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.
| Phase |
Duration |
Role of Coachee |
Role of Coach |
| Situation |
5 min |
Present the account situation: what is happening, what you have tried, where you are stuck |
Listen. Do not problem-solve yet. Understand first |
| Questions |
5 min |
Answer 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?" |
| Perspectives |
10 min |
Listen. Take notes. Do not defend -- absorb |
Offer observations and alternative approaches. "Have you considered..." "In my experience with a similar account..." "What if the issue is actually..." |
| Commitment |
5 min |
State one specific action you will take based on the conversation |
Confirm 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.
| Phase |
Duration |
Content |
| Define the question |
5 min |
What 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 options |
15 min |
Generate as many approaches as possible without evaluating. Quantity over quality in this phase |
| Evaluate |
10 min |
Assess the options: which are realistic, which have the highest probability of success, which can be executed this week |
| Commit |
5 min |
Choose 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.).
| Phase |
Duration |
Content |
| Identify the gap |
5 min |
What skill is the coachee working on? Where are they now vs. where they want to be? |
| Demonstrate |
10 min |
Coach demonstrates the skill using a real or realistic scenario. "Here is how I would approach that executive conversation..." |
| Practice |
10 min |
Coachee practises the skill. Coach observes and provides real-time feedback |
| Debrief |
5 min |
What worked? What to adjust? One thing to practise before the next session |
The Coaching Conversation Rules
These apply regardless of session type:
| Rule |
Why |
| The coachee owns the outcome. The coach does not solve the problem -- they help the coachee think through it |
Dependency 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 telling |
The 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
1---2name: peer-coaching-guide3description: 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.4license: MIT5---67# Peer Coaching Guide89Structures 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.1011## How to Use1213Provide:14- What the coaching session is about (account review, strategy brainstorm, skill development, objection preparation)15- Who is the "coachee" (the person bringing the topic) and who is the "coach" (the person helping)16- Time available (20, 30, or 45 minutes)17- Specific question or challenge (what does the coachee want to walk away with?)1819## Session Types2021### Type 1: Account Review (20-30 min)2223One CSM presents an account situation. The other helps them see what they might be missing.2425| Phase | Duration | Role of Coachee | Role of Coach |26|-------|----------|----------------|--------------|27| Situation | 5 min | Present the account situation: what is happening, what you have tried, where you are stuck | Listen. Do not problem-solve yet. Understand first |28| Questions | 5 min | Answer 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?" |29| Perspectives | 10 min | Listen. Take notes. Do not defend -- absorb | Offer observations and alternative approaches. "Have you considered..." "In my experience with a similar account..." "What if the issue is actually..." |30| Commitment | 5 min | State one specific action you will take based on the conversation | Confirm the action is specific and achievable. Offer to follow up |3132**Coach's rules:**33- Ask before advising. The coachee may have already tried your suggestion34- Offer perspectives, not instructions. "Have you considered..." not "You should..."35- Challenge assumptions gently. "What evidence do you have that the champion is disengaged?" is more useful than "Your champion is probably fine"3637### Type 2: Strategy Brainstorm (30-45 min)3839Both CSMs explore a strategic question together. Less structured, more creative.4041| Phase | Duration | Content |42|-------|----------|---------|43| Define the question | 5 min | What are we trying to solve? Make it specific. "How do I get the CFO engaged at Acme?" not "How do I improve the account?" |44| Explore options | 15 min | Generate as many approaches as possible without evaluating. Quantity over quality in this phase |45| Evaluate | 10 min | Assess the options: which are realistic, which have the highest probability of success, which can be executed this week |46| Commit | 5 min | Choose one approach and define the first action |4748### Type 3: Skill Development (30 min)4950One CSM coaches the other on a specific skill (executive engagement, difficult conversations, commercial acumen, etc.).5152| Phase | Duration | Content |53|-------|----------|---------|54| Identify the gap | 5 min | What skill is the coachee working on? Where are they now vs. where they want to be? |55| Demonstrate | 10 min | Coach demonstrates the skill using a real or realistic scenario. "Here is how I would approach that executive conversation..." |56| Practice | 10 min | Coachee practises the skill. Coach observes and provides real-time feedback |57| Debrief | 5 min | What worked? What to adjust? One thing to practise before the next session |5859## The Coaching Conversation Rules6061These apply regardless of session type:6263| Rule | Why |64|------|-----|65| The coachee owns the outcome. The coach does not solve the problem -- they help the coachee think through it | Dependency on the coach does not build capability. The coachee needs to own the insight |66| Start with questions, not answers. Even if you think you know the solution, ask before telling | The coachee may have context that changes the answer. And questions build understanding faster than advice |67| 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 |68| 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 |69| 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 |7071## Output Format7273```74## Peer Coaching Session75**Date:** [date] | **Type:** [account review / strategy brainstorm / skill development]76**Coachee:** [name] | **Coach:** [name]77**Topic:** [specific question or challenge]78**Duration:** [minutes]7980### Key Insights81[2-3 insights from the conversation]8283### Commitment84[Specific action the coachee will take, with deadline]8586### Follow-Up87Coach will check in: [date]88```8990## Quality Gates9192- 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 question93- Is the coach asking more than telling? A session where the coach talks 80% of the time is advice-giving, not coaching94- Is there a specific commitment at the end? If the coachee leaves without a clear next action, the session was enjoyable but not productive95- Is follow-up scheduled? Without accountability, even the best coaching insight fades within a week9697## Principles9899- 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 time100- The coach benefits as much as the coachee. Articulating how you approach a problem develops your own understanding. Teaching is learning101- 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 honesty102- 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
stephenrogan