To war-game a reorg before you announce it or take it to the board, put the current and proposed org charts, the cost model, the list of people whose role or manager changes, the top customer accounts with their owners, and the announcement plan into one request. Then instruct Pingpong to read the plan from the seats it affects: a leader losing scope, a strong performer moving under a new manager, the account owner on your largest renewal, and the director who asked for the change. Ask what each seat would do in the first two weeks after the announcement, and which questions the board would ask that the plan cannot answer yet.
This page is for chief executives and their heads of people preparing a restructure. For the cash and covenant view of the same plan, see role-play the CFO before you commit to a plan. Executive starting points live under Pingpong for executives.
Seats worth running
The seats that most often expose a problem:
- A leader whose team shrinks or moves, and who decides in the first week whether to start interviewing.
- A high performer who was promised a promotion path that the new chart removes.
- An account owner on a large renewal who now reports to someone the customer has never met.
- A shared team that two new leaders will both try to direct.
- The board member who will ask what the change costs, what it saves, and why now.
Give the model short notes on each seat: tenure, what they were told in their last review, and which customers they own.
A worked example
This example is illustrative and does not describe a customer. A 300-person B2B software company plans to move from functional teams to two business units, one for small business and one for enterprise, each run by a general manager. The chief revenue officer will run small business, and an outside hire will run enterprise. The vice president of customer success role is eliminated, with customer success split between the units. An 18-person platform engineering team stays shared. The board meets in two weeks, and the announcement is planned for the following Monday.
A useful pass starts with span and priority. The enterprise general manager would have 11 direct reports and the small business general manager 4. The platform team reports to the chief technology officer, but both general managers set its priorities, and nothing in the plan says who decides when they disagree.
Then retention and customers. Two customer success directors were told last spring that they were next in line for the eliminated vice president role. The three largest enterprise renewals, worth $4.1 million together, come due in the quarter after the announcement, and their account managers would report to a leader who has not been hired yet.
Then the board. The plan claims $2.2 million in annual savings, but the cost model leaves out the new general manager's compensation and the search fee, which brings the net closer to $1.3 million. A director would also ask why the company is announcing before the enterprise leader is in place.
The chief executive changes the plan before the board meeting. Four enterprise reports move under a deputy. A written rule gives the chief technology officer the tie-break on platform priorities, with a quarterly allocation both units agree to. The two directors and the account managers on the top renewals get retention agreements and individual conversations before the all-hands. The board pack restates savings net of new costs and names the chief revenue officer as interim enterprise lead until the hire starts.
Order of the announcement
A common sequence is the board, then each leader whose role changes, one at a time and a day ahead, then the company, then the top customers through their executive sponsor within 48 hours. Ask the war-game where your sequence leaks, such as a customer hearing from a departing employee.
A request you can copy
Below are our current and proposed org charts, the cost model, notes on each person whose role or manager changes, our top accounts with their owners, and the announcement sequence. Read the plan from each seat I describe and say what that person would likely do in the two weeks after the announcement. Flag spans of control above eight, shared teams with no tie-break, and savings that leave out new costs. List the questions a board member would ask that this plan cannot answer yet. Point out any step in the sequence where people could learn the news from the wrong source.
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. Check every flagged figure against the cost model. For the steps inside the app, see running your first review.
What a model can't war-game
A model does not know who is already talking to recruiters, how a particular customer reacts to account changes, or what notice and consultation rules apply in each country where you employ people. Employment law questions belong with your counsel and head of people.
For seats and scenarios before a board vote, see war-game a decision before the board meeting. More guides live under work decisions before you commit.