Put the coaching into context.
Read an experience-based story about building confidence, or explore an illustrative scenario about coaching through a weakening sponsor relationship.
Confidence, Not Capability When the Sponsor Goes QuietThe Coaching Playbook
Coach the person.
Coach the person.
Strengthen the team.
Good coaching starts with curiosity, not a verdict.
Before deciding what someone needs, understand the person, look at the work together, and ask what is getting in the way.
My approach is to build confidence and judgment, then help turn individual growth into shared team capability. That means clear expectations, practical support, honest feedback, and ownership that stays with the person doing the work.
Explore the approach
Support the person.
A practitioner’s perspective
This is the approach I aim to bring to Customer Success leadership. It is a guide to adapt to the person and situation, not a script every coaching conversation must follow.
Before the first questionLook closer
Look closer
before prescribing.
A missed commitment or a hesitant customer conversation is an observation, not a complete explanation. The next step is to understand whether the person needs a new skill, more confidence, clearer expectations, fewer obstacles, or a combination.
Coaching is not only for something that has gone wrong. A strong performer may be ready for a new capability, a more complex account, or an opportunity to help others grow.
The coaching approach
From understanding to independence.
Six steps to draw from. Support that changes as the person grows.
Start with the person
Understand their strengths, goals, and view of the situation. Use real work to explore whether the issue is skill, confidence, capacity, or process before choosing the support.
Ask“What’s getting in the way?”
Make success clear
Connect the development goal to the customer outcome it should support. Agree on what better looks like in observable terms, what support is needed, and when you will review progress together.
Ask“What would better look like?”
Show the work
Shadow a call, review an account plan, or walk through a customer situation together. Explain what you notice, which questions you ask, and why you choose a particular next step.
Say“Here’s what I’m noticing, and why.”
Practice, then hand back
Let the CSM lead the next attempt. Debrief with specific feedback, then look for whether they can apply the learning in a different situation rather than simply repeat your steps.
Ask“Walk me through your recommendation.”
Help them teach others
Invite people to share a demonstrated strength through peer shadowing, a team discussion, or a reusable playbook. Recognize their contribution and check whether others can use the learning, rather than treating a recorded session as proof of adoption.
Ask“What could others use from this?”
Review and improve
Look for changes in behavior, judgment, and customer progress, not just completed activities. Keep what helps, adjust what does not, and consider whether recurring obstacles call for a better process rather than more individual coaching.
Ask“What changed? What should we adjust?”
Empathy + accountabilityCreate safety.
Create safety.
Keep ownership.
I want people to feel safe asking questions, raising risks, and acknowledging mistakes early. My responsibility is to respond with curiosity, give honest feedback, and help clarify the next step.
Support does not mean removing responsibility. We should leave the conversation knowing who owns the follow-through, what help is available, and when we will reconnect.
- Listen first
- Understand the person’s perspective before deciding on the intervention.
- Make room for different voices
- Offer space for written input and quieter contributions, not just the quickest answer in the room.
- Address persistent gaps
- Be direct when an agreed expectation remains unmet, and distinguish a development conversation from formal performance management.
- Model follow-through
- Hold myself to the commitments I expect from the team.
From experienceFrom the field
An anonymized example from my leadership experience.
DemonstratePracticeTeach
Develop a strength.
Then share the learning.
I worked with a strong CSM who wanted to deepen her fluency in a customer’s cloud environment. This was a development opportunity, not a performance turnaround.
With customer approval, I demonstrated how to review the environment, notice capabilities worth exploring, and turn those observations into questions about how the customer worked. The point was not to make her do every technical task herself. It was to strengthen her judgment about what to ask and when to involve an engineer.
She then applied the approach in another account, and we reviewed her reasoning together. Later, I invited her to share the approach through recorded team enablement.
The progression mattered: see the work, apply it independently, then help others learn. Sharing the session created a learning resource; whether others adopted the approach was a separate question to check.
Follow the evidenceWhat I look for
What I look for
as evidence.
These are signs I look for, not a scorecard to apply identically to every person. The evidence should match the development goal and the work they actually own.
- Stronger discovery
- Questions uncover the customer’s priorities and constraints, not just product requests.
- Independent judgment
- The CSM can explain a recommendation and apply the skill without the manager leading.
- Earlier risk conversations
- Concerns come forward with context and a proposed next step.
- Useful peer learning
- Colleagues can apply what was shared and improve the playbook.
- Customer progress
- The work advances an agreed outcome, not merely a meeting count or completed checklist.
Take it into the conversation
Use this in your next one-on-one.
Start with the person’s agenda, not just your account checklist. Choose the questions that fit the conversation rather than trying to get through them all.
- Start with their agenda
- “What would be most useful for us to talk through today?”
- Explore the work
- “What’s going well, and where are you getting stuck?”
- Build judgment
- “What do you think the next step should be?”
- Clarify support
- “What do you need from me?”
- Close with ownership
- “What are we each committing to before we reconnect?”
Put it into practice
One situation. One useful next step.
You do not need to use every step at once. Start with one observable situation, ask for the person’s perspective, and agree on one useful next step.
Coaching Observation Sheet
Capture what you observed, consider alternative explanations, and agree on practice, support, and a review point.
Open the worksheetKeep coaching notes private, respectful, and focused on development. The worksheet is a conversation aid, not an employee-rating system or a substitute for your organization’s formal processes.
The principle to carry forwardStep in when risk demands it.
Step in when risk demands it.
Coach afterward.
Return ownership.
The goal is not to become the person every decision must pass through. It is to help people build the judgment to lead the next situation with greater independence.
Back to the conversation prompts