Consistency builds relationships. Regular check-ins create rhythm, trust, and momentum. They're the backbone of customer success.

When a customer says "I look forward to our monthly calls," you've created value. When they block time on their calendar and show up prepared, you've built a relationship worth protecting. When they bring their team and tough questions, you've become a trusted advisor.

But too many check-ins waste time. Generic agendas. Surface-level conversation. Box-checking exercises that neither party values. The result? Declining attendance, shortened meetings, and lost opportunities.

Great check-ins are purposeful. You come prepared with insights. You ask questions that matter. You leave with clear next steps. Both sides get value from the time invested.

Regular, valuable check-ins separate good customer success teams from great ones. They're where issues surface early, adoption accelerates, relationships deepen, and expansion opportunities emerge.

Why Check-Ins Matter

You stay connected through consistent touchpoints. The relationship moves from "vendor contact" to "trusted partner" through accumulated interactions over time. When issues arise, you've got goodwill in the bank to draw on.

Problems get caught when they're still small. Usage drops before they become concerning. Team challenges before they impact adoption. Technical hiccups before they frustrate users. Budget concerns before renewal risk. Champion changes before knowledge loss.

A simple "How's everything going?" in a regular check-in surfaces issues that never become support tickets but matter greatly.

You track progress in real-time instead of discovering problems months later. Are they using what they bought? Getting value? What's working well? What needs attention? Where can they optimize? You spot opportunities and challenges through the lens of actual usage.

Learning happens naturally when you show up regularly. You share tips relevant to their usage, introduce features they're not leveraging, answer questions as they arise, and celebrate wins and milestones. Ongoing learning beats one-time training every time.

Growth often starts in casual check-in conversations. New teams that could benefit. Additional use cases emerging. Features they need but don't have. Integrations that would add value. Strategic initiatives you can support. You hear these things because you're there consistently.

Finding the Right Cadence

Balance value and resource by segment. Your enterprise accounts need weekly or bi-weekly touchpoints with a mix of 30-45 minute calls and email check-ins, plus monthly structured meetings and quarterly business reviews.

Mid-market customers typically get bi-weekly or monthly 30-minute calls with quarterly formal reviews and email check-ins between calls. SMB accounts work well with monthly 15-20 minute calls and quarterly check-ins supplemented by email-based touches.

For tech-touch segments, think automated email sequences, in-app check-ins and tips, office hours availability, and surveys for feedback.

Adjust frequency by journey stage. During onboarding (weeks 1-8), check in weekly to ensure success. In early adoption (months 2-6), shift to bi-weekly or monthly to maintain momentum. Once they hit maturity (month 6+), monthly or quarterly works for maintenance. Pre-renewal (90 days out), increase back to bi-weekly or weekly.

Both scheduled and event-triggered touchpoints matter. Scheduled creates consistency and predictability—"We always connect the first Tuesday of the month." Event-triggered responds to signals—"I noticed usage dropped last week. Let's connect." Combine both for comprehensive engagement.

Respect customer preferences. Ask how often they want to connect. Offer calendar time versus on-demand availability. Respect their communication preferences. Adjust based on engagement levels. Make it easy to reschedule when needed.

"What cadence works best for you? Monthly calls? Bi-weekly? More email-based?" Let them guide the rhythm.

And be realistic about capacity. CSM-to-customer ratios determine feasible frequency. Portfolio size affects touch intensity. Plan for team coverage during vacations and overload periods. Use automation for scaled segments. Have clear prioritization when capacity is limited.

Don't commit to cadences you can't maintain consistently.

Different Types of Check-Ins

Quick pulse checks take 15 minutes for a fast health check, answering burning questions, and maintaining rhythm. These work great as phone or video calls with a casual, focused format. How's it going? Any issues or questions? Quick tip or update. Next steps. Use these for frequent touchpoints with busy customers between deeper meetings.

Your workhorse is the standard 30-minute check-in. This gives you time for a comprehensive update, usage review, and two-way discussion. Plan for video calls with a balanced structure and collaborative tone. Spend 5 minutes following up from last time, 10 minutes on usage and progress review, 10 minutes on customer questions and discussion, and 5 minutes on next steps and planning. This cadence works for regular touchpoints with most customer segments.

Deep dives run 60 minutes when you need to solve complex challenges, do strategic planning, or work on optimization. These are video calls with screen sharing, workshop-style format, and multiple stakeholders. Focus on one specific topic or challenge. Do detailed analysis and discussion. Work collaboratively on problem-solving. Create an action plan together. Schedule these for addressing specific needs, launching initiatives, or working on optimization projects.

