The Ultimate Sales Coaching Session Checklist

A Complete Guide to Running High-Impact Coaching Sessions That Drive Results

Sales coaching is one of the most powerful tools in a manager's arsenal, yet 73% of sales managers spend less than 5% of their time actually coaching their teams. The difference between average and exceptional sales teams often comes down to the quality and consistency of coaching sessions.

This comprehensive checklist provides a proven framework for structuring coaching sessions that deliver measurable results. Whether you're a new sales manager wondering what to cover in your first coaching session, or a seasoned leader looking to optimize your approach, this guide gives you everything you need to conduct coaching sessions that actually move the needle.

What's Inside This Coaching Session Checklist

This downloadable resource answers the most common questions sales managers ask about coaching sessions and provides actionable frameworks you can implement immediately:

1. How to Structure Your Coaching Sessions

Most managers struggle with structuring effective coaching conversations. Should they be 30 minutes or an hour? Weekly or monthly? What should you cover first?

The checklist includes:

• A proven 30-minute and 60-minute session template with time allocations
• The optimal frequency for coaching based on rep experience level
• How to balance structure with flexibility
• Pre-session preparation checklist for both manager and rep
• The difference between coaching sessions, 1:1s, and performance reviews

Research shows that structured coaching programs lead to 28% higher win rates. Having a clear framework ensures you don't waste time or miss critical development opportunities.

2. What Topics to Cover (And What to Skip)

One of the biggest mistakes managers make is trying to address too many issues in a single session. The checklist helps you prioritize effectively.

You'll learn:

• The 8 core coaching topics every manager should cover
• How to identify which topic to focus on for each rep
• The "one thing" principle: why coaching to a single aspect works better
• When to address strengths vs. weaknesses (and the 5:1 ratio)
• Call review best practices: what to look for and how long to spend

The checklist includes specific scenarios like "What to do when a rep says they have no challenges" and "How much time to spend on metrics vs. skill development."

3. The Exact Questions to Ask

Great coaching isn't about telling—it's about asking the right questions that drive self-discovery and behavioral change. This section provides over 50 proven coaching questions organized by purpose.

Question categories include:

• Opening questions to start the session and build rapport
• Self-evaluation questions that help reps assess their own performance
• Ownership-building questions that drive accountability
• Deal coaching questions for opportunity reviews
• Motivational questions that uncover personal drivers
• Diagnostic questions for when you're stuck

For example, instead of saying "You need to ask better discovery questions," the checklist shows you how to ask: "What do you think went well in that discovery call? What would you do differently next time?" This approach leads to 3x better retention of coaching lessons.

4. Proven Coaching Frameworks

The checklist breaks down three battle-tested frameworks you can use immediately:

The Did-Doing-Do Framework:

• Did: Review commitments from last session (5 min)
• Doing: Discuss current priorities and activities (40 min)
• Do: Set specific action items for next period (10 min)

The GROW Model:

• Goal: What do you want to achieve?
• Reality: Where are you now?
• Options: What could you do?
• Way Forward: What will you do?

The 5-Section Coaching Session:

• Check-in (5 min)
• Metrics review (5 min)
• Call/performance review (15 min)
• Skill development (10 min)
• Action items and close (5 min)

Each framework includes real-world examples and specific timing recommendations.

5. How to Review Calls Effectively

Call reviews are where coaching rubber meets the road, but many managers waste time reviewing entire hour-long calls or provide vague feedback.

The checklist covers:

• How to select which calls to review (wins vs. losses)
• The 7 key evaluation areas to focus on
• Using conversation intelligence tools to identify coachable moments
• How to get reps to self-assess before sharing your observations
• Role-play techniques for practicing improvements
• What to listen for: talk-listen ratio, question quality, objection handling

Elite-performing sales organizations are 2.2x more likely to have managers who excel at call coaching. This section ensures you're in that top tier.

6. Metrics & Data-Driven Coaching

Coaching without data is just opinion. But data without context is just numbers. The checklist shows you how to balance both.

