North star: How can I help this person feel more confident and capable about their money goals or challenges?
"This session is really about getting a sense of where things are at for you — what's working, what's unclear, and anything you'd like to feel more confident or intentional about. We can take it in whatever direction is most useful for you."
Lower the stakes before the conversation begins. The member may be nervous or unsure what coaching even is. This opening tells them: there is no wrong answer here.
"What prompted you to book this session?"
"What's been on your mind financially lately?"
"Is there something you've been wanting to get clarity on or improve?"
"Or something that's been sitting in the background for a while?"
Do not rush. The thing they say after a pause is often the real thing. Let them find their own words — you are creating space for them to say the thing they might not have said to anyone else.
"How does your day-to-day money management feel at the moment?"
"Do you feel like it's working the way you want it to?"
"Do you feel like you're making proactive decisions, or more reacting as things come up?"
"When you're making financial decisions, how do you usually approach them?"
"Do you tend to feel confident in those decisions, or do you find yourself second-guessing?"
"Are there any areas you tend to avoid or put off?"
"Or things that take more energy than you feel they should?"
Notice the language they use. Avoidance, anxiety, embarrassment, the need for control — these patterns reveal themselves in how people talk about money. Hold what you observe. You are building the picture that Coaching Insights will later hold for you.
"When you think about where you're heading financially — what feels clear or on track?"
"And what feels less defined — or something you haven't quite got to yet?"
"Is there anything you know you should look at, but haven't yet?"
"From everything we've talked about — where do you feel there's the biggest opportunity to improve things?"
"Where would making progress have the biggest impact for you?"
Do not prescribe. Wait for them. If there is silence, let it sit. The member needs to own the priority — if they name it themselves it has far more power than if you suggest it.
"What I'm hearing is… you've got [strength / what's working]… and the main area we could focus on together is [the opportunity they named]. Does that feel right to you?"
If it does not feel right to them, adjust. Their version of the summary is the right one. This reflection makes the member feel genuinely heard and creates the shared understanding that session 2 builds on.
"A good place to start might be [simplifying / clarifying / taking one small step]."
"Rather than trying to change everything, we could start by getting really clear on [X] — so you're making decisions from a stronger base."
Progress is possible — not through doing everything at once, but through getting clear on one thing and moving from there. Give the member that feeling before you close.
"Next session, we can go a level deeper into this and start shaping how you'd want to approach it longer term."
Set any tasks — keep them light at this stage. Let the member know their session summary will come through after the session. After publishing the summary, review what the platform captured and prepare for session 2.
North star: How can I help this person feel more confident and capable about their money goals or challenges?
"What stayed with you after our last session?"
"Did anything shift — even slightly — in how you're thinking about things?"
"Or anything you noticed during the week?"
Listen before you move. The answer here often tells you more than anything from session 1. Do not re-engage on the topic immediately — honour what they bring first.
"Before we get into it — one thing I want to make sure we cover today is what working together beyond these two sessions could look like. We'll come back to that later, but I just wanted to flag it so we can make sure we get there."
That is it — then move straight on. The seed is planted. The member now knows the conversation is coming without it feeling like an ambush at the end of the session.
"Last time we identified [X] as an area to focus on. How does that feel now?"
"Is that still the most important place to focus, or has anything changed?"
This is not a formality. If the answer has shifted, follow it. Trust the member's instinct — a week of reflection sometimes changes the picture.
"Let's unpack that a bit more — what feels hardest or most unclear about this right now?"
"What have you tried so far?"
"What's worked well?"
"What hasn't quite worked the way you'd hoped?"
"When this comes up, what do you tend to do?"
"What usually gets in the way of making progress here?"
"What would 'doing this well' actually look like for you?"
"What would need to change for this to feel easier or more consistent?"
Watch for the gap between what they say they want and what they are actually doing. Do not call it out directly — hold it as a thread. This contradiction is one of the most important coaching signals.
"What are you already doing well in this area?"
"Where do you feel most confident right now?"
Especially important for aspirational members. Capability needs to be reinforced — people lose sight of what they are already doing well when they are focused on what is not working.
"If we were to focus on making meaningful progress from here — what would you want that to look like?"
"We could focus on building clarity in [X], creating structure around [Y], or mapping out [Z] — what resonates most?"
"What's come up today is really clear — you know what you're working toward, and the work to get there has real shape to it. This is exactly where a coaching plan becomes valuable, because we can map out the sessions you need, in the right order, and work through it together step by step rather than trying to do it all at once."
"From here I can build you a plan around [goal] — it gives us both a structure to work from, and you get a clear picture of where we're going and how we're going to get there."
"How does that feel as a direction?"
"What I'm noticing is that there's a lot here — and what you actually need isn't just a list of tasks, it's a proper space to work through it. Coaching works best when we have time to go beneath the surface and keep building on what we uncover, rather than starting from scratch each session."
"What I'd suggest from here is building a plan around you — not a fixed goal track, but something shaped around where you are right now and what would make the biggest difference. The AI looks at everything we've talked about across these sessions and helps me build something that's genuinely personalised to you."
"Would it be useful to explore what that could look like?"
"It sounds like you've got some real clarity from these two sessions, which is great. A lot of people feel that way at this point — and some are ready to go off and action things themselves. That's completely fine."
"The question I'd ask is: six months from now, what's the version of this where you look back and feel like you really moved the needle? Because the clarity from a conversation like this is valuable — but without something to keep you accountable and help you navigate the moments where things get hard or complicated, it can be easy to slip back into old patterns."
"I'm not suggesting you commit to anything right now. What I would suggest is that you have a look at the plan I put together for you — you'll see it in your dashboard — and if it resonates, you can start it when you're ready. Nothing locks in until you decide."
Read the room. Use one talk track — not all three. Some members will be ready immediately. Others need more time. Plant the seed and let them come to it. Do not push for a commitment in the session.
Do not quote specific dollar amounts in session. Pricing can change and the member should see their options in context on the platform. Your job is to frame the decision, not to close a sale.
"Your employer has funded your coaching — you can see how many sessions you have available in your Session Bank inside your dashboard. Starting a plan doesn't cost you anything additional — it just gives a structure to the sessions you already have access to."
"You've still got [X] sessions available through your employer package. Starting a plan now means we can make the most of those in the most structured way. If you want to continue beyond that, we can look at options when we get closer."
"Your Fast Start package covered these two sessions. From here, if you'd like to continue, the platform will show you the options when you go to start your plan — you can choose to purchase individual sessions as you go, or if you want better value and ongoing access, there's a membership option that gives you four sessions over the year, plus messaging access to me between sessions and a discount on any additional sessions you book. The options will be clear when you log in — and nothing locks in until you decide."
"I'd point you to the platform for the exact pricing — it's presented clearly when you go to start the plan and will show you what makes sense based on your situation. What I can tell you is that the membership option works out significantly better value than booking sessions individually if you want regular access."
"How does that direction feel to you?"
Confirm next steps — coaching plan, follow-up session, or continuing session by session. Set tasks. Let the member know their summary will come through after the session.