stephenrogan/peer-coaching-guide

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