What Would Make This Conversation Worthwhile?

Every coach has had this moment: partway into a session, you're listening to a client's story about something that came up for them spontaneously and you realize you don't actually know what they want to take away from the conversation.

This isn't a failure on your part. Sometimes clients come in fired up and launch straight into whatever's grabbed their attention that week, or they want to use you to get something off their chest. But that still begs the question of how they're hoping you can help and what difference the session will make for them.

Think of hopping into a taxi. The driver can't even pull away from the curb without knowing where you want to go. Coaching works the same way.

The solution is to stop and ask, even mid-story: “So how are you hoping I can help? What would tell you our talking had been worthwhile?”

If the answer is vague (“I just want to figure things out”), stay with it: “What would figuring things out look like? Imagine our talking had helped you figure things out: what would be different?” Get specific before moving on.

And if it turns out that you lose the thread again later, simply check back in: “Is this still what would be helpful for you today?”

Every coach has had this moment. You're a few minutes into a session. The client has told you about their week, what's been hard, what they've tried. And you suddenly realize you have no idea what they actually want to take away from the conversation. You don't know how you can help make a difference for them.

This isn't a failure, and it happens to everyone. Sometimes clients come in fired up and launch straight into whatever's grabbed their attention that week. Sometimes they get carried away in a story that has nothing to do with why they booked the session. Either way, you end up listening and maybe asking questions but the conversation doesn't move forward, because you never established where “forward” is.

Think of hopping into a taxi. The driver can't even pull away from the curb without knowing where you want to go. Coaching works the same way.

This is as true in a five-minute patient encounter as it is in a fifty-minute coaching session.

So, as soon as you realize the session has no target to aim for, stop and ask. It can feel awkward, interrupting someone mid-story, admitting you're not sure where things should be headed. You don't have to pretend you've been on track the whole time. Just ask:

You're not done until you can picture what “helpful” and “worthwhile” would actually look like by the end of the session.

Listen for something specific and concrete. If the answer is vague, “I just want to figure things out,” stick with it longer:

Helping the client define what they want to walk away with is the first task for the start of every session, before anything else.

And if it turns out that you lose the thread again later, simply check back in: “Is this still what would be helpful for you today?” That awkward moment of stopping and asking is worth it every time.