The sales landscape shifted dramatically in 2025, and status quo strategies won’t cut it anymore. Only 43% of sales reps hit quota in Q1 2025, deal slippage is costing companies millions in lost revenue, and 70% of sales teams are battling burnout that’s killing engagement. If you’re a sales leader watching your forecasts slip and your team struggle, it’s time to stop guessing and start diagnosing. These 18 questions will help you identify exactly where your performance gaps are and what to do about them.
TLDR:
Only 43% of reps hit quota in Q1 2025, 36% of deals slip past close dates, and 70% of sales teams face burnout that prevents high engagement. These 18 diagnostic questions help sales leaders identify critical performance gaps across prospecting, process, coaching, and mindset. Teams with structured processes, formal coaching, and disciplined CRM use achieve 2-3x better results, including 91.2% quota attainment and 19-28% higher win rates.
The Wake-Up Call Nobody Wants to Hear
Let’s be honest. If your sales team could coast on last year’s playbook, you wouldn’t be reading this right now.
But here’s the reality: 67% of sales reps failed to meet quota by year’s end in 2025. Not because they’re lazy. Not because the economy tanked. But because the game changed faster than most organizations could adapt.
Buyers complete 70% of their research before ever talking to sales. Buying committees now average 10-11 stakeholders, sometimes 15+ for enterprise deals. Your reps aren’t just selling anymore. They’re navigating complex political landscapes, managing marathon sales cycles, and competing against buyer indecision more than actual competitors.
The question isn’t whether you need to change. It’s whether you’re willing to honestly assess where you are before you try to get somewhere better.
Why 2025 Demands a Different Approach
The data doesn’t lie, and it’s telling a story most sales leaders don’t want to hear.
Deal slippage hit 36% in 2025. That means more than one in three forecasted deals didn’t close when expected. Worse? When deals extend beyond two months, win rates plummet by 113%. And only 62% of delayed deals ever close at all.
Burnout is crushing engagement. Seventy percent of sales staff experience burnout that actively prevents high performance. Fifty-two percent of sales leaders rate overall team engagement as “very low.” This isn’t a morale problem. It’s a revenue problem.
Buyers have evolved, but most sales teams haven’t. According to research from top industry analysts, buyers now complete 57-70% of their research before contacting sales. They’re bringing 10-11 decision-makers into the process. And 52% of those buying committees include VP-level or higher executives.
Your team can’t wing it anymore. They need structure, coaching, and accountability, or they’ll keep losing to organizations that figured this out first.
The Cost of Maintaining Status Quo
Let’s talk dollars and sense for a minute.
When deals slip past their projected close dates, you’re not just delaying revenue. You’re watching win rates crater. According to Harvard Business Review research on sales performance, low-performing reps are 217% more likely to experience deal slippage than high performers. That’s not a small gap. That’s a chasm.
And what about your people? Twenty percent of new sales reps churn within the first 45 days when training and onboarding fall short. Forty-four percent of salespeople are planning to leave their jobs within two years. Every time you lose a rep, you’re flushing 6-9 months of productivity and tens of thousands in recruiting and training costs down the drain.
Here’s the math that should keep you up at night: 84% of sales training content is forgotten within three months without proper reinforcement. You’re investing in development that evaporates before it can drive results.
The cost of doing nothing? Lost deals. Lost talent. Lost market position. And a team that’s working harder while falling further behind.
18 Essential Questions to Evaluate Your Sales Team’s Readiness
Stop guessing. Start measuring. A comprehensive sales team evaluation begins with these 18 critical questions that separate high-performing sales teams from the ones stuck in mediocrity:
1. How strong is your prospecting ability? (New business + account expansion)
Why it matters: 76% of deals lack compelling events to drive urgency. If your team can’t create pipeline momentum, they’re already behind.
2. Can your team reach true decision-makers? (Not just single contacts)
Why it matters: Buying committees average 10-11 stakeholders, and 52% include VP+ executives. Single-threading is a death sentence.
