To war-game a decision before a board or leadership meeting, write the ask in one sentence, name the people in the room who can stop it, and play the plan against the strongest move each of them could make, plus the two or three ways the world could turn against you after the vote. Do it while the ask, the numbers, and the fallback can still change.
This page is for chief executives, founders, and senior operators preparing a decision that a board or executive team will approve, reject, or reshape. Executive starting points also live under Pingpong for executives.
What war-gaming a decision means
A document review asks whether the deck is accurate. A war-game asks what happens next. You treat the meeting as a contest with turns: you present, a director pushes back, you answer, and the decision either survives or bends. Then you run the decision forward a few quarters and ask which outside events would make the room regret it.
Three pieces matter. The seats are the specific people who can block or reshape the ask, each with a known concern such as cash, risk, or execution. The scenarios are the plausible bad turns after approval: a key customer leaves, a timeline slips, financing costs rise. The response is what you would change now, before the meeting, so that each objection already has an answer and each scenario already has a trigger and a fallback. The output is a short list of edits to the ask, not a longer deck.
A worked example
This example is illustrative and does not describe a customer. The chief executive of a 300-person specialty components maker plans to ask the board next Tuesday to approve a $14 million acquisition of a smaller competitor. The pre-read includes a board memo, the deal model, a diligence summary, a customer concentration export for the target, and the draft term sheet.
The chief executive puts all of it into one request with three seats: the audit committee chair, an investor director focused on cash runway, and an independent director who has run plants. The request also names three scenarios: the target's largest customer, at 38 percent of revenue, leaves within a year of close; integration slips two quarters; and the floating rate on the acquisition debt rises by two points.
A useful pass turns up concrete problems. The memo assumes 95 percent customer retention, but the diligence summary notes that the largest customer's contract allows termination on change of control. Under the slip scenario, the model breaches the leverage covenant in the fourth quarter after close. The operator director's first question would be who runs the acquired plant on day one, and the memo never names a person.
The chief executive changes the ask before the pre-read goes out: $12.5 million at close plus a $1.5 million earnout tied to that customer renewing, a covenant headroom table under all three scenarios, a named integration lead with a 100-day plan, and a stated walk-away price. The decision the board sees is smaller, sturdier, and easier to approve.
Pick the guide for what you have
- A full board pack due in a few days: review a board pack before the meeting.
- A pre-read and a worry about the room: anticipate the hard questions directors are likely to ask.
- A proposal still shaped as an idea: stress-test a proposal before leadership.
- Slides you will walk the room through: stress-test a pitch or strategy deck.
- A company strategy fork still open: war-game the preferred path before you commit.
- A call inside your own authority with no board vote: review the CEO decision before you announce it.
- A single director seat that can stop the vote: role-play the skeptical director before the meeting.
- Agenda control, process, and fiduciary pressure from the chair seat: role-play the board chair before the meeting.
- A pricing, GTM, or launch plan a named rival would answer: role-play the competitor reading the plan.
- A large B2B deal headed into procurement, security review, and contract redlines: role-play the enterprise buyer before procurement.
- A proposal to a 50 to 500 person company where the owner signs and an operator will use the product: role-play the mid-market buyer before you send it.
- An appeal, reinstatement request, or partnership ask to an app store, marketplace, or payment platform: war-game the message to the platform before you send it.
- An App Review rejection blocking a launch, with a reply or resubmission still in draft: war-game your reply to the app store rejection.
- A monthly or quarterly investor update still in draft: war-game the investor update before you send it.
- A fundraising deck headed to a partner meeting: role-play the skeptical investor before the partner meeting.
- A decision on whether and when to open a fundraise, before any investor hears about it: decide whether the company is ready to fundraise.
- A data room about to open for investors or acquirers, with numbers, folders, and access still to check: war-game the data room before investors open it.
- A secondary sale of founder, employee, or early investor shares that employees and investors are about to hear about: war-game the secondary sale story before employees and investors hear it.
- A fundraising deck whose metrics, runway math, or headlines still need checking against the model: war-game the fundraising deck before investors open it.
