The Process
What to expect from a leadership coaching engagement
A well-structured leadership coaching engagement follows a clear arc, though the specific content is tailored to each leader. Here is what a typical engagement looks like:
Discovery and assessment
The engagement begins with a thorough assessment of your current situation: what transition you're navigating, what feedback you've received, how your stakeholders perceive you, and what specific outcomes you want from coaching. Many engagements include formal assessments (DISC, 360-degree feedback, or stakeholder interviews) to establish a baseline.
Goal-setting and contracting
Together with your coach, you define 3–5 specific development goals with measurable success criteria. The contract clarifies engagement length, session cadence (typically 2x per month, 60 minutes each), confidentiality boundaries, and how progress will be measured.
Structured sessions
Each session is a focused, structured conversation — not a status update, not a venting session, not a pep talk. The coach uses inquiry and challenge to help you think through real leadership situations, practice new behaviors, and commit to specific actions between sessions. For more detail, see what happens in a coaching session.
Midpoint review and adjustment
Halfway through the engagement, coach and leader review progress against the initial goals, gather informal feedback from key stakeholders, and adjust the development plan as needed. This ensures the coaching stays relevant as your situation evolves.
Wrap-up and sustained growth
The engagement concludes with a final assessment of what changed, what new habits were established, and what the leader wants to continue working on independently. The best coaching leaves you with internalized frameworks and self-coaching skills that continue producing returns long after the engagement ends.