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stephenroganstephenrogan/csm-skills/skills/peer-coaching-guide/SKILL.md

peer-coaching-guide

Skill0 starsChanged 8 months agoMITView on GitHub

Structures a coaching conversation between CSMs for peer review of an account situation, strategy brainstorm, or skill development. Provides a framework that makes peer coaching sessions productive and focused rather than unstructured venting. Use when asked to structure a peer coaching session, facilitate an account review between colleagues, build a coaching framework, organise a peer brainstorm, or when two CSMs want to help each other think through a problem. Also triggers for questions about peer coaching, account review sessions, CSM mentoring structures, brainstorm facilitation, or how to make peer conversations more productive.

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  1. Distinctive:

    Ask before advising. The coachee may have already tried your suggestion

    line 37

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SKILL.md

Peer Coaching Guide

Structures coaching conversations between CSMs so they are productive, focused, and developmental -- not just venting sessions or status updates. The most underused development tool in CS is the expertise of the person sitting next to you.

How to Use

Provide:

  • What the coaching session is about (account review, strategy brainstorm, skill development, objection preparation)
  • Who is the "coachee" (the person bringing the topic) and who is the "coach" (the person helping)
  • Time available (20, 30, or 45 minutes)
  • Specific question or challenge (what does the coachee want to walk away with?)

Session Types

Type 1: Account Review (20-30 min)

One CSM presents an account situation. The other helps them see what they might be missing.

PhaseDurationRole of CoacheeRole of Coach
Situation5 minPresent the account situation: what is happening, what you have tried, where you are stuckListen. Do not problem-solve yet. Understand first
Questions5 minAnswer honestly. If you do not know, say "I do not know"Ask questions that surface assumptions: "What does the customer actually say about this?" "Have you asked X directly?" "What would happen if you did nothing?"
Perspectives10 minListen. Take notes. Do not defend -- absorbOffer observations and alternative approaches. "Have you considered..." "In my experience with a similar account..." "What if the issue is actually..."
Commitment5 minState one specific action you will take based on the conversationConfirm the action is specific and achievable. Offer to follow up

Coach's rules:

  • Ask before advising. The coachee may have already tried your suggestion
  • Offer perspectives, not instructions. "Have you considered..." not "You should..."
  • Challenge assumptions gently. "What evidence do you have that the champion is disengaged?" is more useful than "Your champion is probably fine"

Type 2: Strategy Brainstorm (30-45 min)

Both CSMs explore a strategic question together. Less structured, more creative.

PhaseDurationContent
Define the question5 minWhat are we trying to solve? Make it specific. "How do I get the CFO engaged at Acme?" not "How do I improve the account?"
Explore options15 minGenerate as many approaches as possible without evaluating. Quantity over quality in this phase
Evaluate10 minAssess the options: which are realistic, which have the highest probability of success, which can be executed this week
Commit5 minChoose one approach and define the first action

Type 3: Skill Development (30 min)

One CSM coaches the other on a specific skill (executive engagement, difficult conversations, commercial acumen, etc.).

PhaseDurationContent
Identify the gap5 minWhat skill is the coachee working on? Where are they now vs. where they want to be?
Demonstrate10 minCoach demonstrates the skill using a real or realistic scenario. "Here is how I would approach that executive conversation..."
Practice10 minCoachee practises the skill. Coach observes and provides real-time feedback
Debrief5 minWhat worked? What to adjust? One thing to practise before the next session

The Coaching Conversation Rules

These apply regardless of session type:

RuleWhy
The coachee owns the outcome. The coach does not solve the problem -- they help the coachee think through itDependency on the coach does not build capability. The coachee needs to own the insight
Start with questions, not answers. Even if you think you know the solution, ask before tellingThe coachee may have context that changes the answer. And questions build understanding faster than advice
One specific commitment at the end. Not "I will think about it" but "I will email the CFO by Thursday using the framing we discussed"Without a commitment, the session was a conversation, not coaching
Follow up. The coach checks in 1 week later: "Did you send that email? How did it go?"Accountability transforms a good conversation into actual behaviour change
What is said in the session stays in the session (unless both agree otherwise)Psychological safety is the foundation. If the coachee worries their vulnerabilities will be shared, they will not be honest about where they are stuck

Output Format

## Peer Coaching Session
**Date:** [date] | **Type:** [account review / strategy brainstorm / skill development]
**Coachee:** [name] | **Coach:** [name]
**Topic:** [specific question or challenge]
**Duration:** [minutes]

### Key Insights
[2-3 insights from the conversation]

### Commitment
[Specific action the coachee will take, with deadline]

### Follow-Up
Coach will check in: [date]

Quality Gates

  • Does the session have a specific question to answer? "Let me tell you about my accounts" is a status update, not a coaching session. "How should I handle the competitive signal at Acme given the champion's departure?" is a coachable question
  • Is the coach asking more than telling? A session where the coach talks 80% of the time is advice-giving, not coaching
  • Is there a specific commitment at the end? If the coachee leaves without a clear next action, the session was enjoyable but not productive
  • Is follow-up scheduled? Without accountability, even the best coaching insight fades within a week

Principles

  • Peer coaching is the highest-ROI development activity available to CSMs. It costs nothing, requires no management approval, and produces immediately applicable insights. The only cost is 30 minutes of time
  • The coach benefits as much as the coachee. Articulating how you approach a problem develops your own understanding. Teaching is learning
  • Vulnerability is the prerequisite. If the coachee cannot say "I do not know how to handle this" or "I think I messed up," the coaching will stay surface-level. Create the safety for honesty
  • Regular cadence compounds. A one-time session is useful. A weekly 20-minute peer coaching habit transforms both CSMs' capabilities over a quarter. Schedule it. Protect it

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