- An acquisition you are deciding whether to pursue at all, before diligence spending: test the thesis before you acquire.
- A financing term sheet waiting for a signature: prepare the board's questions before you sign the term sheet.
- A funding round in its final weeks, with closing conditions, side letters, and a board resolution to reconcile: reconcile the documents and promises before you close the round.
- A post-close integration plan whose synergy numbers, retention, and systems milestones the board will review: war-game the acquisition integration before the board accepts the synergies.
- A growth or expansion plan whose cash low point and covenant headroom nobody has tested: role-play the CFO before you commit to the plan.
- A runway brief or cash section of the board deck whose months, burn, and covenant floor still need checking: war-game the cash runway brief before the number reaches the board.
- A decision on whether to commit to a burn reduction program and how large it should be: work backward from the runway you need before you cut burn.
- A hiring freeze the board will approve or track, with exceptions, backfills, contractors, and an end trigger to define: war-game the headcount freeze before the board hears it.
- A non-headcount cost reduction whose vendor, cloud, marketing, and travel savings still need testing: war-game the budget cut before the board commits to the savings.
- A mid-year reforecast after actuals moved away from plan, with revenue, hiring, and investments to rebuild: war-game the budget reforecast before you present the new numbers.
- A reset of company objectives and key results for a new half or after a miss: war-game the OKRs reset before you publish the new objectives.
- A price increase or new pricing model for existing customers that the forecast already counts on: war-game the pricing change before the board books the revenue.
- A pricing change still waiting for a commit decision, with grandfathering, notice, and walk-back terms unsettled: decide the policies and the walk-back rule before you change pricing.
- The lowest deal price the company will accept, and who may break it: war-game a pricing floor before the board signs off on discounts.
- Which existing customers keep old prices after a change, and for how long: war-game a pricing grandfather clause before the board approves it.
- A restructure headed to the board or an all-hands, with reporting lines, retention, and announcement order still open: war-game the reorg before you announce it.
- A workforce reduction whose employee, customer, investor, and press messages still need sequencing: war-game the layoff communications plan before the day is set.
- A workforce reduction still waiting for approval, with savings, alternatives, and selection criteria to check: check the decision is ready before you announce layoffs.
- A single involuntary exit, for performance or a role elimination, before HR and counsel set a date: check the reason and the handover before you let someone go.
- A restructure proposal where the first question is whether to reorganize at all: review the reorg proposal before you commit to it.
- A proposed change to the core product, target customer, or business model: answer the board's questions before you pivot.
- A proposal to redefine the ideal customer that sales and marketing pursue, without changing the whole company: test the evidence and write the definition before you change your ICP.
- A board response to a retention miss, with causes, interventions, and owners still to settle: war-game the churn response before the board asks why.
- A plan to start or reset a customer advisory board that the company board will ask about: war-game the customer advisory board before the invitations go out.
- A brand repositioning proposal waiting for a budget, with a new promise, audience, and campaign: war-game the brand repositioning before you fund it.
- A decision on whether to stop a funded internal project that still has advocates: test the evidence against the original bet, before you kill the project.
- A plan to retire a shipped product, edition, or major plan that customers already pay for: check the gates before you announce a sunset.
- A decision to remove one shipped feature from a product that continues: find who still depends on it before you kill the feature.
- A proposal to enter a new country or customer segment while the core business continues: test the demand and the checkpoints before you enter a new market.
- A written go-to-market plan asking for funding, with funnel, ramp, and channel assumptions to test: stress-test the go-to-market plan before the board funds it.
- A major product, feature, or offering about to reach customers: define done and test the adoption cases before you launch.
- A distribution, embedded, co-selling, or technology partnership large enough to shape the company: test what you give, what you get, and the exit before you partner.
- A large vendor, customer, services, or real estate agreement waiting for a signature: price the full term and the exit before you sign the contract.
- A single role or small batch of hires waiting for approval: make the case for the role before you hire.
- A headcount plan headed for board approval, where ramp time, hiring pace, and outcomes per role still need checking: war-game the hiring plan before the board approves it.
- An annual or mid-year compensation review headed for the compensation committee: war-game the compensation review before the committee sees it.