3. Do reps build deep, multi-threaded relationships across accounts?
Why it matters: Low-performing reps are 217% more likely to experience deal slippage. Relationships across the buying committee prevent collapse.
4. Can your team sell value over price?
Why it matters: Teams that embed value-based selling see 19% higher win rates. Price-focused conversations commoditize your solution.
5. Are reps delivering the right content at the right stage?
Why it matters: 85% of salespeople present at the wrong time, and only 18% of buyers think reps are well-prepared for conversations.
6. How well do they manage sales cycles and prevent delays?
Why it matters: 36% of deals slip past close dates. When deals exceed two months, win rates drop 113%.
7. Do you have a custom, milestone-driven sales process?
Why it matters: Milestone-based processes increase quota attainment by 18-31%. Generic processes produce generic results.
8. Is your team disciplined with CRM usage?
Why it matters: 97% of businesses using CRM meet or exceed goals. Sixty-five percent using mobile CRM hit quota versus only 22% who don’t.
9. Do reps ask insightful, challenging questions?
Why it matters: Consultative selling drives 50% higher meeting-to-opportunity conversion. Generic questions get generic responses.
10. How strong are active listening skills?
Why it matters: In complex, multi-stakeholder environments, listening separates order-takers from trusted advisors.
11. Are limiting beliefs holding reps back?
Why it matters: The top 7% of performers have minimal limiting beliefs. Mental roadblocks kill performance faster than skill gaps.
12. Does your team have genuine hunger for success?
Why it matters: Motivation directly correlates with quota attainment and resilience during long sales cycles.
13. Are they committed to doing what it takes ethically?
Why it matters: Discipline and accountability separate high performers from average. No shortcuts, no excuses.
14. What is current morale across your sales team?
Why it matters: 52% of sales leaders rate engagement as “very low,” and 70% face burnout. Low morale = low performance.
15. Do you hear excuses or ownership?
Why it matters: Accountability culture drives performance. Victim mentality kills results and spreads like a virus.
16. How motivated is your team to exceed quotas?
Why it matters: Only 43% of reps hit Q1 quota in 2025. Motivation matters when the going gets tough.
17. How effective are sales leaders at proactive coaching?
Why it matters: Formal coaching drives 91.2% quota attainment versus 84.7% informal. Reps with excellent coaching are 50% more likely to hit quota.
18. Are managers addressing skill gaps with targeted development?
Why it matters: 84% of training is forgotten in three months without reinforcement. Customized, ongoing development doubles effectiveness.
The High-Performance Formula: Clarity + Will + Skill + Process
Here’s what the best sales organizations understand: success isn’t accidental.
High-performing teams know exactly where they are, where they need to go, and what specific capabilities will close the gap. They don’t hope for better results. They engineer them.
The formula is simple. Clarity about current state. Will to change and commit. Skill development that’s targeted and reinforced. Process that creates consistency and accountability.
And here’s the ROI that makes this a no-brainer: sales training delivers 353% ROI, with every dollar spent returning $4.53. Companies that prioritize training are 57% more effective than competitors who don’t.
But here’s the catch: training alone isn’t enough. Without structured processes, consistent coaching, and accountability mechanisms, that investment evaporates. You need the whole formula working together.
What the Data Shows About High-Performing Teams
The gap between high performers and everyone else isn’t small. It’s massive, and it’s measurable.
According to Gallup research on employee engagement, business units in the top quartile for engagement see 23% higher profitability and 18% higher productivity. High-performing teams know exactly where they are, where they need to go, and what specific capabilities will close the gap. They don’t hope for better results. They engineer them.
High-Performing Teams:
- 91.2% quota attainment with formal coaching processes
- 19% higher win rates with value-based selling approach
- 29% revenue increase with disciplined CRM use
- 50% more likely to hit quota with excellent coaching
- 18-31% higher quota attainment with milestone-based processes
Struggling Teams:
- 67% missing quota by year’s end
- 36% deal slippage rates
- 70% experiencing burnout that prevents engagement
- 84% forgetting training within three months
- 217% higher slippage for low performers
The difference? It’s not talent. It’s not market conditions. It’s structure, coaching, accountability, and process.