You'll discover:

• Which individual KPIs to review in each session
• How to use metrics to identify coaching topics (not interrogate reps)
• The right talk ratio: 70% rep, 30% manager
• How to give critical feedback without demotivating
• The "feedback sandwich" technique (when and how to use it)
• Connecting feedback to the rep's personal goals

Top-performing teams use data in 100% of coaching sessions, but spend only 5 minutes on metrics review—the rest is skill development.

7. Creating Accountability Without Micromanaging

One of the most common coaching challenges is holding reps accountable for commitments without becoming a micromanager.

The checklist provides:

• How to end sessions with clear, specific commitments
• The accountability loop: getting reps to document their own action items
• What to do when reps consistently miss commitments
• How to diagnose if the issue is capacity, capability, or motivation
• The power of public commitments (and how to use them)
• Celebrating progress vs. completion

Studies show that when reps write down commitments and send them to their manager, completion rates increase by 67%.

8. Handling Difficult Coaching Situations

Not every coaching session goes smoothly. This section addresses the challenges that trip up even experienced managers.

Scenarios covered:

• Coaching reps who don't want to be coached
• What to do when you don't know how to help
• Coaching someone more experienced than you
• Balancing coaching with pipeline management (they're different!)
• Remote vs. in-office coaching adaptations
• When coaching isn't enough (transitioning to performance management)

Each scenario includes specific dialogue examples and decision frameworks.

9. Role-Plays & Skill Practice

The most effective coaching sessions include live practice, not just discussion. But many managers skip this because they don't know how to facilitate it effectively.

The checklist teaches you:

• How to structure 5-10 minute role-plays
• The 8 most important scenarios to practice
• How to give in-the-moment feedback during role-plays
• Playing the prospect yourself (and why this works better)
• Recording role-plays for self-review
• Overcoming rep resistance to role-playing

Organizations that incorporate role-play into coaching see 34% faster skill development than those relying on discussion alone.

10. Session Documentation & Follow-Up

What you document determines what gets done. The checklist includes templates for tracking coaching effectiveness over time.

Documentation covers:

• What to track from each session
• How to measure if your coaching is working (leading and lagging indicators)
• Quarterly coaching development plan template
• Rep self-assessment worksheets
• Manager observation guides
• Progress tracking dashboards

Elite sales managers review coaching notes before every session and track rep development trajectories over 6-12 months.

Why This Checklist Is Different

Most coaching resources give you theory. This checklist gives you exactly what to do, what to say, and how to structure every minute of your coaching sessions.

Here's what makes it unique:

✓ Based on Real Manager Questions: Every section addresses actual questions sales managers ask when preparing for coaching sessions. This isn't theory—it's practical answers to "What do I actually do?"

✓ Time-Stamped Agendas: No more wondering how to fill 30 or 60 minutes. Get exact time allocations for each section based on what works in thousands of coaching sessions.

✓ Copy-Paste Questions: Over 50 ready-to-use questions organized by coaching objective. Simply select the right questions for your situation.

✓ Framework Comparisons: Understand when to use GROW vs. Did-Doing-Do vs. the 5-Section model based on your coaching objectives and rep needs.

✓ Diagnostic Decision Trees: When you're stuck or facing a difficult situation, use the included flowcharts to diagnose the issue and choose the right approach.

✓ Remote Coaching Adaptations: Specific modifications for coaching distributed teams, including asynchronous coaching techniques and video best practices.

✓ Editable Templates: All worksheets and scorecards are provided in editable formats so you can customize them for your team and sales process.

Common Coaching Session Questions Answered

"How long should a coaching session be?"

Answer: 30-60 minutes depending on the topic complexity. Our checklist provides two session templates:

• 30-minute express session: For weekly check-ins on single topics
• 60-minute comprehensive session: For monthly deep-dives on complex skills

The key is consistency—a 30-minute session every week beats a 2-hour session once a month.

"How often should I coach each rep?"

Answer: It depends on their experience level:

• New reps (0-6 months): Weekly structured coaching
• Mid-level performers: Bi-weekly sessions
• Top performers: Monthly coaching + ad-hoc as needed

The checklist includes a frequency decision matrix based on rep tenure, quota attainment, and skill level.

