This is the meat of the coaching. By now you have established clear goals, and relevant homework items at the end of the previous session.

During these sessions, start by checking in on the homework: how did things go? Was there anything they skipped that should carry over to this week’s homework? Celebrate all big and small wins!

If they skipped an item, do a little inquiry: was it because of any particular barrier? Sometimes a mental block will arise, they need to break the item down into even smaller steps, or they need to carve out dedicated time in their schedule to work on coaching focus areas and homework so that it doesn’t get lost in the scrum of day-to-day tasks.

As always, before each of these mid-point sessions ask, “What would be most helpful to walk away with by the end of today’s session?” Work with the coachee to determine, with their strategic goals in mind and any progress they have made, what the next top priority is.

Each of these sessions should start with the most pressing, important area. If they have two (or more) topics they would like to discuss, set the agenda and prioritize together. For example, “Let’s talk about your upcoming presentation first, then in the last 15 minutes we can do some brainstorming on your morning routine.”

Questions to Consider:

  • Based on their most important goals, what would most bridge the gap between where they are now and where they want to go?

  • What are the remaining stuck points?

  • What are the most important next steps to take?

  • What, if anything, is getting in the way?

  • What would help dismantle those barriers?

  • What would be most helpful to go into a detailed brainstorm on? For any stuck points, brainstorm for quantity, not quality; then narrow down.

When you are halfway through the coaching engagement, consider doing a special mid-point check-in session. As you approach the last session, give them a heads up that the final session will be guided reflection questions for you to discuss together to reflect on the entire coaching engagement.

Coach Preparation

  • Review the coaching notes and the prior week’s homework

  • With their strategic goals in mind, have one or two topics as a backup to discuss in case they come to the call without a clear idea of what they want to discuss.

  • Ask them at the start: what would be most helpful?

  • Start the session by reviewing and reflecting on the previous week’s homework


The homework for these sessions will be highly specific to the individual and his or her goals. Work with them to decide what 3-5 next actions would most move them forward toward the strategic 3-month goals you set together.