Real-World Impact: The ASLI Approach
We worked with a mid-market technology company whose sales team was stuck at 58% quota attainment. They had smart people, a strong product, and plenty of pipeline. But deals kept slipping, reps were burning out, and leadership didn’t know where to start.
We began with a comprehensive evaluation, asking these same 18 questions and digging into the data. What we found: no structured sales process, inconsistent coaching, weak CRM discipline, and reps who were great at getting meetings but terrible at multi-threading across buying committees.
Within 90 days of implementing a milestone-based sales process, structured weekly coaching, and CRM accountability, quota attainment jumped to 79%. Six months later, they hit 87%. Deal slippage dropped by half. Burnout metrics improved dramatically.
The key? We didn’t try to fix everything at once. We identified the 3-5 gaps with the biggest revenue impact and addressed them systematically. That’s what targeted sales training and development delivers when it’s customized to your team’s actual gaps.
FAQ: What Sales Leaders Need to Know
Q: How do we know which gaps to address first?
A: Start with a comprehensive sales team evaluation. Identify the 3-5 gaps with the biggest revenue impact, usually process, coaching, or CRM discipline. Companies using structured assessments see faster, more sustainable improvement than those who guess.
Q: What’s the ROI on investing in sales training and coaching?
A: Sales training delivers 353% ROI on average. Every dollar spent returns $4.53. Teams with formal coaching achieve 91.2% quota attainment versus 84.7% for informal approaches. The question isn’t whether you can afford it. It’s whether you can afford not to.
Q: Why do so many sales training programs fail?
A: Because 84% of training content is forgotten within three months without reinforcement. One-and-done training events don’t stick. Effective programs use spaced repetition, coaching reinforcement, and application tools to ensure retention and behavior change.
Q: How long does it take to see improvement?
A: With targeted coaching and process implementation, teams typically see measurable improvement in 60-90 days. High-growth companies prioritize customized, ongoing development, not one-time events. Think marathon, not sprint.
Q: Can you really fix low quota attainment?
A: Yes. Teams that implement milestone-based processes see 18-31% higher quota attainment. Adding structured coaching increases win rates by 19-28%. But it requires commitment from leadership and accountability from reps.
Q: What if our CRM adoption is low?
A: This is critical to address immediately. Ninety-seven percent of CRM users meet or exceed sales goals, and mobile CRM users are three times more likely to hit quota. Start with training, accountability, and making CRM the central hub for all sales activity.
Q: How do we reduce deal slippage?
A: Focus on qualification, compelling events, and multi-threading. Seventy-six percent of deals lack urgency, and low performers are 217% more likely to experience slippage. Structured processes and disciplined pipeline management make the difference.
Q: What about sales team burnout?
A: This is a performance killer you can’t ignore. Seventy percent of sales staff experience burnout that prevents high engagement. Address it through realistic quotas, consistent coaching, recognition, and removing obstacles to success. Burned-out reps don’t hit quota. Period.
Key Takeaways
- Only 43% of sales reps hit quota in Q1 2025. Status quo strategies no longer work.
- Teams with formal coaching achieve 91.2% quota attainment and 28% higher win rates.
- Milestone-based sales processes increase quota attainment by 18-31%.
- Sales training delivers 353% ROI, but 84% is forgotten without proper reinforcement.
- 97% of businesses using CRM effectively meet or exceed sales goals.
- Deal slippage costs revenue: when deals exceed two months, win rates drop 113%.
Your sales team’s performance in 2025 won’t improve by hoping for better results. It requires honest assessment, targeted development, and accountability. At Accelerated Sales & Leadership Institute, we’ve spent 25+ years helping organizations answer these 18 critical questions and transform the answers into measurable growth. If you’re ready to move from diagnosis to results, let’s talk. Schedule a consultation with ASLI today and discover exactly what it takes to build a high-performing sales team that consistently exceeds quota.
