The Customer Success Check-In Prompt Pack

Write a short, warm check-in message from [YOUR NAME] at [COMPANY NAME] to a new customer named [CUSTOMER FIRST NAME] who signed up [NUMBER] days ago. Their stated goal when signing up was [CUSTOMER'S STATED GOAL, e.g. 'reduce time spent on client reporting']. They are on the [PLAN NAME] plan. The message should: (1) reference their specific goal by name, not in generic terms, (2) ask one focused question about whether they have hit a first milestone related to that goal, (3) offer one specific resource that helps with that exact goal, such as [NAME OF RELEVANT GUIDE, TEMPLATE, OR FEATURE]. Keep it under 80 words. No subject line needed. Do not use the phrase 'just checking in'. Do not start with 'I hope this finds you well'. Tone: direct, warm, as if from a real person who read their sign-up notes.

Write a check-in email from [YOUR NAME] to [CUSTOMER FIRST NAME] who joined [COMPANY NAME] [NUMBER] days ago. They signed up wanting to [CUSTOMER'S STATED GOAL]. Usage data shows they have [COMPLETED / NOT YET COMPLETED] the following step: [SPECIFIC SETUP STEP, e.g. 'connected their first data source']. If they have completed it: acknowledge that win, ask what they are working on next related to their goal. If they have not completed it: do not shame them, instead name the step simply and ask if they ran into anything. Either way: offer a 15-minute call to walk through it if useful. Keep the email under 100 words. Subject line: '[CUSTOMER FIRST NAME], quick one' or similar. No em dashes. No generic praise.

Write a brief celebration message from [YOUR NAME] at [COMPANY NAME] to [CUSTOMER FIRST NAME]. They have just completed [SPECIFIC MILESTONE, e.g. 'their first automated workflow' or 'their first report export']. When they signed up, their goal was [CUSTOMER'S STATED GOAL]. The message should: (1) name the milestone they completed, (2) connect it directly to the goal they came in with, so they feel the progress, (3) tee up the natural next step, which is [NEXT LOGICAL STEP IN THE PRODUCT]. Under 75 words. Enthusiastic but not over the top. No exclamation points after the first sentence.

Write a one-month check-in email from [YOUR NAME] to [CUSTOMER FIRST NAME] at [CUSTOMER COMPANY NAME]. They joined [COMPANY NAME] [NUMBER] weeks ago. Their original goal was [CUSTOMER'S STATED GOAL]. At the time they said their biggest challenge was [CUSTOMER'S STATED CHALLENGE]. Structure the email as: (1) one sentence acknowledging the month, (2) one focused question about whether they have made progress on [SPECIFIC METRIC OR OUTCOME TIED TO THEIR GOAL, e.g. 'hours saved per week' or 'number of leads captured'], (3) one offer, either a tip, a resource, or a short call. Keep it under 120 words. Subject line should reference their goal, not the date. Tone: peer-to-peer, not corporate.

Write a quarterly check-in email from [YOUR NAME] at [COMPANY NAME] to [CUSTOMER FIRST NAME]. It has been [NUMBER] months since they started. Their original goal was [CUSTOMER'S STATED GOAL AT SIGN-UP]. The message should: (1) acknowledge that goals shift, (2) ask what they are most focused on in the next 90 days, specifically in relation to [BROAD OUTCOME AREA, e.g. 'client delivery', 'revenue growth', 'team efficiency'], (3) tell them you want to make sure the way they are using [PRODUCT/SERVICE NAME] actually fits where they are now. Keep it under 130 words. This is a genuine question, not a renewal prompt. Do not mention pricing or plans.

Write a re-engagement message from [YOUR NAME] to [CUSTOMER FIRST NAME] who has been on [PRODUCT/SERVICE NAME] for [NUMBER] months but has not logged in or engaged in [NUMBER] weeks. Their goal when they joined was [CUSTOMER'S STATED GOAL]. Do not open with 'we noticed you have not been active'. Instead: open by naming their original goal, ask one question about whether that goal has changed or whether something got in the way, and offer one concrete way you can help in the next two weeks. Keep it under 100 words. Tone: genuinely curious, not sales-y. No urgency language. No 'limited time' framing.

