To war-game a legal strategy memo before the board acts on it, put the memo, the contracts and documents it relies on, the business facts it touches (affected customers, revenue, insurance, management time), and the decision the board is being asked to make into one request. Then instruct Pingpong to read the memo as a careful director would: find facts the memo assumes but does not show, documents that conflict with its reasoning, costs and outcomes left vague, and business consequences it does not address. Ask for a list of questions to send counsel before the meeting. Pingpong helps you read and question the memo. Your lawyers give the legal advice, and the board makes the call.
This page is for chief executives, general counsel, and directors reviewing advice on litigation, a settlement offer, a contract dispute, or intellectual property risk. Before you paste a privileged memo into any outside tool, ask counsel whether doing so affects privilege. For a filing that goes to an agency, see war-game a regulatory filing before it reaches the examiner. Executive starting points live under Pingpong for executives.
Seven questions a board should be able to answer
- What outcomes are realistic, and how likely does counsel think each one is?
- What will each stage cost, through to the end of the strategy?
- How much management time will this take, and whose?
- Which customers, partners, or employees are affected while it runs?
- Which facts are uncertain, and who is checking them?
- What would change counsel's recommendation?
- When will the board revisit the decision?
If the memo does not answer one of these, that gap goes on your list for counsel.
A worked example
This example is illustrative and does not describe a customer. A 350-person software company terminated a reseller agreement last year. The former reseller has sued, claiming unpaid commissions and damages, and has offered to settle. Outside counsel's memo recommends rejecting the offer and moving for summary judgment, describing the company's position as strong. The board will decide at its next meeting.
The general counsel pastes the memo, the original reseller agreement, a later amendment, the termination notice, the list of customers the reseller still supports, and the company's insurance summary.
A useful pass finds that the memo's main argument relies on a termination clause in the original agreement, while the amendment pasted alongside it appears to change the notice period. The memo assumes the notice was delivered correctly, but the notice in the materials is addressed to an office the reseller had left. Neither point is a legal conclusion. Both are facts for counsel to confirm.
The pass then turns to what the board needs. The memo estimates fees through summary judgment but gives no estimate if the motion fails and the case goes to trial. "Strong" is not translated into a range. The memo does not mention that the reseller still supports 40 shared customers, that discovery could expose pricing data to a reseller now working with a competitor, or whether the company's insurance covers any of the claim. It sets no point at which the board would reconsider settlement.
The general counsel sends outside counsel nine questions before the meeting. Counsel confirms the amendment changed the notice period and revises the analysis. The updated memo gives a rough probability range, fee estimates for each stage through trial, and a note on protecting pricing data in discovery. The insurer is notified. The head of partnerships drafts a plan for the shared customers, and the board agrees to revisit settlement after the key depositions.
A request you can copy
Below are a legal strategy memo from our counsel, the documents it relies on, the business facts it affects, and the decision our board is being asked to make. Read the memo as a careful director. List facts it assumes without showing, documents that seem to conflict with its reasoning, costs or outcomes left vague, and business consequences it leaves out. Do not give legal conclusions. Turn each issue into a clear question for our counsel, and note which of the seven board questions below the memo does not yet answer.
Paste the seven questions from this page under the request.
How Pingpong runs the 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. Treat every flagged issue as a question for counsel. For the steps inside the app, see running your first review.
What a model can't war-game
A model is not your lawyer. It does not know the court, the judge, opposing counsel, or how similar cases have been resolved, and it cannot weigh legal risk the way experienced counsel can. Use it to make sure the memo answers what the board needs, then let counsel advise and the board decide.
When the strategy goes to a board vote, see war-game a decision before the board meeting. More guides live under work decisions before you commit.