Sales Coaching Checklist

A complete 22-item checklist for sales manager 1:1 sessions. Check off items as you go, track your completion rate, and print a summary for your records. Covers prep, pipeline, call review, skill development, and action items.

Session Progress

Completed: 0 / 22 items (0%)

Pre-Meeting Prep

0/4 complete

• Review the rep's pipeline and deal notes before the session
• Come in with context - do not make the rep brief you on every deal from scratch. Glancing at CRM notes 10 minutes before saves 15 minutes of catch-up.
• Pull the rep's call recordings or scores from the last 2 weeks
• Coaching without call evidence is coaching by anecdote. Having specific clips or scores anchors feedback in observable reality rather than general impressions.
• Identify one or two specific development areas to focus on this session
• Trying to cover everything in one session means improving nothing. Pick the one area where focused improvement will have the highest impact on their near-term results.
• Check in on action items from the last 1:1
• Following up on previous actions signals that coaching is cumulative, not a one-off. It also quickly reveals whether the rep is executing on commitments.

Pipeline Review

0/5 complete

• Walk through every deal in active stages - not just the big ones
• Focusing only on high-value deals allows smaller deals to stall quietly. A quick pass across all active opportunities surfaces stuck deals before they die.
• Ask for the most recent customer interaction on each deal
• Deal velocity drops when interaction gaps open up. Asking 'when did you last speak to them?' surfaces deals that are going cold without the rep flagging it.
• Challenge deals with no clear next step
• Deals without a calendar-confirmed next step are not progressing. Make it a rule: no deal survives pipeline review without a specific date, attendee list, and agenda.
• Identify deals at risk and agree on a recovery action
• For every at-risk deal, leave the session with a specific action the rep will take in the next 48 hours. Vague recovery plans do not recover deals.
• Validate forecast accuracy against committed and best-case tiers
• Compare what the rep is forecasting against the evidence - champion access, economic buyer engagement, timeline confirmation. Teach forecast discipline as a skill, not just a reporting exercise.

Call Review

0/5 complete

• Play a specific call clip rather than describing it from memory
• Clip-based coaching is 3x more effective than summary-based coaching. Hearing the exact moment lets the rep self-assess before you give feedback.
• Ask the rep to evaluate the call before giving your assessment
• Self-evaluation builds metacognition. Reps who can identify their own mistakes are far more likely to adjust behavior than reps who are told what went wrong.
• Give one positive observation and one specific improvement
• The 'sandwich' approach dilutes feedback. Instead, give one clear positive and one clear improvement with specific language - not 'ask more questions' but 'try an implication question after they name a pain.'
• Connect call feedback to a deal outcome where possible
• Reps internalise feedback faster when it connects to a tangible consequence. 'That monologue in minute 18 is why the next step was vague' is more motivating than generic coaching.
• Share a clip from a top-performer call showing the better approach
• Seeing is more effective than being told. If you have a clip of a top rep asking a great implication question, show it. It removes ambiguity about what good looks like.

Skill Development

0/4 complete

• Agree on one skill to focus on for the next 2 weeks
• Skill development compounds when it is specific and sustained. One focused area for two weeks beats five areas never revisited.
• Role-play the specific scenario the rep is struggling with
• Verbal coaching tells reps what to do. Role-play forces them to do it. A 5-minute role-play practice is worth more than a 20-minute explanation.
• Identify a resource - playbook, call clip, or framework - to support the skill
• Self-directed skill development requires a reference point. Point the rep to a specific resource they can revisit between sessions.
• Connect skill improvement to a specific upcoming deal or call
• Abstract skill development is forgotten. 'Practice this on your call with [Company] on Thursday' gives the rep a real-world application that makes the learning stick.

Action Items

0/4 complete

• Write down all agreed actions before the session ends
• Verbal commitments have a half-life of about two days. Written action items - with the rep's name and a deadline - survive the session.
• Assign a specific deadline to each action item
• Actions without deadlines are intentions. 'By end of day Friday' is an action. 'This week when you can' is not.
• Confirm the rep understands the priority order of all actions
• If a rep has five actions, they need to know which three matter most. Prioritising prevents the most important things from being displaced by the most urgent.
• Set the date for the next 1:1 before closing the session
• Coaching continuity depends on regular cadence. Before the rep leaves the call, the next session should be on both calendars.

Questions about sales coaching

1. How long should a sales manager 1:1 be?
   Best practice is 30-45 minutes weekly for each rep. Shorter sessions work if you cover the essentials; longer sessions can become unfocused. The cadence matters more than the duration - weekly 30-minute sessions beat monthly hour-long sessions for rep development.

2. What is the most common mistake in sales coaching sessions?
   Talking about deals rather than coaching skills. Many 1:1s become pipeline update meetings where the manager does the thinking for the rep. Effective sessions use pipeline review as a lens for coaching - not as the goal of the meeting.

3. How many reps can a sales manager effectively coach?
   Research from CEB/Gartner suggests the optimal span of control is 6-8 direct reports per manager for effective coaching. Above 10, coaching quality drops significantly because managers do not have enough time to review calls, prepare for sessions, and follow up on development areas.

4. How does Airspeed automate call review and coaching moments?
   Airspeed analyses every call and surfaces specific coaching moments - a missed implication question, an unanswered objection, a monologue that went too long - with the exact timestamp. Managers see a coaching feed across all reps without pulling individual recordings. This makes the call review portion of every 1:1 faster, more specific, and more impactful.