Write a check-in email from [YOUR NAME] to [DECISION MAKER FIRST NAME], who is the [TITLE, e.g. CEO, Director, Founder] at [CUSTOMER COMPANY NAME]. They approved the purchase of [PRODUCT/SERVICE NAME] [NUMBER] weeks ago. The goal they bought it to achieve was [BUSINESS GOAL, e.g. 'reduce time spent on manual reporting by 50%']. They may not be the day-to-day user. The message should: (1) speak at the business outcome level, not the feature level, (2) ask whether [PRODUCT/SERVICE NAME] is moving the needle on that goal from their vantage point, (3) offer a 20-minute business review call. Under 120 words. No product jargon. No walk-through offers. This person wants results, not tutorials.

Write a check-in message from [YOUR NAME] to [USER FIRST NAME], who is the main user of [PRODUCT/SERVICE NAME] at [CUSTOMER COMPANY NAME]. Their role is [USER ROLE, e.g. marketing manager, operations lead, VA]. The outcome their team is working toward is [TEAM'S STATED GOAL]. The message should: (1) acknowledge that they are the person doing the actual work, (2) ask what is taking the most time or feeling most clunky right now, (3) offer one specific tip or shortcut relevant to [MOST-USED FEATURE OR WORKFLOW BASED ON THEIR ROLE]. Under 100 words. Casual and direct. This is peer-to-peer, not account manager to user.

Write a check-in email from [YOUR NAME] at [COMPANY NAME] to [MAIN CONTACT FIRST NAME], who manages a team of [NUMBER] people using [PRODUCT/SERVICE NAME]. The team's goal is [SHARED TEAM GOAL]. The message should: (1) ask how the broader team is getting on, not just the main contact, (2) offer to run a 30-minute team Q and A session to help everyone get more out of the tool, (3) ask if there is a use case their team is trying to solve that they have not figured out yet. Under 120 words. Position this as a hands-on offer, not a generic check-in.

Write a short message from [YOUR NAME] to [CUSTOMER FIRST NAME] triggered by the fact that they just used [SPECIFIC FEATURE NAME] for the first time. Their goal when they signed up was [CUSTOMER'S STATED GOAL]. This feature is relevant because [ONE SENTENCE EXPLAINING HOW THIS FEATURE CONNECTS TO THEIR GOAL]. The message should: (1) acknowledge the specific feature they just used, not in a surveillance-y way but in a 'glad you found it' way, (2) give one tip for getting more from it, (3) ask if they have any questions on the back of using it. Under 80 words. Subject line: something action-specific, not generic. No corporate tone.

Write a check-in from [YOUR NAME] to [CUSTOMER FIRST NAME] at [CUSTOMER COMPANY NAME]. They have had a significant increase in their usage of [PRODUCT/SERVICE NAME] in the past [NUMBER] days, specifically [DESCRIBE THE SPIKE, e.g. 'they have created 3x more workflows than usual' or 'their team has added 4 new users']. Their goal is [CUSTOMER'S STATED GOAL]. The message should: (1) acknowledge the activity without making them feel tracked, phrase it as 'looks like things are picking up on your end', (2) ask what is driving it, (3) offer to make sure their setup scales well if they are in a growth phase. Under 110 words. This is a check-in, not an upsell prompt.

Write a re-engagement message from [YOUR NAME] to [CUSTOMER FIRST NAME]. They have been a customer for [NUMBER] months. They have not used [PRODUCT/SERVICE NAME] in [NUMBER] weeks. Do not open with guilt or urgency. Instead: (1) lead with the goal they originally signed up for, (2) ask a simple yes or no question about whether that goal is still live for them, (3) if it is, offer one specific thing you will do together in the next call or message to get them moving. If the goal has shifted, say you want to make sure the product is still the right fit. Under 100 words. Honest. No pressure.

