When I deal directly with a founder, I want to know whether to believe what they say, so I do not build my plans on someone's optimism.

Job context

Who

A buyer dealing directly with a founder

When

In every conversation

Trigger

A promise that did not materialise

Situation

Whoever promises is both sincere and not in control

Constraints

There is nobody else to check against

5 Pains

• Promises are sincere and still unkept

  High

  Because the company's situation keeps changing.

  Root cause: A small company's priorities move with the next customer and the money left

• Nobody else in the company to check with

  High

  Everything comes through one person.

  Root cause: At a very small company one person holds every role

• Founders are more optimistic than the facts

  High

  And that optimism is a condition of them continuing.

  Root cause: Nobody does this work while seeing the odds accurately

• A personal relationship makes demanding harder

  Medium

  Because you genuinely like them.

  Root cause: At this scale the business and personal relationships are the same one

• No idea how much money the company has left

  Medium

  And it is the most decisive fact.

  Root cause: Nothing obliges disclosure of the financial position

5 Desired Outcomes

• Know which promises are firm enough to plan on

  Functional

• Have a second source inside the company

  Social

• Understand the optimism well enough to discount it

  Functional

• Make demands without damaging the relationship

  Social

• Know how long the company can continue

  Functional

5 Existing Solutions

A solution is not the same thing as a product, a customer can hire a behaviour or a workaround too.

• Put every commitment in writing

  Behaviour

  The only protection with force, and it makes the relationship more formal.

• Ask plainly about money and runway

  Behaviour

  The most decisive question, requiring trust already established.

• Talk to someone else in the company

  Behaviour

  Gives a second view, and at a very small company there is nobody else.

• Discount every estimate yourself

  Workaround

  What experienced buyers do, and it is a guess.

• Plan for them not delivering

  Behaviour

  The soundest preparation, at effort for something that may never be needed.

2 Opportunity Gaps

• Whoever describes the company's future is the founder, and the optimism that skews the description is the same thing that keeps them going.

  Why existing solutions fail: This is not dishonesty but a necessary feature of the role, a founder seeing the odds accurately would stop, so a buyer cannot wait for descriptions to become accurate and must discount them themselves.

  Potential opportunity: Asking questions with checkable answers, current customers, months of runway, rather than about plans.

• At this scale the business relationship and the personal one are the same relationship, so every legitimate demand passes through a personal cost.

  Why existing solutions fail: That closeness is the greatest advantage of buying from a small company and also what makes a buyer reluctant to demand what they are fully entitled to, so the advantage and the weakness are the same thing.

  Potential opportunity: Putting commitments in writing at the start, while the relationship is not yet close enough for it to be awkward.