When Your Key Executive Quits: Build a Company That Keeps Running

1. Read the facts: you are CEO of Hartwell Industrial Services, a $23 million mechanical contracting firm. On a Tuesday morning your VP of Operations, 19 years in, quits without warning. He knew every client, vendor and process; most of it lived only in his head. No key-man insurance, no accurate operations manual, no second-in-command. Two weeks later three client accounts ask for him by name and a critical vendor refuses to negotiate. Inside, four senior leaders think they are next, alliances form and meetings turn political. The all-hands is two weeks away.
2. In groups, take ten minutes to write your next three to five moves.
3. Sort your moves into: first 48 hours, first two weeks, and before the all-hands.
4. Check that your plan covers all four audiences: customers, vendors, the four senior leaders, and every department at the all-hands.
5. Present and grade each plan (par, birdie, eagle), rewarding moves nobody else said.
6. Finish by swapping the fictional VP for your own most critical person and re-running the plan.

Finish with: A time-boxed continuity plan you have already rehearsed against your own key-person risk.

Copy exercise

1. List every person whose sudden departure would hurt the company for more than a week.
2. For each, list what only they know or do: clients, vendors, processes, passwords, relationships, judgment calls.
3. Mark each item green (documented and someone else can do it), yellow (partly), or red (only in their head).
4. Name the interim and the number two for each role. Leave blanks where none exists.
5. Turn every red item and every blank into a dated task with an owner.

Finish with: A one-page map of where your company is held hostage and a task list to fix it.

Copy exercise

1. Write the list of customers and vendors you would call personally, ranked by revenue and criticality.
2. Draft the call in three sentences: what happened, who is in place, and that you personally guarantee continuity of quality and service.
3. Draft the internal message to senior leaders that names the interim and their own role in the response.
4. Draft the all-hands update: fast, clear, one paragraph per department.
5. Store all three drafts where you can find them in a crisis.

Finish with: Ready-to-use scripts for customers, vendors, leaders and the all-hands.

Copy exercise

1. Choose the one person whose knowledge is most concentrated.
2. Book them for one hour a week for four weeks.
3. Week 1: document the top 20 client relationships (contact, history, quirks, open issues) in the CRM. Week 2: vendors and negotiation history. Week 3: the five most critical processes as step-by-step SOPs. Week 4: the judgment calls they make that nobody else knows about.
4. Have their number two run one process from the documents alone and note every gap.
5. Repeat with the next most concentrated person.

Finish with: A shared, tested body of documentation for your most critical role, and a repeatable method for the rest.

Copy exercise

1. Export the last two years of invoices and, using a spreadsheet or an AI tool, produce a ranked list of transacting customers by spend.
2. Confirm in writing (with legal or HR) your policy for reviewing a departed employee's company email for prospects and open conversations before the account is closed.
3. Confirm you can pull every open opportunity from the CRM without a specific person's login.
4. Time how long the whole drill takes. Anything over a day is a gap to close.
5. Assign the drill to someone other than the person who owns the data.

Finish with: Proof that the customer and prospect picture can be rebuilt in hours, and a list of access gaps.

Copy exercise

1. Name the interim leader for the vacated role.
2. Assign four senior leaders one workstream each: (1) the operations manual and systems, (2) client relations, (3) internal office affairs and morale, (4) developing future people.
3. Hold twenty-minute huddles to list everything the departed person did and assign each item to a workstream.
4. Set a recurring operational-resilience check-in (weekly until the all-hands, then monthly) to measure the transition and catch dropped balls.
5. Report progress at the all-hands with a clear update for every department.

Finish with: An organised response with owners, a dependency list and a cadence for checking nothing is missed.

Copy exercise

1. Ask yourself honestly: was this a surprise? If yes, why did nobody tell you?
2. Meet each remaining senior leader one on one and ask what discontent or turmoil they saw and when.
3. Ask what the departed person's strengths and downfalls were, so the replacement is an upgrade.
4. Write down the cultural issue the departure exposed and one change you will make.
5. Decide whether this is a case of addition by subtraction before you rush to hire.

Finish with: A clear diagnosis of why the person really left and a better brief for the replacement.

Copy exercise