The 30/60/90-Day Sales Coaching Plan
Most sales coaching is reactive and inconsistent. This three-phase arc gives you a structured way to develop individual reps — from baseline assessment through measurable improvement.
Why most sales coaching doesn't work
Most sales managers coach reactively — when a deal is in trouble, when a rep is struggling, when a number is off. That's crisis management, not development. It addresses symptoms, not skills.
Structured coaching works differently. It starts with an honest assessment of where the rep actually is, identifies the 1–2 highest-leverage development areas, and works them consistently over 90 days. The improvement is measurable because the baseline was documented.
The Three Phases
Each phase has a distinct goal, manager actions, rep milestones, and a coaching focus. Don't skip phases — they build on each other.
Assess & Establish
Understand where the rep actually is — not where you think they are. Establish the coaching relationship and cadence.
Manager actions
- Complete a baseline skills assessment across the 7 hiring scorecard dimensions
- Review the last 90 days of CRM data — activity levels, pipeline movement, win/loss patterns
- Listen to or observe 3–5 sales calls or meetings
- Establish the weekly 1-on-1 cadence and run the first 3 sessions
- Identify the 1–2 highest-leverage development areas (not a list of everything)
- Share your assessment with the rep — no surprises
Rep milestones
- Understands the coaching cadence and what to expect from 1-on-1s
- Has articulated their own development goals
- Has made and kept their first 3 weekly commitments
Coaching focus
Observation and diagnosis. Don't coach yet — listen. You can't develop what you haven't accurately assessed.
Skipping the assessment and jumping straight to coaching based on assumptions. You'll coach the wrong things.
Focus & Develop
Work the 1–2 development areas identified in Phase 1. Deliberate, specific, consistent.
Manager actions
- Dedicate the development block of every 1-on-1 to the identified focus areas
- Observe in the field or on calls at least twice — give specific behavioral feedback within 24 hours
- Role-play the specific skill in 1-on-1s before the rep uses it in the field
- Track the rep's weekly commitments — are they following through?
- Adjust the focus if the initial assessment was wrong or the rep has made rapid progress
- Document what you're observing — you'll need it for the 60-day review
Rep milestones
- Can articulate the skill they're developing and why it matters
- Has attempted the new approach in at least 3 real situations
- Is showing early signs of improvement — even if inconsistent
Coaching focus
Deliberate practice. The rep should be trying the new approach in real situations, not just discussing it. Failure is expected — debrief it.
Coaching too many things at once. One or two development areas, done consistently, produces results. Five areas produces overwhelm and no change.
Reinforce & Measure
Measure progress against the baseline. Reinforce what's working. Set the next development priority.
Manager actions
- Conduct a formal 90-day coaching review — compare current state to the Day 1 baseline
- Acknowledge specific improvements with specific evidence ("In your last 3 discovery calls, you've been asking about decision process before moving to solution — that's a real change")
- Identify the next development priority based on what you've observed
- Decide whether to continue active coaching or transition to a maintenance cadence
- Update the coaching plan for the next 90 days
Rep milestones
- Can self-assess their progress accurately — not just optimistically
- Has internalized the skill enough to use it without prompting
- Has articulated what they want to work on next
Coaching focus
Measurement and recognition. Reps who see their own progress stay motivated. Make the improvement visible — don't assume they know.
Skipping the formal review because things are going well. The review is how you close the loop and set up the next cycle.
Coaching Conversation Frameworks
Two frameworks that work in different situations. Use them as structures, not scripts.
The GROW Model
For development conversations where the rep needs to find their own answer
GROW works best when the rep has enough experience to generate their own options. For new reps, you may need to provide more direction.
The SBI Feedback Model
For giving specific behavioral feedback after observing a call or meeting
SBI keeps feedback grounded in observable behavior rather than interpretation. "You seemed nervous" is interpretation. "You spoke faster and didn't pause for their response" is behavior.
Accountability Checkpoints
Coaching without accountability is conversation. These checkpoints close the loop.
Review the commitment from last 1-on-1. Did they do it? What happened?
Baseline assessment complete. Development focus identified and shared with rep.
Progress check on development focus. Adjust if needed. Document what you're observing.
Formal coaching review. Compare to baseline. Set next 90-day development priority.
Performance vs. quota review. Coaching plan updated for next quarter.
The weekly commitment review happens in every 1-on-1 meeting. The 30/60/90-day checkpoints are formal reviews — document them.
Related Resources
Sales 1-on-1 Meeting Framework
The weekly meeting where coaching happens
Sales Hiring Scorecard
The baseline assessment dimensions for new hires
Sales Weekly Meeting Agenda
The team meeting cadence that runs alongside 1-on-1s
Pipeline & Capacity Planner
Check pipeline coverage and model rep capacity against your target
Fractional Sales Manager
Get the full coaching cadence built and run for you
Sales Leadership Operating System
The full SLOS hub — all tools in one place
Need Someone to Run the Coaching?
Building a coaching plan is straightforward. Executing it consistently — week after week, rep by rep — is where most managers fall short. A fractional sales manager can run the full coaching cadence as part of the Sales Leadership Operating System.
Talk to Leaman