Quarterly business reviews are formal QBRs for strategic alignment. These provide big-picture assessment, value demonstration, and future planning. Structure it as a presentation plus discussion with executive attendance and formal materials. Review the quarter's results and achievements. Assess current state. Plan forward with goals. Have strategic discussion. These work best for enterprise and mid-market accounts when you want to elevate the relationship.

Don't forget ad-hoc touchpoints for specific needs. Address immediate needs or capitalize on opportune moments with flexible format based on what's needed. Schedule these for issue resolution, feature releases, customer requests, or expansion discussions.

Preparing for the Call

Spend 5-10 minutes before every check-in reviewing customer data and health. Look at current health score and trends, recent activity and login patterns, feature usage and adoption rates, support ticket history, and team member engagement. This prep time makes the call 10x more valuable.

Recent activity review identifies your talking points. What are they using heavily? What have they not touched? Any concerning patterns? Positive trends to celebrate? Opportunities to highlight?

Come with specifics: "I noticed your sales team logged in 45 times last week, but marketing hasn't logged in yet. What's going on there?"

Check previous action item status to ensure follow-through. Did we deliver what we promised? Did they complete their commitments? What's still pending? What needs to be addressed? Show that you remember and follow through. Build credibility through consistency.

Identify discussion topics that create value. Think about questions they might have based on usage, tips relevant to their patterns, features they should explore, upcoming releases they'll care about, and industry insights applicable to them. Don't just ask "how's it going?" Come with something valuable to share.

Have relevant materials ready. Usage summary or dashboard. Relevant documentation or resources. Feature demos if appropriate. Case studies or examples. Notes from last conversation. Have it ready to share or reference, but don't make it a presentation.

Structuring the Conversation

Start human for 2-3 minutes. Ask about them, their work, their company. Build connection before diving into business.

"How was the product launch last week? I know your team's been working hard on that."

Make it genuine. Remember details. Care about them as people.

Then spend 5-8 minutes on progress since last check-in. Review what's happened since you last spoke: action items completed, changes or improvements, wins or milestones, challenges encountered. Celebrate progress. Acknowledge effort. Keep momentum.

Current usage and adoption takes 8-10 minutes. Discuss what's happening now:

"I looked at your usage data before our call. Your team is really maximizing [feature]. That's great. I noticed [other area] is light. Is that intentional, or is there a challenge there?"

Make data conversational, not confrontational.

Open 8-10 minutes for their questions, issues, or concerns:

"What questions have come up since we last talked?" "Any frustrations or challenges I should know about?" "Is there anything keeping you from getting full value?"

Listen more than you talk. This is their time.

Use 5-7 minutes to add value proactively with tips, best practices, or education:

"Based on how you're using [feature], here's a tip that other customers find valuable..." "Have you seen [recent release]? Given your use case, I think it could help with [specific need]."

Make it relevant to them specifically. Not generic product updates.

Finish with 3-5 minutes creating clear commitments for next steps and action items. What will you do? What will they do? When will it happen? When will you connect next?

"So I'll send you the integration guide by Thursday, you'll review it with your team next week, and we'll reconnect on the 15th to see how it went. Sound good?"

Getting Better at Check-Ins

Aim for a 60/40 or 70/30 split in their favor. You're there to understand their world, not pitch yours. Ask questions. Pause after asking. Let silence work. Don't fill every gap.

Open-ended questions unlock valuable information.

Instead of asking "Is everything working okay?" (which gets you yes/no), ask "What's working well, and where are you hitting friction?" (which gets you a discussion).

Instead of "Do you have any questions?" (usually gets "No"), ask "What questions have come up for your team?" (gets specifics).

Instead of "Are you happy?" (too vague), ask "How is the product helping you achieve [their specific goal]?" (gets concrete answers).

Take notes during or immediately after the call, before details fade. Capture key discussion points, action items with owners, customer feedback and sentiment, concerns or risks surfaced, opportunities identified, and next steps with timing.

Confirm understanding to prevent miscommunication:

"Let me make sure I've got this right. You're saying [summary]. Is that accurate?"

"So the main challenge is [issue], and you'd like us to [request]. Do I have that correct?"

Show you're listening. Verify alignment.

Make commitments specific. Not "We'll look into that." Instead: "I'll check with engineering and email you their response by Friday."

Not "You should explore that feature." Instead: "I'll send you a 3-minute video on how to set up that automation, and we'll review it together on our next call."

Make commitments you can keep. Then keep them.

