Most clients don’t quit a program in a session. They quit in the quiet days between sessions, when the motivation you built together slowly leaks out and the old story creeps back in. A short, well-timed message can close that gap, but writing one that feels personal instead of canned takes effort you don’t always have at 9pm on a Tuesday.
This prompt writes a coaching encouragement message that meets your client exactly where you left them: it names a real moment from the last session, reconnects them to this week’s step, and sounds like you, not a customer-service bot. By the end of this page you’ll also understand why it lands, so the messages you send get sharper every time.
When to use this
- Mid-program, when a client is between sessions and you want to keep momentum without hovering.
- After a session where someone was vulnerable or had a breakthrough you don’t want to lose.
- When a client committed to a specific action and you want to reinforce it midweek.
- When you sense someone is wobbling, discouraged, or going quiet, and a generic ‘how’s it going?’ won’t cut it.
The prompt
Copy this whole block into ChatGPT, Claude, or Gemini:
You are an experienced coach who writes short, sincere check-in messages that keep clients motivated between sessions. Your job is to write ONE encouragement message I can send my client today.
Before writing, ask me up to 3 clarifying questions if anything below is unclear or missing. Otherwise, proceed.
CONTEXT
- Client's name: {{CLIENT_NAME}}
- What we're working on: {{PROGRAM_FOCUS}}
- A specific win or moment from our last session: {{LAST_SESSION_WIN}}
- What they committed to this week: {{THIS_WEEK_GOAL}}
- Where they are emotionally right now: {{CLIENT_STATE}}
- Channel I'll send it on: {{CHANNEL}}
- My tone: {{TONE}}
TASK
Write ONE between-session encouragement message that:
1. Opens by naming something specific and true from our last session, so it never feels like a template.
2. Reflects back one concrete strength or piece of progress I can be proud of on their behalf.
3. Gently reconnects them to this week's goal as a small, doable next step, not a verdict on their worth.
4. Closes with a low-pressure line that invites a reply but does not demand one.
5. Sounds like a real human coach texting a client, matched to my tone.
CONSTRAINTS
- Fit the channel: keep it short and skimmable for {{CHANNEL}} (3-6 short sentences or lines).
- No toxic positivity, no 'you've got this!' filler, no exclamation overload.
- Do not invent results, numbers, or events that I did not give you.
- No emojis unless my tone is casual.
After the message, give me 2 alternative opening lines I could swap in, and one shorter one-line version for a quick nudge.
How to customize it
Replace the seven {{VARIABLES}} before you send it:
| Variable | What to put | Example |
|---|---|---|
{{CLIENT_NAME}} |
Your client’s first name | Maya |
{{PROGRAM_FOCUS}} |
What you’re coaching them on | building a consistent strength-training habit |
{{LAST_SESSION_WIN}} |
A specific moment from last session | she admitted she skips workouts out of fear of doing them ‘wrong’ |
{{THIS_WEEK_GOAL}} |
What they committed to | two 20-minute beginner sessions, form over intensity |
{{CLIENT_STATE}} |
Where they are emotionally | motivated but easily discouraged when results feel slow |
{{CHANNEL}} |
Where you’ll send it | |
{{TONE}} |
How you sound | warm, encouraging, no pressure |
The single most important field is {{LAST_SESSION_WIN}}. A real, specific detail is what turns a forgettable message into one your client screenshots.
See it in action (full example)
Here is the exact prompt, filled in for a health coach. This is the whole input, nothing hidden:
You are an experienced coach who writes short, sincere check-in messages that keep clients motivated between sessions. Your job is to write ONE encouragement message I can send my client today.
Before writing, ask me up to 3 clarifying questions if anything below is unclear or missing. Otherwise, proceed.
CONTEXT
- Client's name: Maya
- What we're working on: building a consistent strength-training habit after years of all-or-nothing dieting
- A specific win or moment from our last session: she admitted she's been skipping workouts out of fear of doing them 'wrong', and we reframed the first set as a 'rehearsal' that can't be failed
- What they committed to this week: two 20-minute beginner strength sessions, form over intensity
- Where they are emotionally right now: motivated but easily discouraged when results feel slow
- Channel I'll send it on: WhatsApp
- My tone: warm, encouraging, no pressure
TASK
Write ONE between-session encouragement message... [rest of the prompt unchanged]
And here is the complete output the model returns:
Hi Maya, I’ve been thinking about something you said last week.
You told me you’ve been skipping workouts because you were scared of doing them ‘wrong’. The fact that you could name that out loud is a bigger deal than any set you’ll lift this week, that took real honesty.
Remember, the plan this week is just two 20-minute sessions, and every single one of them is a rehearsal. There’s no wrong version of showing up.
No need to reply, but if you do one and want to tell me how it felt, I’d love to hear about it.
2 alternative opening lines: 1. “Hi Maya, quick note between sessions, no homework attached.” 2. “Hey Maya, one thing from last week has stuck with me and I wanted to send it your way.”
One-line nudge version: “Hi Maya, just a reminder that this week’s two sessions are rehearsals, not tests, you can’t do them wrong. Cheering you on.”
That is ready to send. A five-second tweak to sound exactly like you, and it’s in her inbox.
Why this works
Three LLM principles are doing the heavy lifting here. Learn them and every prompt you write gets better:
- Role priming. The opening line (“You are an experienced coach who writes short, sincere check-in messages”) tells the model which slice of its training to draw from. “Write a motivational message” pulls the bland, greeting-card average of the internet. Casting it as an experienced coach pulls warmer, more grounded language. Always assign a role first.
- Specificity in, specificity out. The model can only be as personal as your input. The
{{LAST_SESSION_WIN}}field is the engine of the whole thing: feed it the vague “she’s doing okay” and you get a generic note; feed it “she admitted she skips workouts out of fear of doing them wrong” and the message names that exact moment back to her. The personal feel you want is capped by the detail you give. - Constraints are quality control. The “no toxic positivity, no ‘you’ve got this!’ filler” and “do not invent results” lines aren’t decoration, each one removes a specific way AI encouragement goes wrong: hollow cheerleading and made-up progress. Telling the model what NOT to do is as powerful as telling it what to do. And the “ask me up to 3 clarifying questions first” line lets it fill gaps by asking rather than guessing, which is the single biggest fix for messages that sound generic.
Do this now
- Pick one client who’s between sessions right now.
- Copy the prompt above into ChatGPT or Claude.
- Fill in the seven variables, especially one true, specific moment from your last session.
- Send it. If the model asks clarifying questions, answer them, then tweak the message into your own voice and hit send today.
Pro tips
- Mine your session notes. The best
{{LAST_SESSION_WIN}}is a near-quote of something the client actually said. Keep a one-line note after each session and you’ll never start from blank. - Keep the clarifying-questions line. It’s the difference between a message that sounds like you and one that sounds like every coach with a ChatGPT tab open.
- Match the channel. A WhatsApp note and a formal email need different lengths and rhythm. Always set
{{CHANNEL}}so the model formats accordingly. - Never auto-send. Read it once for truth and tone before it goes out. The prompt does the drafting; your judgment makes it land.
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