Before the First Session: The Diagnostic

A serious coaching engagement starts with a diagnostic — not a sales conversation, but a real assessment of the business. This typically involves a structured interview covering the business model, revenue, team, key challenges, and what the founder is actually trying to change. The output is a shared picture of where the constraints are and what the coaching will focus on.

This diagnostic is where you find out quickly whether the coach understands your business. If their questions feel generic, their assessment probably will be too.

The First Month: Establishing Clarity

The first month of coaching is rarely about solving problems. It's about establishing a clear-eyed picture of reality — what's actually happening in the business versus what the founder believes is happening. These are often different.

Sessions in the first month typically cover: what the business's actual constraint is, what the founder's role should be versus what it currently is, and what the most important priorities are for the next 90 days. The output is a clear focus for the engagement.

Months Two and Three: Working the Problems

Once priorities are clear, sessions shift to working through them. A typical session looks like: 10 minutes reviewing what was committed to last session and what actually happened, 40 minutes working through the current priority — diagnosing, thinking through options, stress-testing decisions, 10 minutes setting specific commitments for the following week.

The between-session work is where most of the value is created. Implementation happens in the business, not in the coaching session. The session is where you think clearly. The week is where you act.

What Makes the Difference

The coaching relationships that produce the best results have one thing in common: the founder shows up to sessions having done the work. They tried the thing they committed to. They reported honestly on what happened. They came with real questions rather than hoping the coach would provide all the direction.

Coaching is collaborative. The coach brings experience, frameworks, and an honest outside perspective. The founder brings knowledge of their specific business and the willingness to act on what they discover.