Write a pre-renewal check-in from [YOUR NAME] to [CUSTOMER FIRST NAME] at [CUSTOMER COMPANY NAME]. Their renewal is in [NUMBER] weeks. Do not mention the renewal date in this message. Instead: (1) open by naming a specific outcome they have achieved since joining, if you have the data use [SPECIFIC OUTCOME OR METRIC, e.g. '14 workflows automated' or '3 months of reports generated'], (2) ask what they are planning to focus on in the next [RENEWAL PERIOD, e.g. 6 or 12 months], (3) say you want to make sure [PRODUCT/SERVICE NAME] is set up to support that. Under 120 words. This is a value conversation, not a retention push.

Write a message from [YOUR NAME] to [CUSTOMER FIRST NAME] at [CUSTOMER COMPANY NAME] who is on the [CURRENT PLAN] and has been a customer for [NUMBER] months. They are hitting [DESCRIBE THE GROWTH SIGNAL, e.g. 'the upper limit of their current plan' or 'regularly using the features most relevant to teams of their size']. The message should: (1) acknowledge what they have built or achieved, (2) ask one open question about where they want to take things next in [RELEVANT AREA, e.g. 'team capacity', 'client volume', 'automation coverage'], (3) say you would like to show them what is possible at the next level if that is useful. Under 110 words. No pitch. No pricing. Just curiosity about their direction.

Write a message from [YOUR NAME] to [CUSTOMER FIRST NAME] who has just achieved [SPECIFIC OUTCOME, e.g. 'their first 100 leads captured through the platform' or 'a full quarter of automated reporting with no manual hours']. The message should: (1) celebrate that specific outcome briefly, (2) ask if they know anyone else working on the same kind of problem, and describe that person in specific terms, e.g. '[IDEAL REFERRAL PROFILE, e.g. a founder running a service business who is still doing their reporting manually]', (3) tell them what you would do for that person if they introduced you. Under 100 words. This is a genuine ask, not a referral scheme prompt.

Write a follow-up message from [YOUR NAME] to [CUSTOMER FIRST NAME] sent [NUMBER] days after a support ticket was resolved. The issue was [BRIEF DESCRIPTION OF THE ISSUE, e.g. 'an integration that was not syncing correctly']. Their goal with [PRODUCT/SERVICE NAME] is [CUSTOMER'S STATED GOAL]. The message should: (1) check that the fix is still holding, (2) ask if the issue got in the way of anything they were working toward, (3) offer to walk through the relevant workflow together if useful. Under 90 words. Do not re-apologise for the issue. Do not use the phrase 'sorry for any inconvenience'. Simply be helpful.

Write a follow-up message from [YOUR NAME] to [CUSTOMER FIRST NAME] sent [NUMBER] days after a conversation where they pushed back on [PRICING / CONTRACT TERMS / SCOPE]. The conversation ended with [BRIEF DESCRIPTION OF OUTCOME, e.g. 'they agreed to stay on the current plan for now' or 'they asked for a week to think it over']. The message should: (1) not reference the pricing conversation directly unless they brought something up that needs a response, (2) focus instead on what they are trying to achieve in [NEXT TIMEFRAME, e.g. 'this quarter'], (3) offer one concrete thing you can help with in the next two weeks. Under 100 words. No pressure. No re-pitching.

Write a message from [YOUR NAME] to [CUSTOMER FIRST NAME] who has just [PAUSED THEIR ACCOUNT / MOVED TO A LOWER PLAN]. Do not make them feel they made the wrong decision. The message should: (1) acknowledge their choice simply and without drama, (2) ask one honest question about what changed for them, either in their business or in how they were using [PRODUCT/SERVICE NAME], (3) tell them the door is open and name one specific way you would work differently with them if they came back. Under 100 words. Respectful. Short. This is a long-game message, not a save attempt.

