responding), customer intimacy (the mid-market pattern: solving one customer's problem, then the next), or operational excellence (IKEA, Costco, Walmart). All three need attention. Only one can lead.
- The real question: what drives the business? Strategy, targets, or the plan? You need all three—but only one can have primacy.
- Target-driven is the common failure. Numbers are lag indicators. Chasing them under pressure produces reactive decisions, short-termism and a workforce that describes its job as making money for the owners. Engagement dwindles; burnout rises.
- Plan-driven is the other. Two versions: the five-year public-sector plan held as a security blanket long after it stopped being relevant, and—more damaging—the leader who runs a genuine-looking strategy session and then quietly pursues their own predetermined plan. High turnover and leadership-team dysfunction follow.
- Both can work in the short run. That is the trap. You cannot see the performance you are missing until someone changes the philosophy.
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Chapter Three
Getting into Strategy and What Makes It Work
If a business is making money, a strategy is already in play. It may be unarticulated and almost certainly unoptimized—but an offer is winning buyers over the alternatives, and that is something to build on.
- The entrepreneurial model is the original model. IKEA's eighty-year arc shows it: flat-pack came from an employee removing a table's legs to fit it in a car; unique in-house design came from being boycotted by Swedish furniture retailers; Polish sourcing came from being unable to fill a chair-leg order at home. Each accident was converted into positioning. It has never tried to win on product leadership or customer intimacy.
- Development and execution are one dance. Separating them is like treating a chronic illness by fragmenting care across specialists and never asking what the whole system needs.
- Change how you use the board. Reams of slides that exist only to clear an approval gate are waste. Send a succinct summary in advance with questions, alternatives and scenarios—then use the room for the conversation, not a page-by-page walk-through.
- Commitment compounds. One fifty-year-old private company built local plants and hired local people in every market while competitors offshored for margin. When COVID-19 hit, it was often the only player able to supply.
- Trend lines are visible early. Kodak invented the digital camera and overweighted the threat to film. Sony assumed technical brilliance would keep mattering. Bookstores watched the online wave arrive. None were resource-constrained.
- Match the thinking style to the moment. Systems thinking for developing strategy—exploring, speculating, pattern-reading. Linear thinking for planning—sequencing, prioritizing, committing. Most of the friction in strategy work comes from applying the wrong one, and the damage multiplies when it is the leader over-using a preference they cannot see.
Strategy development and execution go hand in hand in a dynamic dance where each informs the other.Chapter 3
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Chapter Four
The Importance of the Human Element
The longest chapter in the book, and its center of gravity. Founders are usually unconsciously skilled—like elite athletes who can play but cannot coach. When they leave, the gap they filled becomes visible all at once.
- The founder gap is predictable, and therefore preventable. In one client, a capable COO and executive team missed a major shift in buying behavior while the founder was on vacation. The founder had been tracking a handful of lead indicators privately, on instinct. Several leaders sensed something was wrong but did not know where to look.
- De-risk the transition while the founder is still there. Bring in a strong external COO with CEO-grade capability to bridge between founder instinct and organizational capability. Moving the founder to chair, with successors coached internally, works well in long-lived private companies.
- Four fields of conversation. Talking nice—agreement without agreement, usually because people have learned it is not safe to challenge. Debate—my truth versus yours, corrosive in strategy work. Reflective dialogue—where strategy conversations should start, and where people can be understood without needing to be agreed with. Generative dialogue—collective meaning-making, which cannot be manufactured but can emerge.
- Shift positions deliberately. Stuck in debate? A "what" or "how" question moves people into second position (the other's shoes) or third position (on the balcony, looking at the whole).
- Read the room (Kantor). Four action modes—mover, follower, opposer, bystander—all necessary, none good or bad. Three operating systems—closed, open, random. Three communication domains—power (getting it done), affect (people and relationships), meaning (logic and purpose). Teams that can hear all three languages have a real advantage.
- Two loops of learning. Single-loop corrects the behavior; double-loop questions the assumptions and goals themselves. Double-loop is where innovation lives, and it requires the openness Argyris described as Model II.
Shared understanding does not mean agreement. It means knowing what is agreed, what isn't, and what needs a decision we all live by.On layered conversations
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Chapter Five
Your Competitive Strategy
The technical core. Competitive strategy is an integrated set of choices that uniquely positions a firm to create sustainable advantage and superior value relative to the competition. Every word in that definition is load-bearing.
