What an executive coaching engagement should include

An engagement that works carries structure from the first conversation through to your last session. Without it, coaching can drift into occasional chats that feel good but shift little. The right framework tells you what to expect, how the coach will track progress, and when you'll know the investment has paid off.

A strong engagement begins before any session happens. Your coach should spend time understanding your context: the role you're in, the specific challenge or gap you're working on, your organisation's culture, and what success looks like for you personally. This isn't small talk. They're learning whether they're the right fit and gathering the detail needed to tailor their approach. Some coaches use a discovery call or written intake; others conduct a deeper initial meeting. Either way, you should feel heard and assessed, not rushed into a generic plan.

The opening weeks set the tone

Once you've committed, the first few sessions establish how you'll work together. Your coach should be explicit about the cadence (weekly, fortnightly, monthly—whatever makes sense for your goal), the format (one-to-one, virtual or in-person, length of session), and the rough timeframe. They'll often use psychometric tools, 360-degree feedback, or structured conversations to build a baseline. This isn't busywork. It gives both of you a clear picture of where you're starting from and what patterns or blind spots matter most. You should walk away from these early sessions with a written coaching plan or agreement that names your focus area, what progress looks like, and how you'll measure it.

The middle phase: deliberate practice and accountability

This is where most of the real work happens. In each session, a good coach doesn't hand you answers. Instead, they ask questions that help you see your situation differently, surface your own insights, and identify concrete actions you'll take before the next session. They listen carefully, sometimes challenge your thinking, and keep bringing you back to your stated goal when you drift. Between sessions, you're doing the work—trying new approaches, noticing what shifts, gathering feedback from colleagues or your team. Your coach reviews what happened, acknowledges what you learned, and builds on it.

You should expect accountability without judgment. The coach asks what you committed to and what actually happened. If you didn't do it, that's data too—worth exploring rather than glossing over. This cycle of action, reflection, and refinement is what creates lasting change. A coach who lets you off the hook isn't serving you.

What sits outside a coaching engagement

It's also worth knowing what a coach won't do. They're not your therapist if you're wrestling with mental health concerns—that needs a qualified psychologist or counsellor. They're not your boss, so they're not evaluating your performance for promotion or pay. They're not a substitute for learning new technical skills; coaching works alongside training, not instead of it. And they're not there to fix your organisation's systems or culture, though coaching might help you lead within imperfect ones more effectively.

The wind-down and beyond

Toward the end of your engagement, a skilled coach begins stepping back deliberately. You're applying your learning without prompting. Sessions might move to check-ins rather than deep dives. Some engagements have a formal closing meeting where you reflect on what's shifted, what you'll keep doing, and how you'll sustain progress without weekly sessions. Others taper more gradually. Either way, the relationship shouldn't feel like a cliff edge where you're suddenly without support. Some coaches offer a follow-up session months later, or you revisit coaching when a new challenge emerges.

When you're vetting coaches, listen for this level of structure and intentionality in how they describe their process. Ask about their approach to measurement and what they do in the early sessions. If they're vague or promise fast fixes, that's a sign. The coaches worth your time can walk you through exactly what the engagement will look like, why each phase matters, and how you'll know it's working. Strove's verified coaches can articulate this clearly—it's worth finding someone who does before you commit your time and resources.