I am going to paste raw CRM notes from a customer account below. Use these notes to write a personalised check-in email from [YOUR NAME] at [COMPANY NAME] to this customer. Requirements: (1) reference at least two specific details from the notes, their role, their goal, or a recent conversation, (2) ask one focused question about their progress toward the goal mentioned, (3) offer one relevant resource or action, (4) keep it under 120 words. Do not invent any details not in the notes. If the notes mention a pain point, reference it. If they mention a win, open with it. CRM NOTES: [PASTE CRM NOTES HERE]

I am going to paste a transcript or summary from a recent call with a customer below. Use it to write a follow-up message from [YOUR NAME] that: (1) references the most important thing they said they wanted to achieve, using their words where possible, (2) confirms any actions you said you would take, (3) names the one thing they should do next before you speak again, (4) keeps the whole message under 150 words. Do not summarise the call for them. They were there. Just confirm direction and next step. TRANSCRIPT OR SUMMARY: [PASTE HERE]

I am going to give you a table of customer data. For each row, write a personalised check-in message of under 90 words from [YOUR NAME] at [COMPANY NAME]. Each message must: (1) open by referencing that customer's specific goal or situation, not a generic opener, (2) ask one focused question relevant to where they are in their journey, (3) close with a specific offer or next step. Format each message as: Customer name, Subject line, Message body. Do not use the same opening line for any two customers. TABLE: [PASTE TABLE WITH COLUMNS: NAME, GOAL, STAGE, LAST TOUCHPOINT, ANY NOTES]

Write a check-in email from [YOUR NAME] to [CUSTOMER FIRST NAME], who is a [COACH / CONSULTANT / FRACTIONAL PROFESSIONAL] serving [THEIR CLIENT TYPE]. They came to [YOUR PRODUCT OR SERVICE] wanting to [CUSTOMER'S STATED GOAL, e.g. 'spend less time on client admin and more time on delivery']. It has been [NUMBER] weeks. The message should: (1) ask how their client work is going right now, specific to [NICHE AREA, e.g. 'onboarding new clients' or 'delivering monthly reports'], (2) connect their answer back to the goal they had for [YOUR PRODUCT OR SERVICE], (3) offer one specific shortcut or workflow tip for [THEIR MOST COMMON BOTTLENECK]. Under 110 words.

Write a check-in from [YOUR NAME] at [COMPANY NAME] to [CUSTOMER FIRST NAME] who runs an e-commerce or product business. They are using [PRODUCT OR SERVICE NAME] to [CUSTOMER'S STATED GOAL, e.g. 'automate their post-purchase email sequence' or 'reduce return processing time']. It has been [NUMBER] months. Ask: (1) how their [RELEVANT METRIC, e.g. repeat purchase rate, cart abandonment rate, fulfilment speed] is looking compared to when they started, (2) whether the [SPECIFIC FEATURE OR WORKFLOW THEY USE] is doing what they needed, (3) whether they have anything coming up, a launch, a sale, a seasonal push, where they want support. Under 110 words.

Write a check-in from [YOUR NAME] to [CUSTOMER FIRST NAME] who runs a [AGENCY TYPE OR FREELANCE DISCIPLINE, e.g. 'social media agency' or 'copywriting freelance practice']. They came to [PRODUCT OR SERVICE NAME] wanting to [CUSTOMER'S STATED GOAL, e.g. 'stop losing hours to client reporting' or 'scale without hiring']. It has been [NUMBER] months. Ask: (1) how their capacity is looking right now, (2) whether [SPECIFIC FEATURE OR PROCESS FROM YOUR PRODUCT] has made a difference to [THE SPECIFIC BOTTLENECK THEY NAMED]. Offer one idea for how they could extend what they are already doing to [ADJACENT OUTCOME, e.g. 'save another two hours a week']. Under 110 words.