When you hold a strategy memo or plan that you still control, put it through several model perspectives in sequence and ask each seat to name what would make the plan unacceptable, what evidence is missing, and which claims the attached exhibits do not support. Do this from the chief executive or strategy seat before you socialize the plan, lock a budget line, or put slides into a board pack.
This guide is for that private collision of seats on one strategy document. For a deck headed to directors, see reviewing a board pack before the meeting. For a second read of an email or chatbot answer, see getting a second opinion on a draft. For a staff-meeting proposal, see stress-testing a proposal before leadership. For a finished package headed to a vote or signature, see reviewing a high-stakes decision package. Executive starting points live under Pingpong for executives.
What this review is for
A strategy memo usually leaves the drafting group with one preferred reading of the market, the cost, and the timeline. Finance, counsel, operations, and the customer seat will each treat a different line as decisive. Hearing those seats while the memo can still change costs less than hearing them after the plan is on the calendar. Pick three to six seats that will matter. Name the function and the question that seat will ask first. Attach the same source pack to every seat so the conflict is about priorities and interpretation. If one seat needs a document the others should not see, run that seat as a separate pass with clear redaction rules.
A worked example
This example is illustrative and does not describe a customer. The chief executive of a 120-person software company has an eight-page strategy memo proposing mid-market expansion into two new regions over eighteen months, with a $2.1 million investment ask. Before sharing the memo with leadership, the chief executive puts five things into one request:
- The strategy memo and the one-page investment summary.
- Last four quarters of revenue and margin by segment, plus current capacity by region.
- The draft hiring plan and the contractor budget the memo assumes.
- The ask in one sentence: approve the expansion plan and first-year spend, with a go or stop review after nine months.
- One instruction: read the memo in turn as the chief financial officer, the head of sales for existing regions, and a skeptical enterprise buyer in a new region; for each seat, list every claim the exhibits do not support, quote the line, and list the first five questions that seat would ask.
A review that helps points at concrete gaps. It might find that page 3 claims the new regions will reach the company's current mid-market win rate in two quarters, while the segment table only covers existing regions. It might notice that the investment summary treats contractor spend as flexible while the hiring plan locks six full-time roles in month one with no stop gate. The chief executive checks each flag, replaces the win-rate claim with a pilot target and nine-month stop condition, and splits hiring into cohorts tied to pipeline.
A request you can copy
Below are a strategy memo or plan, the decision I am about to commit to, and the exhibits the memo relies on. Read the memo in turn as each of these seats: [list three to six functions, for example chief financial officer, head of operations, general counsel, and a skeptical buyer]. For each seat, list every claim the attached exhibits do not support, quoting the page or line. Then list the first five questions that seat would ask, and for each one say whether the memo already answers it and where. After all seats, list the conflicts between seats that the current draft papers over. Don't rewrite the memo.
Leave the exhibits in. Strategy objections often come from a gap between the narrative and the backup, and a reviewer that only sees the memo cannot find it.
How the Pingpong web review app runs it
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. An early pass might list unsupported claims for the first seat; a later pass might score those claims from the next seat or check whether a flagged number holds up across files. You get a final answer and can open each earlier pass. A confident mistake in the first pass can carry forward, so check every flagged figure against the source file before you change the memo.
What a model review can't check
A model does not know which operator already decided against the expansion, what was said in a closed session last week, or which disclosure counsel already cleared. Legal, tax, accounting, and personnel matters belong with the person responsible for those answers before you commit. Use the review to list questions and document gaps for those conversations.
If you are still choosing among alternatives, see reviewing a decision between options. If a director already asked a follow-up and you are about to send the written answer, see reviewing a reply to a board question. For the steps in the app, see running your first review. More guides live under work decisions before you commit.