"What if this person resigned tomorrow?" A succession exercise for small companies

Most founders can name the two or three people the business could not do without. Almost none can name who would cover them. The gap between those two facts is the entire subject, and it does not need a framework to close.

The exercise

Two hours, a list of roles, and honesty. Do it with one other person — a co-founder or a senior colleague — because the conversation is better with two views and the findings should not live in one head.

1. 1

   List the roles, not the people

   Every role in the business, by function. Roles rather than names, because the question is about the position's exposure, not the individual's loyalty.

2. 2

   Ask the question of each

   If the person in this role resigned tomorrow, what happens? Three answers: we manage, it hurts for a while, or something genuinely stops. Only the third category matters here.

3. 3

   For each critical role, ask who covers

   Name someone internal. If the honest answer is nobody, write nobody — that is the finding and softening it defeats the purpose.

4. 4

   Ask what readiness would require

   For each named cover: what would they need to be ready, and how long would it take? Usually one or two specific gaps, not a development programme.

5. 5

   Ask what leaves with the person

   Relationships, undocumented knowledge, system access, supplier or customer trust. This is often more exposing than the role itself.

6. 6

   Pick two actions

   Not a plan for every role. Two things you will actually do this quarter.

The output fits on a page

ROLE               IF THEY LEFT      COVER        READY?   GAP
-------------------------------------------------------------------
                   stops / hurts /                Y/N/     what is
                   we manage                      partly   missing

Example:
Plant in-charge    stops             Shift lead A partly   commercial
                                                           decisions
Key account owner  stops             nobody       -        relationships
                                                           undocumented
Payroll + records  hurts             HR exec      partly   statutory
                                                           calendar
Founder            stops             nobody       -        everything

WHAT LEAVES WITH THEM (per critical role):
  relationships ___  knowledge ___  access ___  trust ___

Four or five rows is normal for a business under two hundred people. If you have fifteen, the definition of critical has slipped and the exercise will not produce action.

The finding nobody wants

The founder's own row is usually the most exposed, and it is the one most often skipped. Approvals, relationships, pricing judgement and institutional memory concentrate there by default, and no successor exists because none has ever been needed.

The realistic response is not to appoint a deputy. It is to reduce what only you can do — which is the same work as writing down approval limits and naming who decides what. Founders who do the succession exercise honestly usually find themselves doing organisation design work as a result, because the exposure is structural rather than personal.

Readiness is the work

Naming a successor takes a minute and changes nothing. What changes something is closing the specific gap, and the gaps are usually narrower than people expect.

• Exposure — the person has never sat in the meeting, seen the numbers, or met the customer. Cheapest to fix and most often neglected.
• Decision practice — they have never had to make the call. Let them make it while the incumbent is still there to catch it.
• A specific skill — commercial judgement, a technical certification, a system. Nameable and trainable.
• Standing — the team or the customer does not yet see them in that role, which takes visible responsibility over time rather than an announcement.

Pick one gap for one successor and close it this quarter. That single step converts the exercise from a document into an actual reduction in risk, and is where succession and leadership development work concentrates its effort.

Capture what would leave

Some of the exposure is not the person's capability but what only they know. That part can be reduced without any successor being ready.

Ask each critical person to write a page: what they do that is not written down, which relationships matter, what falls due and when, what would break first if they were away for a month. It takes an hour and most people have thought about it already — nobody has asked.

Do it while nothing is happening. Asked during a notice period it becomes a handover under pressure, and the material is worse.

Repeat it annually

Roles change, people develop, and the exposure moves. An hour once a year keeps the register true, and the second year is faster because the format exists.

One warning about what to do with it. This register is sensitive: it names people as cover and, by omission, names people who are not. Keep it between you and whoever helped build it, and do not turn it into an announcement. What can be shared is the individual half — telling someone they are being developed toward a bigger role is motivating, and is usually the point at which succession and leadership development work starts producing something visible.

What the exercise tends to reveal beyond succession

Two findings turn up almost every time, and neither is about successors.

The first is that several critical roles are critical because of accumulated informal work rather than the role itself. Someone has absorbed three adjacent responsibilities over four years and nobody noticed. That is a structure question, and it often resolves by redistributing rather than by finding a successor.

The conversation you cannot have

The exercise produces a list of critical people, and then a question that stops most businesses: how much of this can you say out loud.

Telling someone they are a single point of failure is generally received well — it is a statement of value. Telling someone they are not on the succession list for a role they expect to get is a different matter, and doing it badly loses the person immediately.

The practical position is that the list itself stays confidential and the development that follows from it does not. Nobody needs to know they are named as a successor; they do need to know what they are being developed toward and why. Where those two diverge — someone being developed for a role they will not get — that is a problem with the plan rather than with the communication.

The exception worth handling deliberately is the person who believes they are next and is not. Leaving that unaddressed until the role is filled externally guarantees losing them, and usually with a legitimate grievance. Saying it early, with what would need to change, is difficult and keeps more people than silence does.

One further use for the list is worth mentioning, because it costs nothing. A named single point of failure is a good reason to insist that person takes their leave, properly and without being contactable. Nothing exposes an undocumented dependency faster than a fortnight without the person, and finding it that way is considerably cheaper than finding it through a resignation.

The second is that the business has no written record of what these people actually do. The one-page capture described above is usually the first time it exists, and it turns out to be useful for far more than succession — it is the basis of a job description, an induction for the next person, and a handover if anyone does leave. That overlap is why succession and leadership development work so often starts by producing documentation nobody had got round to, and why it pairs naturally with role design and job descriptions.