Don't end with "we'll talk soon." Schedule it: "Let's get our next call on the calendar. How's the first week of March?" Consistent cadence beats sporadic outreach every time.

Questions Worth Asking

"How is the product working for you?" is open-ended and invites honest feedback. It surfaces both positives and negatives. Follow up with "What's working particularly well? Where do you wish it worked differently?"

"What's changed in your business?" uncovers context that affects their needs. Team changes, priority shifts, new initiatives, budget situations, strategic direction. Changes create both risks and opportunities.

"Are you seeing the value you expected?" gets to ROI and satisfaction. Are they achieving their goals? What does success look like to them? Where are they exceeding or missing expectations? If not seeing expected value, you need to know immediately.

"What challenges are you facing?" invites problem-sharing. With the product specifically, in their business generally, with their team or processes. You can't help if you don't know what they're struggling with.

"What features are you curious about?" reveals interest and opportunities. Natural expansion discussions, education opportunities, optimization possibilities. Let them pull information rather than you pushing it.

"How can we better support you?" gives direct feedback opportunity. Communication preferences, resource needs, relationship satisfaction, unmet needs. Shows you care about improving the partnership.

After the Call

Document immediately after every call. Log call date and attendees, key discussion summary, customer sentiment and health signals, issues or concerns raised, opportunities identified, action items (yours and theirs), and next touchpoint scheduled. Make it searchable and useful for anyone who needs context later.

Track action items to ensure accountability. Log them in your CRM or task system. Set reminders for follow-through. Track customer commitments. Update status as completed. Highlight blockers or delays. Never let action items fall through cracks.

Share relevant resources quickly. Same day or next day, send documentation or guides mentioned, video tutorials or demos, case studies or examples, product update notes, and contact information for referrals. Strike while interest is hot.

Coordinate internally when needed. Alert the account team to opportunities. Escalate issues to support or product. Share feedback with relevant teams. Request help from specialists. Update forecasts based on conversations. Check-ins inform your whole company's engagement strategy.

Follow through on commitments to build credibility. Do what you said you'd do when you said you'd do it. Update customers if timelines change. Proactively communicate progress. Over-deliver when possible. Reliability is the foundation of trust.

Scaling Beyond One-to-One

You can't have live calls with everyone. Automation makes consistency possible for low-touch segments: automated email check-ins with response tracking, in-app messages and tips, usage-based outreach triggers, survey and feedback automation, and self-service resource recommendations. Technology enables reach beyond human capacity.

Email-based check-ins work for scaled segments. Send monthly or quarterly emails that summarize their usage trends, highlight opportunities, share relevant resources, ask specific questions, and offer easy ways to respond or book time. Make one-to-many feel one-to-one through personalization.

Use survey and feedback tools to gather insights efficiently. NPS surveys at key milestones. Feature feedback requests. Health check questionnaires. Preference centers. Quarterly satisfaction surveys. You get structured feedback at scale.

Office hours and group sessions create efficiency. Weekly office hours customers can drop into, monthly user group meetings, quarterly training webinars, topic-specific workshops, and community discussions give you one-to-many engagement that still feels personal.

Self-service resources empower customers to "check in" on their own terms. Knowledge base and documentation, video library, community forums, in-app help and guides, and chatbots for common questions let customers get help when they need it.

A Real Example

Here's what a good check-in looks like in practice.

Sarah is a CSM for a project management tool. She's about to have her monthly check-in with TechStart, a 50-person startup using the product for their engineering and product teams.

Before the call, she spends 7 minutes reviewing their data. She notices engineering is using the product heavily (80 logins last week), but the product team barely touched it (5 logins total). She also sees they've started using the time tracking feature, which wasn't part of their initial setup. Previous action items: she was supposed to send them the API documentation (done), and they were going to add three more users (not done yet).

The call starts at 2pm. Sarah opens with "Hey Alex, how did your product launch go last week? I saw on LinkedIn that you shipped the new mobile features."

Alex lights up. "It went great! We had a few last-minute bugs, but the team pulled together. Actually, that's part of why we turned on time tracking—we wanted to see where the crunch time was happening."

"That's smart," Sarah says. "I noticed you started using that feature. How's it working? I've got a couple tips if you want them."

They spend a few minutes talking about time tracking. Sarah shares how another customer uses it for sprint planning. Then she shifts: "I also noticed your product team isn't logging in much. What's going on there?"

Alex sighs. "Yeah, they're still in Trello. They keep saying they'll switch, but it hasn't happened. I think they're just comfortable with what they know."

