Leadership

Give your business coach a clearer view

John Roberts, CEO of Worker.ai
November 2026 · 2 min read
Leadership

One CEO joked that his coach had tried to graduate the company, but the team kept refusing to leave. It valued having someone outside the business who could challenge its thinking.

Before a coaching session, the COO’s recurring job is to give the coach an accurate account of what happened since the last conversation. That can mean recovering decisions, finding changes to the plan and asking managers to explain why a commitment moved.

A coach’s time is more useful when that history is already available. The team can then spend the session examining the decision it needs to make.

Suppose a process change was meant to speed up customer handoffs, but delays continue. A briefing for this made-up case could be this short:

  • Intended change: Sales now hands each new customer to the service team with one intake form, so the first visit can be booked sooner.
  • What happened: Forms reach the service team the same day. Customers still wait about as long for their first visit.
  • Where we disagree: Sales thinks scheduling is the bottleneck. Service thinks the forms arrive without site details, so visits get rebooked. Neither view has been tested yet.
  • Decision we need help with: Do we fix the form first, or change how visits are scheduled?

Writing it takes three records: the original decision, the results since then and the team’s competing explanations. Pull them together and have the people closest to the work check the account. The coach can see what happened, what the team disagrees about and which decision needs help.

Keep the disagreement in. A polished account that hides it gives the coach less to work with.

Use the session for the challenge you value in a coach: testing an explanation, weighing a tradeoff or deciding what to do next.

Before the next session, choose a decision the team wants help making and include the evidence that challenges your preferred explanation. Begin there. Afterward, keep the decision with the work it concerns, so the problem builds a history the next session can use.

Written by John Roberts
CEO of Worker.ai

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