- Anchor before you choose. Scan the external environment starting with what your own people already know—political, economic, regulatory, competitive, technological, social and buying-behavior factors, then the implications. Research afterwards, better targeted.
- Two tools worth the time. Porter's Five Forces, to locate where power actually sits. SWOT, to surface the opportunities you have a real shot at.
- Competitor Games. Split teams, assign each a competitor, hand over public information, and have them build that competitor's strategy for winning against you. Include sales and marketing—they usually know more than the executive team does.
- Two meta-questions first. What is the source of your advantage—lowest cost or differentiation? And if differentiation, on what basis: product leadership, customer intimacy, or operational excellence?
- What business are you in? Confronting because it challenges identity. The railroads defined themselves as rail rather than transportation. A newsroom of veteran editors circled the question for two uncomfortable hours before reframing themselves as a channel rather than a print product.
- Playing to Win, five questions. Winning aspiration; where to play; how to win; what capabilities; what management systems. Not linear—it is usually easier to start at two and three, then test the aspiration against them. Follow every "where to play" with: and what gives us the right to say that?
- Capabilities must be institutionalized. Two to four at most, each genuinely essential and genuinely best-in-class. If the winning capability lives in the founder's head or relationships, it can walk out the door at exit.
- Question five is the weakest link. "What management systems are required" usually collapses into a wish list of tactical stuff. Done properly it is the bridge to the Middle Ground and the strategic pillars.
- Traps. Sometimes there is genuinely no strategy—only an accumulation of decisions. And branding strategy is not competitive strategy: the first is your internal articulation of how you will win, the second is how that story reaches the market.
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Chapter Six
Translating Strategy into Executable Form
Around 70 percent of projects and initiatives still fail to deliver on their promises—a figure that has barely moved in decades. Part of the reason is that leaders fear that naming a failure will cost them their job, so the learning never happens and the same mistakes recycle.
- The Middle Ground is the missing layer. It sits between the meta-thinking of competitive strategy and the micro level of doing. It connects and aligns effort across the system, filters out activity that is not sufficiently aligned, and preserves the parts of the strategy that actually differentiate.
- What goes wrong without it. Organizations leap from conceptual strategic decisions straight to plans, timelines and KPIs. It looks trackable and accountable. But the competitive teeth have already been left behind, and projects become entities unto themselves—resourced by whoever argues hardest, in a contest of my project versus yours.
- Six elements. Build out the plan. Engage team members. Run everything through the portal of culture. Understand the magnitude and nature of the change. Measure, track and report. Build institutional know-how.
- Culture is the portal. Its primary shapers are strategy, structure, leadership, governance, planning and measurement, processes, systems and technology, people practices, communication, training, and brand. A culture that is not aligned to the strategy is worth very little.
- Change comes in four buckets. Stop something, start something, do more, do less. One-size-fits-all handling is suboptimal for all four.
- Governance traps. No declared owner of the governing process. Lists of lag metrics. Check-the-box reviews that leaders quietly disengage from. Monitoring the human side matters as much as the numbers.
No useful strategy remains static. Attention to the Middle Ground enables plans to follow suit quickly enough to adapt and steadily enough to deliver.Chapter 6
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Chapter Seven
More on Building the Middle Ground Plan
The most operational chapter in the book—a working method for getting from strategy to a plan that still has competitive teeth in it.
- Freeze time to build it. Plans live in a dynamic environment, but the best ones are built at a standstill. Pause the new ideas, establish a base, then iterate.
- Pictures of success. Assume you have won. Describe the three- or five-year horizon in full sensory detail, then come back to one year, then to any event horizon that matters—an exit, an acquisition, an ownership change. Do it in groups of four to seven, eyes closed while the questions are read, then a silent private brainstorm, then capture on a flip chart by hand.
- Strategic pillars. Four to eight, each starting with a verb. Typically four driving growth and two building capability and capacity. The trap is naming the things you have always worked on rather than the things that will make you more likely to win.
- A cautionary example. One client's four growth pillars covered new segments, a new line of business and export markets. The core business—over 90 percent of revenue and a strong EBITDA—appeared nowhere. Attention slipped, performance followed, and a fifth pillar was added: protect and grow the core. What gets attention gets done.