"Want to do a quick onboarding session with them? Sometimes having a CSM walk them through it makes the switch easier. I've got 30 minutes next Tuesday if that works."

They schedule it. Sarah then asks, "What else is coming up for you? Any big projects or priorities I should know about?"

Alex mentions they're hiring 10 more engineers in Q2. Sarah's ears perk up. "That's exciting. Do you want to chat about how to onboard that many people at once? I've got some templates that might help."

They wrap up after 28 minutes. Sarah will send the onboarding templates today, schedule the product team session for Tuesday, and they'll reconnect in three weeks to see how the expanded team is doing.

That's what a good check-in looks like. Prepared. Conversational. Valuable. Specific next steps. Both sides got something from it.

Templates and Resources

Cadence Planning Matrix

Segment During Onboarding Early Adoption Maturity Pre-Renewal
Enterprise Weekly calls (30 min) Bi-weekly calls (30 min) Monthly calls (30-45 min) + Quarterly QBRs Bi-weekly calls (30 min)
Mid-Market Bi-weekly calls (20 min) Monthly calls (30 min) Monthly or bi-monthly calls (30 min) + Quarterly reviews Monthly calls (30 min)
SMB Weekly email + optional calls Bi-weekly email + monthly calls (20 min) Monthly email + quarterly calls (20 min) Bi-weekly email + monthly calls
Tech-Touch Automated emails 2x/week Automated weekly emails Automated monthly emails Automated bi-weekly emails

Standard Check-In Agenda Template

Pre-Call Preparation Checklist:

  • Review health score and recent trends
  • Check usage data for patterns
  • Review previous call notes and action items
  • Identify 2-3 relevant tips or insights
  • Prepare any materials or resources

Call Structure (30 minutes):

Opening (3 min)

  • Personal check-in and relationship building
  • Agenda confirmation

Follow-Up (5 min)

  • Action items from last call
  • Progress on commitments

Usage Review (8 min)

  • Current usage patterns and adoption
  • Wins and positive trends
  • Areas of concern or opportunity

Customer Discussion (10 min)

  • Their questions and needs
  • Challenges they're facing
  • Changes in their business
  • Feedback and suggestions

Value-Add (4 min)

  • Relevant tip or best practice
  • Feature highlight based on their needs
  • Resource or content sharing

Next Steps (3 min)

  • Action items (who, what, when)
  • Schedule next check-in
  • Confirm communication plan

Question Bank by Topic

Usage and Adoption:

  • How is your team finding the [feature/product] so far?
  • What workflows are working really well?
  • Where are you running into friction or challenges?
  • Are there features you're curious about but haven't explored yet?

Value and ROI:

  • What wins have you seen since we last talked?
  • How is this helping you achieve [their stated goal]?
  • Are you tracking any metrics that show impact?
  • What would make this even more valuable for you?

Challenges and Support:

  • What questions have come up for your team?
  • Is there anything blocking you from getting full value?
  • What's the biggest challenge you're facing right now?
  • How can I better support you?

Relationship and Satisfaction:

  • How do you feel about the partnership overall?
  • Is our communication cadence working for you?
  • What could we be doing better?
  • Is there anything I should know about your experience?

Future and Strategy:

  • What's on your roadmap for the next quarter?
  • How do you see your usage evolving?
  • Are there other teams that could benefit?
  • What features or capabilities would be most valuable next?

Documentation Template (CRM)

Check-In Summary

Date: [Date of call] Attendees: [Customer names and roles] + [Your name] Type: [Standard check-in / Quick pulse / Deep dive] Duration: [Actual time]

Summary: [2-3 sentence overview of call]

Key Discussion Points:

  • [Point 1]
  • [Point 2]
  • [Point 3]

Health Signals:

  • Overall sentiment: [Positive / Neutral / Concerning]
  • Adoption progress: [On track / Needs attention / Strong]
  • Relationship strength: [Strong / Moderate / At risk]

Issues/Concerns:

  • [Any concerns raised]

Opportunities:

  • [Expansion or optimization opportunities]

Action Items:

  • [Action item 1] - Owner: [Name] - Due: [Date]
  • [Action item 2] - Owner: [Name] - Due: [Date]

Next Touchpoint:

  • Scheduled for: [Date and time]
  • Purpose: [Standard check-in / Specific topic]

Regular check-ins are the heartbeat of customer success. They create consistency, build trust, surface issues early, and drive ongoing value. When done well, they're the meetings customers actually want to attend.

Make every check-in count. Come prepared. Listen actively. Add value. Follow through. That's how you turn routine touchpoints into relationship-building moments.