If you’re wondering whether sales training will actually move the needle—or just burn calendar—these are the seven questions I hear most from CEOs and what I recommend.
1) What outcomes should we expect—and by when?
Think in behavior first, revenue second. Early wins show up as:
- Higher activity quality (fewer no-shows, cleaner discovery notes)
- Improved conversion rates at a single stage (e.g., Stage 2→3 +5–10%)
- Shorter cycle time on comparable deals
Revenue impact typically lags behavior by one to two quarters depending on cycle length.
2) What should a modern program include?
A credible program blends:
- Role-specific skill blocks (prospecting, discovery, negotiation, account growth)
- Live practice with realistic scenarios and rubrics
- Manager enablement (coaching playbooks, scorecards, call review cadence)
- Tools & templates your team actually uses (emails, talk tracks, deal reviews)
- Reps-only time protected for application, not just lectures
3) How do we measure effectiveness?
Use a simple stacked view:
- Leading indicators: coaching participation, practice reps completed, certification scores
- Behavior indicators: discovery depth, multi-threading rate, MEDDICC completeness, next-step quality
- Lagging indicators: stage conversion %, win-rate, average deal size, cycle time
Set baselines first, then compare cohorts (trained vs. not yet trained) for a clean read.
4) How much should we budget?
Rules of thumb:
- Initial build (SMB/Mid-market): $25k–$100k depending on scope and assets
- Enterprise/global rollout: $100k–$350k including localization and manager tracks
- Expect ~1–3% of annual OTE per seller in ongoing reinforcement if you want retention of skills.
5) Do we buy off-the-shelf or build our own?
- Buy when you need foundations fast or lack internal enablement bandwidth.
- Build/Customize when your motion is unique (complex enterprise, PLG + enterprise hybrid, or heavy partner influence).
Most teams do a hybrid: proven core frameworks + custom scenarios and artifacts.
6) How do we avoid “one-and-done” training decay?
- Treat training as an operating system, not an event.
- Add weekly coaching loops (call reviews, 1:1 scorecards, pipeline inspection checklists).
- Tie certifications to manager sign-off and enablement to deal health metrics, not attendance.
7) What role should managers play?
Managers are the multiplier:
- Coach to one focus behavior per rep per month
- Run deal reviews that inspect next steps, stakeholders, and risk, not just forecast numbers
- Model the behaviors in their own calls and emails
If managers aren’t enabled, training won’t stick. Period.
Implementation roadmap (quick start)
- Baseline metrics and call a shot (which stage will improve first?).
- Pilot with one region or team for 6–8 weeks.
- Certify reps and managers; publish the rubric.
- Roll out in waves; report behavior and conversion changes every two weeks.
- Evolve: keep what works, cut what doesn’t, add scenarios from live deals.
What “good” looks like in 90 days
- 70–80% of reps certified on discovery or negotiation
- Stage conversion up 5–10% where you targeted change
- Forecast risk flagged sooner; fewer late-stage stalls
- Managers spending ~30–40% of time on coaching, not just reporting