- Ownership has three levels. A sponsor per pillar, an owner per initiative, a responsible person per task—each with a by-whom and a by-when. Going deeper than that starts to feel like micromanagement.
- Build it on a wall. One sheet per month, split into halves. The first pass will be mile-wide and inch-deep, with far too much crammed into the opening weeks. That is normal and predictable—people overestimate near-term capacity and hate saying no.
- Then de-risk it. Where are the capability gaps? The capacity gaps? The single-point human dependencies? The critical dependencies between initiatives? What needs investment, what needs change management, what could accelerate you?
- Size the keep-the-lights-on work. It does not belong in the plan, but its share of everyone's time does—otherwise resourcing is wrong from the start. And resist a separate business-as-usual plan: it becomes a hiding place for pet projects that did not survive prioritization.
- Prioritization is downstream. Until the Middle Ground plan exists, prioritization is guesswork. A workable plan takes four to six weeks; longer usually means the skills or the commitment are missing.
In one hospital's strategy, car parking for visiting surgeons was not a sidebar issue—it was the linchpin of the differentiation. What looks trivial can be central.Chapter 7
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Chapter Eight
Change
Every strategy implies change, and every execution involves it. The discipline emerged in the 1980s and 1990s after high-profile technology and restructuring failures—and the failure rate has stayed stubbornly high, largely because reviews that would produce learning are career-risky to publish.
- Three agendas, separately articulated. The intellectual agenda (strategic intent, vision, business strategy), the management agenda (structures, networks, technology, systems, resourcing) and the behavioral agenda (values, ethics, leadership style, skills, learning systems, people practices). Over-weighting any one is a standard failure mode—usually a structural or technology program launched without reference to the competitive strategy.
- Continuous versus extraordinary. Day-to-day change still deserves a moment of scrutiny. One organization centralized the office trash cans; within days bins became a coveted commodity, hidden in filing cabinets. People need the why.
- Diagnose before you act (Cynefin). Simple, complicated, complex, chaotic, disorder. Best practice works in the first; expertise in the second; experimentation and iteration in the third; immediate stabilizing action in the fourth. AI sits squarely in the complex domain for most businesses—stay and play, learn, figure it out.
- Resistance is feedback. When change is announced most people focus on what they will lose, not what they will gain. Resistance signals that something else needs to be understood before people can embrace it.
- A three-round conversation that works. Round one: what stands out, what resonates, what are the benefits. Round two: what changes are implied, what concerns you, what will concern others. Round three: what do we need to address, and what would help. Ten minutes each, small groups, debrief between rounds, feed the output into the plan.
- Choice preserves dignity. In a restructure eliminating hundreds of middle-management roles, leaders were walked through the consequences of their own possible responses—positive, neutral or negative—and what support each would attract. Most chose to stay engaged until they had secured new roles.
- From-To shifts. One to four high-impact shifts, identified after the plan exists, expressed in language people recognize. Examples from one client: from measuring activity to measuring what matters; from busyness as a badge of honor to working smarter; from nodding agreement to real accountability with consequences.
- Scaling is a transformation. So is moving from founder-owned to institutionally owned. Privately held businesses routinely underestimate this, keep seeing themselves through the lens of a smaller company, and quietly sacrifice the growth.
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Chapter Nine
The Power of Culture
Culture may eat strategy for breakfast—the line was never Drucker's, incidentally—but culture will not make it to dinner if the strategy has not carved out a winning position. Strategy sets the direction; culture supplies the means.
- Strong cultures are easier to change than weak ones. A strong culture sends legible signals: people know what behaviors and decisions mean. A weak one leaves everyone guessing, and you cannot shift something that has no shape.
- Signals move faster than programs. One turnaround CEO wedged the C-suite door permanently open, ended executive cars and drivers, and emailed all staff almost daily on what he was tackling next. The shift was immediate—and it survived genuinely painful cost decisions, because people understood the reasons.
- Build the top team on trust and team-mindedness. In a crisis under external scrutiny there is no time to watch your back. A trust-based team can carry less experienced executives who share the values; a political one cannot carry anyone.
