Deloitte’s 2026 Global Chief Strategy Officer Survey found that only 35 percent of CSOs say they either co-lead or fully own strategic decision-making for their organization’s own top priorities. More than half report managing too many priorities with too little time to execute any of them well. (Deloitte, February 12, 2026)
Read that as a documentation statistic, because that is what it is.
A chief strategy officer who does not own the decisions behind the strategy is not managing a strategy. They are managing a slide deck other people occasionally consult. If the person whose title is strategy cannot say the priorities belong to them, no function leader two levels down is executing against a shared plan. They are executing against whatever they last heard in a hallway.
This is the starting concept of the Enterprise Value Playbook, and it opens the arc for a reason. Every other pillar inherits this one. Leadership decisions get made against the strategy. Capital gets allocated according to it. Growth targets exist because of it. When the strategy itself is undocumented or unowned, every pillar downstream inherits that instability, whether the people working inside those pillars ever trace the cause back here or not.
GROSS MARGINS HAVE COMPRESSED FOR SIX STRAIGHT QUARTERS. YOUR NEGOTIATING SCRIPT HAS NOT.
I built the Price Pressure Playbook scaling fifteen organizations, five million to five hundred million. In October I am running it live for the first time: one virtual session, two in-person sessions, NYC and Austin. Price increases each week between now and the first session. This week is the lowest it will ever be.
This week’s concept sits in Pillar 1, Strategy + AI: strategy is documented, communicated, and tied to measurable priorities across every function.
Where You Stand Ask five function leaders, independently and without letting them confer, to state the company’s top three strategic priorities. Five different answers, or four vague ones and one confident wrong one, is your actual score. The deck in the shared drive does not get a vote.
The Failure Pattern Strategy lives in a deck, not in the operating rhythm. Priorities shift with the loudest voice in the room instead of a documented plan. Sales optimizes for volume. Finance optimizes for margin. Operations optimizes for utilization. Each function is executing a defensible strategy in isolation, and none of them are executing the same one. Leadership reacts to markets instead of tracking a defined KPI rhythm, so by the time a shift is visible, the company is already behind it.
The Kotter Principle at Work John Kotter’s research on why transformation efforts fail identifies two steps leaders habitually skip, and both show up here. Step 1, Create Urgency, is usually assumed rather than built. Leadership believes the strategy is obviously important and skips making the case for why now. Step 4, Communicate the Vision, is where most strategies actually die. Kotter’s finding, consistently reproduced, is that leaders under-communicate vision by an order of magnitude relative to what it actually takes to stick. The fix is not a better deck. It is a guiding coalition, a small group of leaders across functions who repeat the strategy in their own words, in their own meetings, on their own cadence, translating it into specific priorities for every function and reviewing it on a quarterly cadence against measurable KPIs, not an annual one.
The Win Condition Every function leader, asked independently, states the same top three strategic priorities in their own words. Quarterly KPI reviews reference the documented plan by name rather than reconstructing priorities from memory. When a market shift occurs, the strategy adjusts inside a single review cycle, not a full fiscal year.
FROM THE CHAIRMAN
“Walk me through how a decision made in sales this quarter connects to what you told the board strategy looked like eighteen months ago. If you cannot draw a straight line, either the strategy changed and nobody told me, or it never left the deck it was written in. Which one is it, and how do you know?”
MARKET INTELLIGENCE
Three signals from this week across Venture Capital, Private Equity, Family Offices, and Capital:
KKR agreed to sell USI Insurance Services to Aon for $17 billion, ending a nearly decade-long hold that began with a $4.3 billion investment in 2017. (Bloomberg, August 31, 2026) KKR did not improvise this outcome. It made three subsequent capital investments to become USI’s largest shareholder and executed a single, sustained thesis long enough to produce a 3.4 times return. That is what a documented strategy actually looks like when someone is still executing it a decade later.
Apollo Global Management agreed to sell Kelvion, a data center cooling manufacturer, to SLB for $4.1 billion, just eight months after acquiring it. (Apollo Global Management, August 31, 2026, apollo.com/insights-news/pressreleases) Apollo named one priority at acquisition, data center cooling infrastructure, and did not dilute it. The eight-month hold is unusually short for a deal this size, and it is short because the strategy was never in question long enough to need re-explaining to a buyer.
Global startup investment hit a record $510 billion in the first half of 2026, but OpenAI and Anthropic alone accounted for 43 percent of it. (Crunchbase, September 1, 2026) Capital is not spreading out. It is concentrating on the handful of companies whose strategic thesis is specific enough for an investor to underwrite in one sentence. Everyone else is competing for what is left of the other 57 percent.
WHY ONLY 100 PEOPLE WILL EVER GET THIS
This newsletter has run for over a year, most recently built around the Price Pressure Playbook framework. Starting this month, I am building a second home for this work on Substack, with a new Enterprise Value Playbook focus and a paid tier alongside the free issues you already receive.
The paid tier is called From the Tip of the Spear: Executive Briefings. Every month I release one Executive Briefing Framework, thirteen in total, each a board-ready deck answering the only question my work is built around: how you scale the organization and maximize enterprise value. Membership also includes a monthly Insider group briefing with live Q&A.
Founding Member seats are capped at 100, priced once at $1,200 for lifetime access. Annual access is $400. Seats will not reopen once the cap is reached.
Reply “Briefings” for early access before the general list opens, and I will send you the first one free. The free weekly edition continues without interruption either way.
FROM THE TIP OF THE SPEAR
A strategy you cannot state is not a strategy you have. It is a strategy you once approved.
Thirty-five percent of chief strategy officers actually own the decisions behind their own strategy. The other sixty-five percent are custodians of a document, not authors of an operating rhythm. That distinction sounds academic until you watch what happens downstream. Capital gets allocated off instinct instead of a defined bet. Leadership hires against whatever gap felt urgent last quarter. Growth targets get set by aspiration instead of by a documented plan anyone could recite. Every pillar in this playbook inherits the instability of pillar one, and almost nobody traces it back that far.
KKR held one thesis on USI for nine years and moved three times to reinforce it. Apollo held one thesis on Kelvion for eight months and never needed to defend it twice. Neither firm won because the market was kind to them. They won because the strategy was legible enough that everyone downstream, including the eventual buyer, could see exactly what it was.
The test is not whether you have a strategy document. The test is whether five people in five different functions, asked cold, describe the same one. If they do not, you do not have a strategy. You have an artifact nobody is managing against.
Documentation is not the finish line. It is the floor. Communicate it until the coalition repeats it back to you in their own words, and revisit it on a cadence tight enough that a market shift gets absorbed in one review cycle instead of discovered a year late.
I WANT YOUR SCAR TISSUE IN MY NYU CLASSROOM
The discipline behind this newsletter is the same discipline I teach at NYU, across two courses: Scaling and Exiting the Business for Maximum Value, and Funding and Legal Approaches for Start-Ups. Each semester I bring operators into the classroom, live in NYC or virtual, to sit with graduate students working through the same problem from the practitioner side.
If you have scaled a company, exited one, raised capital, negotiated the legal terms of a deal, or sat across the table at the moment it was won or lost, I want to hear from you.
From the Tip of the Spear is my weekly publication for executives who are building something real. One issue, every Tuesday. A field report from active operator engagements, one principle with supporting data, and market intelligence from across my VC, PE, and family office network.
