When I tell people I transitioned from project management into coaching, the response is usually some version of: that's quite a jump. It isn't. The core move in both disciplines is identical: you help someone build something that doesn't yet exist, using a structure that can hold the weight of what they're trying to make.
The project charter and the coaching agreement
Every project starts with a charter. The charter defines scope, constraints, stakeholders, and success criteria. It is not a wish list. It is a document that forces clarity before the work begins. Most projects that fail do so because the charter was vague, assumed, or skipped entirely.
A coaching engagement starts the same way. In the first session, we establish: what are we building? What's in scope? What are the constraints? How will we know when we've moved far enough to call this a win? Vague answers here produce vague outcomes later.
Milestones are a coaching tool
In project management, milestones are the checkpoints that tell you whether the project is on track or drifting. When a milestone is missed, the question is never just 'what happened?' It's 'what does this tell us about the plan?'
The job of a project manager is not to prevent problems. It's to detect them early enough that they can be redesigned rather than managed.
What twelve years taught me about asking questions
Running projects across Lebanon, the UAE, and beyond taught me one thing above all others: the quality of a project is determined by the quality of the questions asked in the first meeting. Not the quality of the plan. Not the quality of the team. The quality of the questions.
Coaching is the same. The practitioner's job in the first session is not to provide direction. It's to ask the questions that surface what the client already knows but hasn't yet articulated. The plan comes after the questions. Never before.