"What's the difference between coaching and just giving feedback?"

Coaching uses questions to help reps discover solutions themselves. Feedback tells them what to do. The checklist shows you how to transform every directive into a coaching question.

For example:

• Feedback: "You need to ask more discovery questions."
• Coaching: "How might deeper discovery questions have changed that conversation?"

Coaching leads to 3x better behavior change because reps develop the skill, not just follow instructions.

"Should I focus on their strengths or weaknesses?"

Both, but in the right ratio. Use the 5:1 framework:

• Highlight 5 things they did well
• Address 1 specific area for improvement

The checklist explains how to use strengths as leverage for addressing weaknesses, and when to focus exclusively on reinforcing what's working.

"What if my rep doesn't want to be coached?"

This signals a trust or relevance issue. The checklist provides a 4-step process:

1. Build trust through consistency
2. Connect coaching to THEIR goals (not just company goals)
3. Start with their strengths to build confidence
4. Give them choices in what to work on

If resistance persists after 3 sessions using this approach, the checklist includes scripts for direct conversations about expectations.

"How do I find time to coach when I'm so busy?"

Coaching IS your job as a sales manager—it's not extra. The checklist shows you how to:

• Use AI tools to cut call review time by 90% (10-minute review vs. 90 minutes)
• Leverage group coaching for common challenges
• Block "non-negotiable" coaching time first when planning your calendar
• Recognize that 1 hour of coaching prevents 3 hours of future firefighting

Remember: organizations with consistent coaching see 7% higher annual revenue growth. That's not a cost—it's an investment.

"What questions should I ask in a coaching session?"

The checklist provides 50+ questions organized by objective, but here are the essentials:

Opening (build rapport):

• "How are you feeling about your performance this week?"
• "What wins are you proud of?"

Self-Evaluation (drive awareness):

• "How do you think that call went?"
• "What would you do differently next time?"

Ownership (create accountability):

• "What could you have done differently to change the outcome?"
• "What will you do in your next similar situation?"

Motivation (uncover drivers):

• "Why is this goal important to you?"
• "What happens when you knock this out of the park?"

The checklist shows you exactly when to use each question type.

"How do I balance coaching with pipeline management?"

These are two different activities that require separate time:

• Pipeline reviews: Focus on deals, next steps, forecast accuracy
• Coaching sessions: Focus on skills, behaviors, development

The checklist includes a simple rule: If you're problem-solving a specific deal, that's pipeline management. If you're building a repeatable skill, that's coaching.

Many managers try to do both simultaneously and end up doing neither well.

"What do I do if I don't know how to help my rep improve?"

The checklist provides a 5-step "I'm Stuck" protocol:

1. Be honest: "I don't have the answer, but let's figure it out together"
2. Leverage peer coaching: connect them with a top performer
3. Research together: find training resources or best practices
4. Focus on their self-discovery: "What else could you try?"
5. Seek input from other managers or coaches

Great coaches don't have all the answers—they know how to find them.

How to Use This Checklist

Before your first coaching session:

1. Read through the entire checklist once
2. Select which framework you'll use (Did-Doing-Do or GROW)
3. Prepare your session agenda using the templates
4. Review the rep's metrics to identify coaching topics
5. Pre-select 1-2 calls to review together

During the session:

1. Keep the checklist open as a reference
2. Use the question bank when you need to probe deeper
3. Follow the time allocations (set a timer!)
4. Document commitments using the action item template
5. Schedule the next session before ending

After the session:

1. Send a summary email with action items
2. Track progress in your coaching log
3. Review notes before the next session
4. Adjust your approach based on what worked

Over time:

1. The frameworks will become second nature
2. You'll internalize the key questions
3. You'll develop your own coaching style
4. You'll need the checklist less frequently

But always keep it handy for difficult situations or when you're stuck.

