This is Part 3 of 3 posts addressing how to improve your coaching skills by Marley Wagner, head of customer success programs and strategy at EverHealth. Read Part 1: How to coach CSMs who solve problems. and Part 2: Decision boundaries: Creating guardrails that help CSMs improve customer experience.
Quick summary: A coaching culture builds in stages. Start with habits in the first 30-60 days, turning customer situations into coaching moments and recognizing judgment as well as results.
Building a coaching culture doesn’t happen overnight. It requires a deliberate progression. This roadmap covers what to build first and what success should look like at six months. The first 30-60 days involve building strong coaching habits. Then your work shifts to building and sustaining a strong coaching culture.
30-60 days: Build coaching habits.
You won’t overhaul your team’s culture in this short timeframe, but you will establish some core practices that make coaching feel natural.
1. Turn customer situations into coaching opportunities.
The good news: your best coaching material already exists. Review renewal conversations, QBRs and executive business reviews (EBRs), difficult customer emails, angry customer calls and executive conversations.
Let your CSMs do the work. Ask questions and set the stage for them to learn and lead. Things like: “What message are you trying to communicate?” “What do you think the customer is looking for?” “I’ll join, but you’re leading.”
Afterward, focus on their decision-making process: specifically, what they did right and what could be improved
2. Normalize uncertainty.
Customer success is about knowing how to investigate, who to involve and how to communicate confidently while working toward a solution.
One of the most important phrases a CSM can learn is: “Let me validate that and come back with the best path forward.”
Customers expect confidence, transparency and follow-through.
3. Recognize the judgment behind the result.
Sometimes customers churn despite excellent work.
Celebrate behaviors like thoughtful problem-solving, proactive communication, strong prioritization and effective stakeholder management.
For example, imagine your dashboard shows a customer is green. Ask your CSM: “Do you agree?” If they say no and can explain what context the data doesn’t capture, that’s good judgment.
Teach your team to use dashboards as inputs that inform a decision, not a decision on their own.
What intentional coaching looks like after six months:
- CSMs come with recommendations.
- Escalations are thoughtful.
- Customers trust your team more because CSMs are more confident.
- Decisions happen faster.
- You spend more time developing people and focusing on strategic customer initiatives.
60+ days: Focus on culture.
Now that your CSMs have the foundational habits they need to work confidently, shift your focus from individual coaching to building a team-wide coaching culture. This will involve systematizing what you’ve learned, amplifying peer coaching and measuring progress in ways that matter.
1. Build confidence through repetition.
Experienced CSMs need role-playing as much as new hires do. Make it part of your team’s operating rhythm by incorporating it into team meetings, one-on-ones and peer-to-peer sessions.
Use role-playing to practice common scenarios like renewal negotiations, executive conversations, pricing objections, product roadmap discussions and stakeholder turnover.
Don’t stop after someone gives the “right” answer. Throw in curveballs. “What if procurement joins the call?” “What if the customer mentions a competitor?” “What if the executive sponsor disagrees?”
These conversations are where judgment develops.
2. Create peer coaching opportunities.
Some of your best coaches are your top CSMs. Encourage experienced CSMs to review calls, shadow meetings, share what’s worked for them and mentor newer teammates.
Peer coaching scales without relying on your time and effort as a leader, and it recognizes top performers, strengthens collaboration, brings new ideas and helps prepare the next generation of leaders.
3. Measure coaching success.
Don’t evaluate coaching based solely on how many escalations CSMs are bringing to you. Look for indicators that your team is becoming more independent: fewer avoidable escalations, increased CSM ownership, high-quality customer conversations, faster decision-making and issue resolution, and greater confidence in handling complex situations.
This roadmap is a flexible framework. Some teams will progress faster; others may need more time at each stage. What matters is approaching the process intentionally and recognizing that a strong coaching culture develops gradually through consistent, systematic effort.
To start on the path to a strong coaching culture, pick the first habit from the 30-60 day list. Commit to it for two weeks. Then add the second. Then start shifting the culture. Your team’s confidence, your calendar and your renewal rates will thank you.
