Executive coaching: pilot proposal
Use this pilot proposal exercise to design a small engagement that resolves a real uncertainty and has a clear stop or proceed decision. You are discussing a structured leadership coaching programme with a founder preparing to manage a growing leadership team. The point of the practice is to make a useful decision together, including recognising when the offer is not a fit.
Agree a bounded trial with evidence requirements and a review date, without implying expansion is automatic.
The situation
In this fictional brief, important decisions return to the founder even after delegation. The buyer wants clearer decision ownership and a repeatable reflection routine. Your offer is a structured leadership coaching programme, but you must first establish whether its scope addresses the actual need.
A relevant delivery constraint is that personal discussions must have explicit confidentiality boundaries. Treat that as a fact in the exercise; do not remove it to make the sale easier.
| Your counterpart | a founder preparing to manage a growing leadership team |
|---|---|
| Offer under discussion | a structured leadership coaching programme |
| Evidence available | a sample session agenda and a client-owned progress journal |
| Terms to clarify | Agree session cadence, confidentiality, cancellation and sponsor reporting. |
How to approach pilot proposal
A useful question for this stage: “What evidence would make you decide not to expand?” Ask it when the conversation creates a reason for it, rather than reciting every question in order.
- Define a narrow scope, a baseline, an owner and success criteria. Include a stop condition and the decision after the pilot.
- Ground the discussion in the buyer’s work. Ask: “Which recurring decision would you like your team to own without you?” Listen for a concrete example before making a claim.
- Use evidence relevant to the decision: a sample session agenda and a client-owned progress journal. Explain what it demonstrates and what remains unverified.
- Agree a bounded trial with evidence requirements and a review date, without implying expansion is automatic.
An industry-specific concern
Buyer: “How can I prove coaching will pay for itself?”
Possible response: “We can agree observable behaviours and review them. We should not present a coaching conversation as a guaranteed financial return.”
Why this response helps: it acknowledges the concern, brings the discussion back to a verifiable requirement and leaves room for a different decision. Adapt the wording to what the buyer actually said.
Run the practice
- Prepare for two minutes. One person takes the seller role and one plays a founder preparing to manage a growing leadership team. Read the offer and constraint separately from your preferred answer.
- Have a five-minute conversation focused on design a small engagement that resolves a real uncertainty and has a clear stop or proceed decision. The buyer should answer consistently with the brief and ask for evidence when a claim is vague.
- Add this challenge: The buyer wants an open-ended free trial. Explain the work involved and propose a finite evaluation with clear responsibilities.
- Pause for feedback. Quote one useful question and one missed opportunity. Repeat the difficult exchange using a different response.
- Finish by writing the actual agreement. A sensible option, when it fits, is to run a clearly scoped introductory session and agree one behaviour to practise. A clear decision to pause is also a useful outcome.
What to avoid
| Common mistake | Calling a discounted full project a pilot without a learning objective. |
|---|---|
| A stronger direction | Let us test the uncertain part first and agree what the result will and will not tell us. |
| Scope and claim boundary | Keep coaching separate from clinical care and avoid psychological diagnoses. |
| What to measure in real work | completion and reflection on agreed behavioural experiments. Establish a baseline and definition before interpreting a change. |
An example conversation
Which question would a small trial need to answer before you considered a wider engagement?
Our concern is that important decisions return to the founder even after delegation. Also, personal discussions must have explicit confidentiality boundaries.
Which recurring decision would you like your team to own without you?
How can I prove coaching will pay for itself?
We can agree observable behaviours and review them. We should not present a coaching conversation as a guaranteed financial return.
What evidence would make you decide not to expand?
Your working sheet.
Make the exercise your own. Notes are saved in this browser when storage is available. Download a copy to keep; avoid confidential information on a shared device.
Example: important decisions return to the founder even after delegation; personal discussions must have explicit confidentiality boundaries.
Example: What evidence would make you decide not to expand? Industry question: Which recurring decision would you like your team to own without you?
Example: a sample session agenda and a client-owned progress journal. Keep coaching separate from clinical care and avoid psychological diagnoses.
Example: Propose a clear next step, such as: run a clearly scoped introductory session and agree one behaviour to practise. Confirm the owner and date.
Review your work
This is a reflection checklist, not an automated assessment.
Questions
Who is this executive coaching exercise for?+
Can I use the example as a script?+
How should I assess the result?+
Fictional training scenario. The dialogue illustrates response choices; it is not a customer testimonial or a record of a real sale.
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