Before a chief executive's annual or crisis letter goes to investors or employees, war-game it sentence by sentence. Mark each sentence as a claim, a number, a promise, or a hedge, check every number against the board pack, and ask which lines you would regret if someone quoted them back a year from now. Then send the reconciled draft to the board before it goes anywhere else. Paste the draft letter, the latest board pack, the operating plan, and any notes on decisions still under discussion into one request. Instruct Pingpong to tag each sentence, flag numbers that differ from the board materials, and find promises the plan does not support. Review your written answers in a second round.
Where the letter touches securities, fundraising, or public disclosure, counsel owns that review. Pingpong checks consistency and readiness.
This page is for chief executives and directors preparing a letter that readers will keep, forward, and reread. Executive starting points live under Pingpong for executives.
Tag every sentence
- Claim: a statement about the company or market. Is there a source, or is it an opinion?
- Number: a figure. Does it match the board pack, with the same definition and period?
- Promise: something the company will do or achieve. Does the plan support it, and on what conditions?
- Hedge: softened language. Is it hiding a fact the reader deserves to know?
Read it a year from now
A letter outlives the moment it was written for. Employees save it, investors forward it, and candidates find it. Picture the next letter, twelve months later, and ask which sentences in this one it would have to walk back. Those are the ones to rewrite now.
A worked example
This example is illustrative and does not describe a customer. The chief executive of a 320-person software company drafts an annual letter to employees and investors after a difficult year: the company missed its plan, cut 8% of staff in the spring, and narrowed its strategy. The draft is warm and confident.
The chief executive pastes the letter, the most recent board pack, next year's operating plan, and a note that the board is still discussing further cost reductions.
A useful pass tags the draft and finds problems in each category. The claim "we are now the clear leader in our category" has no source. The letter says revenue grew 31%, while the board pack shows 24% growth in recurring revenue. The higher figure includes one-time services. It cites 30 months of runway. Finance shows 26 at current burn. It promises profitability next year, while the plan reaches break-even on an adjusted basis in the fourth quarter, if two large renewals close. "The hardest decisions are behind us" conflicts with the board's ongoing discussion of cost reductions. The spring layoff appears only as "rightsizing." The letter also names a customer that has not agreed to be named.
The revised letter cuts the leadership claim and describes two specific customer wins instead. Revenue growth is stated as 24% in recurring revenue, with services reported separately. Runway reads 26 months at current spending. Profitability becomes a target for adjusted break-even in the fourth quarter, with the conditions stated. The line about hard decisions comes out. The layoff gets a direct paragraph acknowledging the people who left. The customer name is removed until permission arrives. The board sees the draft a week before it is sent, and counsel reviews the forward-looking statements because the company expects to raise in the coming year.
For a regular update built around monthly metrics, see war-game an investor update before you send it.
A request you can copy
Below are a draft letter from our chief executive, our latest board pack, next year's operating plan, and notes on decisions still under discussion. Tag each sentence as a claim, a number, a promise, or a hedge. Check every number against the board pack, including definitions and periods. Flag claims without sources, promises the plan does not support, and hedges that hide facts readers should know. List sentences likely to need walking back within a year. Mark disclosure questions for counsel. Stop there so we can answer in writing, then review our answers.
How Pingpong runs the review
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. For the steps inside the app, see running your first review.
What a model can't review
A model does not know how your employees feel after a hard year or what your investors have heard privately. It can check the draft against your documents. The voice and the decision to send belong to you, with the board's input.
When the letter goes to the board, see war-game a decision before the board meeting. More guides live under work decisions before you commit.