The Impact of Consistent Coaching

When you implement the frameworks in this checklist consistently, here's what you can expect:

Within 30 days:

• Reps report feeling more supported and developed
• You have a consistent coaching rhythm established
• Sessions feel more structured and productive
• Less time spent on unproductive ad-hoc conversations

Within 90 days:

• Measurable improvement in individual rep metrics
• Increased rep confidence and autonomy
• Fewer performance issues requiring intervention
• Improved forecast accuracy

Within 6 months:

• 10-20% improvement in team win rates
• Higher rep retention (60% less likely to leave)
• Reps proactively solve their own challenges
• You've developed a coaching culture on your team

Within 12 months:

• 28% higher win rates (industry benchmark for coached teams)
• 7% greater annual revenue growth
• Reduced ramp time for new hires
• You're coaching other managers on your approach

Organizations with structured coaching programs achieve 353% ROI within 18 months: $4.53 returned for every dollar invested in coaching infrastructure and time.

Who Should Use This Checklist

New Sales Managers: If you're transitioning from rep to manager, this checklist provides the coaching foundation your training probably missed. You'll avoid the most common mistakes and build the right habits from day one.

Experienced Managers: If you've been coaching for years, use this to audit your approach. Even small optimizations, like adding the Did-Doing-Do framework or improving your question technique, can significantly improve outcomes.

Sales Leaders: If you manage managers, use this checklist to standardize coaching across your organization. When every manager uses the same frameworks, you can scale best practices and measure coaching effectiveness consistently.

Enablement Teams: This checklist helps you train managers on coaching fundamentals and provides resources they can reference after training ends. It bridges the gap between coaching theory and daily practice.

Remote Sales Teams: Distributed teams need even more structured coaching. This checklist includes specific adaptations for remote coaching, including asynchronous techniques and video best practices.

Download Your Free Checklist

This comprehensive coaching session checklist includes:

✓ Complete session agenda templates (30 min & 60 min)✓ 50+ coaching questions organized by objective✓ 3 proven coaching frameworks with examples✓ Call review evaluation guide✓ Role-play scenario library✓ Rep self-assessment worksheets✓ Action item tracking templates✓ Quarterly development plan template✓ Remote coaching adaptation guide✓ Troubleshooting decision trees✓ Documentation and tracking tools

Everything you need to run coaching sessions that drive measurable improvement in sales performance.

The checklist is available as a downloadable PDF with fillable templates and an editable Word document so you can customize it for your team and sales process.

[Download the Complete Coaching Session Checklist]

Start Coaching with Confidence

You don't need to be a naturally gifted coach to develop your team effectively. You need a proven system, the right questions, and consistent execution.

This checklist gives you all three.

Sales coaching isn't about having all the answers—it's about asking the right questions, creating space for development, and holding your team accountable to their commitments.

When you coach consistently using these frameworks, you'll see tangible results in your team's performance, confidence, and retention. More importantly, you'll develop the coaching muscle that separates average sales managers from exceptional sales leaders.

The reps on your team want to improve. They want guidance. They want to succeed.

Your job is to create the structure that makes their development inevitable.

Download the checklist. Book your first coaching session. And watch your team transform.

Additional Resources

Want to go deeper on sales coaching? Check out our comprehensive guide: The Complete Sales Coaching Guide: Evidence-Based Strategies, Modern Frameworks & AI-Powered Tools for 2025

Looking for coaching training? Our manager development programs teach the skills in this checklist through hands-on practice and real-world application.

Need coaching software? We partner with leading conversation intelligence platforms that automate call review and provide AI-powered coaching insights.

About This Resource

This coaching session checklist was developed based on:

• Analysis of 1,000+ coaching session recordings
• Interviews with 100+ top-performing sales managers
• Research from CSO Insights, Gartner, Sales Executive Council
• Best practices from organizations with 28%+ win rates
• Field testing across 50+ sales organizations
• Input from sales coaching experts and leadership trainers

It represents the condensed wisdom of what actually works in sales coaching, stripped of theory and focused entirely on practical application.

Every question, framework, and technique has been tested in real coaching sessions with measurable results.

This isn't coaching theory. This is coaching practice.

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