How do you fill a 50-minute coaching session?

When I first started coaching, I was terrified because I didn’t know what I was going to talk about. How did I make those minutes really, truly valuable for a client—valuable enough that they would keep coming back and refer their friends?

Over the years, I’ve come up with a simple template. It’s six questions long. I ask these same six questions to every client, every time. And they have never failed me. Now, I list all six questions in a simple pre-session worksheet I send the client 24 hours before we meet. There’s a note at the top that basically says, “I want what’s top-of-mind. Completing these questions should only take five minutes.”

I’m going to give you all six questions. They’re also perfect for one-on-one check-ins with direct reports. Here they are.

1. What were your top three wins since the last time we talked?

We all have a built-in negativity bias. We tend to focus on the problems because that’s how we come up with solutions. That kind of thinking has helped us survive for thousands of years. If your clients are business owners, that survival mindset is probably amplified. They’re trying to keep their company alive, not just themselves.

Here’s the problem: This kind of thinking doesn’t build confidence. When we focus exclusively on the negative, we find ourselves unsatisfied, demoralized, and even anxious. We need to weigh the full picture. The good is incredibly important.

Part of your job as a coach is to help clients realize that they’re winning more than they think. Only then will they be able to take on bigger challenges and scale their businesses. By asking this question first, I help them make the mental shift to realize they’re winning.

2. What is your outlook on things right now? Rate from one to five.

Think of this question like a thermometer. If you go to the doctor, they take all your vitals. This question does the same thing: It reveals how someone is really doing. Here’s how I think about that one to five rating.

  • One means, “I’m stuck. I’m feeling discouraged and overwhelmed.” You’ll be surprised how many of your clients have no one they can confess that stuck-ness to.
  • Two means, “I’m struggling. It’s three steps forward and two steps back.” Don’t we all know what that feels like?
  • Three means, “I’m making progress, but it’s slower or more difficult than I expected.” That’s true for almost everything your clients will attempt. They’ll underestimate the cost, time, and effort necessary. Expect this answer a lot.
  • Four means, “I’m making steady progress on important projects.” I want to see all my clients get here on a consistent basis, but it takes time.
  • Five means, “I love what I do.” I don’t get this often, but when I do, my clients will say, “I’m on fire!” or “I’m winning at work and succeeding at life.”

Whatever the response, normalize the struggle as part of the journey of leadership and being human.

3. What are you currently excited about?

This ia another question to shift a client’s focus. The point isn’t to minimize their struggles or problems but to realize that life is a balance of good and bad. It’s a mixed bag. In the words of Tony Robinson, “Where focus goes, energy flows.” I don’t want some of my clients’ energy to flow toward maximizing what’s working well, not just fixing what isn’t.

4. How far did you get with your commitments from our last session?

I end every session with a summary of the commitments from the last time, and I have my assistant send a reminder of those commitments 24 hours before the next session to support follow-through.

Meeting these commitments is an act of personal integrity for my clients. Can they give their word and follow through? Can they make themselves do it? Can you conform your actions to your words? It’s an invaluable skill, especially for a leader.

What happens if they didn’t follow through? I don’t shame them. I do ask, “Is this commitment still relevant?” If it is, it can stay on the commitment list. If it isn’t, get it off the list.

5. What are you currently putting off or avoiding?

This question gets to the heart of what clients need. Procrastination is frequently a sign that a problem feels too big, and helping them identify manageable steps can help them gain momentum.

6. What is at least one item you want to discuss?

I try to protect 20 minutes for this question. When I first started coaching, I’d discover that a client wouldn’t bring up what they actually wanted to talk about until the last five minutes—and I try to be disciplined about ending on time for the sake of my other commitments. But this question is essential because it’s the heart of coaching.

What do they need help with? That’s your job. If you can help them with at least one issue, it’s been a successful call. All the prior questions were to set them up to win on this issue. Your job is to help clarify exactly what they need to do to move forward.

When I first started coaching, I was worried about how to fill the time. Now I have the opposite problem. We’re racing the clock. And every coaching session feels meaningful and important, to me and to them.

If you want more insights on growing your coaching business, access my free webinar, Land More Coaching Clients, Transform Lives, and Stand Out in a Crowded Market: 5 Impactful Lessons from a 7-Figure CoachClick here to register

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