- Organize around outcomes, not silos. A university department framed a research funding bid around the problem it wanted to solve rather than its own discipline—pulling in medicine, town planning, insurance, superannuation, government, unions and industry. It won.
- Culture and engagement are not the same measurement. Engagement reads the individual's sentiment at a point in time. Culture reads the whole organizational system—and, on Denison's evidence, predicts performance two-plus years out better than anything else. Strong engagement scores in stumbling businesses are a warning, not a comfort.
- Choose a culture instrument carefully. Longitudinal research base, evidence of efficacy, the language of leaders and employees, simple enough to be led by the CEO rather than an army of consultants, action-oriented, and normative data for context.
- Culture as immune system. It resists what does not fit. Superb when it is aligned to a sound strategy. Dangerous when it is serving something else—political power, or simply the way things have always been done.
- Culture is an outcome, not a lever. You cannot change it in one move. You shape it behavior by behavior and decision by decision, and it is the leader's daily interactions that override every formal mechanism when the two disagree.
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Chapter Ten
Governance—Creating Momentum Through Systems
Governance here means the rhythm, forums, information and behaviors that keep execution moving and learning—not a reporting obligation. Getting the first imperfect plan running is hard; the first six months are the hard yards.
- The rhythm. Daily or weekly check-ins, monthly step-backs, quarterly reviews, a substantial six-month review, an annual refresh.
- The strategy execution lead. The CEO's eyes and ears—analytical and financial skills, an understanding of change and transformation, an appreciation of Agile, sensitivity to the human side, strong facilitation, and enough standing to hold ground with senior executives. They need explicit air cover early, because the role attracts resistance and makes an easy scapegoat.
- From Excel to Agile. Mid-market firms often have a formidable spreadsheet muscle that reduces governance to updating a vertical activity list. The mindset shifts required: control to trust, perfection to learning, individual heroes to team performance, project completion to value delivery, predictability to adaptability. Apollo 11 was off course 97 percent of the time and still landed.
- You need a plan for implementing the plan. Routinely skipped in the mid-market. You may be able to bootstrap it while small, but its absence eventually caps what your people are enabled to do—and you will not see the value going unclaimed.
- Track horizontally, in color, in the open. Vertical list-based tools obscure progress over time. Visual, dynamic, transparent reporting invites curiosity and ownership.
- Traps. Control staying at the top. Agile as a word rather than a reality. An execution lead who controls rather than clears the way. Governance drifting into show-and-tell and document-tidying. Undermining the authority of the people you made responsible. Over-formalizing before the organization needs it.
- Meetings are the instrument. Purpose, sequencing, participants, pre-reading, and the room itself—lighting, ceiling height, seating. Circles for team conversations, not hierarchy. And warm the conversation up: you do not walk into a gym and start heavy lifting.
- Go red early. A handful of lead indicators beats a shopping list of lag metrics. People usually sense when something is off before they can articulate it—pay attention to those sediments of knowledge.
- Overdoing it is also a failure. Too much governance can stifle an organization as thoroughly as too little.
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Chapter Eleven
Getting Started—Your Strategic Leadership Tool Kit
Strategy development, the book concedes, is being done better than ever. The gap is in the connective tissue between competitive strategy, execution and governance—and the lynchpin is leadership. Yours.
- Three pillars of execution excellence. The Three Enoughs, matured: clarity about where you are going and who does what; cohesion between culture, capability and direction; disciplines—the governance, planning, measurement and leadership behaviors that sustain performance.
- The entrepreneurial challenge. There is a point—often before $100 million, sometimes before profitability—where the scrappy, informal approach that built the business starts to cap it. The question is not whether to formalize but what, and when, without losing the entrepreneurial spirit.
- Read the environment continuously. Market-facing people should be bringing insight in daily; leadership should be examining it monthly and properly at quarterly reviews.
- Storytelling is an execution capability. Have leaders and team members tell the organization's strategy story from their boots. It runs intention, then telling, then engagement, then meaning-making, then ownership. In one session the person who told it best was an unexpected junior team member—which is the point.
- Pick something uncomfortable. We hone our preferences and get away with it. Find the chapter you dismissed too quickly and start building know-how there.
Eighteen months in, the author concedes the point a client made at the outset: this turned out to be a book about leadership.Chapter 11