- A headcount plan that needs testing against attrition, a midyear freeze, slower ramp, or a bookings miss: stress-test the headcount plan against the ways it can fail.
- A succession plan for the chief executive or a key officer headed for board discussion: war-game the succession plan before the board discusses it.
- A press, podcast, or trade interview that directors and investors will read: war-game the media interview before the board reads the coverage.
- A financing, acquisition, leadership, or launch announcement the board will read: war-game the press release before the announcement goes out.
- An annual or crisis letter from the chief executive to investors or employees: war-game the founder letter before investors and employees read it.
- A live town hall where the chief executive takes employee questions after a board decision: war-game the town hall before you take questions.
- Decision rights between the chief executive, the executive team, and the board: war-game a delegation framework before the board asks who decides.
- A chief executive running hands-on in founder mode, and what the board sees: war-game a founder-mode operating cadence before the board sees it.
- Redesigning the board, committee, and executive meeting calendar: war-game a meeting cadence change before the board approves the calendar.
- The monthly metrics pack the chief executive and board rely on: war-game a metrics review before the board reads the numbers.
- A board review after a quarter comes in below forecast: stress-test a forecast miss review before the board hears it.
- The retention forecast the board plan depends on: war-game a renewal forecast model before the board relies on it.
- Whether the company can deliver what the revenue plan sells: war-game a capacity plan before the board approves the revenue plan.
- The full-year headcount and cost base the board approves: war-game a headcount plan before the board approves the cost base.
- Standing board permission to scale once agreed numbers hold: war-game an expansion trigger rule before the board pre-approves growth.
- The risk register the board or audit committee reviews: stress-test a risk register before the board reviews it.
- A portfolio cut the board will approve or hear about: war-game a roadmap cut before the board approves the list.
- A vendor commitment large enough for board approval: war-game a vendor selection before the board approves the contract.
- Leaving a vendor the company already depends on: stress-test a vendor exit before the board approves it.
- Selling through a major platform marketplace: war-game a marketplace expansion before the board approves the channel.
- Written questions or an interview request from a reporter digging into the company: pretend you are the journalist investigating your company.
- Embargoed press outreach for a financing, partnership, or launch: war-game the press embargo before you brief reporters.
- A breach, outage, product harm report, or leadership allegation you want to rehearse with the executive team and board: run a crisis tabletop before the real incident tests the plan.
- A first public, customer, or board message due within hours while the facts are incomplete: stress-test the crisis holding statement before it goes out.
- A written crisis communications plan the board wants confirmed as current: review the crisis communications plan before the next incident.
- A license application, agency notification, or disclosure filing the board or audit committee will review: war-game the regulatory filing before it reaches the examiner.
- A memo from counsel on litigation, settlement, a contract dispute, or IP risk that the board must act on: war-game the legal strategy memo before the board decides.
- A meeting, exam, or inquiry with a regulator coming up: pretend you are the regulator before the meeting with agency staff.
- A board deck whose slide order, ask clarity, or trap slides still need a pass: war-game the board deck before the meeting.
- A consent agenda where an item might get pulled, or one you plan to take off consent: war-game the board consent items before the meeting.
- A consent block that may be too large for the meeting, or a packet that buries its backup: war-game the board consent agenda before the packet goes out.
- A strategy memo you still control: run it through multiple perspectives.
- A finished package headed to a vote or signature: review a high-stakes decision package.
- A director's follow-up after the meeting: review a reply to a board question.
- A single draft or answer to check line by line: get a second opinion.
How Pingpong runs a war-game
The web review app sends your request through several models in order. Each later model receives the original request and every earlier answer, with instructions to assess the work so far. One pass might play the seats; a later pass might test whether the scenario math holds. A confident mistake can carry forward, so check every flagged figure against the source file. For the steps inside the app, see running your first review.
What a model can't war-game
A model does not know which director has already made up their mind, what was said in the last closed session, or what counsel has cleared. Legal, tax, accounting, and personnel questions belong with the people responsible for those answers. Use the war-game to sharpen the questions you bring to them. More work-decision guides live under work decisions before you commit.